Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H18N4O |
Molecular Weight | 294.351 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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)
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
Sources: http://ibs-care.org/pdfs/ref_105.pdf
Curator's Comment: Alosetron does cross the blood-brain barrier.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1899 |
0.29 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LOTRONEX Approved UseLOTRONEX is indicated only for women with severe diarrhea-predominant irritable bowel syndrome (IBS) who have: chronic IBS symptoms (generally lasting 6 months or longer), had anatomic or biochemical abnormalities of the gastrointestinal tract excluded, and not responded adequately to conventional therapy. Diarrhea-predominant IBS is severe if it includes diarrhea and one or more of the following: frequent and severe abdominal pain/discomfort, frequent bowel urgency or fecal incontinence, disability or restriction of daily activities due to IBS. Because of infrequent but serious gastrointestinal adverse reactions associated with LOTRONEX, the indication is restricted to those patients for whom the benefit-to-risk balance is most favorable. Clinical studies have not been performed to adequately confirm the benefits of LOTRONEX in men. LOTRONEX is a selective serotonin 5-HT3 antagonist indicated only for women with severe diarrhea-predominant irritable bowel syndrome (IBS) who have: chronic IBS symptoms (generally lasting 6 months or longer), had anatomic or biochemical abnormalities of the gastrointestinal tract excluded, and not responded adequately to conventional therapy. (1) Severe IBS includes diarrhea and 1 or more of the following: frequent and severe abdominal pain/discomfort, frequent bowel urgency or fecal incontinence, disability or restriction of daily activities due to IBS. (1) Launch Date9.5005442E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.35 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
40.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
43.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
5 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9 ng/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
36.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
49.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
66.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
1.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874386 |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
ALOSETRON serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18% |
ALOSETRON plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Disc. AE: Constipation, Gastrointestinal discomfort... AEs leading to discontinuation/dose reduction: Constipation (20%) Sources: Page: S3BA2001Gastrointestinal discomfort (3%) Abdominal pain (8%) Nausea (9%) Vomiting (3%) Diarrhea (5%) Headaches (7%) Malaise and fatigue (3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Constipation | 20% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Gastrointestinal discomfort | 3% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Malaise and fatigue | 3% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Vomiting | 3% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Diarrhea | 5% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Headaches | 7% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Abdominal pain | 8% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Nausea | 9% Disc. AE |
8 mg 2 times / day multiple, oral MTD Dose: 8 mg, 2 times / day Route: oral Route: multiple Dose: 8 mg, 2 times / day Sources: Page: S3BA2001 |
unhealthy, 45 n = 68 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 45 Sex: M+F Population Size: 68 Sources: Page: S3BA2001 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive | ||||
Page: 5.0 |
no | |||
no | ||||
no | ||||
no | ||||
Page: 5.0 |
no | |||
Page: 5.0 |
no | |||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | unlikely (co-administration study) Comment: Ketoconazole is a known strong inhibitor of CYP3A4. In a pharmacokinetic study, 38 healthy female subjects received ketoconazole 200 mg twice daily for 7 days, with coadministration of alosetron 1 mg on the last day. Ketoconazole increased mean alosetron plasma concentrations (AUC) by 29%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21107a_Lotronex_clinphrmr_P3.pdf#page=8 Page: 8.0 |
|||
yes | yes (co-administration study) Comment: Fluvoxamine is a known strong inhibitor of CYP1A2 and also inhibits CYP3A4, CYP2C9, and CYP2C19. In a pharmacokinetic study, 40 healthy female subjects received fluvoxamine in escalating doses from 50 to 200 mg/day for 16 days, with coadministration of alosetron 1 mg on the last day. Fluvoxamine increased mean alosetron plasma concentrations (AUC) approximately 6-fold and prolonged the half-life by approximately 3-fold. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21107a_Lotronex_clinphrmr_P3.pdf#page=8 Page: 8.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12873512/ Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
FDA approves restricted marketing of Lotronex. | 2002 Jul-Aug |
|
Return of alosetron. | 2002 May |
|
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 |
|
Condition-specific deactivation of brain regions by 5-HT3 receptor antagonist Alosetron. | 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 |
|
FDA advisers warn of more deaths if drug is relaunched. | 2002 Sep 14 |
|
Alosetron for irritable bowel syndrome. | 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 |
|
Advances in the management of irritable bowel syndrome. | 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. Risks of using alosetron are still unknown. | 2003 Jan 4 |
|
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 |
|
Alosetron and irritable bowel syndrome. | 2003 Nov |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/alosetron.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10776833
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C94726
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WHO-VATC |
QA03AE01
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NDF-RT |
N0000175818
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LIVERTOX |
29
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WHO-ATC |
A03AE01
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NDF-RT |
N0000175817
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C090840
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M1574
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DTXSID6044278
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2296
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C73100
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ALOSETRON
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13Z9HTH115
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CHEMBL1110
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53783
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85248
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2099
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122852-42-0
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Alosetron
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100000087466
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253342
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6906
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13Z9HTH115
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)