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Also known as: Granisetron, 109889-09-0, Exo-granisetron (granisetron impurity f), 1364914-39-5, 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide, Granisetronum [inn-latin]
Molecular Formula
C18H24N4O
Molecular Weight
312.4  g/mol
InChI Key
MFWNKCLOYSRHCJ-UHFFFAOYSA-N

Granisetron
A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.
1 2D Structure

Granisetron

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide
2.1.2 InChI
InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)
2.1.3 InChI Key
MFWNKCLOYSRHCJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C2CCCC1CC(C2)NC(=O)C3=NN(C4=CC=CC=C43)C
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 1-methyl-n-(endo-9-methyl-9-azabicyclo(3.3.1)non-3-yl)-1h-indazole-3-carboxamide

2. 1h-indazole-3-carboxamide, 1-methyl-n-(9-methyl-9-azabicyclo(3.3.1)non-3-yl

3. 1h-indazole-3-carboxamide, 1-methyl-n-(9-methyl-9-azabicyclo(3.3.1)non-3-yl)-, Endo-

4. Brl 43694

5. Brl 43694a

6. Brl-43694

7. Brl-43694a

8. Brl43694

9. Brl43694a

10. Granisetron

11. Granisetron Hydrochloride

12. Granisetron Monohydrochloride

13. Hydrochloride, Granisetron

14. Kytril

15. Monohydrochloride, Granisetron

2.2.2 Depositor-Supplied Synonyms

1. Granisetron

2. 109889-09-0

3. Exo-granisetron (granisetron Impurity F)

4. 1364914-39-5

5. 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide

6. Granisetronum [inn-latin]

7. 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1h-indazole-3-carboxamide

8. Brl 43694

9. Granisetron-d3

10. Granisetron Base

11. [3h]-granisetron

12. Ly-278584

13. [3h]granisetron

14. Apf-530

15. 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-1h-indazole-3-carboxamide

16. 1-methyl-n-{9-methyl-9-azabicyclo[3.3.1]nonan-3-yl}-1h-indazole-3-carboxamide

17. [3h]-brl-43694

18. Schembl445223

19. Chembl289469

20. Chembl519643

21. Gtpl2292

22. 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-indazole-3-carboxamide

23. Dtxsid50861188

24. Chebi:184693

25. Bcp10022

26. Ex-a1291

27. Hy-b0071

28. Bbl036319

29. Bdbm50000483

30. Pdsp1_001266

31. Pdsp2_001250

32. Stl483411

33. Akos015895362

34. Ab07494

35. Cs-1509

36. Sdccgsbi-0633801.p001

37. Ncgc00186041-01

38. Ncgc00186041-09

39. Ls-14665

40. Ft-0626805

41. Ab01274752-01

42. Ab01274752_02

43. Ab01274752_03

44. Aa-504/10505045

45. L000281

46. 1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-7-yl)indazole-3-carboxamide

47. 1-methyl-1h-indazole-3-carboxylic Acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide

48. 1-methyl-1h-indazole-3-carboxylic Acid (9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide

49. 1-methyl-n-((1s,5r)-9-methyl-9-aza-bicyclo[3.3.1]nonan-3-yl)-1h-indazole-3-carboxamide

50. N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-1-methyl-1h-indazole-3-carboxamide

51. (brl 43694)1-methyl-1h-indazole-3-carboxylic Acid (9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide

52. (granisetron)1-methyl-1h-indazole-3-carboxylic Acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide

53. 1-methyl-1h-indazole-3-carboxylic Acid (9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide(brl 43694)

54. 1-methyl-1h-indazole-3-carboxylic Acid (9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide(granisetron)

55. 2-(9-methyl-3,9-diaza-bicyclo[3.3.1]non-3-yl)-1-(1-methyl-1h-indol-3-yl)-ethanone(granisetron)

2.3 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 312.4 g/mol
Molecular Formula C18H24N4O
XLogP32.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass312.19501140 g/mol
Monoisotopic Mass312.19501140 g/mol
Topological Polar Surface Area50.2 Ų
Heavy Atom Count23
Formal Charge0
Complexity442
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Prevention of nausea and vomiting in patients receiving moderately or highly emetogenic chemotherapy, with or without cisplatin, for up to five consecutive days.

Sancuso may be used in patients receiving their first chemotherapy regimen or in patients who have previously received chemotherapy.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Serotonin 5-HT3 Receptor Antagonists

Drugs that bind to but do not activate SEROTONIN 5-HT3 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT3 RECEPTOR AGONISTS. (See all compounds classified as Serotonin 5-HT3 Receptor Antagonists.)


Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Serotonin-3 Receptor Antagonist [EPC]; Serotonin 3 Receptor Antagonists [MoA]
5.3 ATC Code

A04AA02


A - Alimentary tract and metabolism

A04 - Antiemetics and antinauseants

A04A - Antiemetics and antinauseants

A04AA - Serotonin (5ht3) antagonists

A04AA02 - Granisetron


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28-Dec-2023
03-Sep-2024
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