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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (3) Show 10 proteins XML

enzymes (7)transporters (3) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015061

Secondary Accession Numbers

HMDB15061

Metabolite Identification

Common Name

Phenoxybenzamine

Description

Phenoxybenzamine, also known as dibenyline or fenossibenzamina, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. Phenoxybenzamine is a drug which is used for the treatment of phaeochromocytoma (malignant), benign prostatic hypertrophy and malignant essential hypertension. Phenoxybenzamine is a very strong basic compound (based on its pKa). It is also used in complex regional pain syndrome (CRPS) type 1 due to its anti-adrenergic affects. Phenoxybenzamine forms a permanent covalent bond with adrenergic receptors. This results in further vasodilation, pupil constriction, an increase in GI tract motility and secretions, and glycogen synthesis. This causes vasodilatation in blood vessels, due to its antagonistic effect at the alpha-1 adrenoceptor found in the walls of blood vessels, resulting in a drop in blood pressure.

Structure

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

HMDB0015061
     RDKit          3D
Phenoxybenzamine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.2822   -0.3538   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.1949    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    1.1382    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.4899   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    0.9804   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188   -0.0717    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558   -0.5865   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510   -0.0186   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.0402   -2.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753    1.5404   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -0.4720    1.3922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724   -1.8372    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -2.8205    1.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294   -2.5134    3.4147 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    0.4341    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    0.6488    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -0.2361    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -0.0716   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.9589   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.8569   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    1.6676   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105   -1.0031   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    0.6838   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217   -0.7227   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258   -0.9901    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102    1.9541    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3923    1.1407    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -0.5646    0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -1.4323    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5393   -0.4329   -1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5973    1.4615   -2.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    2.3741   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547   -1.9405    2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709   -2.1716    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921   -3.8255    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7049   -2.9233    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    0.0573    2.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299    1.4534    1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297   -1.0683    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6439   -0.7750   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5395    1.0887   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    2.6656   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    2.3919   -0.3483 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  5  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

925
  Mrv0541 02231215062D          

 21 22  0  0  1  0            999 V2000
    5.2218   -0.8249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7930    1.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -3.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    3.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015061

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3

> <INCHI_KEY>
QZVCTJOXCFMACW-UHFFFAOYSA-N

> <FORMULA>
C18H22ClNO

> <MOLECULAR_WEIGHT>
303.826

> <EXACT_MASS>
303.138992038

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.09244520583415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl(2-chloroethyl)(1-phenoxypropan-2-yl)amine

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.6397570586666665

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.970203783069623

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
88.91500000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenoxybenzamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015061
     RDKit          3D
Phenoxybenzamine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.2822   -0.3538   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.1949    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    1.1382    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.4899   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    0.9804   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188   -0.0717    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558   -0.5865   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510   -0.0186   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.0402   -2.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753    1.5404   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -0.4720    1.3922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724   -1.8372    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -2.8205    1.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294   -2.5134    3.4147 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    0.4341    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    0.6488    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -0.2361    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -0.0716   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.9589   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.8569   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    1.6676   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105   -1.0031   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    0.6838   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217   -0.7227   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258   -0.9901    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102    1.9541    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3923    1.1407    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -0.5646    0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -1.4323    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5393   -0.4329   -1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5973    1.4615   -2.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    2.3741   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547   -1.9405    2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709   -2.1716    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921   -3.8255    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7049   -2.9233    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    0.0573    2.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299    1.4534    1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297   -1.0683    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6439   -0.7750   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5395    1.0887   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    2.6656   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    2.3919   -0.3483 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  5  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 925                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.747  -1.540   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.080   3.080   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.747   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.080  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.080   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.413   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.413  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.414   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.413  -6.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.747   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.747   6.159   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.081   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.081   5.390   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    7   13                                                       
CONECT    3    4    5    6                                                  
CONECT    4    3    7    8                                                  
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    2    4                                                       
CONECT    8    4                                                            
CONECT    9    5   11   12                                                  
CONECT   10    1    6                                                       
CONECT   11    9   14                                                       
CONECT   12    9   15                                                       
CONECT   13    2   17   18                                                  
CONECT   14   11   16                                                       
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
CONECT   17   13   19                                                       
CONECT   18   13   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015061
HETATM    1  C1  UNL     1      -0.282  -0.354  -1.038  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.233  -0.195   0.370  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.877   1.138   0.577  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.818   1.490  -0.348  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.037   0.980  -0.656  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.619  -0.072   0.004  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.856  -0.586  -0.318  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.551  -0.019  -1.356  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.996   1.040  -2.039  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.775   1.540  -1.715  1.00  0.00           C  
HETATM   11  N1  UNL     1      -0.720  -0.472   1.392  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.172  -1.837   1.387  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.093  -2.821   1.783  1.00  0.00           C  
HETATM   14 CL1  UNL     1       0.529  -2.513   3.415  1.00  0.00          CL  
HETATM   15  C12 UNL     1      -1.762   0.434   1.637  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.766   0.649   0.577  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.827  -0.236   0.526  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.804  -0.072  -0.427  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.757   0.959  -1.342  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.711   1.857  -1.315  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.744   1.668  -0.347  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.410  -1.003  -1.624  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.299   0.684  -1.484  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.322  -0.723  -1.090  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.026  -0.990   0.485  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.110   1.954   0.737  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.392   1.141   1.604  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.148  -0.565   0.859  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.274  -1.432   0.245  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.539  -0.433  -1.609  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.597   1.461  -2.863  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.338   2.374  -2.251  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.955  -1.941   2.184  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.571  -2.172   0.411  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.592  -3.825   1.816  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.705  -2.923   1.026  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.311   0.057   2.562  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.430   1.453   1.950  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.930  -1.068   1.219  1.00  0.00           H  
HETATM   40  H19 UNL     1      -5.644  -0.775  -0.461  1.00  0.00           H  
HETATM   41  H20 UNL     1      -5.539   1.089  -2.105  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.668   2.666  -2.029  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.931   2.392  -0.348  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   11   25
CONECT    3    4   26   27
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   32
CONECT   11   12   15
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   15   16   37   38
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
CONECT   21   43
END

HMDB0015061
     RDKit          3D
Phenoxybenzamine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.2822   -0.3538   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -0.1949    0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    1.1382    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.4899   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    0.9804   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188   -0.0717    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558   -0.5865   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510   -0.0186   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956    1.0402   -2.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753    1.5404   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -0.4720    1.3922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724   -1.8372    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -2.8205    1.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294   -2.5134    3.4147 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7619    0.4341    1.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    0.6488    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -0.2361    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8045   -0.0716   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574    0.9589   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7110    1.8569   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443    1.6676   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105   -1.0031   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2992    0.6838   -1.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217   -0.7227   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0258   -0.9901    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102    1.9541    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3923    1.1407    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -0.5646    0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -1.4323    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5393   -0.4329   -1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5973    1.4615   -2.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    2.3741   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547   -1.9405    2.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709   -2.1716    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5921   -3.8255    1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7049   -2.9233    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3109    0.0573    2.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299    1.4534    1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297   -1.0683    1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6439   -0.7750   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5395    1.0887   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    2.6656   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312    2.3919   -0.3483 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 10  5  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fenossibenzamina	HMDB
Dibenyline	HMDB
Hydrochloride, phenoxybenzamine	HMDB
Dibenylene	HMDB
Dibenziran	HMDB
Goldshield brand OF phenoxybenzamine hydrochloride	HMDB
Link brand OF phenoxybenzamine hydrochloride	HMDB
Esparma brand OF phenoxybenzamine hydrochloride	HMDB
Dibenzyline	HMDB
Phenoxybenzamine hydrochloride	HMDB
Wellspring brand OF phenoxybenzamine hydrochloride	HMDB
Dibenzylin	HMDB
Dibenzyran	HMDB

Chemical Formula

C₁₈H₂₂ClNO

Average Molecular Weight

303.826

Monoisotopic Molecular Weight

303.138992038

IUPAC Name

benzyl(2-chloroethyl)(1-phenoxypropan-2-yl)amine

Traditional Name

phenoxybenzamine

CAS Registry Number

59-96-1

SMILES

CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3

InChI Key

QZVCTJOXCFMACW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Benzylamine
Phenoxy compound
Phenol ether
Phenylmethylamine
Alkyl aryl ether
Aralkylamine
Tertiary aliphatic amine
Tertiary amine
Ether
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Amine
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic amine (CHEBI:8077 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015061)

Source

Exogenous

Exogenous (HMDB: HMDB0015061)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	39 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.01 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	4.26	ALOGPS
logP	4.64	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.92 m³·mol⁻¹	ChemAxon
Polarizability	34.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.565	30932474
DeepCCS	[M-H]-	169.207	30932474
DeepCCS	[M-2H]-	202.094	30932474
DeepCCS	[M+Na]+	177.659	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	173.8	32859911
AllCCS	[M+HCOO]-	173.6	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.	8.01 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5294 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1893.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	360.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	619.8 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	593.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	507.5 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	1399.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	254.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	169.0 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenoxybenzamine	CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1	3222.6	Standard polar	33892256
Phenoxybenzamine	CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1	2241.2	Standard non polar	33892256
Phenoxybenzamine	CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1	2325.0	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 - Phenoxybenzamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7930000000-384c032e9b77eb66c749	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenoxybenzamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 10V, Positive-QTOF	splash10-0udi-4029000000-388f1c34ddb95b1ee009	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 20V, Positive-QTOF	splash10-0006-9231000000-ec96011b63bed09eb912	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 40V, Positive-QTOF	splash10-0006-9000000000-56a30aa5b92d840f5281	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 10V, Negative-QTOF	splash10-0udi-4029000000-387751e302c4f69be132	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 20V, Negative-QTOF	splash10-0006-9121000000-8f4d9ec9ea1e13488b14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 40V, Negative-QTOF	splash10-0006-9000000000-6ea07a460948ae16252b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 10V, Positive-QTOF	splash10-0udi-0009000000-0ae6b7497ff7182fb842	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 20V, Positive-QTOF	splash10-0006-9702000000-5ffc7c8dda8bb19ba742	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 40V, Positive-QTOF	splash10-0006-9200000000-209610c0ebfc4d88a446	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 10V, Negative-QTOF	splash10-001i-9100000000-4d9bc979eb54eab7bcac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 20V, Negative-QTOF	splash10-000x-9000000000-89136960ac0373c92e2c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenoxybenzamine 40V, Negative-QTOF	splash10-0006-9000000000-f58b743d198c36a0fc6f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00925	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00925	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00925

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4604

KEGG Compound ID

C07435

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenoxybenzamine

METLIN ID

Not Available

PubChem Compound

4768

PDB ID

Not Available

ChEBI ID

141434

Food Biomarker Ontology

Not Available

VMH ID

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MarkerDB ID

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Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
Caine M, Perlberg S, Meretyk S: A placebo-controlled double-blind study of the effect of phenoxybenzamine in benign prostatic obstruction. Br J Urol. 1978 Dec;50(7):551-4. [PubMed:88984 ]

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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]

Enzyme Details

3. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]

Enzyme Details

4. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]

Enzyme Details

5. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Cimino M, Weiss B: Characteristics of the binding of phenoxybenzamine to calmodulin. Biochem Pharmacol. 1988 Jul 15;37(14):2739-45. [PubMed:3134891 ]
Suko J, Wyskovsky W, Pidlich J, Hauptner R, Plank B, Hellmann G: Calcium release from calmodulin and its C-terminal or N-terminal halves in the presence of the calmodulin antagonists phenoxybenzamine and melittin measured by stopped-flow fluorescence with Quin 2 and intrinsic tyrosine. Inhibition of calmodulin-dependent protein kinase of cardiac sarcoplasmic reticulum. Eur J Biochem. 1986 Sep 15;159(3):425-34. [PubMed:3758070 ]
Lukas TJ, Marshak DR, Watterson DM: Drug-protein interactions: isolation and characterization of covalent adducts of phenoxybenzamine and calmodulin. Biochemistry. 1985 Jan 1;24(1):151-7. [PubMed:3994963 ]
Earl CQ, Prozialeck WC, Weiss B: Interaction of alpha adrenergic antagonists with calmodulin. Life Sci. 1984 Jul 30;35(5):525-34. [PubMed:6146911 ]
Kuromi H, Yoshihara M, Kidokoro Y: An inhibitory role of calcineurin in endocytosis of synaptic vesicles at nerve terminals of Drosophila larvae. Neurosci Res. 1997 Feb;27(2):101-13. [PubMed:9100252 ]

Enzyme Details

6. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Stam WB, Van der Graaf PH, Saxena PR: Analysis of alpha 1L-adrenoceptor pharmacology in rat small mesenteric artery. Br J Pharmacol. 1999 Jun;127(3):661-70. [PubMed:10401556 ]
Michel MC, Hanft G, Gross G: Functional studies on alpha 1-adrenoceptor subtypes mediating inotropic effects in rat right ventricle. Br J Pharmacol. 1994 Feb;111(2):539-46. [PubMed:7911719 ]
Yu Y, Koss MC: Functional characterization of alpha-adrenoceptors mediating pupillary dilation in rats. Eur J Pharmacol. 2003 Jun 20;471(2):135-40. [PubMed:12818701 ]
Salles J, Gascon S, Badia A: Sustained increase in rat myocardial alpha 1A-adrenoceptors induced by 6-hydroxydopamine treatment involves a decelerated receptor turnover. Naunyn Schmiedebergs Arch Pharmacol. 1996 Mar;353(4):408-16. [PubMed:8935707 ]
Suzuki E, Tsujimoto G, Tamura K, Hashimoto K: Two pharmacologically distinct alpha 1-adrenoceptor subtypes in the contraction of rabbit aorta: each subtype couples with a different Ca2+ signalling mechanism and plays a different physiological role. Mol Pharmacol. 1990 Nov;38(5):725-36. [PubMed:1978244 ]

Enzyme Details

7. Alpha-2C adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins
Gene Name:: ADRA2C
Uniprot ID:: P18825
Molecular weight:: 49521.6

References

Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]

Enzyme Details

2. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

3. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]

Showing metabocard for Phenoxybenzamine (HMDB0015061)

MOL for HMDB0015061 (Phenoxybenzamine)

3D MOL for HMDB0015061 (Phenoxybenzamine)

3D SDF for HMDB0015061 (Phenoxybenzamine)

3D-SDF for HMDB0015061 (Phenoxybenzamine)

PDB for HMDB0015061 (Phenoxybenzamine)

3D PDB for HMDB0015061 (Phenoxybenzamine)

SMILES for HMDB0015061 (Phenoxybenzamine)

INCHI for HMDB0015061 (Phenoxybenzamine)

Structure for HMDB0015061 (Phenoxybenzamine)

3D Structure for HMDB0015061 (Phenoxybenzamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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