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

General Information of Drug (ID: DR0877)
Drug Name
Ipecac
Synonyms Ipecac; Ipecac [USP]; Ipecac syrup; Ipecacuanha; Syrup of ipecac, U.S.P; UNII-62I3C8233L; Ipsatol; SCHEMBL20484348; 62I3C8233L; 8012-96-2; EINECS 232-385-8
Indication Pulmonary tuberculosis [ICD11: 1B10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 420 Topological Polar Surface Area 102
Heavy Atom Count 29 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
135314942
TTD Drug ID
D03FEO
Formula
C20H30ClN7O
Canonical SMILES
CC1CCN(C(C1)C(=O)C(CC(C)C)N)NCC2=C(C=CC(=C2)Cl)N3C=NN=N3
InChI
1S/C20H30ClN7O/c1-13(2)8-17(22)20(29)19-9-14(3)6-7-27(19)24-11-15-10-16(21)4-5-18(15)28-12-23-25-26-28/h4-5,10,12-14,17,19,24H,6-9,11,22H2,1-3H3
InChIKey
RMSPDXQDMUBKTG-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
10-O-demethylemetine DM002572 N. A. Oxidation - Demethylation 1 [3] , [4]
9-O-demethylemetine DM002570 N. A. Oxidation - Demethylation 1 [3] , [4]
Cephaeline DM002568
9426
Oxidation - Demethylation 1 [3] , [4]
9-O-demethylemetine glucuronide metabolite DM002571 N. A. Conjugation - Glucuronidation 2 [3]
Cephaeline 6'-O-glucuronide metabolite DM002569 N. A. Conjugation - Glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003497 Ipecac Cephaeline Oxidation - Demethylation CYP2D6 ... [3], [4]
MR003499 Ipecac 9-O-demethylemetine Oxidation - Demethylation CYP3A4 [3], [4]
MR003501 Ipecac 10-O-demethylemetine Oxidation - Demethylation CYP3A4 [3], [4]
MR003500 9-O-demethylemetine 9-O-demethylemetine glucuronide metabolite Conjugation - Glucuronidation Unclear [3]
MR003498 Cephaeline Cephaeline 6'-O-glucuronide metabolite Conjugation - Glucuronidation Unclear [3]
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 Ipecac syrup abuse, morbidity, and mortality: isn't it time to repeal its over-the-counter status? J Adolesc Health. 2005 Sep;37(3):256-60.
2 Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. doi: 10.1002/9781118105955.ch13
3 Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol Pharm Bull. 2001 Jun;24(6):678-82.
4 Biotransformation of the ipecac alkaloids cephaeline and emetine from ipecac syrup in rats Eur J Drug Metab Pharmacokinet. 2002 Jan-Mar;27(1):29-35. doi: 10.1007/BF03190402.

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