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

General Information of Drug (ID: DR1353)
Drug Name
Promethazine
Synonyms
Phargan; Phenargan; Phenerzine; Phensedyl; Pilothia; Pilpophen; Proazaimine; Proazamine; Procit; Promazinamide; Promergan; Promesan; Prometasin; Prometazin; Prometazina; Promethacon; Promethazin; Promethazinum; Promethegan; Promethiazine; Promezathine; Prorex; Protazine; Prothazin; Provigan; Pyrethia; Pyrethiazine; Tanidil; Thiergan; Vallergine; Antiallersin; Aprobit; Atosil; Avomine; Camergan; Dimapp; Diphergan; Diprazine; Diprozin; Fargan; Fenazil; Fenetazina; Fenetazine; Hiberna; Histargan; Iergigan; Isophenergan; Lilly 1516; promethazine; 60-87-7
Indication Functional nausea/vomiting [ICD11: DD90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 284.4 Topological Polar Surface Area 31.8
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4927
PubChem SID
9608 ; 89596 ; 616468 ; 5236627 ; 7847560 ; 7980398 ; 8153034 ; 10529464 ; 11335180 ; 11360419 ; 11363762 ; 11366324 ; 11368886 ; 11372096 ; 11374835 ; 11377048 ; 11406271 ; 11461391 ; 11466916 ; 11468036 ; 11484535 ; 11486631 ; 11488656 ; 11490834 ; 11492963 ; 11494682 ; 14848899 ; 24434790 ; 26752304 ; 29224005 ; 46507798 ; 47216602 ; 47216603 ; 47216604 ; 47290955 ; 47588815 ; 47885231 ; 48110274 ; 48184815 ; 48259042 ; 48416477 ; 49698886 ; 49854482 ; 50105224 ; 56313067 ; 56313700 ; 56459433 ; 57322528 ; 75806049 ; 85088938
ChEBI ID
ChEBI:8461
CAS Number
60-87-7
TTD Drug ID
D0T2XU
Formula
C17H20N2S
Canonical SMILES
CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C
InChI
1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
InChIKey
PWWVAXIEGOYWEE-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
Desmethylpromethazine DM003001
169959
Oxidation - N-Demethylation 1 [4] , [5]
Promethazine Hydroxy metabolite DM003002 N. A. Oxidation - Hydroxylation 1 [4] , [5] , [6]
Promethazine Sulphoxide DM003000
63032
Oxidation - Sulphoxidation 1 [4] , [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002180 Promethazine Promethazine Sulphoxide Oxidation - Sulphoxidation Unclear [4], [5], [6]
MR002181 Promethazine Desmethylpromethazine Oxidation - N-Demethylation Unclear [4], [5]
MR002182 Promethazine Promethazine Hydroxy metabolite Oxidation - Hydroxylation CYP2D6 [4], [5], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
References
1 Promethazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics. 2003 Oct;13(10):619-26.
3 Akathisia with combined use of midodrine and promethazine. JAMA. 2006 May 3;295(17):2000-1. Letter
4 An HPLC-ESI-MS method for simultaneous determination of fourteen metabolites of promethazine and caffeine and its application to pharmacokinetic study of the combination therapy against motion sickness J Pharm Biomed Anal. 2012 Mar 25;62:119-28. doi: 10.1016/j.jpba.2011.12.033.
5 A liquid chromatographic method for the simultaneous determination of promethazine and three of its metabolites in plasma using electrochemical and UV detectors J Chromatogr Sci. 2001 Feb;39(2):70-2. doi: 10.1093/chromsci/39.2.70.
6 CYP2D6 is the principal cytochrome P450 responsible for metabolism of the histamine H1 antagonist promethazine in human liver microsomes. Pharmacogenetics. 1996 Oct;6(5):449-57.

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