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Anisotropine methobromide

Synopsis, Chemistry

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Also known as: Octatropine methylbromide, Valpin, Valpin 50, 80-50-2, Methyloctatropine bromide, Endovalpin

Molecular Formula

C₁₇H₃₂BrNO₂

Molecular Weight

362.3 g/mol

InChI Key

QSFKGMJOKUZAJM-JXMYBXCISA-M

FDA UNII

62M960DHIL

1 2D Structure

Anisotropine methobromide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,5R)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide

2.1.2 InChI

InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1/t14-,15+,16?;

2.1.3 InChI Key

QSFKGMJOKUZAJM-JXMYBXCISA-M

2.1.4 Canonical SMILES

CCCC(CCC)C(=O)OC1CC2CCC(C1)[N+]2(C)C.[Br-]

2.1.5 Isomeric SMILES

CCCC(CCC)C(=O)OC1C[C@H]2CC[C@@H](C1)[N+]2(C)C.[Br-]

2.2 Other Identifiers

2.2.1 UNII

62M960DHIL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anisotropine Methylbromide, (endo)-isomer

2. Octatropine

3. Octotropine Methylbromide

4. Valpin

2.3.2 Depositor-Supplied Synonyms

1. Octatropine Methylbromide

2. Valpin

3. Valpin 50

4. 80-50-2

5. Methyloctatropine Bromide

6. Endovalpin

7. Octotropine Methylbromide

8. Anisotropine Methyl Bromide

9. Mls000028664

10. Mls001146935

11. 62m960dhil

12. Octatropini Methylbromidum

13. Methyloctatropine Bromide (jan)

14. Octatropine Methylbromide (inn)

15. Octatropine Methylbromide [inn]

16. Lytispasm

17. Methylbromure D'octatropine

18. Metilbromuro De Octatropina

19. Anisotropine Methylbromide (usan)

20. 8-methyltropinium Bromide 2-propylpentanoate

21. Smr000058851

22. Dsstox_cid_2612

23. Anisotropine (methobromide)

24. 8-azoniabicyclo(3.2.1)octane, 8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-, Bromide, Endo-

25. Dsstox_rid_76659

26. Dsstox_gsid_22612

27. Methyloctatropine Bromide [jan]

28. Cas-80-50-2

29. Anisotropine Methylbromide [usan]

30. Octatropone Bromide

31. Valpin (tn)

32. Valpin 50 (tn)

33. Ncgc00021394-03

34. Ncgc00021394-04

35. 2-propylpentanoyltropinium Methylbromide

36. Unii-62m960dhil

37. Methylbromure D'octatropine [inn-french]

38. Metilbromuro De Octatropina [inn-spanish]

39. Hsdb 3010

40. Einecs 201-285-6

41. Octatropini Methylbromidum [inn-latin]

42. Anisotropine Methylbromide [usan:inn:jan]

43. Opera_id_1463

44. 1alphah,5alphah-tropanium, 3alpha-hydroxy-8-methyl-, Bromide, 2-propylvalerate

45. 3-alpha-hydroxy-8-methyl-1-alpha-h,5-alpha-h-tropanium Bromide 2-propylvalerate

46. 3alpha-hydroxy-8-methyl-1alphah,5alphah-tropanium Bromide 2-propylvalerate

47. Chembl1578

48. Mls006010788

49. Schembl250226

50. Schembl1650394

51. Dtxsid8022612

52. Regid_for_cid_657201

53. Hms2230n16

54. Hy-b1475

55. Tox21_110871

56. Tox21_113475

57. Akos015916559

58. Anisotropine Methylbromide [mi]

59. Ccg-268189

60. (3-endo)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azoniabicyclo[3.2.1]octane Bromide

61. Anisotropine Methylbromide [hsdb]

62. Octatropine Methylbromide [mart.]

63. Anisotropine Methylbromide [vandf]

64. Octatropine Methylbromide [who-dd]

65. Smr004701473

66. Mls-0002939.p022

67. Cs-0013173

68. Anisotropine Methylbromide [orange Book]

69. C06830

70. D00232

71. Anisotropine Methylbromide(octatropine Methylbromide)

72. Q7076760

73. (1r,3r,5s)-8,8-dimethyl-3-(2-propylpentanoyloxy)-8-azoniabicyclo[3.2.1]octane Bromide

74. (3s)-8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium Bromide

75. [(1s,5r)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide

76. 1-alpha-h,5-alpha-h-tropanium, 3-alpha-hydroxy-8-methyl-, Bromide, 2-propylvalerate

77. 3.alpha.-hydroxy-8-methyl-1.alpha.h,5.alpha.h-tropanium Bromide 2-propylvalerate

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₃₂BrNO₂
Molecular Weight	362.3 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	7
Exact Mass	361.16164 g/mol
Monoisotopic Mass	361.16164 g/mol
Topological Polar Surface Area	26.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	318
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Therapeutic Uses

Parasympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

...ANTIMUSCARINIC DRUG. IT APPEARS TO BE RELATIVELY SELECTIVE FOR GI TRACT... IT IS USED IN TREATMENT OF MUCOUS COLITIS & IRRITABLE COLON, SPASTIC COLITIS, SPLENIC FLEXURE SYNDROME, BILIARY DYSKINESIA, CHOLELITHIASIS, PYLOROSPASM, GASTRITIS, DUODENITIS, ENTEROCOLITIS, & PEPTIC ULCER.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 849

VALPIN 50-PB INDICATED FOR USE AS ADJUNCTIVE THERAPY IN PEPTIC ULCER; IRRITABLE BOWEL SYNDROME (IRRITABLE COLON, SPASTIC COLON, MUCOUS COLITIS, ACUTE ENTEROCOLITIS, & FUNCTIONAL GI DISORDERS).

PDR; 33RD EDITION, 1979, MEDICAL ECONOMICS CO, LITTON INDUST, ORADELL, NJ 07649, 871-872

VALPIN 50-PB EFFECTIVELY PRODUCES VISCERAL SMOOTH MUSCLE RELAXATION. CONTROLS SMOOTH MUSCLE SPASM SEEN IN MOTILITY DISORDERS OF GI TRACT, SUCH AS SPASTIC COLON & FUNCTIONAL GI DISORDERS.

PDR; 33RD EDITION, 1979. MEDICAL ECONOMICS CO, LITTON INDUST, ORADELL, NJ 07649, 871-872

For more Therapeutic Uses (Complete) data for ANISOTROPINE METHYLBROMIDE (11 total), please visit the HSDB record page.

4.2 Drug Warning

ALTHOUGH INCIDENCE & INTENSITY OF SIDE EFFECTS IS LESS THAN THOSE OF METHANTHELINE BROMIDE, THEY ARE QUALITATIVELY SAME.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 849

...NO DRUG OF THIS CLASS HAS YET BEEN SHOWN TO PRODUCE ADEQUATE CONTROL OF GASTRIC SECRETION OR GI MOTILITY @ DOSES THAT ARE DEVOID OF SIGNIFICANT SIDE EFFECTS DUE TO MUSCARINIC BLOCKADE @ OTHER SITES. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158

...USED WITH GREAT CAUTION, & IN SOME CASES MAY BE CONTRAINDICATED, IN PATIENTS WITH REFLUX ESOPHAGITIS, ACHALASIA, PARTIAL GASTRIC OUTLET OBSTRUCTION, PARALYTIC ILEUS, INTESTINAL OBSTRUCTION, NARROW ANGLE GLAUCOMA, & PROSTATISM. /ANTISPASMODICS/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1041

ANTICHOLINERGIC ANTISPASMODICS SHOULD BE USED WITH CAUTION IN PATIENTS WITH PROSTATIC HYPERTROPHY, PYLORIC OBSTRUCTION, OBSTRUCTION OF BLADDER NECK, CONGESTIVE HEART FAILURE WITH TACHYCARDIA, & ACHALASIA (CARDIOSPASM). /ANTICHOLINERGIC AGENTS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 935

For more Drug Warnings (Complete) data for ANISOTROPINE METHYLBROMIDE (11 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

5.2 Absorption, Distribution and Excretion

...POORLY & UNRELIABLY ABSORBED AFTER ORAL ADMIN... PENETRATION OF CONJUNCTIVA IS ALSO POOR, SO THAT...CMPD ARE OF LITTLE VALUE IN OPHTHALMOLOGY. CENTRAL EFFECTS ARE GENERALLY LACKING, BECAUSE THESE AGENTS DO NOT READILY PASS BLOOD-BRAIN BARRIER. ...LITTLE...KNOWN OF FATE & EXCRETION... /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158

WHOLE-BODY AUTORADIOGRAPHY OF MICE GIVEN SC, ORAL, OR IP DOSES OF ANTISPASMODIC, [(14)C]ANISOTROPINE METHBROMIDE SHOWED THAT PARENTERAL DOSES WERE DISTRIBUTED MAINLY IN EXCRETORY ORGANS (KIDNEYS, LIVER, SALIVARY GLANDS, & INTESTINES).

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 123

SOME (14)C /ANISOTROPINE METHBROMIDE/ WAS...PRESENT IN STOMACH MUCOSA, PANCREAS, OVIDUCTS, UTERUS, & SPERMATIC DUCTS /AFTER ADMIN TO MICE/. CATION WOULD NOT BE EXPECTED TO DIFFUSE EASILY ACROSS BIOLOGICAL MEMBRANES...DID NOT APPEAR READILY TO CROSS BLOOD-BRAIN OR PLACENTAL BARRIERS, OR GASTROINTESTINAL EPITHELIUM.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 123

5.3 Mechanism of Action

THERE IS CLINICAL IMPRESSION THAT QUATERNARY AMMONIUM CMPD HAVE RELATIVELY GREATER EFFECT ON GASTROINTESTINAL ACTIVITY & THAT DOSES NECESSARY TO TREAT GASTROINTESTINAL DISORDERS ARE, CONSEQUENTLY...MORE READILY TOLERATED; THIS HAS BEEN ATTRIBUTED TO ADDITIONAL ELEMENT OF GANGLIONIC BLOCK. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158-9

RATIO OF GANGLIONIC BLOCKING TO ANTIMUSCARINIC ACTIVITY IS GREATER FOR CMPD WITH QUATERNARY AMMONIUM STRUCTURE BECAUSE OF THEIR GREATER POTENCY AT NICOTINIC RECEPTORS; SOME OF SIDE EFFECTS SEEN AFTER HIGH DOSES ARE DUE TO GANGLIONIC BLOCKADE. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 159

ANTISPASMODICS ARE COMPETITIVE ANTAGONISTS OF ACETYLCHOLINE, WHICH IS RELEASED @ ENDINGS OF PARASYMPATHETIC NERVES SUPPLYING GI TRACT. ...THESE DRUGS CAUSE MEAN REDUCTION OF BASAL ACID OUTPUT OF ABOUT 50%. THEY ALSO REDUCE MAXIMAL ACID OUTPUT BY 15 TO 50%. /ANTISPASMODICS/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1039