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Pilocarpine

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

SOLUTION;OPHTHALMIC - 1%, SOLUTION;OPHTHALMIC - 2%, SOLUTION;OPHTHALMIC - 4%, TABLET;ORAL - 5MG, TABLET;ORAL - 7.5MG

SOLUTION;OPHTHALMIC - 1%
SOLUTION;OPHTHALMIC - 2%
SOLUTION;OPHTHALMIC - 4%
TABLET;ORAL - 5MG
TABLET;ORAL - 7.5MG

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Also known as: 54-71-7, (+)-pilocarpine hydrochloride, Pilocarpine hcl, Almocarpine, Salagen, Adsorbocarpine

Molecular Formula

C₁₁H₁₇ClN₂O₂

Molecular Weight

244.72 g/mol

InChI Key

RNAICSBVACLLGM-GNAZCLTHSA-N

FDA UNII

0WW6D218XJ

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

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

RNAICSBVACLLGM-GNAZCLTHSA-N

2.1.4 Canonical SMILES

CCC1C(COC1=O)CC2=CN=CN2C.Cl

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

0WW6D218XJ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydrochloride, Pilocarpine

2. Isopilocarpine

3. Isoptocarpine

4. Nitrate, Pilocarpine

5. Ocusert

6. Pilocarpine

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

8. Pilocarpine Nitrate

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

10. Salagen

2.3.2 Depositor-Supplied Synonyms

1. 54-71-7

2. (+)-pilocarpine Hydrochloride

3. Pilocarpine Hcl

4. Almocarpine

5. Salagen

6. Adsorbocarpine

7. Pilocarpal

8. Pilocar

9. Pilocar Smp

10. Pilocarpine Monohydrochloride

11. Pilomiotin

12. Pilovisc

13. Pilocel

14. Sno Pilo

15. Mistura P

16. Pilocarpine Muriate

17. Epicar

18. Mi-pilo Ophth Sol

19. Pilopine Hs

20. Vistacarpin N

21. Pilocarpine, Hydrochloride

22. Spersacarpine Hydrochloride

23. Pilokarpin Monohydrochloride

24. Pilopine

25. Pilocarpine Chloride

26. Pilocarpine (hydrochloride)

27. Pilo

28. Pilocarpinum Muriaticum

29. Pilocarpine, Monohydrochloride

30. Pilocarpine Hydrochlororide

31. Mls000069454

32. 0ww6d218xj

33. Isoptocarpine

34. (3s,4r)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydrochloride

35. Nsc5746

36. Smr000059053

37. Isopto Carpine

38. Isopto-carpine

39. Ami-pilo

40. Amistura P

41. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, Monohydrochloride, (3s,4r)-

42. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, Monohydrochloride, (3s-cis)-

43. Pilopine Hs Gel

44. Nsc 5746

45. (3s,4r)-3-ethyl-4-((1-methyl-1h-imidazol-5-yl)methyl)dihydrofuran-2(3h)-one Hydrochloride

46. (3s,4r)-3-ethyl-4-[(1-methyl-1h-imidazol-5-yl)methyl]dihydrofuran-2(3h)-one Hydrochloride

47. Einecs 200-212-5

48. Unii-0ww6d218xj

49. Pilocarpine-hcl

50. Ai3-61859

51. Sr-01000000054

52. Mi-pilo

53. Component Of Epicar

54. Salagen (tn)

55. Sanpilo (tn)

56. Component Of Pilocar

57. Pilocarpine Hydrochloride [usp:jan]

58. Vuity

59. Pilopine Hs (tn)

60. Isopto Carpine (tn)

61. Nsc-5746

62. Pilocarpini Hydrochloridum

63. Regid855931

64. Opera_id_1616

65. Schembl41427

66. Mls000758210

67. Mls001076314

68. Mls001424017

69. Nsc 5746 Hcl

70. Pilocarpine Hcl [vandf]

71. Chembl1200330

72. Dtxsid2041096

73. Chebi:141029

74. Hy-b0726

75. Tox21_500950

76. S4231

77. Pilocarpine Hydrochloride [mi]

78. Pilocarpinum Muriaticum [hpus]

79. Akos005267231

80. Pilocarpine Hydrochloride (jp17/usp)

81. Ccg-100757

82. Lp00950

83. Nc00007

84. Pilocarpine Hydrochloride [jan]

85. (3s,4r)-3-ethyl-4-[(1-methylimidazol-5-yl)methyl]-3,4,5-trihydrofuran-2-one, C Hloride

86. Ncgc00094254-01

87. Ncgc00261635-01

88. Pilocarpine Hydrochloride [mart.]

89. Pilocarpine Hydrochloride [vandf]

90. Ac-33119

91. Pilocarpine Hydrochloride [usp-rs]

92. Pilocarpine Hydrochloride [who-dd]

93. Pilocarpine Hydrochloride [who-ip]

94. Eu-0100950

95. Sw196587-4

96. D02200

97. D91961

98. P 6503

99. Pilocarpine Hydrochloride [ep Impurity]

100. Pilocarpine Hydrochloride [ep Monograph]

101. Pilocarpine Hydrochloride [orange Book]

102. Pilocarpine Hydrochloride [usp Impurity]

103. 2(3h)-furanone, Monohydrochloride, (3s-cis)-

104. Pilocarpine Hydrochloride [usp Monograph]

105. Pilocarpini Hydrochloridum [who-ip Latin]

106. Wln: T5ovtj C2 D1- Dt5n Cnj C1 &gh

107. Sr-01000000054-3

108. Sr-01000075339-1

109. Pilocarpine Hydrochloride, >=98% (titration), Powder

110. Q23059847

111. Betoptic Pilo Component Pilocarpine Hydrochloride

112. Pilocarpine Hydrochloride Component Of Betoptic Pilo

113. Pilocarpine Hydrochloride, Meets Usp Testing Specifications

114. Pilocarpine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

115. (3s,4r)-3-ethyl-4-[(1-methyl-1h-imidazol-5-yl)methyl]oxolan-2-one Hydrochloride

116. Pilocarpine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

117. Pilocarpine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

118. (3s-cis)-3-ethyldihydro-4-[(1-methyl-1h-imidazol-5-yl)methyl]-2(3h)-furanone Hydrochloride

119. 2(3h)-furanone, 3-ethyldihydro-4-((1-methyl-1h-imidazol-5-yl)methyl)-, Hydrochloride (1:1), (3s,4r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₇ClN₂O₂
Molecular Weight	244.72 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	244.0978555 g/mol
Monoisotopic Mass	244.0978555 g/mol
Topological Polar Surface Area	44.1 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	245
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 Drug Information

1 of 8
Drug Name	Isopto carpine
PubMed Health	Pilocarpine
Drug Classes	Dental Agent, Direct Acting Miotic
Drug Label	Isopto Carpine (pilocarpine hydrochloride ophthalmic solution) is a cholinergic agonist prepared as a sterile topical ophthalmic solution. The active ingredient is represented by the chemical structure:Established name: pilocarpine hydrochlorideChe...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Solution
Route	Ophthalmic
Strength	1%; 2%; 4%
Market Status	Prescription
Company	Alcon Res

2 of 8
Drug Name	Pilocarpine hydrochloride
PubMed Health	Pilocarpine
Drug Classes	Dental Agent, Direct Acting Miotic
Drug Label	Pilocarpine hydrochloride tablets contain pilocarpine hydrochloride, a cholinergic agonist for oral use. Pilocarpine hydrochloride is a hygroscopic, odorless, bitter tasting white crystal or powder, which is soluble in water and alcohol and virtually...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	7.5mg; 5mg
Market Status	Prescription
Company	Corepharma; Roxane; Lannett; Impax Labs

3 of 8
Drug Name	Pilopine hs
Drug Label	SALAGEN Tablets contain pilocarpine hydrochloride, a cholinergic agonist for oral use. Pilocarpine hydrochloride is a hygroscopic, odorless, bitter tasting white crystal or powder which is soluble in water and alcohol and virtually insoluble in mos...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Gel
Route	Ophthalmic
Strength	4%
Market Status	Prescription
Company	Alcon

4 of 8
Drug Name	Salagen
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	7.5mg; 5mg
Market Status	Prescription
Company	Eisai

5 of 8
Drug Name	Isopto carpine
PubMed Health	Pilocarpine
Drug Classes	Dental Agent, Direct Acting Miotic
Drug Label	Isopto Carpine (pilocarpine hydrochloride ophthalmic solution) is a cholinergic agonist prepared as a sterile topical ophthalmic solution. The active ingredient is represented by the chemical structure:Established name: pilocarpine hydrochlorideChe...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Solution
Route	Ophthalmic
Strength	1%; 2%; 4%
Market Status	Prescription
Company	Alcon Res

6 of 8
Drug Name	Pilocarpine hydrochloride
PubMed Health	Pilocarpine
Drug Classes	Dental Agent, Direct Acting Miotic
Drug Label	Pilocarpine hydrochloride tablets contain pilocarpine hydrochloride, a cholinergic agonist for oral use. Pilocarpine hydrochloride is a hygroscopic, odorless, bitter tasting white crystal or powder, which is soluble in water and alcohol and virtually...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	7.5mg; 5mg
Market Status	Prescription
Company	Corepharma; Roxane; Lannett; Impax Labs

7 of 8
Drug Name	Pilopine hs
Drug Label	SALAGEN Tablets contain pilocarpine hydrochloride, a cholinergic agonist for oral use. Pilocarpine hydrochloride is a hygroscopic, odorless, bitter tasting white crystal or powder which is soluble in water and alcohol and virtually insoluble in mos...
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Gel
Route	Ophthalmic
Strength	4%
Market Status	Prescription
Company	Alcon

8 of 8
Drug Name	Salagen
Active Ingredient	Pilocarpine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	7.5mg; 5mg
Market Status	Prescription
Company	Eisai

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Cholinergic Muscarinic Agonists [MoA]; Cholinergic Receptor Agonist [EPC]; Cholinergic Agonists [MoA]