Laropiprant
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MedKoo CAT#: 319908

CAS#: 571170-77-9

Description: Laropiprant, aslo known as MK-0524, was a drug used in combination with niacin to reduce blood cholesterol (LDL and VLDL) that is no longer sold, due to increases in side-effects with no cardiovascular benefit. Laropiprant itself has no cholesterol lowering effect, but it reduces facial flushes induced by niacin. Laropiprant acts as a selective DP1 antagonist, reducing the vasodilation.

Chemical Structure

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Laropiprant
CAS# 571170-77-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319908
Name: Laropiprant
CAS#: 571170-77-9
Chemical Formula: C21H19ClFNO4S
Exact Mass: 435.07
Molecular Weight: 435.890
Elemental Analysis: C, 57.87; H, 4.39; Cl, 8.13; F, 4.36; N, 3.21; O, 14.68; S, 7.35

Price and Availability

Size Price Availability Quantity
10mg USD 190 Ready to ship
25mg USD 350 Ready to ship
50mg USD 550 Ready to ship
100mg USD 950 Ready to ship
200mg USD 1550 Ready to ship
500mg USD 2950 Ready to ship
1g USD 4250 Ready to ship
2g USD 6850 Ready to ship
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Synonym: MK-0524; MK0524; MK 0524; Laropiprant. Trade name: Cordaptive, Tredaptive.

IUPAC/Chemical Name: ((3R)-4-(4-Chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic acid

InChi Key: NXFFJDQHYLNEJK-CYBMUJFWSA-N

InChi Code: 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

SMILES Code: O=C(O)C[C@H]1CCC2=C1N(CC3=CC=C(Cl)C=C3)C4=C2C=C(F)C=C4S(=O)(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: MK 0524 is a potent, selective DP1 receptor antagonist
In vitro activity: Following 7 days of multiple-dose administration, coadministration of laropiprant with ER niacin did not increase urinary 11-dTxB(2) levels compared to ER niacin alone in healthy, hypercholesterolemic, or diabetic subjects. In hypercholesterolemic and diabetic subjects, laropiprant did not increase urinary 11-dTxB(2) levels compared to placebo. These results demonstrate that laropiprant does not enhance in vivo platelet reactivity, either alone or in combination with niacin. Lauring B, Dishy V, Luo WL, Laterza O, Patterson J, Cote J, Chao A, Larson P, Gutierrez M, Wagner JA, Lai E. Laropiprant in combination with extended-release niacin does not alter urine 11-dehydrothromboxane B2, a marker of in vivo platelet function, in healthy, hypercholesterolemic, and diabetic subjects. J Clin Pharmacol. 2009 Dec;49(12):1426-35. doi: 10.1177/0091270009339593. Epub 2009 Oct 15. PMID: 19833861.
In vivo activity: The putative effect of laropiprant on limiting hematoma expansion was tested by an in vivo tail bleeding cessation method and an ex vivo coagulation method. Finally, the roles of laropiprant on gliosis and iron accumulation were also investigated. A significant decrease in the injury volume was observed in DP1-/- as well as laropiprant-treated WT mice. The tail bleeding time was significantly lower in laropiprant group as compared with the vehicle group. Significantly lower Iba-1 and Perls' iron staining in DP1-/- and laropiprant-treated WT groups were observed. Altogether, the data suggest that laropiprant treatment post-ICH attenuates brain damage by targeting primary as well as secondary injuries. Reference: Ahmad AS, Mendes M, Hernandez D, Doré S. Efficacy of Laropiprant in Minimizing Brain Injury Following Experimental Intracerebral Hemorrhage. Sci Rep. 2017 Aug 25;7(1):9489. doi: 10.1038/s41598-017-09994-5. PMID: 28842638; PMCID: PMC5573370.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 45.88
DMF 20.0 45.88
DMSO:PBS (pH 7.2) (1:1) 0.5 1.45
Ethanol 5.0 11.47

Preparing Stock Solutions

The following data is based on the product molecular weight 435.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: Lauring B, Dishy V, Luo WL, Laterza O, Patterson J, Cote J, Chao A, Larson P, Gutierrez M, Wagner JA, Lai E. Laropiprant in combination with extended-release niacin does not alter urine 11-dehydrothromboxane B2, a marker of in vivo platelet function, in healthy, hypercholesterolemic, and diabetic subjects. J Clin Pharmacol. 2009 Dec;49(12):1426-35. doi: 10.1177/0091270009339593. Epub 2009 Oct 15. PMID: 19833861.
In vitro protocol: Lauring B, Dishy V, Luo WL, Laterza O, Patterson J, Cote J, Chao A, Larson P, Gutierrez M, Wagner JA, Lai E. Laropiprant in combination with extended-release niacin does not alter urine 11-dehydrothromboxane B2, a marker of in vivo platelet function, in healthy, hypercholesterolemic, and diabetic subjects. J Clin Pharmacol. 2009 Dec;49(12):1426-35. doi: 10.1177/0091270009339593. Epub 2009 Oct 15. PMID: 19833861.
In vivo protocol: Ahmad AS, Mendes M, Hernandez D, Doré S. Efficacy of Laropiprant in Minimizing Brain Injury Following Experimental Intracerebral Hemorrhage. Sci Rep. 2017 Aug 25;7(1):9489. doi: 10.1038/s41598-017-09994-5. PMID: 28842638; PMCID: PMC5573370.

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1: El Khoury P, Waldmann E, Huby T, Gall J, Couvert P, Lacorte JM, Chapman J, Frisdal E, Lesnik P, Parhofer KG, Le Goff W, Guerin M. Extended-Release Niacin/Laropiprant Improves Overall Efficacy of Postprandial Reverse Cholesterol Transport. Arterioscler Thromb Vasc Biol. 2016 Feb;36(2):285-94. doi: 10.1161/ATVBAHA.115.306834. Epub 2015 Dec 17. PubMed PMID: 26681758.

2: Cioni G, Mannini L, Liotta AA, D'Alessandri G, Fatini C, Bandinelli B, Costanzo M, Abbate R, Marcucci R. Detrimental effects of niacin/laropiprant on microvascular reactivity and red cell deformability in patients with elevated lipoprotein(a) levels. J Thromb Thrombolysis. 2015 Aug 20. [Epub ahead of print] PubMed PMID: 26289089.

3: Hu M, Yang YL, Chan P, Tomlinson B. Pharmacogenetics of cutaneous flushing response to niacin/laropiprant combination in Hong Kong Chinese patients with dyslipidemia. Pharmacogenomics. 2015;16(12):1387-97. doi: 10.2217/pgs.15.79. Epub 2015 Jul 31. PubMed PMID: 26226939.

4: McKenney J, Bays H, Gleim G, Mitchel Y, Kuznetsova O, Sapre A, Sirah W, Maccubbin D. Safety and tolerability of extended-release niacin-laropiprant: Pooled analyses for 11,310 patients in 12 controlled clinical trials. J Clin Lipidol. 2015 May-Jun;9(3):313-25. doi: 10.1016/j.jacl.2015.02.006. Epub 2015 Mar 2. PubMed PMID: 26073389.

5: Hu M, Yang YL, Masuda D, Yamashita S, Tomlinson B. Effect of Extended-Release Niacin/Laropiprant Combination on Plasma Adiponectin and Insulin Resistance in Chinese Patients with Dyslipidaemia. Dis Markers. 2015;2015:154014. doi: 10.1155/2015/154014. Epub 2015 Apr 29. PubMed PMID: 26063948; PubMed Central PMCID: PMC4429190.

6: Bays HE, Brinton EA, Triscari J, Chen E, Maccubbin D, MacLean AA, Gibson KL, Ruck RA, Johnson-Levonas AO, O'Neill EA, Mitchel YB. Extended-release niacin/laropiprant significantly improves lipid levels in type 2 diabetes mellitus irrespective of baseline glycemic control. Vasc Health Risk Manag. 2015 Feb 24;11:165-72. doi: 10.2147/VHRM.S70907. eCollection 2015. PubMed PMID: 25750540; PubMed Central PMCID: PMC4348131.

7: Bloomfield HE. ACP Journal Club: adding niacin plus laropiprant to statins did not reduce vascular events and increased serious adverse events. Ann Intern Med. 2014 Nov 18;161(10):JC8. doi: 10.7326/0003-4819-161-10-201411180-02008. PubMed PMID: 25402541.

8: Krishna R, Guo Y, Schulz V, Cord-Cruz E, Smith S, Hair S, Nahm WK, Draelos ZD. Non-obligatory role of prostaglandin D2 receptor subtype 1 in rosacea: laropiprant in comparison to a placebo did not alleviate the symptoms of erythematoelangiectaic rosacea. J Clin Pharmacol. 2015 Feb;55(2):137-43. doi: 10.1002/jcph.383. Epub 2014 Sep 4. PubMed PMID: 25142778.

9: Kei A, Elisaf M. Nicotinic acid/laropiprant reduces platelet count but increases mean platelet volume in patients with primary dyslipidemia. Arch Med Sci. 2014 Jun 29;10(3):439-44. doi: 10.5114/aoms.2014.43738. Epub 2014 Jun 27. PubMed PMID: 25097572; PubMed Central PMCID: PMC4107250.

10: Huynh K. Dyslipidaemia: Niacin-laropiprant fails to reduce the risk of vascular events. Nat Rev Cardiol. 2014 Oct;11(10):558. doi: 10.1038/nrcardio.2014.116. Epub 2014 Aug 5. PubMed PMID: 25093436.

11: HPS2-THRIVE Collaborative Group, Landray MJ, Haynes R, Hopewell JC, Parish S, Aung T, Tomson J, Wallendszus K, Craig M, Jiang L, Collins R, Armitage J. Effects of extended-release niacin with laropiprant in high-risk patients. N Engl J Med. 2014 Jul 17;371(3):203-12. doi: 10.1056/NEJMoa1300955. PubMed PMID: 25014686.

12: Farnier M, Chen E, Johnson-Levonas AO, McCrary Sisk C, Mitchel YB. Effects of extended-release niacin/laropiprant, simvastatin, and the combination on correlations between apolipoprotein B, LDL cholesterol, and non-HDL cholesterol in patients with dyslipidemia. Vasc Health Risk Manag. 2014 May 7;10:279-90. doi: 10.2147/VHRM.S58694. eCollection 2014. PubMed PMID: 24855368; PubMed Central PMCID: PMC4019613.

13: Lauring B, Dishy V, De Kam PJ, Crumley T, Wenning L, Liu F, Sisk C, Wagner J, Lai E. Effects of Extended-Release Niacin and Extended-Release Niacin/Laropiprant on the Pharmacokinetics of Simvastatin in Healthy Subjects. Am J Ther. 2015 Sep-Oct;22(5):367-76. doi: 10.1097/MJT.0000000000000051. PubMed PMID: 24832384.

14: Nasser Figueiredo V, Vendrame F, Colontoni BA, Quinaglia T, Roberto Matos-Souza J, Azevedo Moura F, Coelho OR, de Faria EC, Sposito AC. Short-term effects of extended-release niacin with and without the addition of laropiprant on endothelial function in individuals with low HDL-C: a randomized, controlled crossover trial. Clin Ther. 2014 Jun 1;36(6):961-6. doi: 10.1016/j.clinthera.2014.03.012. Epub 2014 Apr 24. PubMed PMID: 24768191.

15: Mayor S. Nicotinic acid plus laropiprant suspended for dyslipidaemia. Lancet Diabetes Endocrinol. 2013 Aug;1 Suppl 1:s6. doi: 10.1016/S2213-8587(13)70129-3. Epub 2013 Sep 18. PubMed PMID: 24622598.

16: Kei A, Tellis C, Liberopoulos E, Tselepis A, Elisaf M. Effect of switch to the highest dose of rosuvastatin versus add-on-statin fenofibrate versus add-on-statin nicotinic acid/laropiprant on oxidative stress markers in patients with mixed dyslipidemia. Cardiovasc Ther. 2014 Aug;32(4):139-46. doi: 10.1111/1755-5922.12072. PubMed PMID: 24618208.

17: Aye MM, Kilpatrick ES, Afolabi P, Wootton SA, Rigby AS, Coady AM, Sandeman DD, Atkin SL. Postprandial effects of long-term niacin/laropiprant use on glucose and lipid metabolism and on cardiovascular risk in patients with polycystic ovary syndrome. Diabetes Obes Metab. 2014 Jun;16(6):545-52. doi: 10.1111/dom.12255. Epub 2014 Feb 9. PubMed PMID: 24401089.

18: Cenarro A, Puzo J, Ferrando J, Mateo-Gallego R, Bea AM, Calmarza P, Jarauta E, Civeira F. Effect of Nicotinic acid/Laropiprant in the lipoprotein(a) concentration with regard to baseline lipoprotein(a) concentration and LPA genotype. Metabolism. 2014 Mar;63(3):365-71. doi: 10.1016/j.metabol.2013.10.014. Epub 2013 Nov 6. PubMed PMID: 24333007.

19: De Kam PJ, Luo WL, Wenning L, Ratcliffe L, Sisk CM, Royalty J, Radziszewski W, Wagner JA, Lai E. The effects of laropiprant on the antiplatelet activity of co-administered clopidogrel and aspirin. Platelets. 2014;25(7):480-7. doi: 10.3109/09537104.2013.836747. Epub 2013 Nov 8. PubMed PMID: 24206527.

20: Yang YL, Hu M, Chang M, Tomlinson B. A high incidence of exanthematous eruption associated with niacin/laropiprant combination in Hong Kong Chinese patients. J Clin Pharm Ther. 2013 Dec;38(6):528-32. doi: 10.1111/jcpt.12096. Epub 2013 Sep 10. PubMed PMID: 24020480.