General Information of Drug (ID: DMJCP1Y)

Drug Name
Yohimbine Drug Info
Synonyms
APHRODINE; Actibine; Aphrodyne; Aphrosol; Corynine; Johimbin; Quebrachin; Quebrachine; Thybine; Yocon; Yohimar; Yohimbin; Yohimex; Yoman; Yovital; Dayto himbin; Yohimbic acid methyl ester; Baron-X; Trans-Quinolizidine yohimbine; Yohimbine (DCF); Methyl 17alpha-hydroxyyohimban-16alpha-carboxylate; Yohimbol-16alpha-carboxylic acid, methyl ester (6CI); Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.; Methyl (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylate; Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI); Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-(9CI); Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester; (+)-Yohimbin; (+)-Yohimbine; (16alpha,17alpha)-17-Hydroxy-yohimban-16-carboxylic acid methyl ester; (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester; 17-Hydroxy-yohimbane-16-carboxylic acid methyl ester; 17-Hydroxyyohimban-16-carboxylic acid methyl ester; 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester; 2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
Indication
Disease Entry ICD 11 Status REF
Erectile dysfunction HA01.1 Approved [1]
Therapeutic Class
Mydriatics
Cross-matching ID
PubChem CID
8969
ChEBI ID
CHEMBL15245
CAS Number
CAS 146-48-5
TTD Drug ID
DMJCP1Y
VARIDT Drug ID
DR01191
INTEDE Drug ID
DR1722

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [6]
Meperidine DMX4GND Pain MG30-MG3Z Approved [7]
Lofexidine DM1WXA6 Heroin and opiate withdrawal 6C43 Approved [8]
Sodium chloride DMM3950 Skin burns ME65.0 Approved [6]
Guanfacine extended release DMB1CZ8 Attention deficit hyperactivity disorder 6A05.Z Approved [9]
Dexmedetomidine DM93L4X Irritability MB24 Approved [10]
Guanabenz DM5QWEL High blood pressure BA00 Approved [11]
Tizanidine DMR2IQ4 Spasm MB47.3 Approved [12]
Oxymetazoline DM8ZXT6 Arrhythmia BC9Z Approved [13]
Brimonidine DMQLT4N Ocular hypertension 9C61.01 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2D6 (CYP2D6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [24]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [25]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [26]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [23]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [27]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [28]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [29]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [30]
Propranolol DM79NTF Angina pectoris BA40 Approved [31]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Flupentixol DM0DJ9O Schizophrenia 6A20 Approved [32]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [33]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [34]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [35]
Cepharanthine DM9Y5JB N. A. N. A. Approved [36]
Itraconazole DMCR1MV Aspergillosis 1F20 Approved [37]
Clozapine DMFC71L Schizophrenia 6A20 Approved [38]
Midostaurin DMI6E0R Acute myeloid leukaemia 2A60 Approved [39]
Trifluoperazine DMKBYWI Anxiety Approved [40]
Olanzapine DMPFN6Y Bipolar depression Approved [38]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [5]

References

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3 Human sympathetic activation by alpha2-adrenergic blockade with yohimbine: bimodal, epistatic influence of cytochrome P450-mediated drug metabolism. Clin Pharmacol Ther. 2004 Aug;76(2):139-53.
4 Relationship of cytochrome P450 pharmacogenetics to the effects of yohimbine on gastrointestinal transit and catecholamines in healthy subjects. Neurogastroenterol Motil. 2008 Aug;20(8):891-9.
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8 Clinical pharmacokinetics of lofexidine, the alpha 2-adrenergic receptor agonist, in opiate addicts plasma using a highly sensitive liquid chromatography tandem mass spectrometric analysis. Am J DrugAlcohol Abuse. 2008;34(5):611-6.
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10 Dexmedetomidine in intensive care unit: a study of hemodynamic changes. Middle East J Anesthesiol. 2002 Oct;16(6):587-95.
11 Centrally acting sympathetic inhibitors for therapy of patients with hypertension. Nippon Rinsho. 1997 Aug;55(8):2081-5.
12 Tizanidine. A review of its pharmacology, clinical efficacy and tolerability in the management of spasticity associated with cerebral and spinal disorders. Drugs. 1997 Mar;53(3):435-52.
13 Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55.
14 Increased alpha2-adrenergic constriction of isolated arterioles in diffuse scleroderma. Arthritis Rheum. 2000 Aug;43(8):1886-90.
15 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
20 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
23 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
24 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
25 Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
26 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
27 Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
28 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
29 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
30 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
31 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
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33 Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein. Toxicol Lett. 2013 Feb 27;217(2):137-42. doi: 10.1016/j.toxlet.2012.12.012. Epub 2012 Dec 27.
34 Editor's Highlight: PlacentalDisposition and Effects of Crizotinib: An Ex Vivo Study in the Isolated Dual-Side Perfused Human Cotyledon. Toxicol Sci. 2017 Jun 1;157(2):500-509. doi: 10.1093/toxsci/kfx063.
35 Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs. Pharmacogenet Genomics. 2008 May;18(5):390-402. doi: 10.1097/FPC.0b013e3282f85e36.
36 Cepharanthine potently enhances the sensitivity of anticancer agents in K562 cells. Cancer Sci. 2005 Jun;96(6):372-6. doi: 10.1111/j.1349-7006.2005.00057.x.
37 Clinical pharmacokinetic monitoring of itraconazole is warranted in only a subset of patients. Ther Drug Monit. 2005 Jun;27(3):322-33. doi: 10.1097/01.ftd.0000150135.22645.ea.
38 Evaluation of antipsychotic drugs as inhibitors of multidrug resistance transporter P-glycoprotein. Psychopharmacology (Berl). 2006 Sep;187(4):415-23. doi: 10.1007/s00213-006-0437-9. Epub 2006 Jun 30.
39 Actions of the selective protein kinase C inhibitor PKC412 on B-chronic lymphocytic leukemia cells in vitro. Haematologica. 2002 Feb;87(2):167-76.
40 Characterization of the ATPase activity of the Mr 170,000 to 180,000 membrane glycoprotein (P-glycoprotein) associated with multidrug resistance in K562/ADM cells. Cancer Res. 1988 Sep 1;48(17):4926-32.