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Alosetron Hydrochloride

Alosetron Hydrochloride

Synopsis, Chemistry

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Also known as: 122852-69-1, Alosetron hcl, Lotronex, Gr 68755c, Alosetron (hydrochloride), Alosetron hydrochloride(1:x)

Molecular Formula

C₁₇H₁₉ClN₄O

Molecular Weight

330.8 g/mol

InChI Key

FNYQZOVOVDSGJH-UHFFFAOYSA-N

FDA UNII

2F5R1A46YW

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.

1 2D Structure

Alosetron Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one;hydrochloride

2.1.2 InChI

InChI=1S/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

2.1.3 InChI Key

FNYQZOVOVDSGJH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(N=CN1)CN2CCC3=C(C2=O)C4=CC=CC=C4N3C.Cl

2.2 Other Identifiers

2.2.1 UNII

2F5R1A46YW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,3,4,5-tetrahydro-5-methyl-2-((5-methylimidazol-4-yl)methyl)-1h-pyrido(4,3-b)indol-1-one Monohydrochloride

2. Alosetron

3. Alosetron Monohydrochloride

4. Gr 68755

5. Gr68755

6. Lotronex

2.3.2 Depositor-Supplied Synonyms

1. 122852-69-1

2. Alosetron Hcl

3. Lotronex

4. Gr 68755c

5. Alosetron (hydrochloride)

6. Alosetron Hydrochloride(1:x)

7. Lotrpnex

8. Alosetron Hydrochloride [usan]

9. 132414-02-9

10. 5-methyl-2-[(5-methyl-1h-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one Hydrochloride

11. Gr 68755

12. Alosetron (hydrochloride(1:x))

13. 5-methyl-2-[(5-methyl-1h-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one;hydrochloride

14. Gr 68755x

15. Gr-68755c

16. 2f5r1a46yw

17. 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)

18. 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1h-imidazol-4-yl)methyl]-1h-pyrido[4,3-b]indol-1-one Hydrochloride

19. Gr 68755;gr 68755x

20. 122852-69-1 (hcl)

21. Dsstox_cid_24208

22. Dsstox_rid_80120

23. Dsstox_gsid_44208

24. 1h-pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-2-((5-methyl-1h-imidazol-4-yl)methyl)-, Monohydrochloride

25. 2,3,4,5-tetrahydro-5-methyl-2-((5-methylimidazol-4-yl)methyl)-1h-pyrido(4,3-b)indol-1-one Monohydrochloride

26. Alosetron Hydrochloride (usan)

27. Mls001401464

28. Gr 68755 (hydrochloride(1:x));gr 68755x (hydrochloride(1:x))

29. Chebi:53783

30. Cas-122852-69-1

31. Hsdb 7055

32. Ncgc00167528-01

33. Smr000469211

34. Unii-2f5r1a46yw

35. Lotrpnex (tn)

36. 5-methyl-2-((5-methyl-1h-imidazol-4-yl)methyl)-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indol-1-one Hydrochloride

37. 5-methyl-2-[(5-methyl-1h-imidazol-4-yl)methyl]-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indol-1-one Hydrochloride

38. Schembl806

39. Alosetron Hcl [vandf]

40. Regid_for_cid_60758

41. Alosetron Hydrochloride- Bio-x

42. Chembl1200885

43. Dtxsid8044208

44. Amy33432

45. Bcp08834

46. Alosetron Hydrochloride [mi]

47. Tox21_112525

48. Ac-022

49. Hy-70050c

50. Mfcd03453647

51. S4694

52. Alosetron Hydrochloride [hsdb]

53. Akos015889472

54. Akos015961658

55. Tox21_112525_1

56. Alosetron Hydrochloride [mart.]

57. Ccg-100910

58. Ccg-267816

59. Cs-0642

60. Nc00160

61. Alosetron Hydrochloride [usp-rs]

62. Alosetron Hydrochloride [who-dd]

63. Ncgc00167528-02

64. 1h-pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-2((5-methyl-1h-imidazol-4-yl)methyl)-, Monohydrochloride

65. Alosetron Hydrochloride, >=98% (hplc)

66. Ba166465

67. Bs-42103

68. Gr-68755

69. Alosetron Hydrochloride [orange Book]

70. Ft-0631109

71. Ft-0661526

72. A14989

73. Alosetron Hydrochloride [usp Monograph]

74. D02829

75. D88551

76. 852a691

77. A804978

78. Q-200613

79. Q27124209

80. Gr 68755c; Gr 68755; Gr 68755x;gr68755c; Gr68755; Gr68755x

81. 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1-h-imidazol-4-yl)methyl]-1h-pyrido[4,3-b]indol-1-one Hydrochloride

82. 5-methyl-2-((5-methyl-1h-imidazol-4-yl)methyl)-3,4-dihydro-2h-pyrido[4,3-b]indol-1(5h)-one Hydrochloride

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₉ClN₄O
Molecular Weight	330.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	330.1247389 g/mol
Monoisotopic Mass	330.1247389 g/mol
Topological Polar Surface Area	53.9 Å²
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

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Lotronex
PubMed Health	Alosetron (By mouth)
Drug Classes	Antidiarrheal, Gastrointestinal Agent
Drug Label	The active ingredient in LOTRONEX Tablets is alosetron hydrochloride (HCl), a potent and selective antagonist of the serotonin 5-HT3 receptor type. Chemically, alosetron is designated as 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methy...
Active Ingredient	Alosetron hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 0.5mg base; eq 1mg base
Market Status	Prescription
Company	Prometheus Labs

2 of 2
Drug Name	Lotronex
PubMed Health	Alosetron (By mouth)
Drug Classes	Antidiarrheal, Gastrointestinal Agent
Drug Label	The active ingredient in LOTRONEX Tablets is alosetron hydrochloride (HCl), a potent and selective antagonist of the serotonin 5-HT3 receptor type. Chemically, alosetron is designated as 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methy...
Active Ingredient	Alosetron hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 0.5mg base; eq 1mg base
Market Status	Prescription
Company	Prometheus Labs

4.2 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/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1041

... 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/

PMID:11060667 Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)

4.3 Drug Warning

Plasma concentrations of alosetron are 30 to 50% lower in men than in women given the same oral dose. In patients with irritable bowel syndrome, concentrations of alosetron are influenced by gender. Efficacy has not been established in men at any dose. /Salt not specified/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 58

/Alosetron/ should not be used in irritable bowel syndrome patients currently constipated or whose predominant bowel symptom in constipation because constipation is a frequent side effect of alosetron. /Salt not specified/

... Constipation is the most frequent adverse event, with a higher incidence of transient constipation in alosetron-treated patients, typically occurring in the first month of treatment. /Salt not specified/

PMID:11280555 Wolfe SG, et al; Am J Gastroenterol 96(3): 803-811 (2001)

Significant side effects have been noted with the use of alosetron including severe constipation, fecal impaction, & ischemic colitis. ...A case of ischemic colitis in a male patient with IBS who was briefly treated with alosetron /is described/. Clinical, endoscopic, & pathologic features of the focal colitis strongly suggested ischemia. Symptoms correlated temporally with alosetron use, & symptoms abated with discontinuation of the drug. Endoscopic & pathologic resolution of the colitis were documented. /salt not specified/

PMID:11159896 Friedel D, et al; Gastroenterology 120(2): 557-560 (2001)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Gastrointestinal Agents

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

Serotonin Antagonists

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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

5.3 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/

PMID:11060667 Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)

5.4 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/

PMID:11060667 Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)

Alosetron is extensively metabolized by multiple cytochrome P450 (CYP) enzymes, including CYP2C9 & CYP3A4.

PMID:11304903 D'Souza DL, et al; J Clin Pharmacol 41(4): 455-458 (2001)

5.5 Biological Half-Life

Plasma half life is about 1.5 hours.

PMID:11060667 Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)

5.6 Mechanism of Action

Serotonin 5HT3-receptor antagonist /Salt not specified/

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 56

... 5-HT3 antagonists delay colonic transit, incr colonic compliance, & incr small intestinal water absorption. ... /Salt not specified/

PMID:10886042 Thumshirn M, et al; Aliment Pharmacol Ther 14(7): 869-878 (2000)

Alosetron (Lotronex) is a potent, highly selective 5-HT(3) antagonist. ... /Salt not specified/

PMID:11060667 Camilleri M; Expert Opin Investig Drugs 9(1): 147-159 (2000)