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Basic information
- CAS
122852-69-1- Standard SMILES
Cc1[nH]cnc1CN1CCc2c(c3ccccc3n2C)C1=O.Cl- InChIKey
FNYQZOVOVDSGJH-UHFFFAOYSA-N- Molecular formula
- C17H19ClN4O
- Average molar mass
- 330.8 g/mol
Overview
Alosetron Hydrochloride is the hydrochloride salt form of alosetron, a potent and selective 5-HT3 receptor antagonist. Alosetron blocks the actions of serotonin at 5-HT3 sites in the peripheral nervous system, particularly on enteric and nociceptive sensory neurons, thereby affecting the regulation of visceral pain, decreasing gastrointestinal contraction and motility, and decreasing gastrointestinal secretions. This agent is used to treat diarrhea-predominant irritable bowel syndrome in women.
Names & identifiers
- Preferred name
- Alosetron Hydrochloride
- IUPAC
- 5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one;hydrochloride
Names & synonyms
Show more names
Database identifiers
- CAS
122852-69-1- PubChem CID
- 60758
- DTXSID
DTXSID8044208- ChEMBL
CHEMBL1200885- UNII
- 2F5R1A46YW
- EC Number
- 802-450-0
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 53.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 442
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
FDA Requirements
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl alosetron hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions
... /A study was conducted/ to examine the potential for alosetron to alter the pharmacokinetics of theophylline by inhibiting its metab, as suggested by in vitro & in vivo effects on CYP1A2 activity. ... Ten healthy female volunteers received theophylline 200 mg twice daily alone for 8 days & with alosetron 1 mg twice daily for 15 days in this randomized, placebo-controlled, two-way-crossover study. ... Alosetron had no significant effect on theophylline plasma concns (Cmax approx 9 microg/ml), AUC approx 90 microg/ml-hr) or oral formation clearance of 3 major metabolites produced via CYP1A2: 3-methylxanthine, 1-methylurate & 1,3-dimethylurate (5, 7 & 16 ml/min, respectively). Concomitant admin of alosetron & theophylline was well tolerated. ... The absence of a clinical drug interaction involving inhibition of theophylline metab by alosetron was not predicted by in vitro & in vivo metabolic probe data. /Salt not specified/
Lotronex (alosetron hydrochloride) is a 5-HT3 receptor antagonist indicated for the treatment of irritable bowel syndrome (IBS) in females whose predominant bowel habit is diarrhea. Alosetron is extensively metabolized by multiple cytochrome P450 (CYP) enzymes, including CYP2C9 & CYP3A4. Fluoxetine is an antidepressant that is administered as a racemic mixture of equipotent R- & S-enantiomers. Fluoxetine metab involves CYP2D6 & CYP2C9 in the formation of its major metabolite, norfluoxetine. This metabolite is also present as two enantiomers, of which only the S-enantiomer exhibits comparable antidepressant activity. This study was conducted to assess the potential for an effect of alosetron on the pharmacokinetics of fluoxetine. This was an open-label, two-period, nonrandomized, crossover study in 12 healthy female & male volunteers. The pharmacokinetics for both enantiomers of fluoxetine & norfluoxetine were examined following single oral doses of 20 mg fluoxetine, given alone & in combination with alosetron 1 mg twice daily for 15 days. The results showed small delays in peak concn but no clinically significant effect of alosetron on the pharmacokinetics of S- & R-fluoxetine or S- & R-norfluoxetine. Coadministration of alosetron & fluoxetine was well tolerated by all subjects.
Lotronex (alosetron hydrochloride) is a 5-HT3 receptor antagonist indicated for the treatment of irritable bowel syndrome (IBS) in females whose predominant bowel habit is diarrhea. Alosetron is extensively metabolized by multiple cytochrome P450 (CYP) enzymes, including CYP 2C9 & 3A4. Alprazolam is a short-acting benzodiazepine commonly prescribed for the treatment of anxiety disorders & a potential comedication in patients with IBS. Alprazolam is extensively metabolized by CYP3A4. This clinical study was conducted to assess the potential for a metabolic drug interaction between these two CYP3A4 substrates. This was an open-label, randomized, two-period, crossover study in 12 healthy female & male volunteers to determine the effect of concomitant admin of alosetron at the recommended dose of 1 mg /orally/ bid on the pharmacokinetics of alprazolam following a single oral 1 mg dose. The results showed no effect of alosetron on the pharmacokinetics of alprazolam. Mean alprazolam AUC was 210 & 202 ng/h/ml in the absence & the presence of alosetron, respectively. Therefore, alprazolam may be safely coadministered with alosetron without the need for dosage adjustment.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Alosetron hydrochloride
vLess-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Regulatory information
FDA Requirements
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl alosetron hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Chemistry & industry
Pharmacology
Mechanism of Action
Serotonin 5HT3-receptor antagonist /Salt not specified/
... 5-HT3 antagonists delay colonic transit, incr colonic compliance, & incr small intestinal water absorption. ... /Salt not specified/
Alosetron (Lotronex) is a potent, highly selective 5-HT(3) antagonist. ... /Salt not specified/
Metabolism/Metabolites
/Alosetron/ metab is rapid & extensive with N-demethylation, hydroxylation & oxidation. The drug, or its two principal metabolites, is equally excreted through the biliary tract & kidneys. Alosetron has proved safe in a range of toxicity studies; at high repeated dosing, clinical signs were transient & repeated admin produced no significant adverse effects on fertility, reproductive performance or fetal development. ... /Salt not specified/
Alosetron is extensively metabolized by multiple cytochrome P450 (CYP) enzymes, including CYP2C9 & CYP3A4.
FDA Pharmacological Classification
ALOSETRON HYDROCHLORIDE
Serotonin-3 Receptor Antagonist [EPC]; Serotonin 3 Receptor Antagonists [MoA]
MeSH Pharmacological Classification
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.
Absorption, Distribution and Excretion
Absorption is rapid and ranges from 30 to > 90% after oral administration. /Salt not specified/
Alosetron ... is absorbed rapidly after oral admin & is widely distributed throughout tissues after oral or iv. dosing in animals. Its metab is rapid & extensive with N-demethylation, hydroxylation & oxidation. The drug, or its two principal metabolites, is equally excreted through the biliary tract & kidneys. Alosetron has proved safe in a range of toxicity studies; at high repeated dosing, clinical signs were transient & repeated admin produced no significant adverse effects on fertility, reproductive performance or fetal development. In pharmacokinetic studies, bioavailability of alosetron in healthy volunteers is approx 60% & the plasma half-life is about 1.5 hr. There are some gender differences in the pharmacokinetic profile, with 30-50% higher alosetron concns in females. No consistent differences in alosetron serum concns between the young & elderly were observed. The pharmacokinetics of single, oral doses of alosetron are linear up to 8 mg. ... /Salt not specified/
Uses & manufacturing
Suppliers100 total
Related reactions
Compound notes
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