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Pilocarpine Nitrate

Pilocarpine Nitrate

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Also known as: 148-72-1, Pilagan, Pilofrin, Pilocarpine mononitrate, Pilocarpine nitrate salt, Pilocarpine (nitrate)

Molecular Formula

C₁₁H₁₇N₃O₅

Molecular Weight

271.27 g/mol

InChI Key

PRZXEPJJHQYOGF-GNAZCLTHSA-N

FDA UNII

M20T465H6J

A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.

1 2D Structure

Pilocarpine Nitrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;nitric acid

2.1.2 InChI

InChI=1S/C11H16N2O2.HNO3/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2;2-1(3)4/h5,7-8,10H,3-4,6H2,1-2H3;(H,2,3,4)/t8-,10-;/m0./s1

2.1.3 InChI Key

PRZXEPJJHQYOGF-GNAZCLTHSA-N

2.1.4 Canonical SMILES

CCC1C(COC1=O)CC2=CN=CN2C.[N+](=O)(O)[O-]

2.1.5 Isomeric SMILES

CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C.[N+](=O)(O)[O-]

2.2 Other Identifiers

2.2.1 UNII

M20T465H6J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydrochloride, Pilocarpine

2. Isopilocarpine

3. Isoptocarpine

4. Nitrate, Pilocarpine

5. Ocusert

6. Pilocarpine

7. Pilocarpine Hydrochloride

8. Pilocarpine Mononitrate, (3s-cis)-isomer

9. Pilocarpine, Monohydrochloride, (3s-cis)-isomer

10. Salagen

2.3.2 Depositor-Supplied Synonyms

1. 148-72-1

2. Pilagan

3. Pilofrin

4. Pilocarpine Mononitrate

5. Pilocarpine Nitrate Salt

6. Pilocarpine (nitrate)

7. Pilocarpinum Nitricum

8. Pilocarpine Subnitrate

9. Pilocarpine Nitrate [usp]

10. Nsc-757282

11. 2(3h)-furanone, 3-ethyldihydro-4-[(1-methyl-1h-imidazol-5-yl)methyl]-, (3s,4r)-, Nitrate (1:1)

12. Mls000069669

13. M20t465h6j

14. (3s,4r)-3-ethyl-4-((1-methyl-1h-imidazol-5-yl)methyl)dihydrofuran-2(3h)-one Nitrate

15. Smr000058498

16. Pilocarpine Nitrate (usp)

17. (3s,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;nitric Acid

18. Pilocarpini Nitras

19. Pilocarpin Nitrate

20. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, (3s-cis)-, Mononitrate

21. Sr-01000075339

22. P. V. Carpine Liquifilm

23. Unii-m20t465h6j

24. Sr-01000000054

25. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, (3s,4r)-, Nitrate (1:1)

26. Prestwick_282

27. Einecs 205-723-7

28. Pilagan (tn)

29. Mfcd00078497

30. Pilocarpine, Mononitrate

31. Regid855878

32. Opera_id_1243

33. Schembl41889

34. Spectrum1500487

35. Chembl1213136

36. Pilocarpine Nitrate [mi]

37. Hms501b20

38. Dtxsid80883277

39. Hms1569i20

40. Hms1920h14

41. Hms2091p18

42. Hms2096i20

43. Hms2235p11

44. Hms3262p22

45. Hms3713i20

46. Pharmakon1600-01500487

47. Pilocarpine Nitrate [vandf]

48. Hy-b1006

49. Pilocarpine Nitrate [mart.]

50. Pilocarpinum Nitricum [hpus]

51. Tox21_500960

52. Ccg-38830

53. Nsc757282

54. Pilocarpine Nitrate [usp-rs]

55. Pilocarpine Nitrate [who-dd]

56. Pilocarpine Nitrate [who-ip]

57. Akos016009842

58. Cs-4503

59. Lp00960

60. Nsc 757282

61. Ncgc00094261-01

62. Ncgc00261645-01

63. Pilocarpine Nitrate [ep Impurity]

64. Pilocarpine Nitrate [ep Monograph]

65. Pilocarpini Nitras [who-ip Latin]

66. Pilocarpine Nitrate [usp Monograph]

67. Eu-0100960

68. D05478

69. P 6628

70. T71804

71. Pilocarpine Nitrate Salt, >=98% (tlc), Powder

72. Sr-01000000054-7

73. Sr-01000075339-2

74. Sr-01000075339-5

75. Pilocarpine Nitrate Salt, Tested According To Ph.eur.

76. Pilocarpine Nitrate, Meets Usp Testing Specifications

77. Q27283365

78. Sr-01000075339-10

79. Pilocarpine Nitrate, British Pharmacopoeia (bp) Reference Standard

80. Pilocarpine Nitrate, European Pharmacopoeia (ep) Reference Standard

81. Pilocarpine Nitrate, United States Pharmacopeia (usp) Reference Standard

82. Pilocarpine Nitrate For System Suitability, European Pharmacopoeia (ep) Reference Standard

83. Pilocarpine Nitrate, Pharmaceutical Secondary Standard; Certified Reference Material

84. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, (3s,4r)-, Mononitrate

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇N₃O₅
Molecular Weight	271.27 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	271.11682065 g/mol
Monoisotopic Mass	271.11682065 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	270
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Miotics

Agents causing contraction of the pupil of the eye. Some sources use the term miotics only for the parasympathomimetics but any drug used to induce miosis is included here. (See all compounds classified as Miotics.)

Muscarinic Agonists

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)