General Information of Drug (ID: DMJCP1Y)

Drug Name
Yohimbine
Synonyms
APHRODINE; Actibine; Aphrodyne; Aphrosol; Corynine; Johimbin; Quebrachin; Quebrachine; Thybine; Yocon; Yohimar; Yohimbin; Yohimex; Yoman; Yovital; Dayto himbin; Yohimbic acid methyl ester; Baron-X; Trans-Quinolizidine yohimbine; Yohimbine (DCF); Methyl 17alpha-hydroxyyohimban-16alpha-carboxylate; Yohimbol-16alpha-carboxylic acid, methyl ester (6CI); Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.; Methyl (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylate; Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI); Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-(9CI); Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester; (+)-Yohimbin; (+)-Yohimbine; (16alpha,17alpha)-17-Hydroxy-yohimban-16-carboxylic acid methyl ester; (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester; 17-Hydroxy-yohimbane-16-carboxylic acid methyl ester; 17-Hydroxyyohimban-16-carboxylic acid methyl ester; 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester; 2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
Indication
Disease Entry ICD 11 Status REF
Erectile dysfunction HA01.1 Approved [1]
Therapeutic Class
Mydriatics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 354.4
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 14.6 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 36 minutes [3]
Metabolism
The drug is metabolized via the liver []
Unbound Fraction
The unbound fraction of drug in plasma is 0.2% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.48 L/kg [3]
Chemical Identifiers
Formula
C21H26N2O3
IUPAC Name
methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Canonical SMILES
COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
InChI
InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-N
Cross-matching ID
PubChem CID
8969
ChEBI ID
CHEBI:10093
CAS Number
146-48-5
DrugBank ID
DB01392
TTD ID
D0H4JM
VARIDT ID
DR01191
INTEDE ID
DR1722
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor Alpha-2 (ADRA2) TTQ8AFT NOUNIPROTAC Antagonist [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Gene/Protein Processing [7]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [8]
Prolactin (PRL) OTWFQGX7 PRL_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 102).
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Acute neurotoxicity after yohimbine ingestion by a body builder. Clin Toxicol (Phila). 2009 Sep;47(8):827-9.
5 Human sympathetic activation by alpha2-adrenergic blockade with yohimbine: bimodal, epistatic influence of cytochrome P450-mediated drug metabolism. Clin Pharmacol Ther. 2004 Aug;76(2):139-53.
6 Relationship of cytochrome P450 pharmacogenetics to the effects of yohimbine on gastrointestinal transit and catecholamines in healthy subjects. Neurogastroenterol Motil. 2008 Aug;20(8):891-9.
7 In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks. Toxicol Lett. 2017 Apr 15;272:84-93.
8 A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line. Mol Pharmacol. 1995 Oct;48(4):682-9.
9 Anxiogenic effect of yohimbine in healthy subjects: comparison with caffeine and antagonism by clonidine and diazepam. Int Clin Psychopharmacol. 1988 Jul;3(3):215-29. doi: 10.1097/00004850-198807000-00003.