Alosetron Hydrochloride

HCID 60758

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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

ALOSETRON HYDROCHLORIDE122852-69-1Alosetron HClGR 68755cLotrpnexDTXSID8044208GR-68755C2F5R1A46YWDTXCID60242082,3,4,5-Tetrahydro-5-methyl-2-((5-methylimidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one monohydrochloride1H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-2((5-methyl-1H-imidazol-4-yl)methyl)-, monohydrochlorideCHEBI:53783
Show more names
RefChem:58091132414-02-9Alosetron hydrochloride [USAN]Alosetron (Hydrochloride)Alosetron Hydrochloride(1:X)1H-Pyrido[4,3-b]indol-1-one, 2,3,4,5-tetrahydro-5-methyl-2-[(4-methyl-1H-imidazol-5-yl)methyl]-, hydrochloride (1:1)Alosetron (Hydrochloride(1:X))5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one;hydrochloride

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

Experimental & physicochemical properties

SolubilityWhite to beige solid with a solubility of 61 mg/ml in water, 42 mg/ml in 0.1M hydrochloric acid, 0.3 mg/ml in pH 6 phosphate buffer, and <0.1 mg/ml in pH 8 phosphate buffer /Hydrochloride/
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point288-291 °C
Other Experimental PropertiesMol wt: 294.35. /Alosetron/

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 1 item

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.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety & protection

Disposal Methods · 1 item

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 · 3 items

... /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 · 6 items

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 · 1 item

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 · 3 items

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/

Biological Half-LifePlasma half life is about 1.5 hours.
Metabolism/Metabolites · 2 items

/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 · 2 items

ALOSETRON HYDROCHLORIDE

Serotonin-3 Receptor Antagonist [EPC]; Serotonin 3 Receptor Antagonists [MoA]

MeSH Pharmacological Classification · 2 items

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 · 2 items

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

UsesMedication
Methods of ManufacturingPreparation: I.H. Coates et al., EP 306323; eidem, US 5360800 (1989, 1994 both to Glaxo)
Formulations/PreparationsThe main ingredient in the drug Lotronex ... (tablets)

Suppliers100 total

郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海策嵘生物科技有限公司[email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

Related reactions

4 records

Compound notes

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