yohimbine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 33 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.48 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 14.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

None

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

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
MeSH PA D009184 Mydriatics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
MeSH PA D064804 Urological Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Impotence off-label use 397803000
Hypocupremia contraindication 19577007
Depressive disorder contraindication 35489007
Low blood pressure contraindication 45007003
Heart disease contraindication 56265001 DOID:114
Kidney disease contraindication 90708001 DOID:557
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Psychiatric Disturbance contraindication

Acid dissociation constants calculated using MoKa v3.0.0

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:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Viatrexx-Adipose HUMAN PRESCRIPTION DRUG LABEL 10 73069-024 INJECTION 31 [kp_C] INTRAVENOUS unapproved drug other 11 sections