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Showing metabocard for Tolazoline (HMDB0014935)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:20 UTC
HMDB IDHMDB0014935
Secondary Accession Numbers
  • HMDB14935
Metabolite Identification
Common NameTolazoline
DescriptionTolazoline, also known as priscoline or divascol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Tolazoline is a drug which is used for the treatment of pulmonary artery anomalies. Tolazoline is a very strong basic compound (based on its pKa). It is however most commonly used in veterinary medicine, to reverse xylazine-induced sedation. It is a vasodilator that is used to treat spasms of peripheral blood vessels (as in acrocyanosis). It has also been used (in conjunction with sodium nitroprusside) successfully as an antidote to reverse the severe peripheral vasoconstriction which can occur as a result of overdose with certain 5-HT2A agonist drugs such as 25I-NBOMe, DOB and Bromodragonfly (prolonged severe vasoconstriction can lead to gangrene if untreated). Tolazoline is a non-selective competitive α-adrenergic receptor antagonist.
Structure
Data?1676999899
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014935 (Tolazoline)

797
  Mrv0541 02231215002D          

 12 13  0  0  0  0            999 V2000
    3.1651    1.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324    0.5269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0014935 (Tolazoline)

HMDB0014935
     RDKit          3D
Tolazoline
 24 25  0  0  0  0  0  0  0  0999 V2000
    3.3459   -0.4808   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515   -1.5629   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469   -1.3433    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -0.0725    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    0.0994    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    0.1718    0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -0.6741    0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -0.3737    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    0.5751   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6804    1.1221   -0.2132 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    0.9854    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454    0.8025   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.6267   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -2.5599   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0586   -2.2439    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -0.7259    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724    1.0380    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434    0.1887    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377   -1.2818   -0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    1.3519   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -0.0565   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335    2.0376   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    1.9846    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    1.6450   -1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 12  1  1  0
 10  6  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0014935 (Tolazoline)

797
  Mrv0541 02231215002D          

 12 13  0  0  0  0            999 V2000
    3.1651    1.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8324    0.5269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    1.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643    0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014935

> <DATABASE_NAME>
hmdb

> <SMILES>
C(C1=NCCN1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)

> <INCHI_KEY>
JIVZKJJQOZQXQB-UHFFFAOYSA-N

> <FORMULA>
C10H12N2

> <MOLECULAR_WEIGHT>
160.2157

> <EXACT_MASS>
160.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.938060793252507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-benzyl-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.2036401929999996

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.2476773435235

> <JCHEM_POLAR_SURFACE_AREA>
24.39

> <JCHEM_REFRACTIVITY>
49.06930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolazoline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0014935 (Tolazoline)

HMDB0014935
     RDKit          3D
Tolazoline
 24 25  0  0  0  0  0  0  0  0999 V2000
    3.3459   -0.4808   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515   -1.5629   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469   -1.3433    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -0.0725    0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0544    0.0994    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    0.1718    0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -0.6741    0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -0.3737    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054    0.5751   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6804    1.1221   -0.2132 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    0.9854    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454    0.8025   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.6267   -1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -2.5599   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0586   -2.2439    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -0.7259    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724    1.0380    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434    0.1887    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377   -1.2818   -0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    1.3519   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -0.0565   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335    2.0376   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178    1.9846    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    1.6450   -1.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 12  1  1  0
 10  6  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
M  END
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PDB for HMDB0014935 (Tolazoline)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 797                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.908   3.141   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.154   0.983   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.747   1.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.414   3.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413   0.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.184   2.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.413  -0.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -1.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -1.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -3.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413  -3.780   0.000  0.00  0.00           C+0
CONECT    1    3    4                                                       
CONECT    2    3    6                                                       
CONECT    3    1    2    5                                                  
CONECT    4    1    6                                                       
CONECT    5    3    7                                                       
CONECT    6    2    4                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0014935 (Tolazoline)

COMPND    HMDB0014935
HETATM    1  C1  UNL     1       3.346  -0.481  -0.993  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.652  -1.563  -0.482  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.547  -1.343   0.344  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.128  -0.073   0.666  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.054   0.099   1.550  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.322   0.172   0.778  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.290  -0.674   0.936  1.00  0.00           N  
HETATM    8  C7  UNL     1      -3.404  -0.374   0.062  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.805   0.575  -0.938  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.680   1.122  -0.213  1.00  0.00           N  
HETATM   11  C9  UNL     1       1.841   0.985   0.141  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.945   0.802  -0.685  1.00  0.00           C  
HETATM   13  H1  UNL     1       4.220  -0.627  -1.647  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.983  -2.560  -0.737  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.059  -2.244   0.702  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.048  -0.726   2.275  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.072   1.038   2.162  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.143   0.189   0.667  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.838  -1.282  -0.399  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.516   1.352  -1.277  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.473  -0.056  -1.811  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.234   2.038  -0.397  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.518   1.985   0.389  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.498   1.645  -1.092  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4    4   15
CONECT    4    5   11
CONECT    5    6   16   17
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9   18   19
CONECT    9   10   20   21
CONECT   10   22
CONECT   11   12   12   23
CONECT   12   24
END
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SMILES for HMDB0014935 (Tolazoline)

C(C1=NCCN1)C1=CC=CC=C1
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INCHI for HMDB0014935 (Tolazoline)

InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Benzyl-2-imidazolineChEBI
2-Benzyl-4,5-imidazolineChEBI
2-BenzylimidazolineChEBI
4,5-Dihydro-2-(phenylmethyl)-1H-imidazoleChEBI
TolazineKegg
DivascolHMDB
Tolazoline hydrochlorideHMDB
PridazoleHMDB
Tolazoline monohydrochlorideHMDB
BenzalolinHMDB
Novartis brand OF tolazoline hydrochlorideHMDB
PriscolineHMDB
Ciba vision brand OF tolazoline hydrochlorideHMDB
PriscolHMDB
Chemical FormulaC10H12N2
Average Molecular Weight160.2157
Monoisotopic Molecular Weight160.100048394
IUPAC Name2-benzyl-4,5-dihydro-1H-imidazole
Traditional Nametolazoline
CAS Registry Number59-98-3
SMILES
C(C1=NCCN1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)
InChI KeyJIVZKJJQOZQXQB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Imidolactam
  • Monocyclic benzene moiety
  • 2-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.36 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available135.083http://allccs.zhulab.cn/database/detail?ID=AllCCS00000830
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00797 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00797 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00797
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5303
KEGG Compound IDC07147
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolazoline
METLIN IDNot Available
PubChem Compound5504
PDB IDNot Available
ChEBI ID28502
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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
  1. Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]
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
References
  1. Roll C, Hanssler L: [Interaction of tolazoline and cimetidine in persistent fetal circulation of the newborn infant]. Monatsschr Kinderheilkd. 1993 Apr;141(4):297-9. [PubMed:8487790 ]
Enzyme Details
3. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Teskin O, Uydes-Dogan BS, Enc Y, Alp FI, Kaleli D, Keser S, Iyigun T, Bilgen F, Dagsali S, Ozdemir O: Comparative effects of tolazoline and nitroprusside on human isolated radial artery. Ann Thorac Surg. 2006 Jan;81(1):125-31. [PubMed:16368348 ]
  4. Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]