Identification

Name
Yohimbine
Accession Number
DB01392
Type
Small Molecule
Groups
Approved, Vet Approved
Description

A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]

Structure
Thumb
Synonyms
  • (+)-yohimbine
  • (16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylic acid methyl ester
  • 17alpha-Hydroxyyohimban-16alpha-carboxylic acid methyl ester
  • Aphrodine
  • Corynine
  • Johimbin
  • Quebrachin
  • Quebrachine
  • Yohimbic acid methyl ester
  • Yohimbin
  • Yohimbine
Product Ingredients
IngredientUNIICASInChI Key
Yohimbine hydrochlorideNB2E1YP49F65-19-0PIPZGJSEDRMUAW-VJDCAHTMSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Yocon Tablet 5.4mgTablet5.4 mgOralPalisades Pharmaceuticals Inc.1988-12-312010-07-16Canada
Yohimbine HCl 2mgTablet2 mgOralOdan Laboratories Ltd1992-12-312010-07-19Canada
Yohimbine HCl 5.4mgTablet5.4 mgOralOdan Laboratories Ltd1996-09-092010-07-19Canada
Yohimbine Hydrochloride Tab 2mgTablet2 mgOralOdan Laboratories Ltd1992-12-31Not applicableCanada
Yohimbine Hydrochloride Tablets 5.4mgTablet5.4 mgOralTanta Pharmaceuticals Inc1994-12-312009-09-15Canada
Yohimbine Tab 2mgTablet2 mgOralWelcker Lyster Ltd., Division Of Technilab Inc.1951-12-312005-08-05Canada
Yohimbine Tab 5.4mgTablet5.4 mgOralOdan Laboratories Ltd1991-12-31Not applicableCanada
Yohimbine Tab 6mgTablet6 mgOralRougier Pharma Division Of Ratiopharm Inc1990-12-312003-09-22Canada
Yohimbine-odan 6mgTablet6 mgOralOdan Laboratories Ltd1992-12-31Not applicableCanada
International/Other Brands
Actibine / Aphrodyne / Baron-X / Dayto himbin / Thybine / Yocon / Yohimar / Yohimex / Yoman / Yovital
Categories
UNII
2Y49VWD90Q
CAS number
146-48-5
Weight
Average: 354.4427
Monoisotopic: 354.194342708
Chemical Formula
C21H26N2O3
InChI Key
BLGXFZZNTVWLAY-SCYLSFHTSA-N
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
IUPAC Name
methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
SMILES
[H][[email protected]@]12CC[[email protected]](O)[[email protected]](C(=O)OC)[[email protected]@]1([H])C[[email protected]]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

Pharmacology

Indication

Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.

Structured Indications
Not Available
Pharmacodynamics

Yohimbine is an indolalkylamine alkaloid with chemical similarity to reserpine. Yohimbine blocks presynaptic alpha-2 adrenergic receptors. Its action on peripheral blood vessels resembles that of reserpine, though it is weaker and of short duration. Yohimbine's peripheral autonomic nervous system effect is to increase parasympathetic (cholinergic) and decrease sympathetic (adrenergic) activity. It is to be noted that in male sexual performance, erection is linked to cholinergic activity and to alpha-2 adrenergic blockade which may theoretically result in increased penile inflow, decreased penile outflow or both. Yohimbine exerts a stimulating action on the mood and may increase anxiety. Such actions have not been adequately studied or related to dosage although they appear to require high doses of the drug. Yohimbine has a mild anti-diuretic action, probably via stimulation of hypothalmic center and release of posterior pituitary hormone. Reportedly Yohimbine exerts no significant influence on cardiac stimulation and other effects mediated by (beta)-adrenergic receptors. Its effect on blood pressure, if any, would be to lower it; however, no adequate studies are at hand to quantitate this effect in terms of Yohimbine dosage.

Mechanism of action

Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors.

TargetActionsOrganism
AAlpha-2A adrenergic receptor
antagonist
Human
AAlpha-2B adrenergic receptor
antagonist
Human
AAlpha-2C adrenergic receptor
antagonist
Human
U5-hydroxytryptamine receptor 1A
partial agonist
Human
U5-hydroxytryptamine receptor 1B
antagonist
Human
U5-hydroxytryptamine receptor 1D
antagonist
Human
UD(2) dopamine receptor
antagonist
Human
UD(3) dopamine receptor
antagonist
Human
U5-hydroxytryptamine receptor 2A
antagonist
Human
U5-hydroxytryptamine receptor 2C
antagonist
Human
UATP-sensitive potassium channelNot AvailableHuman
U5-hydroxytryptamine receptor 2B
antagonist
Human
Absorption

Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Yohimbine appears to undergo extensive metabolism in an organ of high flow such as the liver or kidney, however, the precise metabolic fate of yohimbine has not been fully determined.

Route of elimination
Not Available
Half life

Elimination half-life is approximately 36 minutes.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7-NitroindazoleThe therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Yohimbine.Experimental
AbirateroneThe serum concentration of Yohimbine can be increased when it is combined with Abiraterone.Approved
AcebutololYohimbine may decrease the antihypertensive activities of Acebutolol.Approved
AdinazolamThe therapeutic efficacy of Adinazolam can be decreased when used in combination with Yohimbine.Approved
AdipiplonThe therapeutic efficacy of Adipiplon can be decreased when used in combination with Yohimbine.Investigational
AliskirenYohimbine may decrease the antihypertensive activities of Aliskiren.Approved, Investigational
AlprazolamThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Yohimbine.Approved, Illicit, Investigational
AlprenololYohimbine may decrease the antihypertensive activities of Alprenolol.Approved, Withdrawn
AmbrisentanYohimbine may decrease the antihypertensive activities of Ambrisentan.Approved, Investigational
AmineptineThe serum concentration of Yohimbine can be increased when it is combined with Amineptine.Illicit, Withdrawn
AmiodaroneThe metabolism of Yohimbine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Yohimbine can be increased when it is combined with Amitriptyline.Approved
AmlodipineYohimbine may decrease the antihypertensive activities of Amlodipine.Approved
AprepitantThe serum concentration of Yohimbine can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe metabolism of Yohimbine can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Yohimbine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololYohimbine may decrease the antihypertensive activities of Atenolol.Approved
AtomoxetineThe metabolism of Yohimbine can be decreased when combined with Atomoxetine.Approved
BenazeprilYohimbine may decrease the antihypertensive activities of Benazepril.Approved, Investigational
BendroflumethiazideYohimbine may decrease the antihypertensive activities of Bendroflumethiazide.Approved
BenzoctamineThe therapeutic efficacy of Benzoctamine can be decreased when used in combination with Yohimbine.Approved
BepridilYohimbine may decrease the antihypertensive activities of Bepridil.Approved, Withdrawn
BetaxololYohimbine may decrease the antihypertensive activities of Betaxolol.Approved
BethanidineYohimbine may decrease the antihypertensive activities of Bethanidine.Approved
BietaserpineYohimbine may decrease the antihypertensive activities of Bietaserpine.Experimental
BimatoprostYohimbine may decrease the antihypertensive activities of Bimatoprost.Approved, Investigational
BisoprololYohimbine may decrease the antihypertensive activities of Bisoprolol.Approved
BoceprevirThe metabolism of Yohimbine can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Yohimbine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Yohimbine can be decreased when it is combined with Bosentan.Approved, Investigational
BQ-123Yohimbine may decrease the antihypertensive activities of BQ-123.Investigational
BretyliumYohimbine may decrease the antihypertensive activities of Bretylium.Approved
BrimonidineYohimbine may decrease the antihypertensive activities of Brimonidine.Approved
BromazepamThe therapeutic efficacy of Bromazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
BupranololYohimbine may decrease the antihypertensive activities of Bupranolol.Approved
BupropionThe metabolism of Yohimbine can be decreased when combined with Bupropion.Approved
BuspironeThe therapeutic efficacy of Buspirone can be decreased when used in combination with Yohimbine.Approved, Investigational
CadralazineYohimbine may decrease the antihypertensive activities of Cadralazine.Experimental
CafedrineYohimbine may decrease the antihypertensive activities of Cafedrine.Investigational
CamazepamThe therapeutic efficacy of Camazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
Candesartan cilexetilYohimbine may decrease the antihypertensive activities of Candesartan.Approved
CandoxatrilYohimbine may decrease the antihypertensive activities of Candoxatril.Experimental
CaptodiameThe therapeutic efficacy of Captodiame can be decreased when used in combination with Yohimbine.Approved, Investigational
CaptoprilYohimbine may decrease the antihypertensive activities of Captopril.Approved
CarbamazepineThe metabolism of Yohimbine can be increased when combined with Carbamazepine.Approved, Investigational
CarteololYohimbine may decrease the antihypertensive activities of Carteolol.Approved
CarvedilolYohimbine may decrease the antihypertensive activities of Carvedilol.Approved, Investigational
CelecoxibThe metabolism of Yohimbine can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololYohimbine may decrease the antihypertensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Yohimbine can be increased when it is combined with Ceritinib.Approved
ChlordiazepoxideThe therapeutic efficacy of Chlordiazepoxide can be decreased when used in combination with Yohimbine.Approved, Illicit
ChlormezanoneThe therapeutic efficacy of Chlormezanone can be decreased when used in combination with Yohimbine.Approved, Withdrawn
ChloroquineThe metabolism of Yohimbine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorothiazideYohimbine may decrease the antihypertensive activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineThe metabolism of Yohimbine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
ChlorthalidoneYohimbine may decrease the antihypertensive activities of Chlorthalidone.Approved
CholecalciferolThe metabolism of Yohimbine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CicletanineYohimbine may decrease the antihypertensive activities of Cicletanine.Investigational
CilazaprilYohimbine may decrease the antihypertensive activities of Cilazapril.Approved
CimetidineThe metabolism of Yohimbine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Yohimbine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Yohimbine can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Yohimbine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Yohimbine can be decreased when combined with Clemastine.Approved
ClobazamThe therapeutic efficacy of Clobazam can be decreased when used in combination with Yohimbine.Approved, Illicit
ClomipramineThe serum concentration of Yohimbine can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClonidineYohimbine may decrease the antihypertensive activities of Clonidine.Approved
CloranololYohimbine may decrease the antihypertensive activities of Cloranolol.Experimental
ClorazepateThe therapeutic efficacy of Clorazepate can be decreased when used in combination with Yohimbine.Approved, Illicit
ClotiazepamThe therapeutic efficacy of Clotiazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
ClotrimazoleThe metabolism of Yohimbine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CloxazolamThe therapeutic efficacy of Cloxazolam can be decreased when used in combination with Yohimbine.Approved, Investigational
ClozapineThe metabolism of Yohimbine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Yohimbine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Yohimbine can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Yohimbine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Yohimbine can be decreased when combined with Crizotinib.Approved
CryptenamineYohimbine may decrease the antihypertensive activities of Cryptenamine.Approved
CyamemazineThe therapeutic efficacy of Cyamemazine can be decreased when used in combination with Yohimbine.Approved
CyclobenzaprineThe serum concentration of Yohimbine can be increased when it is combined with Cyclobenzaprine.Approved
CyclopenthiazideYohimbine may decrease the antihypertensive activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Yohimbine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclothiazideYohimbine may decrease the antihypertensive activities of Cyclothiazide.Approved
DabrafenibThe serum concentration of Yohimbine can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Yohimbine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Yohimbine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Yohimbine can be increased when it is combined with Dasatinib.Approved, Investigational
DebrisoquinYohimbine may decrease the antihypertensive activities of Debrisoquin.Approved
DeferasiroxThe serum concentration of Yohimbine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelaprilYohimbine may decrease the antihypertensive activities of Delapril.Experimental
DelavirdineThe metabolism of Yohimbine can be decreased when combined with Delavirdine.Approved
DeramciclaneThe therapeutic efficacy of Deramciclane can be decreased when used in combination with Yohimbine.Investigational
DeserpidineYohimbine may decrease the antihypertensive activities of Deserpidine.Approved
DesipramineThe serum concentration of Yohimbine can be increased when it is combined with Desipramine.Approved
DiazepamThe therapeutic efficacy of Diazepam can be decreased when used in combination with Yohimbine.Approved, Illicit, Vet Approved
DiazoxideYohimbine may decrease the antihypertensive activities of Diazoxide.Approved
DibenzepinThe serum concentration of Yohimbine can be increased when it is combined with Dibenzepin.Experimental
diethylnorspermineYohimbine may decrease the antihypertensive activities of diethylnorspermine.Investigational
DihydralazineYohimbine may decrease the antihypertensive activities of Dihydralazine.Investigational
DihydroergotamineThe metabolism of Yohimbine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemYohimbine may decrease the antihypertensive activities of Diltiazem.Approved
DiphenhydramineThe metabolism of Yohimbine can be decreased when combined with Diphenhydramine.Approved
DoramectinThe therapeutic efficacy of Doramectin can be decreased when used in combination with Yohimbine.Vet Approved
DorzolamideYohimbine may decrease the antihypertensive activities of Dorzolamide.Approved
DosulepinThe serum concentration of Yohimbine can be increased when it is combined with Dosulepin.Approved
DoxazosinYohimbine may decrease the antihypertensive activities of Doxazosin.Approved
DoxepinThe serum concentration of Yohimbine can be increased when it is combined with Doxepin.Approved
DoxycyclineThe metabolism of Yohimbine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Yohimbine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Yohimbine can be decreased when combined with Duloxetine.Approved
EfonidipineYohimbine may decrease the antihypertensive activities of Efonidipine.Approved
EliglustatThe metabolism of Yohimbine can be decreased when combined with Eliglustat.Approved
EmylcamateThe therapeutic efficacy of Emylcamate can be decreased when used in combination with Yohimbine.Experimental
EnalaprilYohimbine may decrease the antihypertensive activities of Enalapril.Approved, Vet Approved
EnalaprilatYohimbine may decrease the antihypertensive activities of Enalaprilat.Approved
EndralazineYohimbine may decrease the antihypertensive activities of Endralazine.Experimental
EnzalutamideThe serum concentration of Yohimbine can be decreased when it is combined with Enzalutamide.Approved
EpanololYohimbine may decrease the antihypertensive activities of Epanolol.Experimental
EpoprostenolYohimbine may decrease the antihypertensive activities of Epoprostenol.Approved
EprosartanYohimbine may decrease the antihypertensive activities of Eprosartan.Approved
ErythromycinThe metabolism of Yohimbine can be decreased when combined with Erythromycin.Approved, Vet Approved
EsmirtazapineThe serum concentration of Yohimbine can be increased when it is combined with Esmirtazapine.Investigational
EstazolamThe therapeutic efficacy of Estazolam can be decreased when used in combination with Yohimbine.Approved, Illicit
Ethyl loflazepateThe therapeutic efficacy of Ethyl loflazepate can be decreased when used in combination with Yohimbine.Approved, Illicit
EtifoxineThe therapeutic efficacy of Etifoxine can be decreased when used in combination with Yohimbine.Withdrawn
EtizolamThe therapeutic efficacy of Etizolam can be decreased when used in combination with Yohimbine.Approved
FabomotizoleThe therapeutic efficacy of Fabomotizole can be decreased when used in combination with Yohimbine.Experimental
FelodipineYohimbine may decrease the antihypertensive activities of Felodipine.Approved, Investigational
FenoldopamYohimbine may decrease the antihypertensive activities of Fenoldopam.Approved
Ferulic acidYohimbine may decrease the antihypertensive activities of Ferulic acid.Experimental
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Yohimbine.Approved
FluconazoleThe metabolism of Yohimbine can be decreased when combined with Fluconazole.Approved
FludiazepamThe therapeutic efficacy of Fludiazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
FlunitrazepamThe therapeutic efficacy of Flunitrazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
FluoxetineThe metabolism of Yohimbine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlurazepamThe therapeutic efficacy of Flurazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
FluvoxamineThe therapeutic efficacy of Fluvoxamine can be decreased when used in combination with Yohimbine.Approved, Investigational
FosamprenavirThe metabolism of Yohimbine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Yohimbine can be increased when it is combined with Fosaprepitant.Approved
FosinoprilYohimbine may decrease the antihypertensive activities of Fosinopril.Approved
FosphenytoinThe metabolism of Yohimbine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Yohimbine can be increased when it is combined with Fusidic Acid.Approved
GabapentinThe therapeutic efficacy of Gabapentin can be decreased when used in combination with Yohimbine.Approved, Investigational
GedocarnilThe therapeutic efficacy of Gedocarnil can be decreased when used in combination with Yohimbine.Experimental
GepironeThe therapeutic efficacy of Gepirone can be decreased when used in combination with Yohimbine.Investigational
GuanabenzYohimbine may decrease the antihypertensive activities of Guanabenz.Approved
GuanadrelYohimbine may decrease the antihypertensive activities of Guanadrel.Approved
GuanazodineYohimbine may decrease the antihypertensive activities of Guanazodine.Experimental
GuanethidineYohimbine may decrease the antihypertensive activities of Guanethidine.Approved
GuanfacineYohimbine may decrease the antihypertensive activities of Guanfacine.Approved, Investigational
GuanoclorYohimbine may decrease the antihypertensive activities of Guanoclor.Experimental
GuanoxabenzYohimbine may decrease the antihypertensive activities of Guanoxabenz.Experimental
GuanoxanYohimbine may decrease the antihypertensive activities of Guanoxan.Experimental
HalazepamThe therapeutic efficacy of Halazepam can be decreased when used in combination with Yohimbine.Approved, Illicit, Withdrawn
HaloperidolThe metabolism of Yohimbine can be decreased when combined with Haloperidol.Approved
HexamethoniumYohimbine may decrease the antihypertensive activities of Hexamethonium.Experimental
HydralazineYohimbine may decrease the antihypertensive activities of Hydralazine.Approved
HydrochlorothiazideYohimbine may decrease the antihypertensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideYohimbine may decrease the antihypertensive activities of Hydroflumethiazide.Approved
HydroxyzineThe therapeutic efficacy of Hydroxyzine can be decreased when used in combination with Yohimbine.Approved
IdelalisibThe serum concentration of Yohimbine can be increased when it is combined with Idelalisib.Approved
ImagabalinThe therapeutic efficacy of Imagabalin can be decreased when used in combination with Yohimbine.Investigational
ImatinibThe metabolism of Yohimbine can be decreased when combined with Imatinib.Approved
ImidaprilYohimbine may decrease the antihypertensive activities of Imidapril.Investigational
ImipramineThe serum concentration of Yohimbine can be increased when it is combined with Imipramine.Approved
IndapamideYohimbine may decrease the antihypertensive activities of Indapamide.Approved
IndenololYohimbine may decrease the antihypertensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Yohimbine can be decreased when combined with Indinavir.Approved
IndoraminYohimbine may decrease the antihypertensive activities of Indoramin.Withdrawn
IprindoleThe serum concentration of Yohimbine can be increased when it is combined with Iprindole.Experimental
IrbesartanYohimbine may decrease the antihypertensive activities of Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Yohimbine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Yohimbine can be decreased when combined with Isoniazid.Approved
IsradipineYohimbine may decrease the antihypertensive activities of Isradipine.Approved
ItraconazoleThe metabolism of Yohimbine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Yohimbine can be increased when it is combined with Ivacaftor.Approved
KetanserinYohimbine may decrease the antihypertensive activities of Ketanserin.Investigational
KetazolamThe therapeutic efficacy of Ketazolam can be decreased when used in combination with Yohimbine.Approved
KetoconazoleThe metabolism of Yohimbine can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolYohimbine may decrease the antihypertensive activities of Labetalol.Approved
LacidipineYohimbine may decrease the antihypertensive activities of Lacidipine.Approved
LatanoprostYohimbine may decrease the antihypertensive activities of Latanoprost.Approved, Investigational
LercanidipineYohimbine may decrease the antihypertensive activities of Lercanidipine.Approved, Investigational
LinsidomineYohimbine may decrease the antihypertensive activities of Linsidomine.Experimental
LisinoprilYohimbine may decrease the antihypertensive activities of Lisinopril.Approved, Investigational
LofepramineThe serum concentration of Yohimbine can be increased when it is combined with Lofepramine.Experimental
LofexidineYohimbine may decrease the antihypertensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Yohimbine can be decreased when combined with Lopinavir.Approved
LoprazolamThe therapeutic efficacy of Loprazolam can be decreased when used in combination with Yohimbine.Experimental
LorazepamThe therapeutic efficacy of Lorazepam can be decreased when used in combination with Yohimbine.Approved
LorcaserinThe metabolism of Yohimbine can be decreased when combined with Lorcaserin.Approved
LosartanYohimbine may decrease the antihypertensive activities of Losartan.Approved
LovastatinThe metabolism of Yohimbine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Yohimbine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Yohimbine can be increased when combined with Lumacaftor.Approved
LumefantrineThe metabolism of Yohimbine can be decreased when combined with Lumefantrine.Approved
MacitentanYohimbine may decrease the antihypertensive activities of Macitentan.Approved
ManidipineYohimbine may decrease the antihypertensive activities of Manidipine.Approved
MebicarThe therapeutic efficacy of Mebicar can be decreased when used in combination with Yohimbine.Experimental
MebutamateThe therapeutic efficacy of Mebutamate can be decreased when used in combination with Yohimbine.Approved
MecamylamineYohimbine may decrease the antihypertensive activities of Mecamylamine.Approved
MedazepamThe therapeutic efficacy of Medazepam can be decreased when used in combination with Yohimbine.Experimental
MephenoxaloneThe therapeutic efficacy of Mephenoxalone can be decreased when used in combination with Yohimbine.Experimental
MeprobamateThe therapeutic efficacy of Meprobamate can be decreased when used in combination with Yohimbine.Approved, Illicit
MethadoneThe metabolism of Yohimbine can be decreased when combined with Methadone.Approved
MethoserpidineYohimbine may decrease the antihypertensive activities of Methoserpidine.Experimental
MethotrimeprazineThe metabolism of Yohimbine can be decreased when combined with Methotrimeprazine.Approved
MethyldopaYohimbine may decrease the antihypertensive activities of Methyldopa.Approved
MetipranololYohimbine may decrease the antihypertensive activities of Metipranolol.Approved
MetolazoneYohimbine may decrease the antihypertensive activities of Metolazone.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Yohimbine.Approved, Investigational
MetyrosineYohimbine may decrease the antihypertensive activities of Metyrosine.Approved
MibefradilYohimbine may decrease the antihypertensive activities of Mibefradil.Withdrawn
MidazolamThe therapeutic efficacy of Midazolam can be decreased when used in combination with Yohimbine.Approved, Illicit
MidostaurinThe metabolism of Yohimbine can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Yohimbine can be increased when it is combined with Mifepristone.Approved, Investigational
MinoxidilYohimbine may decrease the antihypertensive activities of Minoxidil.Approved
MirabegronThe metabolism of Yohimbine can be decreased when combined with Mirabegron.Approved
MirtazapineThe serum concentration of Yohimbine can be increased when it is combined with Mirtazapine.Approved
MitotaneThe serum concentration of Yohimbine can be decreased when it is combined with Mitotane.Approved
MoexiprilYohimbine may decrease the antihypertensive activities of Moexipril.Approved
MoxonidineYohimbine may decrease the antihypertensive activities of Moxonidine.Approved
MuzolimineYohimbine may decrease the antihypertensive activities of Muzolimine.Experimental
NabiloneThe therapeutic efficacy of Nabilone can be decreased when used in combination with Yohimbine.Approved, Investigational
NadololYohimbine may decrease the antihypertensive activities of Nadolol.Approved
NaftopidilYohimbine may decrease the antihypertensive activities of Naftopidil.Investigational
NebivololYohimbine may decrease the antihypertensive activities of Nebivolol.Approved, Investigational
NefazodoneThe metabolism of Yohimbine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Yohimbine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Yohimbine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Yohimbine can be increased when combined with Nevirapine.Approved
NicardipineYohimbine may decrease the antihypertensive activities of Nicardipine.Approved
NicorandilYohimbine may decrease the antihypertensive activities of Nicorandil.Approved
NiguldipineYohimbine may decrease the antihypertensive activities of Niguldipine.Experimental
NilotinibThe metabolism of Yohimbine can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineYohimbine may decrease the antihypertensive activities of Nilvadipine.Approved
NimodipineYohimbine may decrease the antihypertensive activities of Nimodipine.Approved
NisoldipineYohimbine may decrease the antihypertensive activities of Nisoldipine.Approved
NitrazepamThe therapeutic efficacy of Nitrazepam can be decreased when used in combination with Yohimbine.Approved
NitrendipineYohimbine may decrease the antihypertensive activities of Nitrendipine.Approved
NitroprussideYohimbine may decrease the antihypertensive activities of Nitroprusside.Approved
NortriptylineThe serum concentration of Yohimbine can be increased when it is combined with Nortriptyline.Approved
OlaparibThe metabolism of Yohimbine can be decreased when combined with Olaparib.Approved
OlmesartanYohimbine may decrease the antihypertensive activities of Olmesartan.Approved, Investigational
OmapatrilatYohimbine may decrease the antihypertensive activities of Omapatrilat.Investigational
OndansetronThe therapeutic efficacy of Ondansetron can be decreased when used in combination with Yohimbine.Approved
OpipramolThe serum concentration of Yohimbine can be increased when it is combined with Opipramol.Investigational
OsimertinibThe serum concentration of Yohimbine can be increased when it is combined with Osimertinib.Approved
OxazepamThe therapeutic efficacy of Oxazepam can be decreased when used in combination with Yohimbine.Approved
OxprenololThe therapeutic efficacy of Oxprenolol can be decreased when used in combination with Yohimbine.Approved
PalbociclibThe serum concentration of Yohimbine can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Yohimbine can be increased when it is combined with Panobinostat.Approved, Investigational
PargylineYohimbine may decrease the antihypertensive activities of Pargyline.Approved
ParoxetineThe metabolism of Yohimbine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Yohimbine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PenbutololYohimbine may decrease the antihypertensive activities of Penbutolol.Approved, Investigational
PentobarbitalThe metabolism of Yohimbine can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoliniumYohimbine may decrease the antihypertensive activities of Pentolinium.Approved
PerindoprilYohimbine may decrease the antihypertensive activities of Perindopril.Approved
PhenobarbitalThe metabolism of Yohimbine can be increased when combined with Phenobarbital.Approved
PhenoxybenzamineYohimbine may decrease the antihypertensive activities of Phenoxybenzamine.Approved
PhentolamineYohimbine may decrease the antihypertensive activities of Phentolamine.Approved
PhenytoinThe metabolism of Yohimbine can be increased when combined with Phenytoin.Approved, Vet Approved
PinacidilYohimbine may decrease the antihypertensive activities of Pinacidil.Withdrawn
PinazepamThe therapeutic efficacy of Pinazepam can be decreased when used in combination with Yohimbine.Experimental
PindololYohimbine may decrease the antihypertensive activities of Pindolol.Approved
PolythiazideYohimbine may decrease the antihypertensive activities of Polythiazide.Approved
PosaconazoleThe metabolism of Yohimbine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrazepamThe therapeutic efficacy of Prazepam can be decreased when used in combination with Yohimbine.Approved, Illicit
PrazosinYohimbine may decrease the antihypertensive activities of Prazosin.Approved
PregabalinThe therapeutic efficacy of Pregabalin can be decreased when used in combination with Yohimbine.Approved, Illicit, Investigational
PrimidoneThe metabolism of Yohimbine can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Yohimbine can be decreased when combined with Promazine.Approved, Vet Approved
PropranololYohimbine may decrease the antihypertensive activities of Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Yohimbine can be increased when it is combined with Protriptyline.Approved
QuinaprilYohimbine may decrease the antihypertensive activities of Quinapril.Approved, Investigational
QuinidineThe metabolism of Yohimbine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Yohimbine can be decreased when combined with Quinine.Approved
RamiprilYohimbine may decrease the antihypertensive activities of Ramipril.Approved
RanolazineThe metabolism of Yohimbine can be decreased when combined with Ranolazine.Approved, Investigational
RemikirenYohimbine may decrease the antihypertensive activities of Remikiren.Approved
RescinnamineYohimbine may decrease the antihypertensive activities of Rescinnamine.Approved
ReserpineYohimbine may decrease the antihypertensive activities of Reserpine.Approved
RifabutinThe metabolism of Yohimbine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Yohimbine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Yohimbine can be increased when combined with Rifapentine.Approved
RilmenidineYohimbine may decrease the antihypertensive activities of Rilmenidine.Investigational
RiociguatYohimbine may decrease the antihypertensive activities of Riociguat.Approved
RitanserinThe therapeutic efficacy of Ritanserin can be decreased when used in combination with Yohimbine.Investigational
RitonavirThe metabolism of Yohimbine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Yohimbine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Yohimbine can be decreased when combined with Ropinirole.Approved, Investigational
SaprisartanYohimbine may decrease the antihypertensive activities of Saprisartan.Experimental
SaquinavirThe metabolism of Yohimbine can be decreased when combined with Saquinavir.Approved, Investigational
SelexipagYohimbine may decrease the antihypertensive activities of Selexipag.Approved
SertralineThe metabolism of Yohimbine can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Yohimbine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Yohimbine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Yohimbine can be increased when it is combined with Simeprevir.Approved
SitaxentanYohimbine may decrease the antihypertensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilYohimbine may decrease the antihypertensive activities of Spirapril.Approved
St. John's WortThe serum concentration of Yohimbine can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Yohimbine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Yohimbine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TalinololYohimbine may decrease the antihypertensive activities of Talinolol.Investigational
TandospironeThe therapeutic efficacy of Tandospirone can be decreased when used in combination with Yohimbine.Investigational
TelaprevirThe metabolism of Yohimbine can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Yohimbine can be decreased when combined with Telithromycin.Approved
TelmisartanYohimbine may decrease the antihypertensive activities of Telmisartan.Approved, Investigational
TemazepamThe therapeutic efficacy of Temazepam can be decreased when used in combination with Yohimbine.Approved
TemocaprilYohimbine may decrease the antihypertensive activities of Temocapril.Experimental, Investigational
TerbinafineThe metabolism of Yohimbine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerlipressinYohimbine may decrease the antihypertensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineYohimbine may decrease the antihypertensive activities of Tetrahydropalmatine.Investigational
TheodrenalineYohimbine may decrease the antihypertensive activities of Theodrenaline.Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Yohimbine.Withdrawn
TianeptineThe serum concentration of Yohimbine can be increased when it is combined with Tianeptine.Approved
TiboloneYohimbine may decrease the antihypertensive activities of Tibolone.Approved
TiclopidineThe metabolism of Yohimbine can be decreased when combined with Ticlopidine.Approved
TicrynafenYohimbine may decrease the antihypertensive activities of Ticrynafen.Withdrawn
TimololYohimbine may decrease the antihypertensive activities of Timolol.Approved
TipranavirThe metabolism of Yohimbine can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Yohimbine can be decreased when it is combined with Tocilizumab.Approved
TofisopamThe therapeutic efficacy of Tofisopam can be decreased when used in combination with Yohimbine.Approved
TolazolineYohimbine may decrease the antihypertensive activities of Tolazoline.Approved, Vet Approved
TolonidineYohimbine may decrease the antihypertensive activities of Tolonidine.Experimental
TorasemideYohimbine may decrease the antihypertensive activities of Torasemide.Approved
TrandolaprilYohimbine may decrease the antihypertensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineThe therapeutic efficacy of Trans-2-Phenylcyclopropylamine can be decreased when used in combination with Yohimbine.Experimental
TranylcypromineThe therapeutic efficacy of Tranylcypromine can be decreased when used in combination with Yohimbine.Approved
TravoprostYohimbine may decrease the antihypertensive activities of Travoprost.Approved
TrazodoneThe therapeutic efficacy of Trazodone can be decreased when used in combination with Yohimbine.Approved, Investigational
TreprostinilYohimbine may decrease the antihypertensive activities of Treprostinil.Approved, Investigational
TriazolamThe therapeutic efficacy of Triazolam can be decreased when used in combination with Yohimbine.Approved
TrichlormethiazideYohimbine may decrease the antihypertensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinYohimbine may decrease the antihypertensive activities of Trimazosin.Experimental
TrimethaphanYohimbine may decrease the antihypertensive activities of Trimethaphan.Approved
TrimipramineThe serum concentration of Yohimbine can be increased when it is combined with Trimipramine.Approved
UnoprostoneYohimbine may decrease the antihypertensive activities of Unoprostone.Approved
UrapidilYohimbine may decrease the antihypertensive activities of Urapidil.Investigational
ValsartanYohimbine may decrease the antihypertensive activities of Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Yohimbine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Yohimbine can be decreased when combined with Verapamil.Approved
VincamineYohimbine may decrease the antihypertensive activities of Vincamine.Experimental
VinpocetineYohimbine may decrease the antihypertensive activities of Vinpocetine.Investigational
VoriconazoleThe metabolism of Yohimbine can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe therapeutic efficacy of Vortioxetine can be decreased when used in combination with Yohimbine.Approved
XipamideYohimbine may decrease the antihypertensive activities of Xipamide.Experimental
XylometazolineYohimbine may decrease the antihypertensive activities of Xylometazoline.Approved
ZiprasidoneThe metabolism of Yohimbine can be decreased when combined with Ziprasidone.Approved
ZofenoprilYohimbine may decrease the antihypertensive activities of Zofenopril.Experimental
ZolazepamThe therapeutic efficacy of Zolazepam can be decreased when used in combination with Yohimbine.Vet Approved
Food Interactions
Not Available

References

Synthesis Reference

Germain Saint-Ruf, Pham Huu Chanh, Buu Hoi, "Yohimbine derivatives, process for their preparation and their applications." U.S. Patent US3940387, issued April, 1960.

US3940387
General References
Not Available
External Links
Human Metabolome Database
HMDB15464
KEGG Compound
C09256
PubChem Compound
8969
PubChem Substance
46504602
ChemSpider
8622
BindingDB
50013515
ChEBI
10093
ChEMBL
CHEMBL15245
Therapeutic Targets Database
DAP000087
PharmGKB
PA451946
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Yohimbine
ATC Codes
G04BE04 — Yohimbine
AHFS Codes
  • 92:92.00 — Other Miscellaneous Therapeutic Agents
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentAutonomic Nervous System Diseases / Hypertensive / Idiopathic orthostatic hypotension1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1RecruitingTreatmentHeroin Dependence / Opioid Use Disorders1
1, 2CompletedTreatmentHealthy Volunteers1
2CompletedNot AvailableDepression, Involutional / Major Depresssion1
2CompletedTreatmentAlcoholism1
2CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)1
2CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentSocial Anxiety Disorder (SAD)1
4CompletedNot AvailableErectile Dysfunction (ED)1
4CompletedTreatmentAutoregulation / Blood Flow Velocity / Physiology, Ocular1
Not AvailableCompletedNot AvailableCocaine Related Disorders1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedBasic ScienceIntrusive Memories1
Not AvailableRecruitingBasic ScienceEarly Life Trauma / Major Depressive Disorder (MDD)1
Not AvailableUnknown StatusBasic SciencePain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral2 mg
TabletOral5.4 mg
TabletOral6 mg
Prices
Unit descriptionCostUnit
Yohimbine hcl powder22.8USD g
Yohimbine 5.4 mg tablet1.04USD tablet
Yocon 5.4 mg tablet0.96USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)241 °CPhysProp
logP2.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.348 mg/mLALOGPS
logP2.36ALOGPS
logP2.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.56 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.63 m3·mol-1ChemAxon
Polarizability40.22 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9782
Blood Brain Barrier-0.5738
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.8762
P-glycoprotein inhibitor IInhibitor0.6002
P-glycoprotein inhibitor IINon-inhibitor0.9318
Renal organic cation transporterInhibitor0.5738
CYP450 2C9 substrateNon-substrate0.8514
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.5677
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9094
CYP450 3A4 inhibitorNon-inhibitor0.8333
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.8681
CarcinogenicityNon-carcinogens0.9696
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7324 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8104
hERG inhibition (predictor II)Non-inhibitor0.6141
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-3921000000-e28dd8692e2b8dd63330

Taxonomy

Description
This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Yohimbine alkaloids
Sub Class
Not Available
Direct Parent
Yohimbine alkaloids
Alternative Parents
Corynanthean-type alkaloids / Beta carbolines / 3-alkylindoles / Aralkylamines / Beta hydroxy acids and derivatives / Benzenoids / Piperidines / Pyrroles / Heteroaromatic compounds / Methyl esters
show 10 more
Substituents
Yohimbine / Corynanthean skeleton / Yohimbine alkaloid / Beta-carboline / Pyridoindole / 3-alkylindole / Indole / Indole or derivatives / Aralkylamine / Beta-hydroxy acid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
methyl 17-hydroxy-20xi-yohimban-16-carboxylate (CHEBI:10093) / Indole alkaloids (C09256)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Thioesterase binding
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Laurila JM, Xhaard H, Ruuskanen JO, Rantanen MJ, Karlsson HK, Johnson MS, Scheinin M: The second extracellular loop of alpha2A-adrenoceptors contributes to the binding of yohimbine analogues. Br J Pharmacol. 2007 Aug;151(8):1293-304. Epub 2007 Jun 11. [PubMed:17558432]
  2. Zadori ZS, Shujaa N, Fulop K, Dunkel P, Gyires K: Pre- and postsynaptic mechanisms in the clonidine- and oxymetazoline-induced inhibition of gastric motility in the rat. Neurochem Int. 2007 Oct;51(5):297-305. Epub 2007 Jun 30. [PubMed:17664022]
  3. Paul BZ, Jin J, Kunapuli SP: Molecular mechanism of thromboxane A(2)-induced platelet aggregation. Essential role for p2t(ac) and alpha(2a) receptors. J Biol Chem. 1999 Oct 8;274(41):29108-14. [PubMed:10506165]
  4. Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [PubMed:12591093]
  5. Ozdogan UK, Lahdesmaki J, Scheinin M: The analgesic efficacy of partial opioid agonists is increased in mice with targeted inactivation of the alpha2A-adrenoceptor gene. Eur J Pharmacol. 2006 Jan 4;529(1-3):105-13. Epub 2005 Dec 2. [PubMed:16325800]
  6. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Epinephrine binding
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 clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Freitag A, Wessler I, Racke K: Adrenoceptor- and cholinoceptor-mediated mechanisms in the regulation of 5-hydroxytryptamine release from isolated tracheae of newborn rabbits. Br J Pharmacol. 1996 Sep;119(1):91-8. [PubMed:8872361]
  2. Cleary L, Vandeputte C, Docherty JR: Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice. Br J Pharmacol. 2002 Jul;136(6):857-64. [PubMed:12110610]
  3. Gyires K, Mullner K, Ronai AZ: Functional evidence that gastroprotection can be induced by activation of central alpha(2B)-adrenoceptor subtypes in the rat. Eur J Pharmacol. 2000 May 19;396(2-3):131-5. [PubMed:10822066]
  4. Takada K, Clark DJ, Davies MF, Tonner PH, Krause TK, Bertaccini E, Maze M: Meperidine exerts agonist activity at the alpha(2B)-adrenoceptor subtype. Anesthesiology. 2002 Jun;96(6):1420-6. [PubMed:12170055]
  5. Alonso E, Garrido E, Diez-Fernandez C, Perez-Garcia C, Herradon G, Ezquerra L, Deuel TF, Alguacil LF: Yohimbine prevents morphine-induced changes of glial fibrillary acidic protein in brainstem and alpha2-adrenoceptor gene expression in hippocampus. Neurosci Lett. 2007 Jan 29;412(2):163-7. Epub 2006 Nov 22. [PubMed:17123717]
  6. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
References
  1. Lalchandani SG, Lei L, Zheng W, Suni MM, Moore BM, Liggett SB, Miller DD, Feller DR: Yohimbine dimers exhibiting selectivity for the human alpha 2C-adrenoceptor subtype. J Pharmacol Exp Ther. 2002 Dec;303(3):979-84. [PubMed:12438517]
  2. Rizzo CA, Ruck LM, Corboz MR, Umland SP, Wan Y, Shah H, Jakway J, Cheng L, McCormick K, Egan RW, Hey JA: Postjunctional alpha(2C)-adrenoceptor contractility in human saphenous vein. Eur J Pharmacol. 2001 Feb 16;413(2-3):263-9. [PubMed:11226402]
  3. Cleary L, Murad K, Bexis S, Docherty JR: The alpha (1D)-adrenoceptor antagonist BMY 7378 is also an alpha (2C)-adrenoceptor antagonist. Auton Autacoid Pharmacol. 2005 Oct;25(4):135-41. [PubMed:16176444]
  4. Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [PubMed:12591093]
  5. Cleary L, Vandeputte C, Docherty JR: Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice. Br J Pharmacol. 2002 Jul;136(6):857-64. [PubMed:12110610]
  6. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
  2. Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
  2. Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
  2. Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
  2. Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
General Function
Phosphatidylinositol-4,5-bisphosphate binding
Specific Function
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than...

Components:
References
  1. Plant TD, Henquin JC: Phentolamine and yohimbine inhibit ATP-sensitive K+ channels in mouse pancreatic beta-cells. Br J Pharmacol. 1990 Sep;101(1):115-20. [PubMed:2282453]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
  2. Bonhaus DW, Weinhardt KK, Taylor M, DeSouza A, McNeeley PM, Szczepanski K, Fontana DJ, Trinh J, Rocha CL, Dawson MW, Flippin LA, Eglen RM: RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist. Neuropharmacology. 1997 Apr-May;36(4-5):621-9. [PubMed:9225287]

Enzymes

Details
1. Cytochrome P450 2D6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on July 08, 2007 11:00 / Updated on October 23, 2017 14:14