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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17N3O.ClH
Molecular Weight 315.797
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAMOSETRON HYDROCHLORIDE

SMILES

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

InChI

InChIKey=XIXYTCLDXQRHJO-RFVHGSKJSA-N
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

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
0.06 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Iribo
Primary
Iribo
Primary
Iribo

PubMed

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.