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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
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

Molecular Formula C17H18N4O
Molecular Weight 294.351
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Primary TargetPharmacologyConditionPotency
0.29 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOTRONEX

Cmax

ValueDoseCo-administeredAnalytePopulation
43.1 ng/mL
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
14.6 ng/mL
2 mg single, oral
ALOSETRON serum
Homo sapiens
40.2 ng/mL
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
9.35 ng/mL
2 mg single, oral
ALOSETRON serum
Homo sapiens
5 ng/mL
1 mg single, oral
ALOSETRON serum
Homo sapiens
9 ng/mL
1 mg single, oral
ALOSETRON serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
66.1 ng × h/mL
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
36.6 ng × h/mL
2 mg single, oral
ALOSETRON serum
Homo sapiens
49.3 ng × h/mL
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
24.6 ng × h/mL
2 mg single, oral
ALOSETRON serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.65 h
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
1.44 h
2 mg single, oral
ALOSETRON serum
Homo sapiens
1.52 h
2 mg single, intravenous
ALOSETRON serum
Homo sapiens
1.45 h
2 mg single, oral
ALOSETRON serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
18%
ALOSETRON plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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.
Substance Class Chemical
Record UNII
13Z9HTH115
Record Status Validated (UNII)
Record Version