yohimbine indications/contra

Stem definitionDrug idCAS RN
3659 146-48-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • yohimbine
  • yohimbin
  • quebrachin
  • quebrachine
  • yohimbine hydrochloride
  • yohimbine HCl
A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.
  • Molecular weight: 354.45
  • Formula: C21H26N2O3
  • CLOGP: 2.17
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 65.56
  • ALOGS: -3.01
  • ROTB: 2

Drug dosage:

DoseUnitRoute
15 mg O

Approvals:

None

FDA Adverse Event Reporting System

None

Pharmacologic Action:

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SourceCodeDescription
ATC G04BE04 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs used in erectile dysfunction
MeSH PA D018663 Adrenergic Agents
MeSH PA D058669 Adrenergic alpha-2 Receptor Antagonists
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
MeSH PA D001337 Autonomic Agents
MeSH PA D009184 Mydriatics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D064804 Urological Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Hypocupremia contraindication 19577007
Depressive disorder contraindication 35489007 DOID:2848
Low blood pressure contraindication 45007003
Heart disease contraindication 56265001 DOID:114
Kidney disease contraindication 90708001 DOID:2527
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Psychiatric Disturbance contraindication
Impotence off-label use 397803000

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.2 acidic
pKa2 7.31 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2A adrenergic receptor GPCR ANTAGONIST Ki 9.38 CHEMBL IUPHAR
Alpha-2B adrenergic receptor GPCR ANTAGONIST Ki 8.70 CHEMBL IUPHAR
Alpha-2C adrenergic receptor GPCR ANTAGONIST Ki 9.30 CHEMBL IUPHAR
5-hydroxytryptamine receptor 1B GPCR ANTAGONIST Ki 7.60 IUPHAR
5-hydroxytryptamine receptor 5A GPCR ANTAGONIST Ki 5.30 IUPHAR
5-hydroxytryptamine receptor 1F GPCR ANTAGONIST Ki 7 IUPHAR
5-hydroxytryptamine receptor 1E GPCR ANTAGONIST Ki 5.90 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 5.60 IUPHAR
D(2) dopamine receptor GPCR Ki 6.16 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.11 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 5.69 DRUG MATRIX
Adenosine receptor A3 GPCR IC50 7.02 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 4.48 CHEMBL
DNA topoisomerase 1 Enzyme IC50 4.52 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 8.80 CHEMBL
Alpha-1A adrenergic receptor GPCR Kd 6.40 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 8.96 CHEMBL
Dual specificity phosphatase Cdc25A Enzyme IC50 4.65 CHEMBL
D(3) dopamine receptor GPCR Ki 5.60 PDSP
5-hydroxytryptamine receptor 1A GPCR ANTAGONIST Ki 7.30 IUPHAR
5-hydroxytryptamine receptor 2B GPCR ANTAGONIST Ki 7.90 IUPHAR
5-hydroxytryptamine receptor 1D GPCR ANTAGONIST Ki 7.70 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 6.18 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 8.36 CHEMBL
D(3) dopamine receptor GPCR Ki 5.61 CHEMBL
Dopamine receptor GPCR Ki 5.70 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 9.22 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 8.44 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.31 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 8.70 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 7.28 CHEMBL
Alpha-2 adrenergic receptor GPCR Ki 9.22 CHEMBL
Voltage-dependent L-type calcium channel subunit alpha-1C Ion channel Ki 7.35 CHEMBL
D(2) dopamine receptor GPCR IC50 5.95 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 5.79 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.90 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 5.91 CHEMBL
5-hydroxytryptamine receptor 1B Unclassified ANTAGONIST Ki 8.30 IUPHAR
5-hydroxytryptamine receptor 1F Unclassified ANTAGONIST IC50 6.20 IUPHAR
5-hydroxytryptamine receptor 5A Unclassified ANTAGONIST Ki 6 IUPHAR
5-hydroxytryptamine receptor 2B GPCR ANTAGONIST Ki 7.30 IUPHAR

External reference:

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IDSource
102 IUPHAR_LIGAND_ID
4022649 VUID
N0000020654 NUI
C0724441 UMLSCUI
D06671 KEGG_DRUG
CHEMBL15245 ChEMBL_ID
2Y49VWD90Q UNII
7315 MMSL
4022649 VANDF
N0000020654 NDFRT
N0000006817 NDFRT
7316 MMSL
398674007 SNOMEDCT_US
73407000 SNOMEDCT_US
d01386 MMSL
220982 RXNORM
002414 NDDF
8969 PUBCHEM_CID
CHEMBL537669 ChEMBL_ID
DB01392 DRUGBANK_ID
65-19-0 SECONDARY_CAS_RN
D015016 MESH_DESCRIPTOR_UI
CHEBI:10093 CHEBI

Pharmaceutical products:

None