Identification

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Name
Ramosetron
Accession Number
DB09290
Type
Small Molecule
Groups
Investigational
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.

Structure
Thumb
Synonyms
Not Available
External IDs
YM 060
Product Ingredients
IngredientUNIICASInChI Key
Ramosetron hydrochloride9551LHD87E132907-72-3XIXYTCLDXQRHJO-RFVHGSKJSA-N
International/Other Brands
IBset / Iribo / Nasea / Nozia
Categories
UNII
7ZRO0SC54Y
CAS number
132036-88-5
Weight
Average: 279.343
Monoisotopic: 279.137162179
Chemical Formula
C17H17N3O
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

Pharmacology

Indication

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

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 3A
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Ramosetron can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Ramosetron is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Ramosetron is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Ramosetron.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Ramosetron is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Ramosetron.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Ramosetron is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Ramosetron.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Ramosetron.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Ramosetron.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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]
External Links
KEGG Drug
D08466
PubChem Compound
108000
PubChem Substance
310265182
ChemSpider
97112
BindingDB
50334454
ChEBI
135156
ChEMBL
CHEMBL1643895
Wikipedia
Ramosetron

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentAnterior Resection Syndrome1
1CompletedNot AvailableHealthy Volunteers / Plasma Concentration of YM0602
2CompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
2CompletedTreatmentCancer of the Ovary / Chemotherapy-Induced Nausea and Vomiting (CINV)1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2Unknown StatusPreventionPost-Operative Nausea and Vomiting (PONV) / Tumors, Solid1
2Unknown StatusSupportive CareMalignancies, Hematologic1
3CompletedPreventionRadiotherapy Induced Nausea and Vomiting1
3CompletedTreatmentDiarrhoea Predominant Irritable Bowel Syndrome2
3CompletedTreatmentNausea / Vomiting1
3CompletedTreatmentPost-Operative Nausea and Vomiting (PONV)1
3Unknown StatusSupportive CareMalignancies1
3Unknown StatusTreatmentUterine Myoma, Ovary Neoplasm, Adenomyosis1
4CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
4CompletedPreventionElectrocardiogram QTc interval prolonged / Ponv1
4CompletedPreventionKnee Osteoarthritis (Knee OA)1
4CompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
4CompletedSupportive CareMalignancies / Tumors1
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1
4RecruitingPreventionPost-Operative Nausea and Vomiting (PONV)1
4RecruitingTreatmentPost-Operative Nausea and Vomiting (PONV)1
4TerminatedPreventionFacial Bones Fracture1
4Unknown StatusPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedNot AvailableDiarrhoea Predominant Irritable Bowel Syndrome1
Not AvailableCompletedPreventionArterial Hypotension / Coronary Artery Bypass Graft Triple Vessel1
Not AvailableCompletedPreventionLaparoscopic Marsupialization of Renal Cyst1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)5
Not AvailableCompletedSupportive CareMalignant Neoplasm of Colon1
Not AvailableCompletedTreatmentAbdominal mass1
Not AvailableNot Yet RecruitingPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableNot Yet RecruitingTreatmentC.Delivery; Surgery (Previous), Gynecological1
Not AvailableNot Yet RecruitingTreatmentChemotherapy-Induced Nausea and Vomiting (CINV)1
Not AvailableRecruitingPreventionHysteroscopy1
Not AvailableRecruitingPreventionProstate Cancer1
Not AvailableUnknown StatusPreventionArterial Hypotension / Nausea and vomiting / Shivering / Vasopressor1
Not AvailableUnknown StatusPreventionLaparoscopic Cholecystectomy / Nausea / Vomiting1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
N-alkylindole / Indole / Aryl ketone / Aryl alkyl ketone / N-methylpyrrole / Substituted pyrrole / Benzenoid / Vinylogous amide / Imidazole / Azole
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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 15:13 / Updated on May 09, 2019 00:15