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

General Information of Drug (ID: DR0951)
Drug Name
ML-3000
Synonyms
Licofelone; Licofelone [INN]; ML 3000; ML-3000; P5T6BYS22Y; 156897-06-2; 2,3-Dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid; 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid; 6-(4-Chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizine-5-acetic acid; BRN 6823674; C23H22ClNO2; CHEMBL300982; UNII-P5T6BYS22Y; [6-(4-CHLOROPHENYL)-2,2-DIMETHYL-7-PHENYL-2,3-DIHYDRO-1H-PYRROLIZIN-5-YL]ACETIC ACID
Indication Osteoarthritis [ICD11: FA00] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 379.9 Topological Polar Surface Area 42.2
Heavy Atom Count 27 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
133021
PubChem SID
6436380 ; 7888616 ; 10243273 ; 12014886 ; 14829304 ; 29311030 ; 50040041 ; 50700417 ; 53788587 ; 57344354 ; 103243188 ; 103945934 ; 104378798 ; 125333743 ; 126645607 ; 126648934 ; 129342134 ; 131300446 ; 134338958 ; 135088300 ; 135692433 ; 137116560 ; 137275875 ; 142116170 ; 144072480 ; 162172234 ; 162476140 ; 163884604 ; 164228207 ; 164761582 ; 175426859 ; 184826912 ; 196105884 ; 198972330 ; 204370171 ; 223392829 ; 223705238 ; 223909705 ; 226588726 ; 251882412 ; 252215695 ; 252450609
CAS Number
156897-06-2
TTD Drug ID
D0N1SU
Formula
C23H22ClNO2
Canonical SMILES
CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C
InChI
1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
InChIKey
UAWXGRJVZSAUSZ-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
Licofelone acyl glucuronide (M1) DM007004 N. A. Conjugation - Acyl glucuronidation 1 [2]
Licofelone M2 DM007006
154699910
Oxidation - Hydrolyzationn 1 [2]
Licofelone M4 DM007002
22500686
Oxidation - Hydrolyzationn 1 [2]
Licofelone M3 DM007005 N. A. Conjugation - Acyl glucuronidation 2 [2]
Licofelone M3 DM007005 N. A. Oxidation - Hydrolyzationn 2 [2]
Licofelone M5 DM007003 N. A. Conjugation - Acyl glucuronidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007630 ML-3000 Licofelone M4 Oxidation - Hydrolyzationn CYP2C8 ... [2]
MR007632 ML-3000 Licofelone acyl glucuronide (M1) Conjugation - Acyl glucuronidation UGT1A3 ... [2]
MR007634 ML-3000 Licofelone M2 Oxidation - Hydrolyzationn CYP2C8 ... [2]
MR007633 Licofelone acyl glucuronide (M1) Licofelone M3 Oxidation - Hydrolyzationn CYP2C8 [2]
MR007635 Licofelone M2 Licofelone M3 Conjugation - Acyl glucuronidation UGT [2]
MR007631 Licofelone M4 Licofelone M5 Conjugation - Acyl glucuronidation UGT [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 10  DME(s)
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003927)
2 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.
3 In vitro metabolism of 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl] acetic acid (licofelone, ML3000), an inhibitor of cyclooxygenase-1 and -2 and 5-lipoxygenase. Drug Metab Dispos. 2008 May;36(5):894-903.

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