Sarpogrelate-d3 HCl | CAS#unknown | Sarpogrelate quantification internal standard

MedKoo Cat#: 464180 | Name: Sarpogrelate-d3 HCl

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Description:

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

Sarpogrelate-d3 is intended for use as an internal standard for the quantification of sarpogrelate (hydrochloride) by GC- or LC-MS. Sarpogrelate is a selective antagonist of the serotonin (5-HT) receptor subtypes 5-HT2A, 5-HT2B, and 5-HT2C. It is selective for 5-HT2 (Ki = 70.8 nM) over 5-HT1 (Ki = >26,000 nM), α1-, α2-, and β-adrenergic (Kis = 640-123,800 nM), and muscarinic receptors (Ki = >40,000 nM). In vitro, it inhibits aggregation of rat whole blood induced by collagen, 5-HT with collagen, and 5-HT with ADP. In vivo, it inhibits leukocyte-endothelial interactions in the femoral artery induced by a high-fat high-fructose diet (HFFD) in mice when administered at a dose of 5 mg/kg per day. Sarpogrelate (5 mg/kg per day) decreases ventricular hypertrophy and infarct size in a rat model of myocardial infarction.

Chemical Structure

Sarpogrelate-d3 HCl

CAS#To be determined

Theoretical Analysis

MedKoo Cat#: 464180

Name: Sarpogrelate-d3 HCl

CAS#: To be determined

Chemical Formula: C24H29D3ClNO6

Exact Mass: 0.0000

Molecular Weight: 468.99

Elemental Analysis: C, 61.46; H, 7.52; Cl, 7.56; N, 2.99; O, 20.47

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Sarpogrelate-d3 HCl; Sarpogrelate d3 HCl; Sarpogrelate-d3 hydrochloride; Sarpogrelate d3 hydrochloride;

IUPAC/Chemical Name

4-((1-(dimethylamino)-3-(2-(3-(methoxy-d3)phenethyl-d3)phenoxy)propan-2-yl)oxy)-4-oxobutanoic acid hydrochloride

InChi Key

POQBIDFFYCYHOB-FJCVKDQNSA-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/i3D3;

SMILES Code

CN(CC(COC1=CC=CC=C1CCC2=CC(OC([2H])([2H])[2H])=CC=C2)OC(CCC(O)=O)=O)C.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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

to be determined

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

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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
	To be determined	0.0	100.00

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 468.99 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: Kim SK, Kim G, Choi BH, Ryu D, Ku SK, Kwak MK. Negative correlation of urinary miR-199a-3p level with ameliorating effects of sarpogrelate and cilostazol in hypertensive diabetic nephropathy. Biochem Pharmacol. 2021 Feb;184:114391. doi: 10.1016/j.bcp.2020.114391. Epub 2020 Dec 23. PMID: 33359069. 2: Ma B, Fan X, Liu P. Therapeutic Effects of Medication Use on Intermittent Claudication: A Network Meta-analysis. J Cardiovasc Pharmacol. 2021 Feb 1;77(2):253-262. doi: 10.1097/FJC.0000000000000956. PMID: 33235027. 3: Liu H, Xu S, Li G, Lou D, Fu X, Lu Q, Hao L, Zhang J, Mei J, Sui Z, Lou Y. Sarpogrelate and rosuvastatin synergistically ameliorate aortic damage induced by hyperlipidemia in apolipoprotein E-deficient mice. Exp Ther Med. 2020 Dec;20(6):170. doi: 10.3892/etm.2020.9300. Epub 2020 Oct 9. PMID: 33093907; PMCID: PMC7571328. 4: Xu J, Pei Z, Yu M, Li X, Wang L, Lin Y, Chen X, Liu X. Combinational Use of Antiplatelet Medication Sarpogrelate with Therapeutic Drug Rosuvastatin in Treating High-Cholesterol Diet-Induced Chronic Kidney Disease in ApoE-Deficient Mice. Biomed Res Int. 2020 Sep 26;2020:1809326. doi: 10.1155/2020/1809326. PMID: 33029491; PMCID: PMC7537702. 5: Tanaka-Totoribe N, Hidaka M, Gamoh S, Yokota A, Nakamura E, Kuwabara M, Tsunezumi J, Yamamoto R. Effects of M-1, a Major Metabolite of Sarpogrelate, on 5-HT-Induced Constriction of Isolated Human Internal Thoracic Artery. Biol Pharm Bull. 2020 Dec 1;43(12):1979-1982. doi: 10.1248/bpb.b20-00591. Epub 2020 Sep 30. PMID: 32999137. 6: Watanabe K, Nagata N, Yanagisawa N, Shimbo T, Okubo H, Imbe K, Yokoi C, Yanase M, Kimura A, Akiyama J, Uemura N. Effect of antiplatelet agent number, types, and pre-endoscopic management on post-polypectomy bleeding: validation of endoscopy guidelines. Surg Endosc. 2021 Jan;35(1):317-325. doi: 10.1007/s00464-020-07402-0. Epub 2020 Feb 6. PMID: 32030553. 7: Wang H, Gao XY, Rao F, Yang H, Wang ZY, Liu L, Kuang SJ, Wu Q, Deng CY, Xu JS. Mechanism of contractile dysfunction induced by serotonin in coronary artery in spontaneously hypertensive rats. Naunyn Schmiedebergs Arch Pharmacol. 2020 Nov;393(11):2165-2176. doi: 10.1007/s00210-020-01813-5. Epub 2020 Jan 24. PMID: 31980857. 8: Hernández-Abreu OI, García-Pedraza JÁ, Rivera-Mancilla E, Villanueva-Castillo B, Morán A, García-Domingo M, Manrique-Maldonado G, Altamirano-Espinoza AH, Villalón CM. Blockade of 5-HT2 receptors with sarpogrelate uncovers 5-HT7 receptors inhibiting the tachycardic sympathetic drive in pithed rats. Clin Exp Pharmacol Physiol. 2020 Mar;47(3):403-411. doi: 10.1111/1440-1681.13227. Epub 2019 Dec 25. PMID: 31846086. 9: Lu Y, Li J, Xie J, Yu Q, Liao L. Effects of sarpogrelate hydrochloride on peripheral arterial disease: A meta-analysis of randomized controlled trials. Medicine (Baltimore). 2019 Nov;98(46):e17266. doi: 10.1097/MD.0000000000017266. PMID: 31725602; PMCID: PMC6867789. 10: Lee HR, Park KY, Jeong YJ, Heo TH. Comparative effectiveness of different antiplatelet agents at reducing TNF-driven inflammatory responses in a mouse model. Clin Exp Pharmacol Physiol. 2020 Mar;47(3):432-438. doi: 10.1111/1440-1681.13211. Epub 2019 Dec 6. PMID: 31713877. 11: Ki YJ, Kwon SA, Kim HL, Seo JB, Chung WY. The Prevention of Contrast Induced Nephropathy by Sarpogrelate: a Prospective Randomized Controlled Clinical Trial. J Korean Med Sci. 2019 Oct 21;34(40):e261. doi: 10.3346/jkms.2019.34.e261. PMID: 31625293; PMCID: PMC6801223. 12: Kim SR, Choi KH, Song YB, Lee JM, Park TK, Yang JH, Hahn JY, Choi JH, Choi SH, Gwon HC. Effect of sarpogrelate and high-dose statin on the reduction of coronary spasm in vasospastic angina: A two by two factorial, pilot randomized study. Clin Cardiol. 2019 Oct;42(10):899-907. doi: 10.1002/clc.23239. Epub 2019 Jul 24. PMID: 31339594; PMCID: PMC6788571. 13: Jeong MJ, Kwon H, Ko GY, Gwon DI, Kim MJ, Han Y, Kwon TW, Cho YP. New predictors of aneurysm sac behavior after endovascular aortic aneurysm repair. Eur Radiol. 2019 Dec;29(12):6591-6599. doi: 10.1007/s00330-019-06306-5. Epub 2019 Jun 27. PMID: 31250171. 14: Wang R, Zhu Z, Qiu X, Bai L, Guo W, Zuo L, Zhao T, Shan G. Determination of epoxide impurity in sarpogrelate hydrochloride intermediate by UHPLC and column- switching liquid chromatography. J Pharm Biomed Anal. 2019 Sep 10;174:57-62. doi: 10.1016/j.jpba.2019.05.053. Epub 2019 May 24. PMID: 31154094. 15: Yoo H, Park I, Kim DJ, Lee S. Effects of sarpogrelate on microvascular complications with type 2 diabetes. Int J Clin Pharm. 2019 Apr;41(2):563-573. doi: 10.1007/s11096-019-00794-7. Epub 2019 Mar 12. PMID: 30864083. 16: Moghaddam RA, Jazaeri F, Abdollahi A, Mohammadjafari R, Dehpour AR, Bakhtiarian A. Evaluation of Isolated Vascular Response to 5HT1A, 5HT1B1D & 5HT2A Receptors Agonist & Antagonist in Chronic Endotoxemic Rats. Drug Res (Stuttg). 2019 Jun;69(6):352-360. doi: 10.1055/a-0800-8391. Epub 2018 Dec 10. PMID: 30536257. 17: Han J, Tian H, Liu Y, Fan F. Sarpogrelate attenuates pulmonary arterial hypertension via calcium/calcineurin axis. Front Biosci (Landmark Ed). 2019 Jan 1;24:607-615. PMID: 30468677. 18: Choi W, Namkung J, Hwang I, Kim H, Lim A, Park HJ, Lee HW, Han KH, Park S, Jeong JS, Bang G, Kim YH, Yadav VK, Karsenty G, Ju YS, Choi C, Suh JM, Park JY, Park S, Kim H. Serotonin signals through a gut-liver axis to regulate hepatic steatosis. Nat Commun. 2018 Nov 16;9(1):4824. doi: 10.1038/s41467-018-07287-7. Erratum in: Nat Commun. 2019 Jan 8;10(1):158. PMID: 30446669; PMCID: PMC6240035. 19: Park KY, Heo TH. Combination therapy with cilostazol and pravastatin improves antiatherogenic effects in low-density lipoprotein receptor knockout mice. Cardiovasc Ther. 2018 Dec;36(6):e12476. doi: 10.1111/1755-5922.12476. Epub 2018 Nov 29. PMID: 30378752. 20: Ding YH, Liu B, Lou JF, Sun JX, Wu M, Zhu XX, Chen GL, Zhang H, Li XJ, Chen H, Liu CJ, Shen ZW, Li CY. Bioequivalence of Sarpogrelate in Healthy Chinese Subjects Under Fasting and Fed Conditions: A 4-Way Replicate Crossover Investigation by a Reference-Scaled Average Bioequivalence Approach. Clin Pharmacol Drug Dev. 2019 Aug;8(6):713-720. doi: 10.1002/cpdd.624. Epub 2018 Oct 16. PMID: 30325583.