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Chemical Product CAS:122852-69-11H-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)

CAS:122852-69-1
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)

  • CAS No:

    122852-69-1
  • Name:

    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)
  • Molecular Formula:

    C17H19ClN4O
  • Molecular Weight:

    330.81
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1H-Pyrido[4,3-b]indol-1-one,2,3,4,5-tetrahydr ( CASNO:122852-69-1 )

Identification and Related Records
Name:
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)
CAS Registry number:
122852-69-1
Iupac name:
5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,
3-b]indol-1-one hydrochloride
Synonyms:
Alosetron HCl
1H-Pyrido[4,3-b]indol-1-one,2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-,monohydrochloride (9CI)
GR 68755C
Molecular Formula:
C17H19ClN4O
Molecular Weight:
330.81
Inchi:
InChI=1/C17H18N4O.ClH/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);1H
Canonical SMILES:
CC1=C(N=CN1)CN2CCC3=C(C2=O)C4=CC=CC=C4N3C.Cl
Chemical and Physical Properties
Appearance:
Off-white powder
Density:
1.34g/cm3
Melting Point:
288-291℃
Boiling Point:
648.1 °C at 760 mmHg
Vapour:
1.1E-16mmHg at 25°C
Flash Point:
345.8 °C
Computed Properties:
Molecular Weight:330.81196 [g/mol]
Molecular Formula:C17H19ClN4O
H-Bond Donor:2
H-Bond Acceptor:1
Rotatable Bond Count:2
Tautomer Count:2
Exact Mass:330.124739
MonoIsotopic Mass:330.124739
Topological Polar Surface Area:53.9
Heavy Atom Count:23
Formal Charge:0
Complexity:442
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2
Safety and Handling
Formulations/Preparations:
The main ingredient in the drug Lotronex ... (tablets)
Exposure Standards and Regulations:
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.
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.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

Preparation: I.H. Coates et al., EP 306323; eidem, US 5360800 (1989, 1994 both to Glaxo)
Usage:
Serotonin 5HT3-receptor antagonist. Used in treatment of irritable bowel syndrome
Biomedical Effects and Toxicity
Pharmacological Action:
- 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.
Therapeutic Uses:
Alosetron, a selective 5-HT3-receptor antagonist, is indicated for the treatment of irritable bowel syndrome in female patients whose predominant symptom is diarrhea. /Salt not specified/
... Animal models have shown it to be active in anxiety, psychosis, cognitive impairment, emesis & drug withdrawal, though its application in humans has been almost entirely restricted to irritable bowel syndrome (IBS). ... Alosetron appears promising in the treatment of abdominal pain & discomfort & normalising of bowel function in patients with non-constipated IBS. It also improves quality of life, has a high degree of tolerability & has an excellent safety profile to date. /Salt not specified/ [Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)]
Biomedical Effects and Toxicity:
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/ [Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)] PubMed Abstract
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