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

General Information of Drug (ID: DR1677)
Drug Name
Vemurafenib
Synonyms
Vemurafenib; Vemurafenib (PLX4032); Vemurafenib (PLX4032, RG7204); Zelboraf; PLX 4032; PLX-4032; PLX4032; RG 7204; RG-7204; RG7204; RO 5185426; RO5185426; 1029872-54-5; 207SMY3FQT; 918504-65-1; CHEBI:63637; N-(3-(5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide; N-(3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl}-2,4-difluorophenyl)propane-1-sulfonamide; NSC761431; UNII-207SMY3FQT
Indication Melanoma [ICD11: 2C30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 489.9 Topological Polar Surface Area 100
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
42611257
PubChem SID
86450036 ; 99207986 ; 99344329 ; 99436933 ; 104245715 ; 123055406 ; 123393726 ; 124757131 ; 125163935 ; 125240992 ; 125312523 ; 125477821 ; 126731467 ; 131408691 ; 131480743 ; 134213431 ; 135267495 ; 135360056 ; 135611115 ; 135626717 ; 135686206 ; 135686207 ; 135686222 ; 135686223 ; 135727433 ; 136367377 ; 136920367 ; 137241152 ; 137275900 ; 138196197 ; 152258377 ; 160647214 ; 160837190 ; 162011358 ; 162037528 ; 162201724 ; 163098027 ; 163345507 ; 163390276 ; 164041819 ; 164193918 ; 164766097 ; 164834160 ; 165826640 ; 170483525 ; 170498105 ; 172087033 ; 172914376 ; 174531480 ; 175267423
ChEBI ID
ChEBI:63637
CAS Number
918504-65-1
TTD Drug ID
D0Y9EW
Formula
C23H18ClF2N3O3S
Canonical SMILES
CCCS(=O)(=O)NC1=C(C(=C(C=C1)F)C(=O)C2=CNC3=C2C=C(C=N3)C4=CC=C(C=C4)Cl)F
InChI
1S/C23H18ClF2N3O3S/c1-2-9-33(31,32)29-19-8-7-18(25)20(21(19)26)22(30)17-12-28-23-16(17)10-14(11-27-23)13-3-5-15(24)6-4-13/h3-8,10-12,29H,2,9H2,1H3,(H,27,28)
InChIKey
GPXBXXGIAQBQNI-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
Hydroxyvemurafenib DM003041 N. A. Oxidation - Hydroxylation 1 [3]
Vemurafenib glucuronide DM003042 N. A. Conjugation - Glucuronidation 1 [3]
Vemurafenib intermediary metabolite DM003043 N. A. Hydrolysis - Hydrolysis 1 [4]
Secondary metabolite of vemurafenib DM003045
156635836
Hydrolysis - Hydrolysis 2 [4]
Secondary metabolite of vemurafenib alternative DM003044
67376769
Oxidation - Dehalogenation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002508 Vemurafenib Hydroxyvemurafenib Oxidation - Hydroxylation CYP3A4 [3]
MR002509 Vemurafenib Vemurafenib glucuronide Conjugation - Glucuronidation Unclear [3]
MR002510 Vemurafenib Vemurafenib intermediary metabolite Hydrolysis - Hydrolysis Unclear [4]
MR002506 Vemurafenib intermediary metabolite Secondary metabolite of vemurafenib alternative Oxidation - Dehalogenation Unclear [4]
MR002507 Vemurafenib intermediary metabolite Secondary metabolite of vemurafenib Hydrolysis - Hydrolysis Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Vemurafenib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Vemurafenib for the treatment of melanoma. Expert Opin Pharmacother. 2012 Dec;13(17):2533-43.
3 Novel rapid liquid chromatography tandem masspectrometry method for vemurafenib and metabolites in human plasma, including metabolite concentrations at steady state Biomed Chromatogr. 2016 Aug;30(8):1234-9. doi: 10.1002/bmc.3672.
4 A single-dose mass balance and metabolite-profiling study of vemurafenib in patients with metastatic melanoma Pharmacol Res Perspect. 2015 Mar;3(2):e00113. doi: 10.1002/prp2.113.

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