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

General Information of Drug (ID: DR1089)
Drug Name
CCRIS-9277
Synonyms
Midomafetamine; Ecstasy; MDMA (unspecified); Methylenedioxymethamphetamine; (+-)-(3,4-Methylenedioxy)methamphetamine; (+-)-N-Methyl-3,4-(methylenedioxy)amphetamine; (RS)-3,4-(methylenedioxy)methamphetamine; 1,3-Benzodioxole-5-ethanamine, N,alpha-dimethyl-; 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine; 3,4-methylenedioxymethamphetamine; 42542-10-9; CHEBI:1391; DEA No. 7405; DL-(3,4-Methylenedioxy)methamphetamine; HSDB 6929; MDMA; N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine; N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE
Indication Posttraumatic stress disorder [ICD11: 6B40] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 193.24 Topological Polar Surface Area 30.5
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
1615
ChEBI ID
CHEBI:1391
CAS Number
42542-10-9
TTD Drug ID
D0F5NJ
Formula
C11H15NO2
Canonical SMILES
CC(CC1=CC2=C(C=C1)OCO2)NC
InChI
1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
InChIKey
SHXWCVYOXRDMCX-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
HHMA DM006823
12611606
Oxidation - O-demethylation 1 [2]
MDA DM006812 N. A. Oxidation - O-demethylation 1 [2]
CCRIS-9277 M7 DM006821
78407
Oxidation - Deamination 2 [2]
HHA DM006813
17005
Oxidation - N-dealkylation 2 [2]
HHA DM006813
17005
Oxidation - O-demethylation 2 [2]
HMMA DM006825 N. A. Oxidation - O-demethylation 2 [2]
CCRIS-9277 M10 DM006826 N. A. Conjugation - Conjugation 3 [2]
CCRIS-9277 M4 DM006818
14515288
Oxidation - Deamination 3 [2]
CCRIS-9277 M6 DM006820 N. A. Conjugation - Sulfation 3 [2]
CCRIS-9277 M8 DM006822
21202694
Conjugation - Conjugation 3 [2]
CCRIS-9277 M9 DM006824 N. A. Conjugation - Sulfation 3 [2]
HMA DM006814 N. A. Oxidation - Deamination 3 [2]
CCRIS-9277 M1 DM006815
24721450
Conjugation - Conjugation 4 [2]
CCRIS-9277 M3 DM006817 N. A. Conjugation - Conjugation 4 [2]
CCRIS-9277 M5 DM006819 N. A. Conjugation - Conjugation 4 [2]
CCRIS-9277 M2 DM006816 N. A. Conjugation - Conjugation 5 [2]
⏷ Show the Full List of 16  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007394 CCRIS-9277 MDA Oxidation - O-demethylation Unclear [2]
MR007405 CCRIS-9277 HHMA Oxidation - O-demethylation CYP2D6 ... [2]
MR007406 HHMA HHA Oxidation - N-dealkylation Unclear [2]
MR007408 HHMA HMMA Oxidation - O-demethylation CYP2D6 ... [2]
MR007395 MDA HHA Oxidation - O-demethylation Unclear [2]
MR007403 MDA CCRIS-9277 M7 Oxidation - Deamination Unclear [2]
MR007404 CCRIS-9277 M7 CCRIS-9277 M8 Conjugation - Conjugation Unclear [2]
MR007396 HHA HMA Oxidation - Deamination Unclear [2]
MR007400 HHA CCRIS-9277 M4 Oxidation - Deamination Unclear [2]
MR007402 HHA CCRIS-9277 M6 Conjugation - Sulfation Unclear [2]
MR007407 HHA CCRIS-9277 M9 Conjugation - Sulfation Unclear [2]
MR007409 HMMA CCRIS-9277 M10 Conjugation - Conjugation Unclear [2]
MR007401 CCRIS-9277 M4 CCRIS-9277 M5 Conjugation - Conjugation Unclear [2]
MR007397 HMA CCRIS-9277 M1 Conjugation - Conjugation Unclear [2]
MR007399 HMA CCRIS-9277 M3 Conjugation - Conjugation Unclear [2]
MR007398 CCRIS-9277 M1 CCRIS-9277 M2 Conjugation - Conjugation Unclear [2]
⏷ Show the Full List of 16 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT00090064) A Test of MDMA-Assisted Psychotherapy in People With Posttraumatic Stress Disorder.
2 Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition. Ther Drug Monit. 2004 Apr;26(2):137-44.
3 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.

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