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Details

Stereochemistry ACHIRAL
Molecular Formula C17H18N4O
Molecular Weight 294.351
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALOSETRON

SMILES

CN1C2=CC=CC=C2C3=C1CCN(CC4=C(C)N=CN4)C3=O

InChI

InChIKey=JSWZEAMFRNKZNL-UHFFFAOYSA-N
InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)

HIDE SMILES / InChI

Description

Alosetron, marketed under the brand name Lotronex, is a 5-HT3 antagonist used for the management of severe diarrhea-predominant irritable bowel syndrome (IBS) in women only. Alosetron is a potent and selective 5-HT3 receptor antagonist. 5-HT3 receptors are nonselective cation channels that are extensively distributed on enteric neurons in the human gastrointestinal tract, as well as other peripheral and central locations. Activation of these channels and the resulting neuronal depolarization affect the regulation of visceral pain, colonic transit and gastrointestinal secretions, processes that relate to the pathophysiology of irritable bowel syndrome (IBS). 5-HT3 receptor antagonists such as alosetron inhibit activation of non-selective cation channels which results in the modulation of the enteric nervous system. Alosetron is used for the treating women with severe irritable bowel syndrome (IBS) accompanied by severe diarrhea (usually lasting for 6 months or more). It is only prescribed to women who do not respond to other medicines and is not to be used by women whose main IBS problem is constipation.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.29 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOTRONEX
PubMed

PubMed

TitleDatePubMed
Adverse drug reaction update.
2002
Contemporary thoughts on the treatment of irritable bowel syndrome.
2002 Aug
The treatment of irritable bowel syndrome.
2002 Aug
Serotonin-transporter polymorphism pharmacogenetics in diarrhea-predominant irritable bowel syndrome.
2002 Aug
From the Food and Drug Administration.
2002 Aug 14
Alosetron (lotronex) revisited.
2002 Aug 5
Patient satisfaction with alosetron for the treatment of women with diarrhea-predominant irritable bowel syndrome.
2002 Dec
Irritable bowel syndrome neuropharmacology. A review of approved and investigational compounds.
2002 Jul
The effect of the 5-HT3 receptor antagonist, alosetron, on brain responses to visceral stimulation in irritable bowel syndrome patients.
2002 Jul
Serotonergic modulating drugs for functional gastrointestinal diseases.
2002 Jul
Alosetron to return to market.
2002 Jul 15
FDA approves restricted marketing of Lotronex.
2002 Jul-Aug
Health-related quality of life among persons with irritable bowel syndrome: a systematic review.
2002 Jun
FDA allows controversial bowel drug back on to market.
2002 Jun 15
Return of alosetron.
2002 May
FDA advisory panels recommend Lotronex be put back on market.
2002 May 4
Systematic review on the management of irritable bowel syndrome in North America.
2002 Nov
Evidence-based position statement on the management of irritable bowel syndrome in North America.
2002 Nov
Excitation of rat colonic afferent fibres by 5-HT(3) receptors.
2002 Nov 1
Gateways to clinical trials.
2002 Oct
FDA OK's two drugs for irritable bowel syndrome. The arsenal of IBS drugs is growing, but diagnosis is tricky.
2002 Oct
New developments in the diagnosis and treatment of irritable bowel syndrome.
2002 Oct
Alosetron: a case study in regulatory capture, or a victory for patients' rights?
2002 Sep 14
Alosetron in irritable bowel syndrome: strategies for its use in a common gastrointestinal disorder.
2003
Tegaserod and other serotonergic agents: what is the evidence?
2003
Irritable bowel syndrome genophenomics: correlation of serotonin-transporter polymorphisms and alosetron response.
2003
Safety, efficacy and costs of pharmacotherapy for functional gastrointestinal disorders: the case of alosetron and its implications.
2003 Apr
Regulatory role of 5-HT and muscarinic receptor antagonists on the migrating myoelectric complex in rats.
2003 Apr 25
Platelet serotonin transporter in patients with diarrhea-predominant irritable bowel syndrome both before and after treatment with alosetron.
2003 Dec
Efficacy of alosetron in irritable bowel syndrome: a meta-analysis of randomized controlled trials.
2003 Feb
Bad medicine. Why data from drug companies may be hard to swallow.
2003 Feb
[Visceral hypersensitivity: a concept within our reach].
2003 Jan
Alosetron (Lotronex) is back: should I use it to treat my patients with irritable bowel syndrome?
2003 Jan
Lipid-induced colonic hypersensitivity in irritable bowel syndrome: the role of 5-HT3 receptors.
2003 Jan
Alosetron for irritable bowel syndrome. Senior vice president of GlaxoSmithKline responds.
2003 Jan 4
Gateways to clinical trials.
2003 Jan-Feb
Irritable bowel syndrome: an overview of diagnosis and pharmacologic treatment.
2003 Jun
Review: tegaserod or alosetron is effective for the irritable bowel syndrome.
2003 Mar-Apr
Incidence of colonic ischemia, hospitalized complications of constipation, and bowel surgery in relation to use of alosetron hydrochloride.
2003 May
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003 Nov 17
Gateways to clinical trials.
2003 Oct
Evaluation of drug treatment in irritable bowel syndrome.
2003 Oct
Re: Brandt et al.--An evidence-based approach to the management of irritable bowel syndrome in North America.
2003 Sep
Treating irritable bowel syndrome: overview, perspective and future therapies.
2004 Apr
5-HT3-receptor antagonist inhibits visceral pain differently in chemical and mechanical stimuli in rats.
2004 Jan
Study design issues in irritable bowel syndrome.
2004 Jan 1
Safety and tolerability of tegaserod in irritable bowel syndrome management.
2004 Jan-Feb
Occurrence of colon ischemia in relation to irritable bowel syndrome.
2004 Mar
New options for soothing an irritable bowel.
2004 Mar
Therapy for irritable bowel syndrome.
2004 Mar 18
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Irritable Bowel Syndrome -Initial dose: 0.5 mg orally twice a day -Maintenance dose: 0.5 mg orally once or twice a day; can be increased up to 1 mg orally twice a day after 4 weeks of treatment.
Route of Administration: Oral
In Vitro Use Guide
Alosetron blocked the fast 5HT3-mediated depolarisation of guinea-pig myenteric and submucosal neurons in vitro, with half-maximal inhibition at approximately 55 nmol/L.
Name Type Language
ALOSETRON
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ALOSETRON [MI]
Common Name English
ALOSETRON [VANDF]
Common Name English
A03AE01
Code English
ALOSETRON [INN]
Common Name English
ALOSETRON [WHO-DD]
Common Name English
1H-PYRIDO(4,3-B)INDOL-1-ONE, 2,3,4,5-TETRAHYDRO-5-METHYL-2-((5-METHYL-1H-IMIDAZOL-4-YL)METHYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C94726
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
WHO-VATC QA03AE01
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
NDF-RT N0000175818
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
LIVERTOX 29
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
WHO-ATC A03AE01
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
NDF-RT N0000175817
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
Code System Code Type Description
MESH
C090840
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
MERCK INDEX
M1574
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY Merck Index
EPA CompTox
122852-42-0
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
IUPHAR
2296
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
NCI_THESAURUS
C73100
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
WIKIPEDIA
ALOSETRON
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
EVMPD
SUB05358MIG
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
DRUG BANK
DB00969
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
ChEMBL
CHEMBL1110
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
RXCUI
85248
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY RxNorm
PUBCHEM
2099
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
CAS
122852-42-0
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY
INN
6906
Created by admin on Mon Oct 21 19:45:14 UTC 2019 , Edited by admin on Mon Oct 21 19:45:14 UTC 2019
PRIMARY