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

General Information of Drug (ID: DR1345)
Drug Name
Prochlorperazine
Synonyms
Prochloroperazine; Prochlorpemazine; Prochlorperazin; Prochlorperazine maleate; Prochlorperazinum; Prochlorperazinum [INN-Latin]; Prochlorpermazine; Prochlorpromazine; Procloperazine; Proclorperazina; Proclorperazina [INN-Spanish]; Proclorperazine; Capazine; Chlormeprazine; Chlorperazine; Combid; Compazine; Compazine Suppositories; Compro; Emelent; Eskatrol; Kronocin; Meterazin; Meterazine; Nipodal; Novamin; SKF 4657; Stemetil; Tementil; Temetid; Vertigon; prochlorperazine; 58-38-8; 6140 RP; Bayer A 173
Indication Functional nausea/vomiting [ICD11: DD90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 373.9 Topological Polar Surface Area 35
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4917
PubChem SID
9607 ; 597374 ; 855827 ; 5236619 ; 7847559 ; 7980391 ; 8153028 ; 10528269 ; 11111685 ; 11111686 ; 11335588 ; 11360827 ; 11363734 ; 11364717 ; 11366296 ; 11367279 ; 11368858 ; 11369841 ; 11371862 ; 11372882 ; 11374482 ; 11375441 ; 11377020 ; 11378005 ; 11427138 ; 11461799 ; 11466427 ; 11467547 ; 11485069 ; 11486274 ; 11489113 ; 11490697 ; 11492787 ; 11494654 ; 14828997 ; 24263035 ; 29223995 ; 46509018 ; 47216713 ; 47216714 ; 47291072 ; 47291073 ; 47662213 ; 47662214 ; 47736410 ; 47810684 ; 47885344 ; 47885345 ; 48035042 ; 48416473
ChEBI ID
ChEBI:8435
CAS Number
58-38-8
TTD Drug ID
D0B2UZ
Formula
C20H24ClN3S
Canonical SMILES
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
InChI
1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
InChIKey
WIKYUJGCLQQFNW-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
N-demethylation DM002980
10451115
Oxidation - N-Demethylation 1 [3] , [4] , [5]
Prochlorperazine 7-hydroxide DM002982
12333094
Oxidation - 7-Hydroxylation 1 [3] , [4] , [5]
Prochlorperazine sulfoxide DM002981
3084059
Oxidation - Sulfoxidation 1 [3] , [4] , [5]
Prochlorperazine sulfoxide 4'-N-oxide DM002983
91668180
Oxidation - Oxidation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002166 Prochlorperazine N-demethylation Oxidation - N-Demethylation CYP2C19 ... [3], [4], [5]
MR002167 Prochlorperazine Prochlorperazine sulfoxide Oxidation - Sulfoxidation CYP2C19 ... [3], [4], [5]
MR002168 Prochlorperazine Prochlorperazine 7-hydroxide Oxidation - 7-Hydroxylation CYP2C19 ... [3], [4], [5]
MR002169 Prochlorperazine Prochlorperazine sulfoxide 4'-N-oxide Oxidation - Oxidation Unclear [5]
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 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Prochlorperazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Potential for drug interactions involving cytochromes P450 2D6 and 3A4 on general adult psychiatric and functional elderly psychiatric wards. Br J Clin Pharmacol. 2004 Apr;57(4):464-72.
3 Influence of cytochrome P450 genotype on the plasma disposition of prochlorperazine metabolites and their relationships with clinical responses in cancer patients Ann Clin Biochem. 2018 May;55(3):385-393. doi: 10.1177/0004563217731432.
4 Simultaneous determination of prochlorperazine and its metabolites in human plasma using isocratic liquid chromatography tandem mass spectrometry Biomed Chromatogr. 2012 Jun;26(6):754-60. doi: 10.1002/bmc.1725.
5 Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route J Clin Pharmacol. 2005 Dec;45(12):1383-90. doi: 10.1177/0091270005281044.

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