Jump To Section:

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-10-17 09:58:23 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005032

Secondary Accession Numbers

HMDB05032

Metabolite Identification

Common Name

Cetirizine

Description

Cetirizine is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth. A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects. Cetirizine hydrochloride is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

341
  Mrv0541 02231214362D          

 27 29  0  0  1  0            999 V2000
    1.6500   -4.1746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 15  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 27  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0005032
     RDKit          3D
Cetirizine
 52 54  0  0  0  0  0  0  0  0999 V2000
    6.3048    1.0572    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2945    0.4364    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379   -0.5508    0.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    0.7530   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    1.7239   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    1.5339    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.2986    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.0140    1.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738    0.9263    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    0.7490    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507   -0.5575    0.1867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -1.0011   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.4551   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274    0.8461   -1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588    1.2641   -3.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    0.3464   -4.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323   -0.9804   -3.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022   -1.3898   -2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8383   -0.7758    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551   -0.2394    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -0.0577    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -0.3833    2.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -0.1596    3.9368 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665   -0.9211    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -1.1041    2.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -1.5110    0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756   -1.3538    1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183   -0.4573    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    1.1063   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195   -0.1918   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    1.5721    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    2.4333    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.5854    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.4213   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    1.9600    1.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2693    0.7072    2.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    1.2481    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672    1.3474   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -2.1306   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441    1.6044   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209    2.3251   -3.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.6737   -5.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426   -1.7061   -4.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3616   -2.4528   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917    0.0442   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9652    0.3639    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -1.1978    4.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -1.5366    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -2.5559    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.4296   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032   -1.6082    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2587   -2.0260    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 11 26  1  0
 26 27  1  0
 27  8  1  0
 18 13  1  0
 25 19  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

341
  Mrv0541 02231214362D          

 27 29  0  0  1  0            999 V2000
    1.6500   -4.1746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2 15  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 27  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005032

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)

> <INCHI_KEY>
ZKLPARSLTMPFCP-UHFFFAOYSA-N

> <FORMULA>
C21H25ClN2O3

> <MOLECULAR_WEIGHT>
388.888

> <EXACT_MASS>
388.155370383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.878150049336554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
0.8598093028281057

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.596630966769094

> <JCHEM_PKA_STRONGEST_BASIC>
7.789172195841928

> <JCHEM_POLAR_SURFACE_AREA>
53.010000000000005

> <JCHEM_REFRACTIVITY>
106.86650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cetirizine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005032
     RDKit          3D
Cetirizine
 52 54  0  0  0  0  0  0  0  0999 V2000
    6.3048    1.0572    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2945    0.4364    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379   -0.5508    0.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    0.7530   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    1.7239   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    1.5339    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.2986    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.0140    1.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738    0.9263    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    0.7490    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507   -0.5575    0.1867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -1.0011   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.4551   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274    0.8461   -1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588    1.2641   -3.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    0.3464   -4.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323   -0.9804   -3.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022   -1.3898   -2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8383   -0.7758    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551   -0.2394    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -0.0577    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -0.3833    2.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -0.1596    3.9368 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665   -0.9211    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -1.1041    2.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -1.5110    0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756   -1.3538    1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183   -0.4573    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    1.1063   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195   -0.1918   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    1.5721    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    2.4333    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.5854    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.4213   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    1.9600    1.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2693    0.7072    2.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    1.2481    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672    1.3474   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -2.1306   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441    1.6044   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209    2.3251   -3.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.6737   -5.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426   -1.7061   -4.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3616   -2.4528   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917    0.0442   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9652    0.3639    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -1.1978    4.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -1.5366    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -2.5559    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.4296   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032   -1.6082    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2587   -2.0260    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 11 26  1  0
 26 27  1  0
 27  8  1  0
 18 13  1  0
 25 19  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 341                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -7.793   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       9.748   3.758   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.416   6.838   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.748   6.838   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.415  -3.172   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.415  -0.092   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748  -2.402   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -4.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -5.483   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748  -5.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -7.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -4.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -4.713   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -7.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -7.793   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -5.483   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416  -5.483   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082  -7.793   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -7.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.416  -7.023   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082   4.528   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.082   6.068   0.000  0.00  0.00           C+0
CONECT    1   24                                                            
CONECT    2   15   26                                                       
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5    7    8   11                                                  
CONECT    6    9   10   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    6    7                                                       
CONECT   10    6    8                                                       
CONECT   11    5   13   14                                                  
CONECT   12    6   15                                                       
CONECT   13   11   16   17                                                  
CONECT   14   11   18   19                                                  
CONECT   15    2   12                                                       
CONECT   16   13   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   14   23                                                       
CONECT   20   16   24                                                       
CONECT   21   17   24                                                       
CONECT   22   18   25                                                       
CONECT   23   19   25                                                       
CONECT   24    1   20   21                                                  
CONECT   25   22   23                                                       
CONECT   26    2   27                                                       
CONECT   27    3    4   26                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0005032
HETATM    1  O1  UNL     1       6.305   1.057   1.358  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.294   0.436   0.272  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.238  -0.551   0.072  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.307   0.753  -0.754  1.00  0.00           C  
HETATM    5  O3  UNL     1       4.402   1.724  -0.472  1.00  0.00           O  
HETATM    6  C3  UNL     1       3.570   1.534   0.611  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.761   0.299   0.411  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.853   0.014   1.485  1.00  0.00           N  
HETATM    9  C5  UNL     1       0.774   0.926   1.626  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.295   0.749   0.562  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.551  -0.557   0.187  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.772  -1.001  -0.315  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.132  -0.455  -1.618  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.227   0.846  -1.992  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.559   1.264  -3.264  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.816   0.346  -4.237  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.732  -0.980  -3.902  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.402  -1.390  -2.637  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.838  -0.776   0.709  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.055  -0.239   0.365  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.997  -0.058   1.358  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.786  -0.383   2.673  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -5.968  -0.160   3.937  1.00  0.00          CL  
HETATM   24  C18 UNL     1      -3.566  -0.921   3.018  1.00  0.00           C  
HETATM   25  C19 UNL     1      -2.620  -1.104   2.022  1.00  0.00           C  
HETATM   26  C20 UNL     1       0.504  -1.511   0.267  1.00  0.00           C  
HETATM   27  C21 UNL     1       1.376  -1.354   1.465  1.00  0.00           C  
HETATM   28  H1  UNL     1       8.218  -0.457   0.219  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.858   1.106  -1.688  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.820  -0.192  -1.119  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.077   1.572   1.600  1.00  0.00           H  
HETATM   32  H5  UNL     1       2.875   2.433   0.587  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.421  -0.585   0.251  1.00  0.00           H  
HETATM   34  H7  UNL     1       2.169   0.421  -0.519  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.174   1.960   1.634  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.269   0.707   2.601  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.229   1.248   0.913  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.067   1.347  -0.301  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.726  -2.131  -0.398  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.044   1.604  -1.242  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.621   2.325  -3.515  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.082   0.674  -5.254  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.943  -1.706  -4.698  1.00  0.00           H  
HETATM   44  H17 UNL     1      -2.362  -2.453  -2.469  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.292   0.044  -0.670  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.965   0.364   1.113  1.00  0.00           H  
HETATM   47  H20 UNL     1      -3.350  -1.198   4.060  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.673  -1.537   2.373  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.080  -2.556   0.252  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.130  -1.430  -0.646  1.00  0.00           H  
HETATM   51  H24 UNL     1       0.803  -1.608   2.363  1.00  0.00           H  
HETATM   52  H25 UNL     1       2.259  -2.026   1.348  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   28
CONECT    4    5   29   30
CONECT    5    6
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   27
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   26
CONECT   12   13   19   39
CONECT   13   14   14   18
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   16   17   42
CONECT   17   18   18   43
CONECT   18   44
CONECT   19   20   20   25
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   22   23   24
CONECT   24   25   25   47
CONECT   25   48
CONECT   26   27   49   50
CONECT   27   51   52
END

HMDB0005032
     RDKit          3D
Cetirizine
 52 54  0  0  0  0  0  0  0  0999 V2000
    6.3048    1.0572    1.3580 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2945    0.4364    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2379   -0.5508    0.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    0.7530   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    1.7239   -0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704    1.5339    0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7610    0.2986    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.0140    1.4845 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738    0.9263    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2953    0.7490    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507   -0.5575    0.1867 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -1.0011   -0.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.4551   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274    0.8461   -1.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588    1.2641   -3.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8161    0.3464   -4.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323   -0.9804   -3.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022   -1.3898   -2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8383   -0.7758    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551   -0.2394    0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -0.0577    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7858   -0.3833    2.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9684   -0.1596    3.9368 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5665   -0.9211    3.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6198   -1.1041    2.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -1.5110    0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756   -1.3538    1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2183   -0.4573    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    1.1063   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195   -0.1918   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    1.5721    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    2.4333    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206   -0.5854    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.4213   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742    1.9600    1.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2693    0.7072    2.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    1.2481    0.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672    1.3474   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -2.1306   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441    1.6044   -1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209    2.3251   -3.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.6737   -5.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426   -1.7061   -4.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3616   -2.4528   -2.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2917    0.0442   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9652    0.3639    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3501   -1.1978    4.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -1.5366    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -2.5559    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.4296   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032   -1.6082    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2587   -2.0260    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 11 26  1  0
 26 27  1  0
 27  8  1  0
 18 13  1  0
 25 19  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 27 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cetirizin	ChEBI
Cetirizina	ChEBI
Cetirizinum	ChEBI
Cetiderm	Kegg
Benaday	HMDB
Cetirizine hydrochloride	HMDB
Humex	HMDB
Reactine	HMDB, MeSH
Virlix	HMDB, MeSH
Zirtek	HMDB, MeSH
Zyrlex	HMDB
Zyrtec	HMDB, MeSH
Alpharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Ceti-puren	MeSH, HMDB
CetiLich	MeSH, HMDB
Cetirigamma	MeSH, HMDB
Cetirizin al	MeSH, HMDB
Dihydrochloride, cetirizine	MeSH, HMDB
glaxo Wellcome brand OF cetirizine dihydrochloride	MeSH, HMDB
TAD brand OF cetirizine dihydrochloride	MeSH, HMDB
UCB brand OF cetirizine dihydrochloride	MeSH, HMDB
Voltric	MeSH, HMDB
CT-Arzneimittel brand OF cetirizine dihydrochloride	MeSH, HMDB
Azupharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Basics brand OF cetirizine dihydrochloride	MeSH, HMDB
Cetalerg	MeSH, HMDB
Dermapharm brand OF cetirizine dihydrochloride	MeSH, HMDB
Krewel brand OF cetirizine dihydrochloride	MeSH, HMDB
Lacer brand OF cetirizine dihydrochloride	MeSH, HMDB
Menarini brand OF cetirizine dihydrochloride	MeSH, HMDB
Pfizer brand OF cetirizine dihydrochloride	MeSH, HMDB
Pfizer consumer healthcare brand OF cetirizine dihydrochloride	MeSH, HMDB
UCB pharma brand OF cetirizine dihydrochloride	MeSH, HMDB
AWD.pharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Aliud brand OF cetirizine dihydrochloride	MeSH, HMDB
Ceti tad	MeSH, HMDB
Cetidura	MeSH, HMDB
Cetirizin azu	MeSH, HMDB
Cetirizine dihydrochloride	MeSH, HMDB
Cetirlan	MeSH, HMDB
Lichtenstein brand OF cetirizine dihydrochloride	MeSH, HMDB
Rodleben brand OF cetirizine	MeSH, HMDB
United drug brand OF cetirizine dihydrochloride	MeSH, HMDB
Wolff brand OF cetirizine dihydrochloride	MeSH, HMDB
(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic acid	MeSH, HMDB
Alerlisin	MeSH, HMDB
Ceterifug	MeSH, HMDB
Cetil von CT	MeSH, HMDB
Cetirizin basics	MeSH, HMDB
Merck dura brand OF cetirizine dihydrochloride	MeSH, HMDB
Sanofi synthelabo brand OF cetirizine dihydrochloride	MeSH, HMDB
Wörwag brand OF cetirizine dihydrochloride	MeSH, HMDB
Zetir	MeSH, HMDB

Chemical Formula

C₂₁H₂₅ClN₂O₃

Average Molecular Weight

388.888

Monoisotopic Molecular Weight

388.155370383

IUPAC Name

2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

Traditional Name

cetirizine

CAS Registry Number

83881-51-0

SMILES

OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)

InChI Key

ZKLPARSLTMPFCP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Chlorobenzene
Halobenzene
N-alkylpiperazine
Aralkylamine
Aryl halide
1,4-diazinane
Aryl chloride
Piperazine
Amino acid
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Monocarboxylic acid or derivatives
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organohalogen compound
Amine
Organochloride
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:3561 )
ether (CHEBI:3561 )
monochlorobenzenes (CHEBI:3561 )
piperazines (CHEBI:3561 )

Ontology

Physiological effect

Health effect

Observation

Irritability (HMDB: HMDB0005032)
Drowsiness (HMDB: HMDB0005032)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Brain (HMDB: HMDB0005032)
Skin (HMDB: HMDB0005032)

Tissue

Epithelium

Epidermis (HMDB: HMDB0005032)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0005032)
Extracellular (HMDB: HMDB0005032)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005032)

Source

Exogenous

Exogenous (HMDB: HMDB0005032)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cetirizine H1-Antihistamine Action (HMDB: HMDB0005032)
Cetirizine H1-Antihistamine Action (PathBank: SMP0059058)

Role

Industrial application

H1-receptor antagonist (HMDB: HMDB0005032)
Anti-allergic agent (HMDB: HMDB0005032)

Pharmaceutical industry

Anti-allergic (HMDB: HMDB0005032)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	112.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	200.8	30932474
[M+H]+	Not Available	198.285	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000754

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	2.98	ALOGPS
logP	0.86	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	7.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.87 m³·mol⁻¹	ChemAxon
Polarizability	41.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.426	30932474
DeepCCS	[M-H]-	184.957	30932474
DeepCCS	[M-2H]-	219.166	30932474
DeepCCS	[M+Na]+	194.606	30932474
AllCCS	[M+H]+	191.2	32859911
AllCCS	[M+H-H2O]+	188.5	32859911
AllCCS	[M+NH4]+	193.6	32859911
AllCCS	[M+Na]+	194.3	32859911
AllCCS	[M-H]-	193.0	32859911
AllCCS	[M+Na-2H]-	193.2	32859911
AllCCS	[M+HCOO]-	193.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cetirizine	OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	4076.7	Standard polar	33892256
Cetirizine	OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	3009.0	Standard non polar	33892256
Cetirizine	OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1	3029.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cetirizine,1TMS,isomer #1	C[Si](C)(C)OC(=O)COCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC1	3104.7	Semi standard non polar	33892256
Cetirizine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)COCCN1CCN(C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)CC1	3312.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-3292000000-e20abaab20740ce81a18	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cetirizine GC-MS (1 TMS) - 70eV, Positive	splash10-0uds-7498000000-d6daecf118171395d6b7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cetirizine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cetirizine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000j-0900000000-9801bb859e79fa9922aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-014b559d56b0f32984ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-213bd47e17d5ab69ad4b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-004r-9006000000-f496e22c8e0e293fe98c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-d8a55ab1a7aff0580a91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-d8a55ab1a7aff0580a91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-dc957bb6f947575ae4fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000b-0900000000-48fc0581ff9fff15e16d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-04ca95fadd952d0aaeb8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-000i-0009000000-014b559d56b0f32984ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-0006-0009000000-26a7769df28c2325ec53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , negative-QTOF	splash10-0006-0009000000-284c2e7b25733d7c9875	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-QFT , negative-QTOF	splash10-000i-0009000000-04befed283d691217ba2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0190000000-14715ff4d57580fbb166	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-0f79-0069000000-431df9c3533b77cf08bc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0090000000-e042b67e2048318e7dbd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0190000000-b0dfb67717c01fd0c0b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-0gb9-0970000000-e2810b242fefb4a419e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cetirizine LC-ESI-ITFT , positive-QTOF	splash10-014i-0900000000-72f7cddc4ff6d45f98c0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 10V, Positive-QTOF	splash10-000i-0019000000-e2cc239f762011eb0c4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 20V, Positive-QTOF	splash10-0w2i-1169000000-185e6899ae017256a767	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 40V, Positive-QTOF	splash10-0udi-3391000000-bfd70499959ae71093eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 10V, Negative-QTOF	splash10-000i-0009000000-caf1604c9603d45a6712	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 20V, Negative-QTOF	splash10-000i-1119000000-61c40cd9a0e9b76b5e91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cetirizine 40V, Negative-QTOF	splash10-056r-9162000000-08731719ee47b215e4c7	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Epidermis

Pathways

Name	SMPDB/PathBank	KEGG
Cetirizine H1-Antihistamine Action		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2577

KEGG Compound ID

C07778

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cetirizine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3561

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Cossement, Eric; Motte, Genevieve; Bodson, Guy; Gobert, Jean. A., Process for preparation of cetirizine, its dihydrochloride, and optical isomers via hydrolysis and corresponding nitriles. Brit. UK Pat. Appl. (1990), 13 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093 ]
Purohit A, Melac M, Pauli G, Frossard N: Comparative activity of cetirizine and desloratadine on histamine-induced wheal-and-flare responses during 24 hours. Ann Allergy Asthma Immunol. 2004 Jun;92(6):635-40. [PubMed:15237765 ]
Ramboer I, Bumtbacea R, Lazarescu D, Radu JR: Cetirizine and loratadine: a comparison using the ED50 in skin reactions. J Int Med Res. 2000 Mar-Apr;28(2):69-77. [PubMed:10898119 ]
Purohit A, Duvernelle C, Melac M, Pauli G, Frossard N: Twenty-four hours of activity of cetirizine and fexofenadine in the skin. Ann Allergy Asthma Immunol. 2001 Apr;86(4):387-92. [PubMed:11345280 ]
Townley RG, Okada C: Use of cetirizine to investigate non-H1 effects of second-generation antihistamines. Ann Allergy. 1992 Feb;68(2):190-6. [PubMed:1346737 ]
Brik A, Tashkin DP, Gong H Jr, Dauphinee B, Lee E: Effect of cetirizine, a new histamine H1 antagonist, on airway dynamics and responsiveness to inhaled histamine in mild asthma. J Allergy Clin Immunol. 1987 Jul;80(1):51-6. [PubMed:2885355 ]
Fadel R, Herpin-Richard N, Rihoux JP, Henocq E: Inhibitory effect of cetirizine 2HCl on eosinophil migration in vivo. Clin Allergy. 1987 Jul;17(4):373-9. [PubMed:2887304 ]
Petersen LJ, Church MK, Rihoux JP, Skov PS: Measurement of interstitial cetirizine concentrations in human skin: correlation of drug levels with inhibition of histamine-induced skin responses. Allergy. 1999 Jun;54(6):607-11. [PubMed:10435475 ]
Siergiejko Z, Michalska I, Rogalewska A, Chyrek-Borowska S: [Effect of cetirizine, selective H1 antagonist of histamine on skin and bronchial reactivity and cellular histamine release in allergic diseases]. Pneumonol Alergol Pol. 1992;60(11-12):22-7. [PubMed:1303774 ]
Atkins PC, Zweiman B, Moskovitz A, von Allmen C, Ciliberti M: Cellular inflammatory responses and mediator release during early developing late-phase allergic cutaneous inflammatory responses: effects of cetirizine. J Allergy Clin Immunol. 1997 Jun;99(6 Pt 1):806-11. [PubMed:9215249 ]
Simons FE, Murray HE, Simons KJ: Quantitation of H1-receptor antagonists in skin and serum. J Allergy Clin Immunol. 1995 Mar;95(3):759-64. [PubMed:7897161 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

2. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

Showing metabocard for Cetirizine (HMDB0005032)

MOL for HMDB0005032 (Cetirizine)

3D MOL for HMDB0005032 (Cetirizine)

3D SDF for HMDB0005032 (Cetirizine)

3D-SDF for HMDB0005032 (Cetirizine)

PDB for HMDB0005032 (Cetirizine)

3D PDB for HMDB0005032 (Cetirizine)

SMILES for HMDB0005032 (Cetirizine)

INCHI for HMDB0005032 (Cetirizine)

Structure for HMDB0005032 (Cetirizine)

3D Structure for HMDB0005032 (Cetirizine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes