Details of the Drug

General Information of Drug (ID: DM5FABJ)

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
Disease Entry ICD 11 Status REF
Coronary heart disease BA80.Z Phase 4 [1]
Arteriosclerosis BD40 Discontinued in Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 435.9
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.21 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 11.8 hours [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1 L/kg [3]
Chemical Identifiers
Formula
C21H19ClFNO4S
IUPAC Name
2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
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
Cross-matching ID
PubChem CID
9867642
ChEBI ID
CHEBI:135942
CAS Number
571170-77-9
DrugBank ID
DB11629
TTD ID
D0WL5V
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
HMG-CoA reductase (HMGCR) TTPADOQ HMDH_HUMAN Inhibitor [4]
Prostacyclin receptor (PTGIR) TTOFYT1 PI2R_HUMAN Inhibitor [5]
Prostaglandin D2 receptor (PTGDR) TTNVEIR PD2R_HUMAN Inhibitor [5]
Prostaglandin D2 receptor 2 (PTGDR2) TTQDMX5 PD2R2_HUMAN Inhibitor [5]
Prostaglandin E2 receptor EP2 (PTGER2) TT1ZAVI PE2R2_HUMAN Inhibitor [5]
Prostaglandin F2-alpha receptor (PTGFR) TTT2ZAR PF2R_HUMAN Inhibitor [5]
Thromboxane A2 receptor (TBXA2R) TT2O84V TA2R_HUMAN Inhibitor [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Regulation of Drug Effects [6]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Regulation of Drug Effects [6]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Biotransformations [6]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Biotransformations [6]
UDP-glucuronosyltransferase 1A9 OTPCHAFX UD19_HUMAN Biotransformations [6]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Biotransformations [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Coronary heart disease
ICD Disease Classification BA80.Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin F2-alpha receptor (PTGFR) DTT PTGFR 8.25E-02 -0.05 -0.14
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 A novel c-Met inhibitor, MK8033, synergizes with carboplatin plus paclitaxel to inhibit ovarian cancer cell growth. Oncol Rep. 2013 May;29(5):2011-8.
5 Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydroc... J Med Chem. 2007 Feb 22;50(4):794-806.
6 Metabolism of MK-0524, a prostaglandin D2 receptor 1 antagonist, in microsomes and hepatocytes from preclinical species and humans. Drug Metab Dispos. 2007 Feb;35(2):283-92. doi: 10.1124/dmd.106.011551. Epub 2006 Nov 28.