Identification
- Summary
Ramosetron is a selective 5-HT3 antagonist used as an antiemetic for chemotherapy- and postoperative-associated nausea and vomiting. It may also possess efficacy in irritable bowel syndrome.
- Generic Name
- Ramosetron
- DrugBank Accession Number
- DB09290
- Background
Ramosetron is a serotonin 5-HT3 receptor antagonist commonly employed to treat nausea and vomiting, in addition to certain diarrheal conditions. It is believed to have higher potency and longer antiemetic action than other 1st generation 5-HT3 antagonists such as ondansetron. Currently, ramosetron is only approved for use Japan and in certain Southeast Asian countries.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Ramosetron (DB09290)
- Weight
- Average: 279.343
Monoisotopic: 279.137162179 - Chemical Formula
- C17H17N3O
- Synonyms
- Ramosetron
- External IDs
- Nor-YM 060
- YM 060
Pharmacology
- Indication
For the treatment of nausea and vomiting and diarrhea-predominant irritable bowel syndrome in males.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Gastrointestinal symptoms caused by cancer treatment •••••••••••• •••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U5-hydroxytryptamine receptor 3A antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Ramosetron is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Ramosetron can be increased when it is combined with Abametapir. Abatacept The metabolism of Ramosetron can be increased when combined with Abatacept. Abiraterone The serum concentration of Ramosetron can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Ramosetron can be decreased when combined with Acenocoumarol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ramosetron hydrochloride 9551LHD87E 132907-72-3 XIXYTCLDXQRHJO-RFVHGSKJSA-N - International/Other Brands
- IBset / Iribo / Nasea / Nozia
Categories
- Drug Categories
- Antidepressive Agents
- Antiemetics
- Autonomic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Substrates
- Gastrointestinal Agents
- Heterocyclic Compounds, Fused-Ring
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Serotonin Agents
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- N-alkylindoles
- Direct Parent
- N-alkylindoles
- Alternative Parents
- Indoles / Aryl alkyl ketones / N-methylpyrroles / Benzenoids / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Indole show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7ZRO0SC54Y
- CAS number
- 132036-88-5
- InChI Key
- NTHPAPBPFQJABD-LLVKDONJSA-N
- InChI
- 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
- IUPAC Name
- (5R)-5-(1-methyl-1H-indole-3-carbonyl)-4,5,6,7-tetrahydro-1H-1,3-benzodiazole
- SMILES
- CN1C=C(C(=O)[C@@H]2CCC3=C(C2)N=CN3)C2=C1C=CC=C2
References
- General References
- Fujii Y, Saitoh Y, Tanaka H, Toyooka H: Ramosetron for preventing postoperative nausea and vomiting in women undergoing gynecological surgery. Anesth Analg. 2000 Feb;90(2):472-5. [Article]
- Lee SH, Cho SY, Yoo KY, Jeong S: Population pharmacokinetics of ramosetron. J Pharmacokinet Pharmacodyn. 2016 Feb;43(1):73-83. doi: 10.1007/s10928-015-9455-8. Epub 2015 Nov 11. [Article]
- External Links
- KEGG Drug
- D08466
- PubChem Compound
- 108000
- PubChem Substance
- 310265182
- ChemSpider
- 97112
- BindingDB
- 50334454
- ChEBI
- 135156
- ChEMBL
- CHEMBL1643895
- ZINC
- ZINC000005116719
- Wikipedia
- Ramosetron
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Irritable Bowel Syndrome (IBS) 1 4 Completed Other Post Operative Nausea and Vomiting (PONV) 1 4 Completed Prevention Female Breast Cancer / Post Operative Nausea and Vomiting (PONV) 1 4 Completed Prevention Nausea / Vomiting 1 4 Completed Prevention Osteoarthritis of the Knee 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral 5 mcg Tablet, film coated 5 mcg Injection Tablet Tablet 0.1 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0696 mg/mL ALOGPS logP 2.22 ALOGPS logP 2.24 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 12.68 Chemaxon pKa (Strongest Basic) 6.36 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 50.68 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 82.14 m3·mol-1 Chemaxon Polarizability 31.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0zgl-4960000000-1a9861736f1b6fb9baa6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-e7d3bed8e1e6d3b67779 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-0e9387bc877316438215 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0190000000-1c854e8d9fa27a0c2970 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0590000000-76ccab94c7a37ead9e08 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001l-0920000000-4d3ec4b22cc6fcf2b49e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05ai-1910000000-4d7a0aad26637d3d2cb0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.2846399 predictedDarkChem Lite v0.1.0 [M-H]- 164.43811 predictedDeepCCS 1.0 (2019) [M+H]+ 179.5380399 predictedDarkChem Lite v0.1.0 [M+H]+ 166.79611 predictedDeepCCS 1.0 (2019) [M+Na]+ 178.7065399 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.24223 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
- Gene Name
- HTR3A
- Uniprot ID
- P46098
- Uniprot Name
- 5-hydroxytryptamine receptor 3A
- Molecular Weight
- 55279.835 Da
References
- Suzuki T, Sugimoto M, Koyama H, Mashimo T, Uchida I: Inhibitory effect of glucocorticoids on human-cloned 5-hydroxytryptamine3A receptor expressed in xenopus oocytes. Anesthesiology. 2004 Sep;101(3):660-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Grover M, Camilleri M: Ramosetron in irritable bowel syndrome with diarrhea: new hope or the same old story? Clin Gastroenterol Hepatol. 2014 Jun;12(6):960-2. doi: 10.1016/j.cgh.2013.12.025. Epub 2014 Jan 3. [Article]
- Swaika S, Pal A, Chatterjee S, Saha D, Dawar N: Ondansetron, ramosetron, or palonosetron: Which is a better choice of antiemetic to prevent postoperative nausea and vomiting in patients undergoing laparoscopic cholecystectomy? Anesth Essays Res. 2011 Jul-Dec;5(2):182-6. doi: 10.4103/0259-1162.94761. [Article]
- Kadokura T, den Adel M, Krauwinkel WJ, Takeshige T, Nishida A: The effect of fluvoxamine on the pharmacokinetics, safety, and tolerability of ramosetron in healthy subjects. Eur J Clin Pharmacol. 2008 Jul;64(7):691-5. doi: 10.1007/s00228-008-0466-x. Epub 2008 Apr 26. [Article]
Drug created at October 29, 2015 21:13 / Updated at February 02, 2024 22:52