You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameYohimbine
Accession NumberDB01392
TypeSmall Molecule
GroupsApproved, 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
External Identifiers Not Available
Approved 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
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActibineNot Available
AphrodyneNot Available
Baron-XNot Available
Dayto himbinNot Available
ThybineNot Available
YoconNot Available
YohimarNot Available
YohimexNot Available
YomanNot Available
YovitalNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Yohimbine hydrochloride
ThumbNot applicableDBSALT001153
Categories
UNII2Y49VWD90Q
CAS number146-48-5
WeightAverage: 354.4427
Monoisotopic: 354.194342708
Chemical FormulaC21H26N2O3
InChI KeyInChIKey=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][C@@]12CC[[email protected]](O)[[email protected]](C(=O)OC)[C@@]1([H])C[C@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
Substituents
  • Yohimbine
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Pyridoindole
  • Beta-carboline
  • Indole or derivatives
  • Indole
  • Aralkylamine
  • Beta-hydroxy acid
  • Benzenoid
  • Piperidine
  • Hydroxy acid
  • Heteroaromatic compound
  • Methyl ester
  • Pyrrole
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationIndicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.
PharmacodynamicsYohimbine 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 actionYohimbine 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.
Related Articles
AbsorptionRapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).
Volume of distributionNot Available
Protein bindingNot 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 eliminationNot Available
Half lifeElimination half-life is approximately 36 minutes.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point241 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 ReferencesNot Available
External Links
ATC CodesG04BE04
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AcebutololYohimbine may decrease the antihypertensive activities of Acebutolol.
AliskirenYohimbine may decrease the antihypertensive activities of Aliskiren.
AlprazolamThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Yohimbine.
AmilorideYohimbine may decrease the antihypertensive activities of Amiloride.
AmitriptylineThe serum concentration of Yohimbine can be increased when it is combined with Amitriptyline.
AmlodipineYohimbine may decrease the antihypertensive activities of Amlodipine.
AmoxapineThe serum concentration of Yohimbine can be increased when it is combined with Amoxapine.
AtenololYohimbine may decrease the antihypertensive activities of Atenolol.
Azilsartan medoxomilYohimbine may decrease the antihypertensive activities of Azilsartan medoxomil.
BenazeprilYohimbine may decrease the antihypertensive activities of Benazepril.
BetaxololYohimbine may decrease the antihypertensive activities of Betaxolol.
BisoprololYohimbine may decrease the antihypertensive activities of Bisoprolol.
BromazepamThe therapeutic efficacy of Bromazepam can be decreased when used in combination with Yohimbine.
BumetanideYohimbine may decrease the antihypertensive activities of Bumetanide.
BuspironeThe therapeutic efficacy of Buspirone can be decreased when used in combination with Yohimbine.
CandesartanYohimbine may decrease the antihypertensive activities of Candesartan.
CaptoprilYohimbine may decrease the antihypertensive activities of Captopril.
CarvedilolYohimbine may decrease the antihypertensive activities of Carvedilol.
ChlordiazepoxideThe therapeutic efficacy of Chlordiazepoxide can be decreased when used in combination with Yohimbine.
ChlorothiazideYohimbine may decrease the antihypertensive activities of Chlorothiazide.
ChlorthalidoneYohimbine may decrease the antihypertensive activities of Chlorthalidone.
CilazaprilYohimbine may decrease the antihypertensive activities of Cilazapril.
ClevidipineYohimbine may decrease the antihypertensive activities of Clevidipine.
ClobazamThe therapeutic efficacy of Clobazam can be decreased when used in combination with Yohimbine.
ClomipramineThe serum concentration of Yohimbine can be increased when it is combined with Clomipramine.
ClonazepamThe therapeutic efficacy of Clonazepam can be decreased when used in combination with Yohimbine.
ClonidineYohimbine may decrease the antihypertensive activities of Clonidine.
ClorazepateThe therapeutic efficacy of Clorazepate can be decreased when used in combination with Yohimbine.
DesipramineThe serum concentration of Yohimbine can be increased when it is combined with Desipramine.
DiazepamThe therapeutic efficacy of Diazepam can be decreased when used in combination with Yohimbine.
DiltiazemYohimbine may decrease the antihypertensive activities of Diltiazem.
DoxazosinYohimbine may decrease the antihypertensive activities of Doxazosin.
DoxepinThe serum concentration of Yohimbine can be increased when it is combined with Doxepin.
EnalaprilYohimbine may decrease the antihypertensive activities of Enalapril.
EnalaprilatYohimbine may decrease the antihypertensive activities of Enalaprilat.
EplerenoneYohimbine may decrease the antihypertensive activities of Eplerenone.
EprosartanYohimbine may decrease the antihypertensive activities of Eprosartan.
EsmololYohimbine may decrease the antihypertensive activities of Esmolol.
EstazolamThe therapeutic efficacy of Estazolam can be decreased when used in combination with Yohimbine.
Etacrynic acidYohimbine may decrease the antihypertensive activities of Ethacrynic acid.
FelodipineYohimbine may decrease the antihypertensive activities of Felodipine.
FlurazepamThe therapeutic efficacy of Flurazepam can be decreased when used in combination with Yohimbine.
FosinoprilYohimbine may decrease the antihypertensive activities of Fosinopril.
FurosemideYohimbine may decrease the antihypertensive activities of Furosemide.
GuanfacineYohimbine may decrease the antihypertensive activities of Guanfacine.
HydralazineYohimbine may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideYohimbine may decrease the antihypertensive activities of Hydrochlorothiazide.
ImipramineThe serum concentration of Yohimbine can be increased when it is combined with Imipramine.
IndapamideYohimbine may decrease the antihypertensive activities of Indapamide.
IrbesartanYohimbine may decrease the antihypertensive activities of Irbesartan.
IsradipineYohimbine may decrease the antihypertensive activities of Isradipine.
LabetalolYohimbine may decrease the antihypertensive activities of Labetalol.
LisinoprilYohimbine may decrease the antihypertensive activities of Lisinopril.
LorazepamThe therapeutic efficacy of Lorazepam can be decreased when used in combination with Yohimbine.
LosartanYohimbine may decrease the antihypertensive activities of Losartan.
MannitolYohimbine may decrease the antihypertensive activities of Mannitol.
MecamylamineYohimbine may decrease the antihypertensive activities of Mecamylamine.
MeprobamateThe therapeutic efficacy of Meprobamate can be decreased when used in combination with Yohimbine.
MethyclothiazideYohimbine may decrease the antihypertensive activities of Methyclothiazide.
MethyldopaYohimbine may decrease the antihypertensive activities of Methyldopa.
MetolazoneYohimbine may decrease the antihypertensive activities of Metolazone.
MetoprololYohimbine may decrease the antihypertensive activities of Metoprolol.
MidazolamThe therapeutic efficacy of Midazolam can be decreased when used in combination with Yohimbine.
MinoxidilYohimbine may decrease the antihypertensive activities of Minoxidil.
MoexiprilYohimbine may decrease the antihypertensive activities of Moexipril.
NadololYohimbine may decrease the antihypertensive activities of Nadolol.
NebivololYohimbine may decrease the antihypertensive activities of Nebivolol.
NicardipineYohimbine may decrease the antihypertensive activities of Nicardipine.
NifedipineYohimbine may decrease the antihypertensive activities of Nifedipine.
NimodipineYohimbine may decrease the antihypertensive activities of Nimodipine.
NisoldipineYohimbine may decrease the antihypertensive activities of Nisoldipine.
NitrazepamThe therapeutic efficacy of Nitrazepam can be decreased when used in combination with Yohimbine.
NitroprussideYohimbine may decrease the antihypertensive activities of Nitroprusside.
NortriptylineThe serum concentration of Yohimbine can be increased when it is combined with Nortriptyline.
OlmesartanYohimbine may decrease the antihypertensive activities of Olmesartan.
OxazepamThe therapeutic efficacy of Oxazepam can be decreased when used in combination with Yohimbine.
PenbutololYohimbine may decrease the antihypertensive activities of Penbutolol.
PerindoprilYohimbine may decrease the antihypertensive activities of Perindopril.
PhenoxybenzamineYohimbine may decrease the antihypertensive activities of Phenoxybenzamine.
PhentolamineYohimbine may decrease the antihypertensive activities of Phentolamine.
PindololYohimbine may decrease the antihypertensive activities of Pindolol.
PrazosinYohimbine may decrease the antihypertensive activities of Prazosin.
PropranololYohimbine may decrease the antihypertensive activities of Propranolol.
ProtriptylineThe serum concentration of Yohimbine can be increased when it is combined with Protriptyline.
QuazepamThe therapeutic efficacy of Quazepam can be decreased when used in combination with Yohimbine.
QuinaprilYohimbine may decrease the antihypertensive activities of Quinapril.
RamiprilYohimbine may decrease the antihypertensive activities of Ramipril.
ReserpineYohimbine may decrease the antihypertensive activities of Reserpine.
SotalolYohimbine may decrease the antihypertensive activities of Sotalol.
SpironolactoneYohimbine may decrease the antihypertensive activities of Spironolactone.
TelmisartanYohimbine may decrease the antihypertensive activities of Telmisartan.
TemazepamThe therapeutic efficacy of Temazepam can be decreased when used in combination with Yohimbine.
TerazosinYohimbine may decrease the antihypertensive activities of Terazosin.
TimololYohimbine may decrease the antihypertensive activities of Timolol.
TorasemideYohimbine may decrease the antihypertensive activities of Torasemide.
TrandolaprilYohimbine may decrease the antihypertensive activities of Trandolapril.
TriamtereneYohimbine may decrease the antihypertensive activities of Triamterene.
TriazolamThe therapeutic efficacy of Triazolam can be decreased when used in combination with Yohimbine.
TrimipramineThe serum concentration of Yohimbine can be increased when it is combined with Trimipramine.
ValsartanYohimbine may decrease the antihypertensive activities of Valsartan.
VerapamilYohimbine may decrease the antihypertensive activities of Verapamil.
Food InteractionsNot Available

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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
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
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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 substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
Gene Name:
HTR1B
Uniprot ID:
P28222
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 substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
Gene Name:
HTR1D
Uniprot ID:
P28221
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
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
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
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-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
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 out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium.
Components:
NameUniProt IDDetails
ATP-sensitive inward rectifier potassium channel 1P48048 Details
ATP-sensitive inward rectifier potassium channel 10P78508 Details
ATP-sensitive inward rectifier potassium channel 11Q14654 Details
ATP-sensitive inward rectifier potassium channel 12Q14500 Details
ATP-sensitive inward rectifier potassium channel 14Q9UNX9 Details
ATP-sensitive inward rectifier potassium channel 15Q99712 Details
ATP-sensitive inward rectifier potassium channel 8Q15842 Details
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 change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins ...
Gene Name:
HTR2B
Uniprot ID:
P41595
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

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]
Comments
comments powered by Disqus
Drug created on July 08, 2007 11:00 / Updated on August 17, 2016 12:23