Ramosetron HCl | YM-060 | 132907-72-3 | 5-HT3 Antagonist

MedKoo Cat#: 328335 | Name: Ramosetron hydrochloride

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Description:

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

Ramosetron hydrochloride, also known as Ramosetron and YM-060, is a serotonin 5-HT3 receptor antagonist used to treat diarrhea-predominant irritable bowel syndrome and nausea.

Chemical Structure

Ramosetron hydrochloride

CAS#132907-72-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 328335

Name: Ramosetron hydrochloride

CAS#: 132907-72-3 (HCl)

Chemical Formula: C17H18ClN3O

Exact Mass: 0.0000

Molecular Weight: 315.80

Elemental Analysis: C, 64.66; H, 5.75; Cl, 11.23; N, 13.31; O, 5.07

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00
25mg	USD 600.00
50mg	USD 900.00

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Related CAS #

132907-72-3 (HCl) 132036-88-5 (free base)

Synonym

Ramosetron hydrochloride; Ramosetron HCl, YM-060; YM 060; YM060

IUPAC/Chemical Name

(R)-(1-methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-5-yl)methanone hydrochloride

InChi Key

XIXYTCLDXQRHJO-RFVHGSKJSA-N

InChi Code

InChI=1S/C17H17N3O.ClH/c1-20-9-13(12-4-2-3-5-16(12)20)17(21)11-6-7-14-15(8-11)19-10-18-14;/h2-5,9-11H,6-8H2,1H3,(H,18,19);1H/t11-;/m1./s1

SMILES Code

O=C([C@H](CC1)CC2=C1NC=N2)C3=CN(C)C4=C3C=CC=C4.[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, DMF, and ethanol

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

Related CAS# 132036-88-5(Ramosetron) 132907-72-3(Ramosetron HCl)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ramosetron is a potent and selective antagonist of 5-HT3 (Ki = 0.06 nM). Ramosetron competitively blocks serotonin-mediated contraction of the colon. It has applications in ameliorating diarrhea-predominant inflammatory bowel syndrome and postoperative nausea and vomiting.

In vitro activity:

A range of partial agonist activities in HEK cells heterologously expressing the h5-HT(3)A receptor were measured for the indazole series. Excellent 5-HT(3) receptor selectivity, favorable in vitro metabolic stability and CYP inhibition properties, and good oral in vivo potency in the murine von Bezold-Jarisch reflex model is exemplified thereby indicating the series to have potential utility as improved IBS agents. Reference: Bioorg Med Chem Lett. 2011 Jan 1;21(1):58-61. https://pubmed.ncbi.nlm.nih.gov/21146988/

In vivo activity:

Therefore, this study indicates that ramosetron is an effective and well tolerated antiemetic that can be used to prevent postoperative nausea and vomiting following spinal surgery in adult patients. Reference: Curr Ther Res Clin Exp. 2022 Mar 25;96:100666. https://pubmed.ncbi.nlm.nih.gov/35464291/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	63.33
	DMF	10.0	31.67
	Ethanol	1.0	3.17

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 315.80 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. Manning DD, Cioffi CL, Usyatinsky A, Fitzpatrick K, Masih L, Guo C, Zhang Z, Choo SH, Sikkander MI, Ryan KN, Naginskaya J, Hassler C, Dobritsa S, Wierschke JD, Earley WG, Butler AS, Brady CA, Barnes NM, Cohen ML, Guzzo PR. Novel serotonin type 3 receptor partial agonists for the potential treatment of irritable bowel syndrome. Bioorg Med Chem Lett. 2011 Jan 1;21(1):58-61. doi: 10.1016/j.bmcl.2010.11.080. Epub 2010 Nov 21. PMID: 21146988. 3. Kiso T, Ito H, Miyata K. Effect of ramosetron on short-circuit current response in rat colonic mucosa. Eur J Pharmacol. 1997 Feb 12;320(2-3):187-92. doi: 10.1016/s0014-2999(96)00893-x. PMID: 9059853. 4. Lin Y, Tiansheng S, Zhicheng Z, Xiaobin C, Fang L. Effects of Ramosetron on Nausea and Vomiting Following Spinal Surgery: A Meta-Analysis. Curr Ther Res Clin Exp. 2022 Mar 25;96:100666. doi: 10.1016/j.curtheres.2022.100666. PMID: 35464291; PMCID: PMC9019236.

In vitro protocol:

In vivo protocol:

1. Kiso T, Ito H, Miyata K. Effect of ramosetron on short-circuit current response in rat colonic mucosa. Eur J Pharmacol. 1997 Feb 12;320(2-3):187-92. doi: 10.1016/s0014-2999(96)00893-x. PMID: 9059853. 2. Lin Y, Tiansheng S, Zhicheng Z, Xiaobin C, Fang L. Effects of Ramosetron on Nausea and Vomiting Following Spinal Surgery: A Meta-Analysis. Curr Ther Res Clin Exp. 2022 Mar 25;96:100666. doi: 10.1016/j.curtheres.2022.100666. PMID: 35464291; PMCID: PMC9019236.

1: Xia J, Chen P. Stability and Compatibility of Ramosetron with Midazolam in 0.9% Sodium Chloride Injection for Postoperative Nausea and Vomiting Administration. Drug Des Devel Ther. 2020 Mar 17;14:1169-1176. doi: 10.2147/DDDT.S244439. PMID: 32256048; PMCID: PMC7085948. 2: He G, Zeng F, Lei K, Xia S, Deng L, Zhang C, Liu D. Compatibility of dexamethasone sodium phosphate with 5-HT3 receptor antagonists in infusion solutions: a comprehensive study. Eur J Hosp Pharm. 2017 May;24(3):162-166. doi: 10.1136/ejhpharm-2016-000980. Epub 2016 Jul 14. PMID: 31156929; PMCID: PMC6451543. 3: Sanmukhani JJ, Pawar P, Mittal R. Ramosetron hydrochloride for the prevention of cancer chemotherapy induced nausea and vomiting: The Indian experience. South Asian J Cancer. 2014 Apr;3(2):132-7. doi: 10.4103/2278-330X.130466. PMID: 24818110; PMCID: PMC4014645. 4: Yamanouchi T, Horiuchi K, Ishii K, Mimura Y, Kato A, Adachi I. [Usefulness of one point measurement method of pediatric dose and UV spectrophotometry for filterability test of in-line filter]. Yakugaku Zasshi. 2014;134(5):671-7. Japanese. doi: 10.1248/yakushi.13-00250. PMID: 24790051. 5: Hirata T, Funatsu T, Keto Y, Akuzawa S, Akiho H, Nishida A, Sasamata M, Miyata K. [Pharmacological and clinical profile of ramosetron hydrochloride (Irribow), a novel therapeutic agent for irritable bowel syndrome with diarrhea]. Nihon Yakurigaku Zasshi. 2009 May;133(5):281-91. Japanese. doi: 10.1254/fpj.133.281. PMID: 19443966. 6: Matsueda K, Harasawa S, Hongo M, Hiwatashi N, Sasaki D. A phase II trial of the novel serotonin type 3 receptor antagonist ramosetron in Japanese male and female patients with diarrhea-predominant irritable bowel syndrome. Digestion. 2008;77(3-4):225-35. doi: 10.1159/000150632. Epub 2008 Jun 10. PMID: 18667823. 7: Matsueda K, Harasawa S, Hongo M, Hiwatashi N, Sasaki D. A randomized, double- blind, placebo-controlled clinical trial of the effectiveness of the novel serotonin type 3 receptor antagonist ramosetron in both male and female Japanese patients with diarrhea-predominant irritable bowel syndrome. Scand J Gastroenterol. 2008;43(10):1202-11. doi: 10.1080/00365520802240255. PMID: 18618371. 8: Voravud N, Sriuranpong V. Phase II trial of ramosetron plus dexamethasone in the prevention of cisplatin-induced nausea and vomiting. J Med Assoc Thai. 2005 Dec;88(12):1790-6. PMID: 16518975. 9: Xie XD, Zheng ZD, Liu DW, Liu YY, Shan XJ. [Effects of Nasea on prevention of gastrointestinal side effects caused by chemotherapeutic drugs]. Zhonghua Yi Xue Za Zhi. 2003 Jul 10;83(13):1180-2. Chinese. PMID: 12921641. 10: Yamamoto S, Tanaka Y, Ito T, Nakai S, Morimoto Y, Kitagawa T, Kurihara Y, Nishimura J. [Weekly administration of paclitaxel with a short course of premedication for advanced or recurrent gastric cancer]. Gan To Kagaku Ryoho. 2003 Jan;30(1):67-71. Japanese. PMID: 12557707. 11: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2002 Jan-Feb;24(1):37-55. PMID: 11980386. 12: Ogata A, Yamada Y, Sugiura M, Takayanagi R, Sawada Y, Iga T. [Analysis of 5-HT3 receptor antagonist, ramosetron hydrochloride, based on receptor occupancy considering its active metabolite]. Yakugaku Zasshi. 2001 Nov;121(11):793-8. Japanese. doi: 10.1248/yakushi.121.793. PMID: 11725547. 13: Zeng XY, Wang AH, Liu YF, Chen Y, Shen Y, Shen ZX. Ramosetron for the management of chemotherapy-induced gastrointestinal events in patients with hematological malignancies. Methods Find Exp Clin Pharmacol. 2001 May;23(4):191-5. doi: 10.1358/mf.2001.23.4.634643. PMID: 11676227. 14: Yahagi R, Machida Y, Onishi H. Mucoadhesive suppositories of ramosetron hydrochloride utilizing Carbopol. Int J Pharm. 2000 Jan 5;193(2):205-12. doi: 10.1016/s0378-5173(99)00338-5. PMID: 10606783. 15: Taguchi T, Tsukamoto F, Watanabe T, Yoneda K, Takamura Y, Hojo S, Shiba E, Noguchi S. [Usefulness of ramosetron hydrochloride on nausea and vomiting in CMF or CEF therapy for breast cancer]. Gan To Kagaku Ryoho. 1999 Jul;26(8):1163-70. Japanese. PMID: 10431583. 16: Tsukagoshi S. [A new antiemetic ramosetron hydrochloride]. Gan To Kagaku Ryoho. 1997 Feb;24(3):371-80. Japanese. PMID: 9051143.