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

General Information of Drug (ID: DR0388)
Drug Name
Cyamemazine
Synonyms
Ciamatil; Ciamemazina [INN-Spanish]; Cianatil; Cyamemazin; Cyamemazine; Cyamemazine (INN); Cyamemazine [INN]; Cyamemazinum [INN-Latin]; Cyamepromazine; Cyamepromezine; Kyamepromazin; Kyamepromazine; RP-7204; TH 2602; Tercian; 10-(3-(Dimethylamino)-2-methylpropyl)phenothiazine-2-carbonitrile; 10-(3-dimethylamino-2-methylpropyl)phenothiazine-2-carbonitrile; 10-[3-(Dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile; 3546-03-0; 7204 R.E.; 7204 RP; BRN 0093261; EINECS 222-594-2; F.I. 6229
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 323.5 Topological Polar Surface Area 55.6
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
62865
PubChem SID
8188334 ; 14826280 ; 43119930 ; 47285901 ; 47880135 ; 50006264 ; 51091644 ; 57314886 ; 75129996 ; 85209840 ; 96099841 ; 104326854 ; 125824719 ; 135019180 ; 135650143 ; 136158994 ; 136352157 ; 137006389 ; 142677092 ; 160676424 ; 162221098 ; 163133724 ; 164838618 ; 164838619 ; 172919690 ; 179225635 ; 184530546 ; 226509842 ; 249924678
ChEBI ID
CHEBI:135379
CAS Number
3546-03-0
TTD Drug ID
D0G7NW
Formula
C19H21N3S
Canonical SMILES
CC(CN1C2=CC=CC=C2SC3=C1C=C(C=C3)C#N)CN(C)C
InChI
1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3
InChIKey
SLFGIOIONGJGRT-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
Cyamemazine sulfoxide DM004928
71315019
Oxidation - Oxidationn 1 [3] , [2]
N-desmethyl cyamemazine DM004927 N. A. Oxidation - N-demethylation 1 [3] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005317 Cyamemazine N-desmethyl cyamemazine Oxidation - N-demethylation CYP3A4 ... [3], [2]
MR005318 Cyamemazine Cyamemazine sulfoxide Oxidation - Oxidationn CYP1A2 ... [3], [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3] , [2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 84).
2 Characterization of human cytochrome P450 enzymes involved in the metabolism of cyamemazine. Eur J Pharm Sci. 2007 Dec;32(4-5):357-66.
3 Active cyamemazine metabolites in patients treated with cyamemazine (Tercian?): influence on cerebral dopamine D2 and serotonin 5-HT (2A) receptor occupancy as measured by positron emission tomography (PET)

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