Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1722)
Drug Name
Yohimbine
Synonyms
Yohimbic acid methyl ester; Yohimbin; Yohimbine; Yohimex; APHRODINE; Actibine; Aphrodyne; Aphrosol; Corynine; Johimbin; Quebrachin; Quebrachine; Thybine; (+)-Yohimbine; 146-48-5; 17-Hydroxyyohimban-16-carboxylic acid methyl ester; 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester; 2Y49VWD90Q; BRN 0097276; CHEBI:10093; CHEMBL15245; EINECS 205-672-0; UNII-2Y49VWD90Q; Yocon; Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-; methyl 17alpha-hydroxyyohimban-16alpha-carboxylate
Indication Erectile dysfunction [ICD11: HA01] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 354.4 Topological Polar Surface Area 65.6
Heavy Atom Count 26 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
8969
PubChem SID
11447 ; 587676 ; 605307 ; 840951 ; 841871 ; 7980901 ; 8156377 ; 11120335 ; 11120823 ; 11121311 ; 11121803 ; 11122283 ; 11362990 ; 11365552 ; 11368114 ; 11371131 ; 11371132 ; 11373715 ; 11376276 ; 11466612 ; 11467732 ; 11486383 ; 11533345 ; 14754428 ; 14852160 ; 29227596 ; 46501178 ; 46504602 ; 47275218 ; 47349036 ; 47573040 ; 47646243 ; 47794706 ; 47869289 ; 48018552 ; 48318057 ; 48393589 ; 49698567 ; 50063657 ; 50104741 ; 50104742 ; 56459445 ; 57325346 ; 79341239 ; 81044603 ; 85787300 ; 85787958 ; 90340710 ; 92308815 ; 92310154
ChEBI ID
ChEBI:10093
CAS Number
146-48-5
TTD Drug ID
D0H4JM
Formula
C21H26N2O3
Canonical SMILES
COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
InChI
1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1
InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-N
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 ClinicalTrials.gov (NCT00975325) Bioequivalence Study Comparing Two Test Products With One Reference Product, All Containing 5 mg Yohimbine.
2 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.
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.

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