Sarpogrelate HCl | MCI-9042 | LS-187,118 | CAS#135159-51-2 | 125926-17-2 | 5HT2A antagonist

MedKoo Cat#: 319608 | Name: Sarpogrelate HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sarpogrelate is a drug which acts as an antagonist at the 5HT2A and 5-HT2B receptors. It blocks serotonin-induced platelet aggregation, and has applications in the treatment of many diseases including diabetes mellitus, Buerger's disease, Raynaud's disease, coronary artery disease, angina pectoris, and atherosclerosis.

Chemical Structure

Sarpogrelate HCl

CAS#135159-51-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 319608

Name: Sarpogrelate HCl

CAS#: 135159-51-2 (HCl)

Chemical Formula: C24H32ClNO6

Exact Mass: 0.0000

Molecular Weight: 465.97

Elemental Analysis: C, 61.86; H, 6.92; Cl, 7.61; N, 3.01; O, 20.60

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 250.00
10mg	USD 450.00
25mg	USD 650.00

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Synonym

MCI-9042; MCI9042; MCI 9042; LS-187,118; LS187,118; LS 187,118; Sarpogrelate, Sarpogrelate HCl; Sarpogrelate hydrochloride. brand name: Anplag.

IUPAC/Chemical Name

4-((1-(dimethylamino)-3-(2-(3-methoxyphenethyl)phenoxy)propan-2-yl)oxy)-4-oxobutanoic acid hydrochloride

InChi Key

POQBIDFFYCYHOB-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H31NO6.ClH/c1-25(2)16-21(31-24(28)14-13-23(26)27)17-30-22-10-5-4-8-19(22)12-11-18-7-6-9-20(15-18)29-3;/h4-10,15,21H,11-14,16-17H2,1-3H3,(H,26,27);1H

SMILES Code

O=C(O)CCC(OC(COC1=CC=CC=C1CCC2=CC=CC(OC)=C2)CN(C)C)=O.[H]Cl

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sarpogrelate HCl is a selective 5-HT2R antagonist, with pKis of 8.52, 6.57, and 7.43 for 5-HT2A, 5-HT2B, and 5-HT2C receptors, respectively. Sarpogrelate HCl displays selectivity over 5-HT1, 5-HT3, 5-HT4, α1-, α2- and β-adrenoreceptor, histamine H1, H2 and muscarinic M3 receptors.

In vitro activity:

These results suggest a protective effect of sarpogrelate on red blood cells, which could have implications for various medical conditions. Sarpogrelate reduced shear stress-induced hemolysis in erythrocytes and potentially safeguarded erythrocytes from mechanical shear stress-induced damage. Sarpogrelate significantly lowered the normalized index of hemolysis compared to the control treatment group. Reference: J Artif Organs. 2010 Sep;13(3):178-81. https://pubmed.ncbi.nlm.nih.gov/20799047/

In vivo activity:

In a diabetic rat model, 14-day sarpogrelate treatment improved polydipsia and polyuria, reduced platelet hyperactivation, plasma 5-HT and the vascular sympathetic tone, and changed 5-HT receptors inhibiting noradrenergic drive. Sarpogrelate had beneficial effects on the diabetic rats. Reference: Biomed Pharmacother. 2022 Sep;153:113276. https://pubmed.ncbi.nlm.nih.gov/35717784/

	Solvent	mg/mL	mM
Solubility
	DMSO	93.0	199.58
	Ethanol	31.0	66.53
	Water	93.0	199.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 465.97 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.

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:

1. Nakamura K, Kawahito K. Erythrocyte-protective effect of sarpogrelate hydrochloride (Anplag ®), a selective 5-HT2 receptor antagonist: an in vitro study. J Artif Organs. 2010 Sep;13(3):178-81. doi: 10.1007/s10047-010-0515-y. Epub 2010 Aug 27. PMID: 20799047. 2. Rashid M, Manivet P, Nishio H, Pratuangdejkul J, Rajab M, Ishiguro M, Launay JM, Nagatomo T. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 2003 May 30;73(2):193-207. doi: 10.1016/s0024-3205(03)00227-3. PMID: 12738034. 3. Yum KS, Kang SG, Lee JW, Cho YI. Effects of sarpogrelate on blood viscosity. Microvasc Res. 2023 Jan;145:104439. doi: 10.1016/j.mvr.2022.104439. Epub 2022 Sep 17. PMID: 36126755. 4. Fernández-González JF, García-Pedraza JÁ, Marín-Quílez A, Bastida JM, Martín ML, Morán A, García-Domingo M. Effect of sarpogrelate treatment on 5-HT modulation of vascular sympathetic innervation and platelet activity in diabetic rats. Biomed Pharmacother. 2022 Sep;153:113276. doi: 10.1016/j.biopha.2022.113276. Epub 2022 Jun 16. PMID: 35717784.

In vitro protocol:

In vivo protocol:

1. Yum KS, Kang SG, Lee JW, Cho YI. Effects of sarpogrelate on blood viscosity. Microvasc Res. 2023 Jan;145:104439. doi: 10.1016/j.mvr.2022.104439. Epub 2022 Sep 17. PMID: 36126755. 2. Fernández-González JF, García-Pedraza JÁ, Marín-Quílez A, Bastida JM, Martín ML, Morán A, García-Domingo M. Effect of sarpogrelate treatment on 5-HT modulation of vascular sympathetic innervation and platelet activity in diabetic rats. Biomed Pharmacother. 2022 Sep;153:113276. doi: 10.1016/j.biopha.2022.113276. Epub 2022 Jun 16. PMID: 35717784.

1: Tullis BE, Ryals RC, Coyner AS, Gale MJ, Nicholson A, Ku C, Regis D, Sinha W, Datta S, Wen Y, Yang P, Pennesi ME. Sarpogrelate, a 5-HT2A Receptor Antagonist, Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2015 Jul;56(8):4560-9. doi: 10.1167/iovs.15-16378. PubMed PMID: 26200496; PubMed Central PMCID: PMC4515947. 2: Yang JS, Kim JR, Cho E, Huh W, Ko JW, Lee SY. A Novel Simultaneous Determination of Sarpogrelate and its Active Metabolite (M-1) in Human Plasma, Using Liquid Chromatography-Tandem Mass Spectrometry: Clinical Application. Ann Lab Med. 2015 Jul;35(4):391-8. doi: 10.3343/alm.2015.35.4.391. Epub 2015 May 21. PubMed PMID: 26131409; PubMed Central PMCID: PMC4446576. 3: Lee SY, Kim JR, Jung JA, Kim TE, Lee SY, Huh W, Lee JW, Jun H, Ko JW. Multiple-Dose Study to Evaluate Pharmacokinetics, Pharmacodynamics, and Safety in Healthy Subjects: A Comparison of Controlled-Release Sarpogrelate and Immediate-Release Sarpogrelate. Pharmacology. 2015;96(1-2):68-75. doi: 10.1159/000430889. Epub 2015 Jun 18. PubMed PMID: 26089136. 4: Chen YX, Wang WD, Song XJ, Gu YQ, Tian HY, Hu HJ, Zhao JC, Li XQ, Liu CW. Prospective Randomized Study of Sarpogrelate Versus Clopidogrel-based Dual Antiplatelet Therapies in Patients Undergoing Femoropopliteal Arterial Endovascular Interventions: Preliminary Results. Chin Med J (Engl). 2015 Jun 20;128(12):1563-6. doi: 10.4103/0366-6999.158285. PubMed PMID: 26063354. 5: Zhang E, Maruyama J, Yokochi A, Mitani Y, Sawada H, Nishikawa M, Ma N, Maruyama K. Sarpogrelate hydrochloride, a serotonin 5HT2A receptor antagonist, ameliorates the development of chronic hypoxic pulmonary hypertension in rats. J Anesth. 2015 Oct;29(5):715-23. doi: 10.1007/s00540-015-2015-y. Epub 2015 May 1. PubMed PMID: 25931318. 6: Park JB, Bae SK, Bae SH, Oh E. Simultaneous determination of sarpogrelate and its active metabolite in human plasma by liquid chromatography with tandem mass spectrometry and its application to a pharmacokinetic study. J Sep Sci. 2015 Jan;38(1):42-9. doi: 10.1002/jssc.201400884. Epub 2014 Nov 29. PubMed PMID: 25354353. 7: Cho DY, Bae SH, Lee JK, Park JB, Kim YW, Lee S, Oh E, Kim BT, Bae SK. Effect of the potent CYP2D6 inhibitor sarpogrelate on the pharmacokinetics and pharmacodynamics of metoprolol in healthy male Korean volunteers. Xenobiotica. 2015 Mar;45(3):256-63. doi: 10.3109/00498254.2014.967824. Epub 2014 Sep 30. PubMed PMID: 25268386. 8: Kusakari Y, Yamasaki K, Aiba S. Painful macules of hand cholesterol crystal embolization successfully treated with oral corticosteroid, statin, and sarpogrelate. J Dermatol. 2014 Jul;41(7):662-4. doi: 10.1111/1346-8138.12530. Epub 2014 Jun 14. PubMed PMID: 24931069. 9: Nagayama D, Ohira M, Saiki A, Shirai K, Tatsuno I. Sarpogrelate hydrochloride decreases cardio-ankle vascular index accompanied by increased serum lipoprotein lipase mass in type 2 diabetic patients. Int Heart J. 2014;55(4):337-41. Epub 2014 Jun 5. PubMed PMID: 24898600. 10: Kim HJ, Shin DH, Lim EA, Kim JS. Sustained-release formulation of sarpogrelate hydrochloride. Arch Pharm Res. 2015 Jan;38(1):35-41. doi: 10.1007/s12272-014-0415-4. Epub 2014 Jun 4. PubMed PMID: 24895147. 11: García-Pedraza JÁ, García M, Martín ML, San Román L, Morán A. The role of endothelium-derived hyperpolarizing factor and cyclooxygenase pathways in the inhibitory serotonergic response to the pressor effect elicited by sympathetic stimulation in chronic sarpogrelate treated rats. Eur J Pharmacol. 2014 May 15;731:80-7. doi: 10.1016/j.ejphar.2014.02.043. Epub 2014 Mar 24. PubMed PMID: 24675150. 12: Kim TE, Kim JR, Jung JA, Kim MJ, Lee SY, Ko JW, Jung WT, Choi YW, Lee HJ, Kim SH, Huh W. Pharmacokinetics of a new once-daily controlled-release sarpogrelate hydrochloride compared with immediate-release formulation and the effect of food. J Clin Pharm Ther. 2014 Apr;39(2):192-5. doi: 10.1111/jcpt.12117. Epub 2013 Dec 11. PubMed PMID: 24325365. 13: Cho DY, Bae SH, Lee JK, Kim YW, Kim BT, Bae SK. Selective inhibition of cytochrome P450 2D6 by Sarpogrelate and its active metabolite, M-1, in human liver microsomes. Drug Metab Dispos. 2014 Jan;42(1):33-9. doi: 10.1124/dmd.113.054296. Epub 2013 Oct 28. PubMed PMID: 24167220. 14: Hamasaki Y, Doi K, Maeda-Mamiya R, Ogasawara E, Katagiri D, Tanaka T, Yamamoto T, Sugaya T, Nangaku M, Noiri E. A 5-hydroxytryptamine receptor antagonist, sarpogrelate, reduces renal tubulointerstitial fibrosis by suppressing PAI-1. Am J Physiol Renal Physiol. 2013 Dec 15;305(12):F1796-803. doi: 10.1152/ajprenal.00151.2013. Epub 2013 Oct 9. PubMed PMID: 24107419. 15: Jung JA, Kim JR, Kim TE, Lee SY, Huh W, Lee JW, Jun H, Ko JW. Effect of food on the pharmacokinetic properties of the oral sarpogrelate hydrochloride controlled-release tablet in healthy male Korean subjects. Clin Ther. 2013 Jul;35(7):1038-44. doi: 10.1016/j.clinthera.2013.06.002. PubMed PMID: 23870611. 16: Shaikh Q, Kamal AK. Sarpogrelate- another new antiplatelet agent? J Pak Med Assoc. 2012 Nov;62(11):1253. PubMed PMID: 23866425; PubMed Central PMCID: PMC4185068. 17: Watada S, Harada H, Matsubara K, Obara H, Matsumoto K, Ando N, Kitagawa Y. Effect of sarpogrelate hydrochloride, a 5-hydroxytryptamine2 receptor antagonist, on allograft arteriosclerosis after aortic transplantation in rats. Transpl Immunol. 2013 Dec;29(1-4):162-6. doi: 10.1016/j.trim.2013.07.001. Epub 2013 Jul 10. PubMed PMID: 23851153. 18: García-Pedraza JÁ, García M, Martín ML, Gómez-Escudero J, Rodríguez-Barbero A, Román LS, Morán A. Peripheral 5-HT₁D and 5-HT₇ serotonergic receptors modulate sympathetic neurotransmission in chronic sarpogrelate treated rats. Eur J Pharmacol. 2013 Aug 15;714(1-3):65-73. doi: 10.1016/j.ejphar.2013.05.045. Epub 2013 Jun 11. PubMed PMID: 23769743. 19: Kawamura M, Ishiguro M, Nagamine T, Houkin K. Sarpogrelate dilates cerebral arteries in the absence of exogenous serotonin. Neurol Med Chir (Tokyo). 2013;53(5):291-8. PubMed PMID: 23708219. 20: Kim HJ, Jeong ES, Seo KA, Shin KJ, Choi YJ, Lee SJ, Ghim JL, Sohn DR, Shin JG, Kim DH. Glucuronidation of a sarpogrelate active metabolite is mediated by UDP-glucuronosyltransferases 1A4, 1A9, and 2B4. Drug Metab Dispos. 2013 Aug;41(8):1529-37. doi: 10.1124/dmd.113.051862. Epub 2013 May 23. PubMed PMID: 23704698.