RAMOSETRON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H17N3O
Molecular Weight	279.3364
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C=C(C(=O)[C@@H]2CCC3=C(C2)N=CN3)C4=C1C=CC=C4

InChI

InChIKey=NTHPAPBPFQJABD-LLVKDONJSA-N

InChI=1S/C17H17N3O/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)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H17N3O
Molecular Weight	279.3364
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB09290
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21146988 | https://www.ncbi.nlm.nih.gov/pubmed/12195819 | https://www.ncbi.nlm.nih.gov/pubmed/25949526

Ramosetron (INN) is a serotonin 5-HT3 receptor antagonist for the treatment of nausea, vomiting. And "diarrhea-predominant irritable bowel syndrome in males" (IBS-D). Ramosetron is licensed for use in India, Japan (Iribo) and selected Southeast Asian countries. In animal studies, ramosetron reduced defecation induced by corticotrophin-releasing hormone and had inhibitory effects on colonic nociception. In two randomized controlled studies including 957 patients with IBS-D, ramosetron increased monthly responder rates of patient-reported global assessment of IBS symptom relief compared with placebo. Ramosetron was also as effective as mebeverine in male patients with IBS-D. In a recent randomized controlled trial with 343 male patients with IBS-D, ramosetron has proved effective in improving stool consistency, relieving abdominal pain/discomfort, and improving health-related quality of life. Regarding safety, ramosetron is associated with a lower incidence of constipation compared with other 5-HT3 receptor antagonists and has not been associated with ischemic colitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3a (5-HT3a) receptor 46 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21146988	Antagonist 2778		0.06 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Chemotherapy induced nausea and vomiting 10 Sources: http://www.mims.com/india/drug/info/ramosetron?type=full&mtype=generic	Primary	Approved 8429	Iribo Approved Use Unknown
Postoperative nausea and vomiting 29 Sources: https://clinicaltrials.gov/ct2/show/NCT02849483	Primary	Phase IV 63	Iribo Approved Use Unknown
Irritable bowel syndrome 60 Sources: http://www.mims.com/india/drug/info/ramosetron?type=full&mtype=generic	Primary	Approved 8429	Iribo Approved Use Unknown

PubMed

Title	Date	PubMed
Ramosetron for preventing postoperative nausea and vomiting in women undergoing gynecological surgery.	2000 Feb	10648342
Evaluation of the pharmacological profile of ramosetron, a novel therapeutic agent for irritable bowel syndrome.	2007 Jul	17652911
Population pharmacokinetics of ramosetron.	2016 Feb	26558626

Patents

Sample Use Guides

In Vivo Use Guide

For treatment Nausea and vomiting associated with cancer chemotherapy in Adult: PO 100 mcg once daily. IV 300 mcg once daily. May administer an additional dose of 300 mcg if necessary. Max: 600 mcg/day. For treatment Irritable bowel syndrome in men PO 5 mcg once daily, may adjust dose according to symptoms. Max: 10 mcg/day.

Route of Administration: Other

In Vitro Use Guide

Mouse L cells and LV500 cells were washed three times with 1.0 mL of incubation buffer (composition (mm ): 141 NaCl, 4 KCl, 2.8 CaCl2, 1MgSO4, 10 d -glucose, 10 HEPES, pH 7.4).We used the same incubation buffer in the uptake study in all the cell lines. The uptake study was initiated by adding 250 L to multidishes of incubation buffer containing [14C]ramosetron (10 m ) or [3H]vinblastine (30 nm ) in the absence or presence of verapamil (10, 50 and 100 m ) or ciclosporin (20 m ). The cells were incubated at 37° C for a specified time. After incubation, the cells were washed three times with 1.0 mL of ice-cold incubation buffer to terminate the uptake. The cells were solubilized with 3 m NaOH and neutralized with 6 m HCl. [14C]ramosetron or [3H]vinblastine was measured by liquid scintillation counting after addition of scintillation fluid.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:27:14 UTC 2023` Edited by `admin` on `Fri Dec 15 16:27:14 UTC 2023`
Record UNII	7ZRO0SC54Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RAMOSETRON

Official Name

English

RAMOSETRON [MI]

Common Name

English

Ramosetron [WHO-DD]

Common Name

English

ramosetron [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267