| Identification | Back Directory | [Name]
MK 0524 | [CAS]
571170-77-9 | [Synonyms]
CS-623
MK 0524
Cardaptive
Laropiprant
Laropiprant, >=99%
Laropiprant(MK0524)
MK-0524(Laropiprant)/
MK0524;LAROPIPRANT;MK-0524
[(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(Methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
(R)-2-(4-(4-chlorobenzyl)-7-fluoro-5-(Methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
(3R)-4-[(4-Chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)cyclopent[b]indole-3-acetic acid
Cyclopent[b]indole-3-acetic acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)-
Cyclopent[b]indole-3-acetic acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)-Laropiprant
(3R)-4-[(4-Chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)cyclopent[b]indole-3-acetic acid Laropiprant MK 0524 | [EINECS(EC#)]
682-424-1 | [Molecular Formula]
C21H19ClFNO4S | [MDL Number]
MFCD11042421 | [MOL File]
571170-77-9.mol | [Molecular Weight]
435.9 |
| Chemical Properties | Back Directory | [Melting point ]
175∶C | [Boiling point ]
710.0±60.0 °C(Predicted) | [density ]
1.48 | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
DMSO:20.0(Max Conc. mg/mL);45.88(Max Conc. mM)
DMF:20.0(Max Conc. mg/mL);45.88(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.45(Max Conc. mM)
Ethanol:5.0(Max Conc. mg/mL);11.47(Max Conc. mM) | [form ]
Powder | [pka]
4.54±0.10(Predicted) | [color ]
White to off-white | [InChIKey]
NXFFJDQHYLNEJK-CYBMUJFWSA-N | [SMILES]
OC(C[C@@H](CC1)C2=C1C3=CC(F)=CC(S(C)(=O)=O)=C3N2CC4=CC=C(C=C4)Cl)=O |
| Hazard Information | Back Directory | [Uses]
Laropiprant is a potent and selective DP receptor antagonist with Ki values of 0.57 nM and 2.95 nM for DP receptor and TP Receptor, respectively[1][2][3]. | [Definition]
ChEBI: Laropiprant is an indolyl carboxylic acid. | [Biological Activity]
MK-0524 is a potent and selective prostaglandin D2 (PGD2) receptor PTGDR (DP1) antagonist with inverse agonist activity (Ki = 570 pM/DP12.95 nM/TP745 nM/DP2>890 nM for EP1/2/3/4FP and IP). MK-0524 inhibits cAMP accumulation in PGD2-challenged human platelets (IC50 = 90 pM) and blocks PGD2-induced nasal congestion in a sheep allergic rhinitis model in vivo (by 99% at 0.1 mg/kg i.v.). MK-0524 decreases DP1-dependent basal cAMP level in HEK293 (1-100 nM) without affecting DP1-dependent basal ERK1/2 phosphorylation (up to 1 μM). | [in vivo]
Laropiprant (0-100 mg/kg; p.o. and i.v.; male Sprague-Dawley rats) exhibits good pharmacokinetic profiles[3].
Pharmacokinetic Analysis in Male Sprague-Dawley rats[3]
| Route | Dose (mg/kg) | AUC0-∞ (μM·hr) | Clp (mL/min/kg) | Vdss (L/kg) | T1/2 (hr) | | PO | 1 | 22.7 | 1.9 | 0.7 | 7.4 | | PO | 5 | 96.0 | 2.1 | 0.9 | 7.6 | | Route | Dose (mg/kg) | AUC0-∞ (μM·hr) | Cmax (μM) | Tmax (hr) | F(%) | | IV | 5 | 52.6 | 15.6 | 1.2 | / |
| [IC 50]
DP: 0.57 nM (Ki); TP Receptor: 2.95 nM (Ki) | [storage]
Store at -20°C | [References]
[1] Labrecque P, et, al. Inverse agonist and pharmacochaperone properties of MK-0524 on the prostanoid DP1 receptor. PLoS One. 2013 Jun 10;8(6):e65767.
[2] Sturino CF, et, al. Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524). J Med Chem. 2007 Feb 22;50(4):794-806. DOI:10.1021/jm0603668
[3] Chang SW, et, al. The pharmacokinetics and disposition of MK-0524, a Prosglandin D2 Receptor 1 antagonist, in rats, dogs and monkeys. Xenobiotica. 2007 May;37(5):514-33. DOI:10.1080/00498250601175565 |
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