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

General Information of Drug (ID: DR3555)
Drug Name
LAROPIPRANT
Synonyms
Laropiprant; 571170-77-9; MK 0524; Cardaptive; MK-0524; UNII-G7N11T8O78; CHEMBL426559; G7N11T8O78; 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid; 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methanesulfonyl-1H,2H,3H,4H-cyclopenta[b]indol-3-yl]acetic acid; Tedaptive; Laropiprant [USAN:INN:BAN]; [14C]-Laropiprant; Laropiprant/MK-0524; Laropiprant (INN/USAN); Laropiprant (MK-0524); SCHEMBL991107; AMOT0189; GTPL3356; KS-00000XIE; CTK8F0660; MK-0524B
Indication Atherosclerosis [ICD11: BA80] Phase 4 [1]
Arteriosclerosis obliterans [ICD11: ICD11: BD40] Discontinued in Phase 3 [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 435.9 Topological Polar Surface Area 84.8
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
9867642
ChEBI ID
CHEBI:135942
CAS Number
571170-77-9
TTD Drug ID
D0WL5V
Formula
C21H19ClFNO4S
Canonical SMILES
CS(=O)(=O)C1=CC(=CC2=C1N(C3=C2CC[C@@H]3CC(=O)O)CC4=CC=C(C=C4)Cl)F
InChI
InChI=1S/C21H19ClFNO4S/c1-29(27,28)18-10-15(23)9-17-16-7-4-13(8-19(25)26)20(16)24(21(17)18)11-12-2-5-14(22)6-3-12/h2-3,5-6,9-10,13H,4,7-8,11H2,1H3,(H,25,26)/t13-/m1/s1
InChIKey
NXFFJDQHYLNEJK-CYBMUJFWSA-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
LAROPIPRANT Metabolite M1 DM016094
44425192
Oxidation - Monohydroxylation 1 [3]
LAROPIPRANT Metabolite M2 DM017752 N. A. Conjugation - Acyl glucuronide conjugation 1 [3]
LAROPIPRANT Metabolite M3 DM015756
11385386
Unclear - Unclear 1 [3]
LAROPIPRANT Metabolite M4 DM015945
16216714
Oxidation - Monohydroxylation 1 [3]
LAROPIPRANT Metabolite M5 DM017755 N. A. Oxidation - N-dealkylation 1 [3]
LAROPIPRANT Metabolite M7 DM017756 N. A. Oxidation - Oxidization 1 [3]
LAROPIPRANT Metabolite M6 DM017751 N. A. Unclear - Unclear 2 [3]
LAROPIPRANT Metabolite M8 DM017753 N. A. Unclear - Unclear 2 [3]
LAROPIPRANT Metabolite M9 DM017754 N. A. Unclear - Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009263 LAROPIPRANT LAROPIPRANT Metabolite M3 Unclear - Unclear Unclear [3]
MR009265 LAROPIPRANT LAROPIPRANT Metabolite M2 Conjugation - Acyl glucuronide conjugation Unclear [3]
MR009267 LAROPIPRANT LAROPIPRANT Metabolite M1 Oxidation - Monohydroxylation CYP3A4 ... [3]
MR009269 LAROPIPRANT LAROPIPRANT Metabolite M4 Oxidation - Monohydroxylation CYP3A4 ... [3]
MR009271 LAROPIPRANT LAROPIPRANT Metabolite M5 Oxidation - N-dealkylation Unclear [3]
MR009272 LAROPIPRANT LAROPIPRANT Metabolite M7 Oxidation - Oxidization Unclear [3]
MR009268 LAROPIPRANT Metabolite M1 LAROPIPRANT Metabolite M9 Unclear - Unclear Unclear [4]
MR009266 LAROPIPRANT Metabolite M2 LAROPIPRANT Metabolite M8 Unclear - Unclear Unclear [3]
MR009264 LAROPIPRANT Metabolite M3 LAROPIPRANT Metabolite M6 Unclear - Unclear Unclear [3]
MR009270 LAROPIPRANT Metabolite M4 LAROPIPRANT Metabolite M9 Unclear - Unclear Unclear [4]
⏷ 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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT01126073) A Double Blind, Randomized Study to Compare Influence of Niacin/Laropiprant on Functional and Morphological Characteristics of Arterial Wall and Parameters of Inflammation in Subjects With Coronary Heart Disease Already Treated With a Statin in Miran Sebestjen, University Medical Centre Ljubljana.
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800023729)
3 Metabolism of MK-0524, a prostaglandin D2 receptor 1 antagonist, in microsomes and hepatocytes from preclinical species and humans
4 Absorption, metabolism, and excretion of [(14)C]MK-0524, a prostaglandin D(2) receptor antagonist, in humans

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