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

General Information of Drug (ID: DR1500)
Drug Name
Sorafenib
Synonyms
Sorafenib; Nexavar; 284461-73-0; 4-(4-(3-(4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL)UREIDO)PHENOXY)-N-METHYLPICOLINAMIDE; 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide; 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide; 9ZOQ3TZI87; BAY 43-9006; CHEMBL1336; N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea; UNII-9ZOQ3TZI87
Indication Renal cell carcinoma [ICD11: 2C90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 464.8 Topological Polar Surface Area 92.4
Heavy Atom Count 32 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
216239
PubChem SID
833589 ; 833590 ; 7886069 ; 9372814 ; 12015507 ; 14720365 ; 14834034 ; 30419984 ; 46505329 ; 46516901 ; 50069824 ; 50070560 ; 50071324 ; 50100118 ; 50112741 ; 53787819 ; 53799234 ; 56312334 ; 56312336 ; 56312338 ; 56312517 ; 56312519 ; 56312521 ; 56394953 ; 57399755 ; 68529952 ; 74382940 ; 75518900 ; 81092852 ; 85174603 ; 85285882 ; 85845166 ; 91148447 ; 92718861 ; 93581025 ; 96025209 ; 99443909 ; 103420820 ; 103904444 ; 104178872 ; 113461200 ; 117695450 ; 117871124 ; 124767621 ; 124893320 ; 124893321 ; 124893322 ; 124893323 ; 124893324 ; 125346960
ChEBI ID
ChEBI:50924
CAS Number
284461-73-0
TTD Drug ID
D0W5HK
Formula
C21H16ClF3N4O3
Canonical SMILES
CNC(=O)C1=NC=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F
InChI
1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChIKey
MLDQJTXFUGDVEO-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
Pyridine N-oxide glucuronide DM006367
131770061
Multi-steps Reaction - Oxidationn; glucuronidation 1 [6] , [3]
Pyridostigmine DM006366
4991
Oxidation - Oxidationn 1 [6]
Sorafenib beta-D-Glucuronide DM006368
71752221
Conjugation - Glucuronidation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006833 Sorafenib Pyridostigmine Oxidation - Oxidationn CYP1A2 ... [6]
MR006834 Sorafenib Pyridine N-oxide glucuronide Multi-steps Reaction - Oxidationn; glucuronidation CYP1A2 ... [6], [3]
MR006835 Sorafenib Sorafenib beta-D-Glucuronide Conjugation - Glucuronidation UGT1A9 [6]
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
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Sorafenib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Ontogeny and sorafenib metabolism. Clin Cancer Res. 2012 Oct 15;18(20):5788-95.
3 Interaction of sorafenib and cytochrome P450 isoenzymes in patients with advanced melanoma: a phase I/II pharmacokinetic interaction study. Cancer Chemother Pharmacol. 2011 Nov;68(5):1111-8.
4 Drug Interactions Flockhart Table
5 Pharmacokinetic interaction involving sorafenib and the calcium-channel blocker felodipine in a patient with hepatocellular carcinoma. Invest New Drugs. 2011 Dec;29(6):1511-4.
6 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.

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