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Chemistry

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Also known as: 51-83-2, Carbamoylcholine chloride, Miostat, Carbamylcholine chloride, Jestryl, Carbachol chloride
Molecular Formula
C6H15ClN2O2
Molecular Weight
182.65  g/mol
InChI Key
AIXAANGOTKPUOY-UHFFFAOYSA-N
FDA UNII
8Y164V895Y

Carbachol
A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.
1 2D Structure

Carbachol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-carbamoyloxyethyl(trimethyl)azanium;chloride
2.1.2 InChI
InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H
2.1.3 InChI Key
AIXAANGOTKPUOY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C[N+](C)(C)CCOC(=O)N.[Cl-]
2.2 Other Identifiers
2.2.1 UNII
8Y164V895Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Carbachol, Isopto

2. Carbacholine

3. Carbamann

4. Carbamoylcholine

5. Carbamylcholine

6. Carbastat

7. Carbocholine

8. Carboptic

9. Doryl

10. Isopto Carbachol

11. Jestryl

12. Miostat

2.3.2 Depositor-Supplied Synonyms

1. 51-83-2

2. Carbamoylcholine Chloride

3. Miostat

4. Carbamylcholine Chloride

5. Jestryl

6. Carbachol Chloride

7. Carbocholine

8. Doryl

9. Carbacholine Chloride

10. Isopto Carbachol

11. Carbacholin

12. Carbacolina

13. Carbamiotin

14. Carbocholin

15. Carbochol

16. Carcholin

17. Coletyl

18. Vasoperif

19. Carbyl

20. Lentin

21. Moryl

22. Carbacholine

23. Choline Carbamate Chloride

24. Carbacholum

25. Karbachol

26. Rilentol

27. Choline Chlorine Carbamate

28. Choline Chloride, Carbamate

29. Mistura C

30. Doryl (pharmaceutical)

31. Carbaminocholine Chloride

32. P. V. Carbachol

33. (2-carbamoyloxyethyl)trimethylammonium Chloride

34. Carbaminoylcholine Chloride

35. Carbacol

36. Lentine

37. Carbachol Hydrochloride

38. Karbamoylcholin Chlorid

39. (2-hydroxyethyl)trimethylammonium Chloride Carbamate

40. Carbamoylcholine-hydrochloride

41. Choline Chloride, Carbamoyl-

42. (2-hydroxyethyl)trimethyl Ammonium Chloride Carbamate

43. Choline, Chloride Carbamate(ester)

44. Carbamoylcholine (chloride)

45. 2-carbamoyloxyethyl(trimethyl)azanium;chloride

46. Carbamic Acid, Ester With Choline Chloride

47. 2-((aminocarbonyl)oxy)-n,n,n-trimethylethanaminium Chloride

48. 2-((aminocarbonyl)oxy)-n,n,n-trimethylethanaminum Chloride

49. Choline Chloride Carbamate

50. Nsc-32865

51. Ethanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride

52. Chebi:3385

53. 2-(carbamoyloxy)-n,n,n-trimethylethanaminium Chloride

54. 8y164v895y

55. Carbacholinum

56. Carbach

57. Dsstox_cid_2730

58. Dsstox_rid_76703

59. Lentine [french]

60. Dsstox_gsid_22730

61. Karbachol [czech]

62. Carbacolo [dcit]

63. Carbacholum Chloratum

64. Carbacholini Chloridum

65. Chembl14

66. Doryl (van)

67. Carbacholinium Chloratum

68. Carbacolo

69. Carbacol [inn-spanish]

70. Carbacholum [inn-latin]

71. Karbamoylcholin Chlorid [czech]

72. Gamma-carbamoyl Choline Chloride

73. Hsdb 6373

74. Cas-51-83-2

75. Sr-01000075312

76. Ncgc00163219-01

77. (2-carbamoyloxy-ethyl)-trimethyl-ammonium

78. Einecs 200-127-3

79. Nsc 32865

80. Tl 457

81. 2-[(aminocarbonyl)oxy]-n,n,n-trimethylethanaminium Chloride

82. Choline, Chloride, Carbamate

83. Choline, Chloride, Carbamate, Hydrochloride

84. (carbachol)(2-carbamoyloxy-ethyl)-trimethyl-ammonium

85. Unii-8y164v895y

86. 2-(trimethylazaniumyl)ethyl Carbamate Chloride

87. Carbachol [usp:inn:ban:jan]

88. Carbachol,(s)

89. Choline, Carbamate

90. Miostat (tn)

91. Mfcd00012011

92. Prestwick_1036

93. Carbachol [inn]

94. Carbachol [jan]

95. Carbachol [mi]

96. Ethanaminium, 2-(aminocarbonyl)oxy-n,n,n-trimethyl-, Chloride

97. Carbachol [hsdb]

98. Carbachol [vandf]

99. Carbachol [mart.]

100. 2-carbamoyloxyethyl(trimethyl)ammonium Chloride

101. Carbachol [usp-rs]

102. Carbachol [who-dd]

103. Schembl2791

104. Carbachol (jan/usp/inn)

105. Mls002153502

106. Spectrum1500158

107. Carbachol [ep Impurity]

108. Carbachol [orange Book]

109. Carbamoylcholine Chloride, 99%

110. Carbachol [ep Monograph]

111. Dtxsid9022730

112. Hms502e07

113. Carbachol [usp Monograph]

114. Choline, Carbamate, Hydrochloride

115. .gamma.-carbamoyl Choline Chloride

116. Hms1570p21

117. Hms1920i15

118. Hms2091o17

119. Hms2097p21

120. Hms2236l04

121. Hms3260b08

122. Hms3372g03

123. Hms3714p21

124. Pharmakon1600-01500158

125. Hy-b1208

126. Nsc32865

127. Tox21_112029

128. Tox21_500243

129. Ccg-38913

130. Nsc755919

131. Akos015909565

132. Akos025149486

133. Tox21_112029_1

134. Cs-4836

135. Lp00243

136. Nsc-755919

137. Wln: Zvo2k1&1&1 &q &g

138. Ncgc00015237-07

139. Ncgc00093705-01

140. Ncgc00093705-02

141. Ncgc00093705-03

142. Ncgc00093705-04

143. Ncgc00093705-05

144. Ncgc00260928-01

145. Smr000058584

146. B7196

147. C0596

148. Eu-0100243

149. Sw197107-3

150. C 4382

151. C-1770

152. D00524

153. D89274

154. 2-aminocarbonyloxyethyl(trimethyl)azanium Chloride

155. A828807

156. Q419401

157. Sr-01000075312-1

158. Sr-01000075312-3

159. Sr-01000075312-6

160. (2-carbamoyloxy-ethyl)-trimethyl-ammonium(carbachol)

161. Z1551429748

162. 2-(carbamoyloxy)-n,n,n-trimethylethan-1-aminium Chloride

163. Carbachol, European Pharmacopoeia (ep) Reference Standard

164. Carbamoylcholine Chloride, >=98% (titration), Crystalline

165. Carbachol, United States Pharmacopeia (usp) Reference Standard

166. Carbachol, Pharmaceutical Secondary Standard; Certified Reference Material

167. Ethanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride (1:1)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 182.65 g/mol
Molecular Formula C6H15ClN2O2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass182.0822054 g/mol
Monoisotopic Mass182.0822054 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity117
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMiostat
PubMed HealthCarbachol
Drug ClassesAntiglaucoma, Direct Acting Miotic
Drug LabelMIOSTAT (carbachol intraocular solution, USP) is a sterile balanced salt solution of carbachol for intraocular injection. The active ingredient is represented by the chemical structure:Established name:CarbacholChemical name:Ethanaminium, 2-[(amino...
Active IngredientCarbachol
Dosage FormSolution
RouteIntraocular
Strength0.01%
Market StatusPrescription
CompanyAlcon

2 of 2  
Drug NameMiostat
PubMed HealthCarbachol
Drug ClassesAntiglaucoma, Direct Acting Miotic
Drug LabelMIOSTAT (carbachol intraocular solution, USP) is a sterile balanced salt solution of carbachol for intraocular injection. The active ingredient is represented by the chemical structure:Established name:CarbacholChemical name:Ethanaminium, 2-[(amino...
Active IngredientCarbachol
Dosage FormSolution
RouteIntraocular
Strength0.01%
Market StatusPrescription
CompanyAlcon

4.2 Therapeutic Uses

Analgesics, Non-Narcotic; Cardiotonic Agents; Cholinergic Agonists; Miotics; Muscarinic Agonists; Nicotinic Agonists; Parasympathomimetics

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


Acetylcholine, 1%, or carbachol, 0.01%, is used in cataract extractions and certain other surgical procedures on the anterior segment when it is desired to produce miosis rapidly; the action of acetylcholine is brief. For the chronic therapy of noncongestive, wide-angle glaucoma, carbachol (0.75 to 3.0%) has been employed.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 105


Carbachol has been used in the treatment of postoperative intestinal atony and postoperative retention of urine, for which it has been given by subcutaneous injection ... or by mouth. It has also been used to stop supraventricular paroxysmal tachycardia when all other measures have failed. Carbachol has a miotic action and eye-drops ... have been used to lower intraocular pressure in glaucoma ... Even in comparatively late cases of sun blindness the symptoms could in many instances be alleviated ... by retrobulbar injection of carbachol.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1038


Pilocarpine (or occasionally carbachol) is used to lower intraocular pressure in the emergency treatment of acute (congestive) angle-closure glaucoma prior to surgery.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1657


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


4.3 Drug Warning

Topical carbachol shares the toxic potentials of the direct-acting miotics, and the usual precautions of miotic therapy should be observed. The manufacturer states that intraocular carbachol does not produce the adverse effects of topically applied carbachol; bullous keratopathy and postoperative iritis following cataract extraction have been reported in some patients.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1660


Corneal edema may occur if excessive amounts of carbachol are introduced into the anterior chamber or if the drug is used in patients with an already compromised endothelium, eg, Fuchs' dystrophy, corneal transplants, cataract surgery that requires more manipulation than usual.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1855


It is recommended that carbachol should not be used as eye-drops in patients with a corneal abrasion as there may be excessive absorption. The sensitivity of asthmatic patients to carbachol bronchoconstriction was increased when inhalation of carbachol was preceded by maximum respiratory maneurvers.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 1038


Drugs of this class should be admin only by the oral or subcutaneous route for systemic effects; they are also used locally in the eye. If they are given intravenously or intramuscularly, their relative selectivity of action no longer holds, and the incidence and severity of toxic side effects are greatly increased. /Choline esters/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 104


For more Drug Warnings (Complete) data for CARBACHOL CHLORIDE (10 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 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.)


Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)


Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)


Cholinergic Agonists

Drugs that bind to and activate cholinergic receptors. (See all compounds classified as Cholinergic Agonists.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cholinergic Receptor Agonist [EPC]; Cholinergic Agonists [MoA]
5.3 ATC Code

N07AB01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N07 - Other nervous system drugs

N07A - Parasympathomimetics

N07AB - Choline esters

N07AB01 - Carbachol


S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EB - Parasympathomimetics

S01EB02 - Carbachol


5.4 Absorption, Distribution and Excretion

Topical carbachol penetrates intact corneal epithelium very poorly; combination with wetting agent ... greatly improves corneal penetration by the drug. ... Carbachol /is/ ... absorbed through intact skin.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1657


5.5 Metabolism/Metabolites

Carbachol, which is an unsubstituted carbamyl ester, is totally resistant to hydrolysis by either acetylcholinesterase or nonspecific cholinesterases; its half-life is thus sufficiently long that it is distributed to areas of low blood flow.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 101


5.6 Mechanism of Action

The pharmacologic effects of all miotics are similar; they differ primarily in ocular and systemic absorption, duration of action and degree of effects. Acetylcholine, an endogenous mediator of nerve impulses, stimulates cholinergic receptors, resulting in muscarinic and nicotinic effects. The action of acetylcholine is transient. ... Pilocarpine, carbachol, and methacholine also directly stimulate cholinergic receptors; however, these drugs have a more prolonged duration of action (several hours) than does acetylcholine. There is some evidence that carbachol also has a weak anticholinesterase effect ... .

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1657


Miotics reduce intraocular pressure in normal and glaucomatous eyes. The mechanism of action of the drugs in lowering intraocular pressure has not been precisely determined. In patients with open-angle (chronic simple, noncongestive) glaucoma, the drugs facilitate aqueous humor outflow, apparently by causing contraction of the ciliary muscle and widening of the trabecular meshwork. ... Miotics decrease activity of extraocular muscles of convergence. ... Systemically absorbed miotics produce parasympathomimetic effects on various body systems. /Miotics/

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 1656


/Carbachol acts/ ... with selectivity on the smooth muscle of the gastrointestinal tract ... Carbachol /also/ retains substantial nicotinic activity, particularly on autonomic ganglia. It is likely that both its peripheral and its ganglionic actions are due, in part, to the release of endogenous acetylcholine from the terminals of cholinergic fibers.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 101


The choline esters /carbachol & bethanechol/ increase ureteral peristalsis, contract the detrusor muscle of the urinary bladder, increase the maximal voluntary voiding pressure, and decrease the capacity of the bladder. In addition, the trigone and external sphincter are relaxed. In animals with experimental lesions of the spinal cord or sacral roots, these drugs bring about satisfactory evacuation of the neurogenic bladder.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 103


For more Mechanism of Action (Complete) data for CARBACHOL CHLORIDE (7 total), please visit the HSDB record page.


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