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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-16 11:45:18 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005000

Secondary Accession Numbers

HMDB05000

Metabolite Identification

Common Name

Loratadine

Description

desloratadine is available off the shelf in Canada); Loratadine is a tricyclic antihistamine, which has a selective and peripheral H1-antagonist action. It has a long-lasting effect and does not normally cause drowsiness because it does not readily enter the central nervous system; An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic; Loratadine is a drug used to treat allergies. It is marketed by Schering-Plough under several trade names such as Claritin, Clarityn or Claratyne depending on the market, by Lek as Lomilan and by Wyeth as Alavert. It is also available as a generic. Its active metabolite, desloratadine, is also on the market, though loratadine itself is the only drug of its class available over the counter (at least in the U.S. as of 2005. Loratadine is available off the shelf in the UK.

Structure

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

455
  Mrv1652305271900192D          

 27 30  0  0  0  0            999 V2000
    1.6500    2.6662    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -2.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014   -2.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.9036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    1.3352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0727    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    2.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428    2.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518    1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    2.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    2.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    2.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1944    2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0032    1.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -2.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2448   -3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  2  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 19  1  0  0  0  0
  5 13  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 18  1  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 20 23  2  0  0  0  0
 21 24  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0005000
     RDKit          3D
Loratadine
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.8304    0.7004   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.1296    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307    0.2113    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0227   -0.3957   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -1.0680   -1.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276   -0.2683   -0.5158 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.8919   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -1.3933   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075   -0.1460   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1324   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.1768   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.1060   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    3.3736   -1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    3.6935   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748    5.3553   -0.0165 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    2.7635    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    1.4395    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.6166    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492   -0.8131    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0935   -1.6320    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203   -2.8958    0.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -3.7443   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -3.4259   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187   -2.2207   -1.2563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -1.4023   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    1.0373   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.5101    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8661    0.8886    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773   -0.0688   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3765    1.6236   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.9316    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212    0.6816    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -1.8253   -1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -0.2134   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.0623   -1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9319   -1.8432   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    1.7347   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    4.0974   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    3.0277    1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125    0.7651    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    1.0860    2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3924   -1.2875    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0165    2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -3.0809    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729   -4.7250   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -4.1289   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    1.8704    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948    1.4082   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681    1.4011    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490   -0.0847    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  9 26  1  0
 26 27  1  0
 27  6  1  0
 25 10  1  0
 17 11  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
 27 50  1  0
M  END

455
  Mrv1652305271900192D          

 27 30  0  0  0  0            999 V2000
    1.6500    2.6662    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -2.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014   -2.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.9036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    1.3352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    1.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0727    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    2.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428    2.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518    1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    2.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    2.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286    1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    2.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1944    2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0032    1.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -2.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2448   -3.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 19  1  0  0  0  0
  2 26  1  0  0  0  0
  3 19  2  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 19  1  0  0  0  0
  5 13  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 18  1  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 20 23  2  0  0  0  0
 21 24  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005000

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3

> <INCHI_KEY>
JCCNYMKQOSZNPW-UHFFFAOYSA-N

> <FORMULA>
C22H23ClN2O2

> <MOLECULAR_WEIGHT>
382.883

> <EXACT_MASS>
382.144805697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.675132935182525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

> <ALOGPS_LOGP>
4.80

> <JCHEM_LOGP>
4.554579307

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.333617086511285

> <JCHEM_POLAR_SURFACE_AREA>
42.43

> <JCHEM_REFRACTIVITY>
116.9769

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005000
     RDKit          3D
Loratadine
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.8304    0.7004   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.1296    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307    0.2113    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0227   -0.3957   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -1.0680   -1.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276   -0.2683   -0.5158 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.8919   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -1.3933   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075   -0.1460   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1324   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.1768   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.1060   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    3.3736   -1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    3.6935   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748    5.3553   -0.0165 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    2.7635    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    1.4395    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.6166    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492   -0.8131    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0935   -1.6320    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203   -2.8958    0.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -3.7443   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -3.4259   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187   -2.2207   -1.2563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -1.4023   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    1.0373   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.5101    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8661    0.8886    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773   -0.0688   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3765    1.6236   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.9316    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212    0.6816    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -1.8253   -1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -0.2134   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.0623   -1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9319   -1.8432   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    1.7347   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    4.0974   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    3.0277    1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125    0.7651    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    1.0860    2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3924   -1.2875    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0165    2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -3.0809    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729   -4.7250   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -4.1289   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    1.8704    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948    1.4082   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681    1.4011    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490   -0.0847    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  9 26  1  0
 26 27  1  0
 27  6  1  0
 25 10  1  0
 17 11  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
 27 50  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 455                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       3.080   4.977   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      10.323  -3.997   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.656  -3.997   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.990  -1.687   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      11.536   2.492   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.990   1.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.323   0.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.656   0.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.990   2.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.323  -0.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.656  -0.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.602   3.602   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.377   3.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.259   5.103   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.220   6.307   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.760   6.307   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.720   5.103   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.443   2.492   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.990  -3.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.734   5.599   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.245   5.599   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.907   2.953   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.550   4.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.430   4.517   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.073   2.953   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.323  -5.537   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.657  -6.307   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   19   26                                                       
CONECT    3   19                                                            
CONECT    4   10   11   19                                                  
CONECT    5   13   25                                                       
CONECT    6    7    8    9                                                  
CONECT    7    6   10                                                       
CONECT    8    6   11                                                       
CONECT    9    6   12   13                                                  
CONECT   10    4    7                                                       
CONECT   11    4    8                                                       
CONECT   12    9   14   18                                                  
CONECT   13    5    9   17                                                  
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   13   16   21                                                  
CONECT   18   12   22                                                       
CONECT   19    2    3    4                                                  
CONECT   20   14   23                                                       
CONECT   21   17   24                                                       
CONECT   22   18   23                                                       
CONECT   23    1   20   22                                                  
CONECT   24   21   25                                                       
CONECT   25    5   24                                                       
CONECT   26    2   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0005000
HETATM    1  C1  UNL     1       6.830   0.700  -0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.031   0.130   0.991  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.631   0.211   0.733  1.00  0.00           O  
HETATM    4  C3  UNL     1       4.023  -0.396  -0.328  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.686  -1.068  -1.142  1.00  0.00           O  
HETATM    6  N1  UNL     1       2.628  -0.268  -0.516  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.906  -0.892  -1.632  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.592  -1.393  -0.984  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.208  -0.146  -0.687  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.465  -0.132  -0.449  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.110   1.177  -0.202  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.669   2.106  -1.119  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.148   3.374  -1.057  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.066   3.694  -0.077  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -3.675   5.355  -0.016  1.00  0.00          CL  
HETATM   16  C12 UNL     1      -3.501   2.764   0.827  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.036   1.440   0.804  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.694   0.617   1.831  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.449  -0.813   1.927  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.094  -1.632   0.778  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.720  -2.896   0.785  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.396  -3.744  -0.244  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.508  -3.426  -1.260  1.00  0.00           C  
HETATM   24  N2  UNL     1      -1.919  -2.221  -1.256  1.00  0.00           N  
HETATM   25  C20 UNL     1      -2.225  -1.402  -0.272  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.653   1.037  -0.478  1.00  0.00           C  
HETATM   27  C22 UNL     1       1.839   0.510   0.421  1.00  0.00           C  
HETATM   28  H1  UNL     1       7.866   0.889   0.238  1.00  0.00           H  
HETATM   29  H2  UNL     1       6.877  -0.069  -0.975  1.00  0.00           H  
HETATM   30  H3  UNL     1       6.376   1.624  -0.552  1.00  0.00           H  
HETATM   31  H4  UNL     1       6.292  -0.932   1.157  1.00  0.00           H  
HETATM   32  H5  UNL     1       6.221   0.682   1.934  1.00  0.00           H  
HETATM   33  H6  UNL     1       2.433  -1.825  -1.931  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.719  -0.213  -2.460  1.00  0.00           H  
HETATM   35  H8  UNL     1       0.138  -2.062  -1.705  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.932  -1.843  -0.034  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.973   1.735  -1.890  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.794   4.097  -1.779  1.00  0.00           H  
HETATM   39  H12 UNL     1      -4.219   3.028   1.586  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.812   0.765   1.686  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.461   1.086   2.831  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.392  -1.288   2.366  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.716  -1.016   2.797  1.00  0.00           H  
HETATM   44  H17 UNL     1      -4.390  -3.081   1.587  1.00  0.00           H  
HETATM   45  H18 UNL     1      -3.873  -4.725  -0.252  1.00  0.00           H  
HETATM   46  H19 UNL     1      -2.277  -4.129  -2.058  1.00  0.00           H  
HETATM   47  H20 UNL     1       0.206   1.870   0.080  1.00  0.00           H  
HETATM   48  H21 UNL     1       1.195   1.408  -1.347  1.00  0.00           H  
HETATM   49  H22 UNL     1       2.368   1.401   0.797  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.349  -0.085   1.190  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   27
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   10   26
CONECT   10   11   25
CONECT   11   12   12   17
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   16
CONECT   16   17   17   39
CONECT   17   18
CONECT   18   19   40   41
CONECT   19   20   42   43
CONECT   20   21   21   25
CONECT   21   22   44
CONECT   22   23   23   45
CONECT   23   24   46
CONECT   24   25   25
CONECT   26   27   47   48
CONECT   27   49   50
END

HMDB0005000
     RDKit          3D
Loratadine
 50 53  0  0  0  0  0  0  0  0999 V2000
    6.8304    0.7004   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.1296    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307    0.2113    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0227   -0.3957   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -1.0680   -1.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276   -0.2683   -0.5158 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.8919   -1.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917   -1.3933   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2075   -0.1460   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4652   -0.1324   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102    1.1768   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    2.1060   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475    3.3736   -1.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    3.6935   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6748    5.3553   -0.0165 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5013    2.7635    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358    1.4395    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.6166    1.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492   -0.8131    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0935   -1.6320    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203   -2.8958    0.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3964   -3.7443   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -3.4259   -1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187   -2.2207   -1.2563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255   -1.4023   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    1.0373   -0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.5101    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8661    0.8886    0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773   -0.0688   -0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3765    1.6236   -0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -0.9316    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212    0.6816    1.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -1.8253   -1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186   -0.2134   -2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -2.0623   -1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9319   -1.8432   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725    1.7347   -1.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    4.0974   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    3.0277    1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125    0.7651    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    1.0860    2.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3924   -1.2875    2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -1.0165    2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -3.0809    1.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8729   -4.7250   -0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -4.1289   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    1.8704    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948    1.4082   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681    1.4011    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3490   -0.0847    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  9 26  1  0
 26 27  1  0
 27  6  1  0
 25 10  1  0
 17 11  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
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  7 34  1  0
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  8 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
 27 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester	ChEBI
Aerotina	ChEBI
Alarin	ChEBI
Alavert	ChEBI
Alerpriv	ChEBI
Allerclear	ChEBI
Civeran	ChEBI
Claratyne	ChEBI
Claritin	ChEBI
Loracert	ChEBI
Loradamed	ChEBI
Loradex	ChEBI
Lorastine	ChEBI
Loratadina	ChEBI
Loratadinum	ChEBI
Loratyne	ChEBI
Wal-itin	ChEBI
4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate ethyl ester	Generator
4-(8-Chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester	MeSH
Clarium	MeSH
Amantadine	HMDB
Anhissen	HMDB
Bonalerg	HMDB
Claritine	HMDB
Clarityn	HMDB
Clarityne	HMDB
Cronopen	HMDB
Flonidan	HMDB
Fristamin	HMDB
Histaloran	HMDB
Klaritin	HMDB
Lertamine	HMDB
Lisino	HMDB
Loranox	HMDB
Loratidine	HMDB
Loratadine wyeth brand	MeSH, HMDB
Wyeth brand OF loratadine	MeSH, HMDB

Chemical Formula

C₂₂H₂₃ClN₂O₂

Average Molecular Weight

382.883

Monoisotopic Molecular Weight

382.144805697

IUPAC Name

ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

Traditional Name

ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

CAS Registry Number

79794-75-5

SMILES

CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2

InChI Identifier

InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3

InChI Key

JCCNYMKQOSZNPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzocycloheptapyridines

Sub Class

Not Available

Direct Parent

Benzocycloheptapyridines

Alternative Parents

Substituents

Benzocycloheptapyridine
Piperidinecarboxylic acid
Aryl chloride
Aryl halide
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
Carbamic acid ester
Carbonic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17156962)

Cellular substructure

Membrane (HMDB: HMDB0005000)
Cell membrane (HMDB: HMDB0005000)

Organ

Brain (HMDB: HMDB0005000)
Skin (HMDB: HMDB0005000)

Tissue

Epithelium

Epidermis (HMDB: HMDB0005000)

Central Nervous System (HMDB: HMDB0005000)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005000)

Source

Exogenous

Exogenous (HMDB: HMDB0005000)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Loratadine H1-Antihistamine Action (HMDB: HMDB0005000)
Loratadine H1-Antihistamine Action (PathBank: SMP0060195)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005000)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 - 136 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	5.20	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	187.4	30932474
[M+H]+	Not Available	185.793	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001050

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.8	ALOGPS
logP	4.55	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	4.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.98 m³·mol⁻¹	ChemAxon
Polarizability	41.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	190.066	30932474
DeepCCS	[M-H]-	187.708	30932474
DeepCCS	[M-2H]-	221.9	30932474
DeepCCS	[M+Na]+	197.128	30932474
AllCCS	[M+H]+	191.1	32859911
AllCCS	[M+H-H2O]+	188.4	32859911
AllCCS	[M+NH4]+	193.6	32859911
AllCCS	[M+Na]+	194.3	32859911
AllCCS	[M-H]-	193.1	32859911
AllCCS	[M+Na-2H]-	192.9	32859911
AllCCS	[M+HCOO]-	192.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.74 minutes	32390414
Predicted by Siyang on May 30, 2022	20.1878 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2676.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	576.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	249.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	291.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	838.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	593.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1689.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	535.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1828.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	575.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	305.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	537.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loratadine	CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2	4411.7	Standard polar	33892256
Loratadine	CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2	2938.9	Standard non polar	33892256
Loratadine	CCOC(=O)N1CCC(CC1)=C1C2=C(CCC3=C1N=CC=C3)C=C(Cl)C=C2	3156.5	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Brain
Epidermis

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.02 +/- 0.33 uM	Adult (>18 years old)	Both	Normal	17156962	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
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

DB00455

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023577

KNApSAcK ID

Not Available

Chemspider ID

3820

KEGG Compound ID

C06818

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loratadine

METLIN ID

1021

PubChem Compound

3957

PDB ID

Not Available

ChEBI ID

6538

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Vilani, Frank J. Antihistaminic 11-(4-piperidylidene)-5H-benzo-(5,6)-cyclohepta-[1,2-b]-pyridines. U.S. (1981), 4 pp. CODEN: USXXAM US 4282233 19810804 CAN 95:203761 AN 1981:603761

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
Green LB, Hornyak JE, Hurvitz EA: Amantadine in pediatric patients with traumatic brain injury: a retrospective, case-controlled study. Am J Phys Med Rehabil. 2004 Dec;83(12):893-7. [PubMed:15624567 ]
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 ]
Kornhuber J, Quack G, Danysz W, Jellinger K, Danielczyk W, Gsell W, Riederer P: Therapeutic brain concentration of the NMDA receptor antagonist amantadine. Neuropharmacology. 1995 Jul;34(7):713-21. [PubMed:8532138 ]
Deep P, Dagher A, Sadikot A, Gjedde A, Cumming P: Stimulation of dopa decarboxylase activity in striatum of healthy human brain secondary to NMDA receptor antagonism with a low dose of amantadine. Synapse. 1999 Dec 15;34(4):313-8. [PubMed:10529725 ]
Strong DK, Eisenstat DD, Bryson SM, Sitar DS, Arbus GS: Amantadine neurotoxicity in a pediatric patient with renal insufficiency. DICP. 1991 Nov;25(11):1175-7. [PubMed:1763530 ]
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 ]
Shiller AD, Burke DT, Kim HJ, Calvanio R, Dechman KG, Santini C: Treatment with amantadine potentiated motor learning in a patient with traumatic brain injury of 15 years' duration. Brain Inj. 1999 Sep;13(9):715-21. [PubMed:10507453 ]
Wilkinson R, Meythaler JM, Guin-Renfroe S: Neuroleptic malignant syndrome induced by haloperidol following traumatic brain injury. Brain Inj. 1999 Dec;13(12):1025-31. [PubMed:10628507 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

3. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

4. 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 Loratadine (HMDB0005000)

MOL for HMDB0005000 (Loratadine)

3D MOL for HMDB0005000 (Loratadine)

3D SDF for HMDB0005000 (Loratadine)

3D-SDF for HMDB0005000 (Loratadine)

PDB for HMDB0005000 (Loratadine)

3D PDB for HMDB0005000 (Loratadine)

SMILES for HMDB0005000 (Loratadine)

INCHI for HMDB0005000 (Loratadine)

Structure for HMDB0005000 (Loratadine)

3D Structure for HMDB0005000 (Loratadine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes