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

General Information of Drug (ID: DR1433)
Drug Name
Rofecoxib
Synonyms
Rofecoxib [USNA]; Rofecoxib (Vioxx); Rofecoxib [INN]; 0QTW8Z7MCR; 162011-90-7; 3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one; 3-phenyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone; 4-(4-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone; 4-(4-(Methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one; MK 0966; MK 966; MK-0966; MK-966; MK0966; 4-[4-(methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone; 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one; CCRIS 8967; CHEBI:8887; CHEMBL122; Ceoxx; HSDB 7262; UNII-0QTW8Z7MCR; Vioxx
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 314.4 Topological Polar Surface Area 68.8
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5090
PubChem SID
9792 ; 535364 ; 5146347 ; 7847634 ; 7980536 ; 8146414 ; 8153131 ; 11341940 ; 11362123 ; 11362973 ; 11364757 ; 11365535 ; 11367319 ; 11368097 ; 11369881 ; 11372304 ; 11372922 ; 11374381 ; 11375481 ; 11376259 ; 11378046 ; 11445527 ; 11484228 ; 11487525 ; 11488262 ; 11490968 ; 11492446 ; 11493933 ; 11528653 ; 12014954 ; 14752370 ; 25819946 ; 26612684 ; 26680170 ; 26719838 ; 26748942 ; 26748943 ; 29224158 ; 46386634 ; 46504787 ; 47365310 ; 47810857 ; 48334605 ; 48416526 ; 49665949 ; 49666006 ; 49681737 ; 49846184 ; 50107491 ; 50107492
ChEBI ID
ChEBI:8887
CAS Number
162011-90-7
TTD Drug ID
D05VLS
Formula
C17H14O4S
Canonical SMILES
CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
InChI
1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChIKey
RZJQGNCSTQAWON-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
4'-Hydroxyrofecoxib-O-bate-D-glucuronide DM017920 N. A. Conjugation - Glucuronidation 1 [7]
5-OH-rofecoxib DM015583
9973893
Other reaction - Hydoxylation 1 [7]
5-OH-rofecoxib DM015583
9973893
Other reaction - Hydoxylation 1 [5]
Dihydro-5-OH-rofecoxib DM015335
644098
Unclear - Unclear 1 [5]
Rofecoxib-erythro-3,4-dihydrohydroxy acid DM016544
119058022
Reduction - Reduction 1 [5]
Rofecoxib-threo-3,4-dihydrohydroxy acid DM016084
44323831
Unclear - Unclear 1 [5]
5-Hydroxyrofecoxib-O-bate-D-glucuronide DM017919 N. A. Conjugation - Glucuronidation 2 [7]
5-OH-rofecoxib O-glucuronide DM017918 N. A. Conjugation - Glucuronidation 2 [5] , [6]
Cis -Dihydrorofecoxib DM016449
101079917
Unclear - Unclear 2 [5]
Rofecoxib-threo-3,4-dihydrohydroxy acid DM016084
44323831
Unclear - Unclear 2 [5]
Trans-Dihydrorofecoxib DM016083
44323766
Unclear - Unclear 2 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013062 Rofecoxib 5-OH-rofecoxib Other reaction - Hydoxylation CYP3A4 ... [5]
MR013064 Rofecoxib Dihydro-5-OH-rofecoxib Unclear - Unclear Unclear [5]
MR013066 Rofecoxib Rofecoxib-erythro-3,4-dihydrohydroxy acid Reduction - Reduction Unclear [5]
MR013068 Rofecoxib Rofecoxib-threo-3,4-dihydrohydroxy acid Unclear - Unclear Unclear [5]
MR013071 Rofecoxib 4'-Hydroxyrofecoxib-O-bate-D-glucuronide Conjugation - Glucuronidation Unclear [7]
MR013070 5-Hydroxyrofecoxib 5-Hydroxyrofecoxib-O-bate-D-glucuronide Conjugation - Glucuronidation Unclear [7]
MR013063 5-OH-rofecoxib 5-OH-rofecoxib O-glucuronide Conjugation - Glucuronidation UGT2B15 ... [5], [6]
MR013065 Dihydro-5-OH-rofecoxib Rofecoxib-threo-3,4-dihydrohydroxy acid Unclear - Unclear Unclear [5]
MR013067 Rofecoxib-erythro-3,4-dihydrohydroxy acid Cis -Dihydrorofecoxib Unclear - Unclear Unclear [5]
MR013069 Rofecoxib-threo-3,4-dihydrohydroxy acid Trans-Dihydrorofecoxib Unclear - Unclear Unclear [5]
⏷ Show the Full List of 10 MR(s)
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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 7  DME(s)
References
1 Rofecoxib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Rofecoxib is a potent inhibitor of cytochrome P450 1A2: studies with tizanidine and caffeine in healthy subjects. Br J Clin Pharmacol. 2006 Sep;62(3):345-57.
3 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
4 Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 Involvement of human UGT2B7 and 2B15 in rofecoxib metabolism
7 The disposition and metabolism of rofecoxib, a potent and selective cyclooxygenase-2 inhibitor, in human subjects

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