All FDA-approved EMA-approved PMDA-approved
Target Card Uniprot Example: P23975

yohimbine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
	3659	146-48-5

Description:

Molecule	Description
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:

Dose	Unit	Route
15	mg	O

ADMET properties:

Property	Value	Reference
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
S (Water solubility)	10 mg/mL	Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	2.132		Moderate	0.79
caco2-efflux	Caco-2 efflux ratio (BA/AB)	2.037		Moderate	0.79
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	19.409	10^-6 cm/s	Moderate	0.79
dh-clint	Dog hepatocyte intrinsic clearance	15.241	uL/min/10^6 cells	Moderate	0.79
dppb	Dog plasma protein binding (% unbound)	32.880	%	Moderate	0.79
fcs-ppb	Fetal calf serum protein binding (% unbound)	34.890	%	Moderate	0.79
herg	hERG pIC50	5.088	pIC50	Moderate	0.79
hh-clint	Human hepatocyte intrinsic clearance	17.906	uL/min/10^6 cells	Moderate	0.79
hlm-clint	Human liver microsomal intrinsic clearance	30.269	uL/min/mg protein	Moderate	0.79
hppb	Human plasma protein binding (% unbound)	24.410	%	Moderate	0.79
kinase-safety-class	ACVR2B,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,JAK3,MAP3K7,MAPK10,MAPK7,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKDC,SIK2,STK33,TEK,TGFBR1,ZAP70	33
kinase-selectivity-class	AXL,EIF2AK3	2
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	5.649		Moderate	0.79
mh-clint	Mouse hepatocyte intrinsic clearance	155.239		Moderate	0.79
mppb	Mouse plasma protein binding (% unbound)	25.610		Moderate	0.79
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	12.618		Moderate	0.79
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pppb	Pig plasma protein binding (% unbound)	35.890	%	Moderate	0.79
rh-clint	Rat hepatocyte intrinsic clearance	161.065	uL/min/10^6 cells	Moderate	0.79
rh-fuinc	Rat hepatocyte fraction unbound in incubation	71.530	%	Moderate	0.79
rppb	Rat plasma protein binding (% unbound)	22.260	%	Moderate	0.79
solubility-dd	Solubility at pH 7.4 in DMSO	636.796	uM	Moderate	0.79

Approvals:

Date	Agency	Company	Orphan
None	FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	G04BE04	GENITO URINARY SYSTEM AND SEX HORMONES UROLOGICALS UROLOGICALS Drugs used in erectile dysfunction
MeSH PA	D000317	Adrenergic alpha-Antagonists
MeSH PA	D009184	Mydriatics
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D018674	Adrenergic Antagonists
MeSH PA	D058669	Adrenergic alpha-2 Receptor Antagonists
MeSH PA	D064804	Urological Agents
CHEBI has role	CHEBI:35469	antidepressant
CHEBI has role	CHEBI:35526	hypoglycemic agent
CHEBI has role	CHEBI:35620	vasodilator agent
CHEBI has role	CHEBI:37890	α-adrenergic antagonist
CHEBI has role	CHEBI:48279	serotonergic antagonist
CHEBI has role	CHEBI:48407	antiparkinson drug
CHEBI has role	CHEBI:50514	vasoconstrictor agent
CHEBI has role	CHEBI:131787	dopamine receptor D<small><sub>2</sub></small> antagonist

Related Drugs by ATC class:

G04BE Drugs used in erectile dysfunction 9 drugs

alprostadilapomorphineavanafilmoxisylytepapaverinesildenafiltadalafiludenafilvardenafil

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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

🐶 Veterinary Drug Use

Species	Use	Relation
Cervidae	To antagonize the effect of xylazine	Indication
Dogs	To antagonize the effect of xylazine	Indication

🐶 Veterinary products

Product	Applicant	Ingredients
Yobine Injection	Akorn Animal Health Inc.	1
Antagonil	Wildlife Laboratories Inc.	1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN	ANTAGONIST	Ki	9.30		CHEMBL	IUPHAR
Alpha-2B adrenergic receptor	GPCR	P18089	ADA2B_HUMAN	ANTAGONIST	Ki	8.70		CHEMBL	IUPHAR
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN	ANTAGONIST	Ki	9.38		CHEMBL	IUPHAR
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN	ANTAGONIST	Ki	7.90		IUPHAR
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	6.11		DRUG MATRIX
5-hydroxytryptamine receptor 7	GPCR	P34969	5HT7R_HUMAN	ANTAGONIST	Ki	5.60		IUPHAR
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN		Kd	6.40		CHEMBL
D(3) dopamine receptor	GPCR	P35462	DRD3_HUMAN		Ki	5.60		PDSP
5-hydroxytryptamine receptor 1B	GPCR	P28222	5HT1B_HUMAN	ANTAGONIST	Ki	7.60		IUPHAR
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN	ANTAGONIST	Ki	7.70		IUPHAR
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	5.69		DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		IC50	7.02		CHEMBL
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN		Ki	8.80		CHEMBL
Alpha-1B adrenergic receptor	GPCR	P35368	ADA1B_HUMAN		Ki	8.96		CHEMBL
5-hydroxytryptamine receptor 5A	GPCR	P47898	5HT5A_HUMAN	ANTAGONIST	Ki	5.30		IUPHAR
5-hydroxytryptamine receptor 1F	GPCR	P30939	5HT1F_HUMAN	ANTAGONIST	Ki	7		IUPHAR
5-hydroxytryptamine receptor 1E	GPCR	P28566	5HT1E_HUMAN	ANTAGONIST	Ki	5.90		IUPHAR
DNA topoisomerase 1	Enzyme	P11387	TOP1_HUMAN		IC50	4.52		CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III)	Ion channel	P35498 Q99250 Q9NY46	SCN1A_HUMAN SCN2A_HUMAN SCN3A_HUMAN		IC50	4.48		CHEMBL
Dual specificity phosphatase Cdc25A	Enzyme	P30304	MPIP1_HUMAN		IC50	4.65		CHEMBL
Beta-2 adrenergic receptor	GPCR	P07550	ADRB2_HUMAN		Ki	10.40		CHEMBL
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	6.16		DRUG MATRIX
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN	ANTAGONIST	Ki	7.30		IUPHAR
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	6.18		DRUG MATRIX
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	5.91		CHEMBL
Alpha-2B adrenergic receptor	GPCR		ADA2B_RAT		Ki	8.70		CHEMBL
Alpha-1D adrenergic receptor	GPCR		ADA1D_RAT		Ki	7.28		CHEMBL
D(2) dopamine receptor	GPCR		DRD2_RAT		IC50	5.95		CHEMBL
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		IC50	6.90		CHEMBL
5-hydroxytryptamine receptor 2A	GPCR		5HT2A_RAT		Ki	5.79		CHEMBL
5-hydroxytryptamine receptor 2B	GPCR		5HT2B_RAT	ANTAGONIST	Ki	7.30		IUPHAR
Voltage-dependent L-type calcium channel subunit alpha-1C	Ion channel		CAC1C_RAT		Ki	7.35		CHEMBL
Alpha-1A adrenergic receptor	GPCR		ADA1A_BOVIN		Ki	8.44		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_PIG		Ki	8.36		CHEMBL
D(3) dopamine receptor	GPCR		DRD3_RAT		Ki	5.61		CHEMBL
Alpha-2A adrenergic receptor	GPCR		ADA2A_BOVIN		Ki	7.31		CHEMBL
Adrenergic receptor alpha-2	GPCR		ADA2B_RAT ADA2C_RAT ADA2A_RAT		Ki	9.22		CHEMBL
Dopamine receptor	GPCR		DRD1_RAT DRD3_RAT DRD5_RAT DRD4_RAT DRD2_RAT		Ki	5.70		CHEMBL
Alpha-2 adrenergic receptor	GPCR		ADA2B_MOUSE ADA2C_MOUSE ADA2A_MOUSE		Ki	9.22		CHEMBL
5-hydroxytryptamine receptor 1B	GPCR		5HT1B_MOUSE	ANTAGONIST	Ki	8.30		IUPHAR
5-hydroxytryptamine receptor 5A	GPCR		5HT5A_MOUSE	ANTAGONIST	Ki	6		IUPHAR
5-hydroxytryptamine receptor 1F	GPCR		5HT1F_RAT	ANTAGONIST	IC50	6.20		IUPHAR

External reference:

ID	Source
4022649	VUID
N0000020654	NUI
D06671	KEGG_DRUG
4018920	VANDF
4022649	VANDF
C0724441	UMLSCUI
CHEBI:10093	CHEBI
CHEMBL15245	ChEMBL_ID
DB01392	DRUGBANK_ID
CHEMBL537669	ChEMBL_ID
D015016	MESH_DESCRIPTOR_UI
8969	PUBCHEM_CID
102	IUPHAR_LIGAND_ID
65-19-0	SECONDARY_CAS_RN
2Y49VWD90Q	UNII
133041	RXNORM
1391	MMSL
5700	MMSL
7315	MMSL
7316	MMSL
d01386	MMSL
002414	NDDF
003550	NDDF
398674007	SNOMEDCT_US
73407000	SNOMEDCT_US
96264005	SNOMEDCT_US
2Y49VWD90Q	INXIGHT DRUGS

Pharmaceutical products:

None