Identification

Name
Ramosetron
Accession Number
DB09290
Type
Small Molecule
Groups
Approved, Investigational
Description

Ramosetron is a serotonin 5-HT3 receptor antagonist for the treatment of nausea and vomiting. It is believed to have higher potency and longer antiemetic action than other 1st generation 5-HT3 antagonists such as ondansetron. Ramosetron is also indicated for a treatment of “diarrhea-predominant irritable bowel syndrome in males”. It is only licensed for use in Japan and selected 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)[[email protected]@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.

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 3A
antagonist
Human
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
DrugInteractionDrug group
AclidiniumAclidinium may increase the constipating activities of Ramosetron.Approved
AlcuroniumAlcuronium may increase the constipating activities of Ramosetron.Experimental
AlfentanilAlfentanil may increase the constipating activities of Ramosetron.Approved, Illicit
AlphacetylmethadolAlphacetylmethadol may increase the constipating activities of Ramosetron.Experimental, Illicit
AlphaprodineAlphaprodine may increase the constipating activities of Ramosetron.Illicit
Anisotropine MethylbromideAnisotropine Methylbromide may increase the constipating activities of Ramosetron.Approved
AtracuriumAtracurium may increase the constipating activities of Ramosetron.Experimental, Investigational
Atracurium besylateAtracurium besylate may increase the constipating activities of Ramosetron.Approved
AtropineAtropine may increase the constipating activities of Ramosetron.Approved, Vet Approved
BenactyzineBenactyzine may increase the constipating activities of Ramosetron.Withdrawn
BenzatropineBenzatropine may increase the constipating activities of Ramosetron.Approved
BezitramideBezitramide may increase the constipating activities of Ramosetron.Experimental, Illicit, Withdrawn
BiperidenBiperiden may increase the constipating activities of Ramosetron.Approved, Investigational
BornaprineBornaprine may increase the constipating activities of Ramosetron.Experimental
BuprenorphineBuprenorphine may increase the constipating activities of Ramosetron.Approved, Illicit, Investigational, Vet Approved
ButorphanolButorphanol may increase the constipating activities of Ramosetron.Approved, Illicit, Vet Approved
ButylscopolamineScopolamine butylbromide may increase the constipating activities of Ramosetron.Approved, Vet Approved
CarfentanilCarfentanil may increase the constipating activities of Ramosetron.Illicit, Investigational, Vet Approved
ChlorphenoxamineChlorphenoxamine may increase the constipating activities of Ramosetron.Withdrawn
CodeineCodeine may increase the constipating activities of Ramosetron.Approved, Illicit
CyclopentolateCyclopentolate may increase the constipating activities of Ramosetron.Approved
DarifenacinDarifenacin may increase the constipating activities of Ramosetron.Approved, Investigational
DesloratadineDesloratadine may increase the constipating activities of Ramosetron.Approved, Investigational
DexetimideDexetimide may increase the constipating activities of Ramosetron.Withdrawn
DextromoramideDextromoramide may increase the constipating activities of Ramosetron.Experimental, Illicit
DextropropoxypheneDextropropoxyphene may increase the constipating activities of Ramosetron.Approved, Illicit, Investigational, Withdrawn
DezocineDezocine may increase the constipating activities of Ramosetron.Approved, Investigational
DicyclomineDicyclomine may increase the constipating activities of Ramosetron.Approved
DihydrocodeineDihydrocodeine may increase the constipating activities of Ramosetron.Approved, Illicit
DihydroetorphineDihydroetorphine may increase the constipating activities of Ramosetron.Experimental, Illicit
DihydromorphineDihydromorphine may increase the constipating activities of Ramosetron.Experimental, Illicit
DiphenoxylateDiphenoxylate may increase the constipating activities of Ramosetron.Approved, Illicit
DPDPEDPDPE may increase the constipating activities of Ramosetron.Experimental
EmeproniumEmepronium may increase the constipating activities of Ramosetron.Experimental
EtanautineEtanautine may increase the constipating activities of Ramosetron.Experimental
EthopropazineEthopropazine may increase the constipating activities of Ramosetron.Approved
EthylmorphineEthylmorphine may increase the constipating activities of Ramosetron.Approved, Illicit
EtorphineEtorphine may increase the constipating activities of Ramosetron.Illicit, Vet Approved
EtybenzatropineEtybenzatropine may increase the constipating activities of Ramosetron.Experimental
FentanylFentanyl may increase the constipating activities of Ramosetron.Approved, Illicit, Investigational, Vet Approved
FesoterodineFesoterodine may increase the constipating activities of Ramosetron.Approved
GallamineGallamine may increase the constipating activities of Ramosetron.Experimental
Gallamine TriethiodideGallamine Triethiodide may increase the constipating activities of Ramosetron.Approved
GlycopyrroniumGlycopyrronium may increase the constipating activities of Ramosetron.Approved, Investigational, Vet Approved
HeroinHeroin may increase the constipating activities of Ramosetron.Approved, Illicit, Investigational
HexamethoniumHexamethonium may increase the constipating activities of Ramosetron.Experimental
HomatropineHomatropine may increase the constipating activities of Ramosetron.Approved
HydrocodoneHydrocodone may increase the constipating activities of Ramosetron.Approved, Illicit
HydromorphoneHydromorphone may increase the constipating activities of Ramosetron.Approved, Illicit
HyoscyamineHyoscyamine may increase the constipating activities of Ramosetron.Approved
Ipratropium bromideIpratropium bromide may increase the constipating activities of Ramosetron.Approved
KetobemidoneKetobemidone may increase the constipating activities of Ramosetron.Approved, Investigational
Levomethadyl AcetateLevomethadyl Acetate may increase the constipating activities of Ramosetron.Approved, Investigational
LevorphanolLevorphanol may increase the constipating activities of Ramosetron.Approved
LofentanilLofentanil may increase the constipating activities of Ramosetron.Illicit
LoperamideLoperamide may increase the constipating activities of Ramosetron.Approved
MazaticolMazaticol may increase the constipating activities of Ramosetron.Experimental
MecamylamineMecamylamine may increase the constipating activities of Ramosetron.Approved
MeptazinolMeptazinol may increase the constipating activities of Ramosetron.Experimental
MethadoneMethadone may increase the constipating activities of Ramosetron.Approved
Methadyl AcetateMethadyl Acetate may increase the constipating activities of Ramosetron.Approved, Illicit
MethanthelineMethantheline may increase the constipating activities of Ramosetron.Approved, Investigational
Methylscopolamine bromideMethylscopolamine bromide may increase the constipating activities of Ramosetron.Approved
MetixeneMetixene may increase the constipating activities of Ramosetron.Approved
MorphineMorphine may increase the constipating activities of Ramosetron.Approved, Investigational
NalbuphineNalbuphine may increase the constipating activities of Ramosetron.Approved
NicomorphineNicomorphine may increase the constipating activities of Ramosetron.Experimental
NormethadoneNormethadone may increase the constipating activities of Ramosetron.Approved, Illicit
OpiumOpium may increase the constipating activities of Ramosetron.Approved, Illicit
OrphenadrineOrphenadrine may increase the constipating activities of Ramosetron.Approved
OtiloniumOtilonium may increase the constipating activities of Ramosetron.Experimental, Investigational
OxitropiumOxitropium may increase the constipating activities of Ramosetron.Investigational
OxybutyninOxybutynin may increase the constipating activities of Ramosetron.Approved, Investigational
OxycodoneOxycodone may increase the constipating activities of Ramosetron.Approved, Illicit, Investigational
OxymorphoneOxymorphone may increase the constipating activities of Ramosetron.Approved, Investigational, Vet Approved
OxyphenoniumOxyphenonium may increase the constipating activities of Ramosetron.Approved
PancuroniumPancuronium may increase the constipating activities of Ramosetron.Approved
PentazocinePentazocine may increase the constipating activities of Ramosetron.Approved, Vet Approved
PentoliniumPentolinium may increase the constipating activities of Ramosetron.Approved
PethidinePethidine may increase the constipating activities of Ramosetron.Approved
PhenazocinePhenazocine may increase the constipating activities of Ramosetron.Experimental
PhenglutarimidePhenglutarimide may increase the constipating activities of Ramosetron.Experimental
PhenoperidinePhenoperidine may increase the constipating activities of Ramosetron.Experimental
PipecuroniumPipecuronium may increase the constipating activities of Ramosetron.Approved
PirenzepinePirenzepine may increase the constipating activities of Ramosetron.Approved
PiritramidePiritramide may increase the constipating activities of Ramosetron.Investigational
ProcyclidineProcyclidine may increase the constipating activities of Ramosetron.Approved
PropanthelinePropantheline may increase the constipating activities of Ramosetron.Approved
PropiverinePropiverine may increase the constipating activities of Ramosetron.Approved, Investigational
QuinidineQuinidine may increase the constipating activities of Ramosetron.Approved
RemifentanilRemifentanil may increase the constipating activities of Ramosetron.Approved
ScopolamineScopolamine may increase the constipating activities of Ramosetron.Approved
SolifenacinSolifenacin may increase the constipating activities of Ramosetron.Approved
SufentanilSufentanil may increase the constipating activities of Ramosetron.Approved, Investigational
TapentadolTapentadol may increase the constipating activities of Ramosetron.Approved
TilidineTilidine may increase the constipating activities of Ramosetron.Experimental
TiotropiumTiotropium may increase the constipating activities of Ramosetron.Approved
TolterodineTolterodine may increase the constipating activities of Ramosetron.Approved, Investigational
TramadolTramadol may increase the constipating activities of Ramosetron.Approved, Investigational
TrihexyphenidylTrihexyphenidyl may increase the constipating activities of Ramosetron.Approved
TrimethaphanTrimethaphan may increase the constipating activities of Ramosetron.Approved, Investigational
TropatepineTropatepine may increase the constipating activities of Ramosetron.Experimental
TropicamideTropicamide may increase the constipating activities of Ramosetron.Approved
TrospiumTrospium may increase the constipating activities of Ramosetron.Approved
TubocurarineTubocurarine may increase the constipating activities of Ramosetron.Approved
UmeclidiniumUmeclidinium may increase the constipating activities of Ramosetron.Approved
VecuroniumVecuronium may increase the constipating activities of Ramosetron.Approved
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
2CompletedPreventionProphylaxis against postoperative nausea and vomiting1
2CompletedTreatmentCancer, Ovarian / Prophylaxis of acute chemotherapy induced nausea and vomiting1
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
2Unknown StatusPreventionProphylaxis against postoperative nausea and vomiting / Tumors, Solid1
2Unknown StatusSupportive CareMalignancies, Hematologic1
3CompletedPreventionRadiotherapy Induced Nausea and Vomiting1
3CompletedTreatmentDiarrhea-predominant Irritable Bowel Syndrome2
3CompletedTreatmentNausea / Vomiting1
3CompletedTreatmentProphylaxis against postoperative nausea and vomiting1
3Unknown StatusSupportive CareCancers / Malignancies1
3Unknown StatusTreatmentUterine Myoma, Ovary Neoplasm, Adenomyosis1
4CompletedNot AvailableIrritable Bowel Syndrome (IBS)1
4CompletedPreventionKnee Osteoarthritis (Knee OA)1
4CompletedPreventionProphylaxis against postoperative nausea and vomiting1
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1
4RecruitingPreventionPonv / Prolonged QTc Interval1
4RecruitingPreventionProphylaxis against postoperative nausea and vomiting1
4RecruitingSupportive CareCancers / Tumors1
4RecruitingTreatmentProphylaxis against postoperative nausea and vomiting1
4TerminatedPreventionFacial Bones Fracture1
4Unknown StatusPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableActive Not RecruitingNot AvailableDiarrhea-predominant Irritable Bowel Syndrome1
Not AvailableCompletedPreventionArterial Hypotension / Coronary Artery Bypass Graft Triple Vessel1
Not AvailableCompletedPreventionLaparoscopic Marsupialization of Renal Cyst1
Not AvailableCompletedPreventionProphylaxis against postoperative nausea and vomiting4
Not AvailableCompletedSupportive CareMalignant Neoplasm of Colon1
Not AvailableCompletedTreatmentAbdominal mass1
Not AvailableNot Yet RecruitingPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableNot Yet RecruitingTreatmentC.Delivery; Surgery (Previous), Gynecological1
Not AvailableNot Yet RecruitingTreatmentProphylaxis of acute chemotherapy induced nausea and vomiting1
Not AvailableRecruitingPreventionProphylaxis against postoperative nausea and vomiting1
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
Human
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]

Drug created on October 29, 2015 15:13 / Updated on December 01, 2017 17:22