Identification

Name
Ramosetron
Accession Number
DB09290
Description

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
Thumb
Weight
Average: 279.343
Monoisotopic: 279.137162179
Chemical Formula
C17H17N3O
Synonyms
  • Ramosetron
External IDs
  • Nor-YM 060
  • YM 060

Pharmacology

Pharmacology
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Indication

For the treatment of nausea and vomiting and diarrhea-predominant irritable bowel syndrome in males.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 3A
antagonist
Humans
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
Medicalerrors
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Ramosetron can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ramosetron can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Ramosetron can be increased when it is combined with Abiraterone.
AcenocoumarolThe metabolism of Ramosetron can be decreased when combined with Acenocoumarol.
AcetaminophenThe metabolism of Ramosetron can be decreased when combined with Acetaminophen.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Ramosetron.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Ramosetron.
AclidiniumThe risk or severity of constipation can be increased when Aclidinium is combined with Ramosetron.
AcyclovirThe metabolism of Ramosetron can be decreased when combined with Acyclovir.
AdalimumabThe metabolism of Ramosetron can be increased when combined with Adalimumab.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ramosetron hydrochloride9551LHD87E132907-72-3XIXYTCLDXQRHJO-RFVHGSKJSA-N
International/Other Brands
IBset / Iribo / Nasea / Nozia

Categories

Drug Categories
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

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
  1. 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. [PubMed:10648342]
  2. 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. [PubMed:26558626]
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
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
4CompletedOtherPost Operative Nausea and Vomiting (PONV)1
4CompletedPreventionNausea / Vomiting1
4CompletedPreventionOsteoarthritis of the Knee1
4CompletedPreventionPonv / Prolonged QT Interval1
4CompletedPreventionPost Operative Nausea and Vomiting (PONV)1
4CompletedSupportive CareMalignancies / Tumors1
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1
4RecruitingPreventionDay Surgery1
4TerminatedPreventionFacial Bones Fracture1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Tablet, film coated
Injection
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0696 mg/mLALOGPS
logP2.22ALOGPS
logP2.24ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.68ChemAxon
pKa (Strongest Basic)6.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.68 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.14 m3·mol-1ChemAxon
Polarizability31.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  1. 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. [PubMed:15329590]

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
  1. 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. [PubMed:24393804]
  2. 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. [PubMed:25885385]
  3. 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. [PubMed:18438654]

Drug created on October 29, 2015 21:13 / Updated on February 21, 2021 18:52