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Chemistry

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Also known as: 101-26-8, Mestinon, Regonol, Kalimin, Kalymin, 3-(dimethylcarbamoyloxy)-1-methylpyridinium bromide
Molecular Formula
C9H13BrN2O2
Molecular Weight
261.12  g/mol
InChI Key
VNYBTNPBYXSMOO-UHFFFAOYSA-M
FDA UNII
KVI301NA53

Pyridostigmine
A cholinesterase inhibitor with a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.
1 2D Structure

Pyridostigmine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1-methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate;bromide
2.1.2 InChI
InChI=1S/C9H13N2O2.BrH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1
2.1.3 InChI Key
VNYBTNPBYXSMOO-UHFFFAOYSA-M
2.1.4 Canonical SMILES
C[N+]1=CC=CC(=C1)OC(=O)N(C)C.[Br-]
2.2 Other Identifiers
2.2.1 UNII
KVI301NA53
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bromide, Pyridostigmine

2. Mestinon

3. Pyridostigmine

2.3.2 Depositor-Supplied Synonyms

1. 101-26-8

2. Mestinon

3. Regonol

4. Kalimin

5. Kalymin

6. 3-(dimethylcarbamoyloxy)-1-methylpyridinium Bromide

7. 3-((dimethylcarbamoyl)oxy)-1-methylpyridin-1-ium Bromide

8. Regonal

9. Mestinon Bromide

10. Pyridostigmini Bromidum

11. Pyridostigmine (bromide)

12. (1-methylpyridin-1-ium-3-yl) N,n-dimethylcarbamate;bromide

13. Nsc-679759

14. Nsc-758435

15. Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, Bromide

16. Mls000028385

17. 3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium Bromide

18. Kvi301na53

19. Pyridinium, 3-[[(dimethylamino)carbonyl]oxy]-1-methyl-, Bromide

20. Ro 1-5130

21. 3-hydroxy-1-methylpyridinium Bromide Dimethylcarbamate

22. Ncgc00094324-02

23. 3-(((dimethylamino)carbonyl)oxy)-1-methylpyridinium Bromide

24. Smr000058605

25. Ro-1-5130

26. 3-(dimethylcarbamyloxy)-1-methylpyridinium Bromide

27. Dsstox_cid_3540

28. 1-methyl-3-hydroxypyridinium Bromide Dimethylcarbamate

29. Dsstox_rid_77069

30. Dsstox_gsid_23540

31. Dimethylcarbamic Acid Ester Of 3-hydroxy-1-methylpyridinium Bromide

32. Chembl812

33. Carbamic Acid, Dimethyl-, Ester With 3-hydroxy-1-methylpyridinium Bromide

34. Unii-19qm69hh21

35. 3-dimethylcarbamoyloxy-1-methylpyridinium Bromide;3-dimethylcarbamoyloxy-1-methylpyridinium Bromide

36. Cas-101-26-8

37. Piridostigmina Bromuro [dcit]

38. Ccris 6798

39. Piridostigmina Bromuro

40. Hsdb 3924

41. Sr-01000003072

42. Bromure De Pyridostigmine

43. Bromuro De Piridostigmina

44. Einecs 202-929-9

45. Pyridostigmini Bromidum [inn-latin]

46. Bromure De Pyridostigmine [inn-french]

47. 3-{[(dimethylamino)carbonyl]oxy}-1-methylpyridinium Bromide

48. Unii-kvi301na53

49. Bromuro De Piridostigmina [inn-spanish]

50. Mestinon-sr

51. Pyridinium, 3-[[(dimethylamino)carbonyl]oxy]-1-methyl-, Bromide (1:1)

52. Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, Bromide (1:1)

53. Mestinon (tn)

54. Pyridostigminebromine

55. Mfcd00079283

56. Pyridinium, 3-hydroxyl-1-methyl-, Bromide, Dimethylcarbamate

57. Opera_id_420

58. 3-hydroxy-1-methylpyridinium Bromide Dimethylcarbamate (ester)

59. Pyridostigmine Bromide [usp:inn:ban:jan]

60. Schembl41147

61. Mls001074080

62. Spectrum1503240

63. Chebi:8666

64. 3-(dimethylaminocarbonyloxy)-1-methylpyridinium Bromide

65. Dtxsid9023540

66. Hms500k09

67. Hy-b0207a

68. Pyridostigmine Bromide (mestinon)

69. Hms1922m05

70. Hms2092p14

71. Hms2234d06

72. Hms3259m16

73. Hms3263o11

74. Hms3369p02

75. Hms3651g13

76. Hms3884m21

77. Pharmakon1600-01503240

78. Pyridostigmine Bromide [mi]

79. Bcp02148

80. Pyridostigmine Bromide [inn]

81. Pyridostigmine Bromide [jan]

82. Tox21_111266

83. Tox21_501035

84. Ccg-40306

85. Nsc679759

86. Nsc758435

87. Pyridinium, 3-hydroxy-1-methyl-, Bromide, Dimethylcarbamate (ester)

88. Pyridostigmine Bromide [hsdb]

89. S1608

90. Akos015895321

91. Pyridostigmine Bromide [mart.]

92. Tox21_111266_1

93. Ac-8143

94. Lp01035

95. Nc00581

96. Nsc 758435

97. Pyridostigmine Bromide [usp-rs]

98. Pyridostigmine Bromide [who-dd]

99. Pyridostigmine Bromide [who-ip]

100. Ncgc00015862-07

101. Ncgc00094324-01

102. Ncgc00094324-03

103. Ncgc00094324-04

104. Ncgc00261720-01

105. Pyridostigmine Bromide (jp17/usp/inn)

106. As-13164

107. Pyridostigmine Bromide [ep Impurity]

108. Pyridostigmine Bromide [orange Book]

109. Eu-0101035

110. Ft-0603307

111. P1339

112. Pyridostigmine Bromide [ep Monograph]

113. Sw199029-2

114. Pyridostigmine Bromide [usp Monograph]

115. Pyridostigmini Bromidum [who-ip Latin]

116. D00487

117. P 9797

118. T71526

119. Q-201644

120. Sr-01000003072-2

121. Sr-01000003072-4

122. Q26840825

123. 3-((dimethylcarbamoyl)oxy)-1-methylpyridin-1-iumbromide

124. Z1541632810

125. Pyridostigmine Bromide, European Pharmacopoeia (ep) Reference Standard

126. Pyridostigmine Bromide, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 261.12 g/mol
Molecular Formula C9H13BrN2O2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass260.01604 g/mol
Monoisotopic Mass260.01604 g/mol
Topological Polar Surface Area33.4 Ų
Heavy Atom Count14
Formal Charge0
Complexity183
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 4  
Drug NameMestinon
PubMed HealthPyridostigmine Bromide (By mouth)
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nerve Gas Antidote
Drug LabelMestinon (pyridostigmine bromide) is an orally active cholinesterase inhibitor. Chemically, pyridostigmine bromide is 3-hydroxy-1-methylpyridinium bromide dimethylcarbamate. Its structural formula is:Mestinon is available in the following forms: Syru...
Active IngredientPyridostigmine bromide
Dosage FormTablet, extended release; Tablet; Syrup; Injectable
RouteInjection; Oral
Strength180mg; 60mg/5ml; 5mg/ml; 60mg
Market StatusPrescription
CompanyValeant Pharm North; Valeant Pharm Intl; Valeant Pharms

2 of 4  
Drug NamePyridostigmine bromide
PubMed HealthPyridostigmine Bromide (By mouth)
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nerve Gas Antidote
Drug LabelPyridostigmine bromide is an orally active, reversible cholinesterase inhibitor. Its chemical name is: 3-hydroxy-1-methylpyridinium bromide dimethylcarbamate.CAS registration number is 101-26-8.Pyridostigmine bromide has a molecular formula of C9H13B...
Active IngredientPyridostigmine bromide
Dosage FormTablet
RouteOral
Strength60mg
Market StatusPrescription
CompanyImpax Labs

3 of 4  
Drug NameMestinon
PubMed HealthPyridostigmine Bromide (By mouth)
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nerve Gas Antidote
Drug LabelMestinon (pyridostigmine bromide) is an orally active cholinesterase inhibitor. Chemically, pyridostigmine bromide is 3-hydroxy-1-methylpyridinium bromide dimethylcarbamate. Its structural formula is:Mestinon is available in the following forms: Syru...
Active IngredientPyridostigmine bromide
Dosage FormTablet, extended release; Tablet; Syrup; Injectable
RouteInjection; Oral
Strength180mg; 60mg/5ml; 5mg/ml; 60mg
Market StatusPrescription
CompanyValeant Pharm North; Valeant Pharm Intl; Valeant Pharms

4 of 4  
Drug NamePyridostigmine bromide
PubMed HealthPyridostigmine Bromide (By mouth)
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nerve Gas Antidote
Drug LabelPyridostigmine bromide is an orally active, reversible cholinesterase inhibitor. Its chemical name is: 3-hydroxy-1-methylpyridinium bromide dimethylcarbamate.CAS registration number is 101-26-8.Pyridostigmine bromide has a molecular formula of C9H13B...
Active IngredientPyridostigmine bromide
Dosage FormTablet
RouteOral
Strength60mg
Market StatusPrescription
CompanyImpax Labs

4.2 Therapeutic Uses

Cholinesterase Inhibitors; Parasympathomimetics

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


A QUATERNARY AMMONIUM ANTICHOLINESTERASE DRUG ...PRINCIPAL USE IS IN THE TREATMENT OF MYASTHENIA GRAVIS. ...

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 842


DOSAGE: THE EQUIVALENT PARENTERAL DOSE OF...PYRIDOSTIGMINE IS APPROX 1/30TH OF THE ORAL DOSE.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1029


PYRIDOSTIGMINE HAS A SLOWER ONSET (13 MIN) THAN EDROPHONIUM (3 MIN) OR NEOSTIGMINE (6-8 MIN), BUT A LONGER DURATION OF ACTION THAN EITHER. FOR THIS REASON, IT HAS BEEN RECOMMENDED FOR PATIENTS WITH RENAL IMPAIRMENT.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 424


For more Therapeutic Uses (Complete) data for PYRIDOSTIGMINE BROMIDE (9 total), please visit the HSDB record page.


4.3 Drug Warning

BROMIDE SENSITIVITY OCCASIONALLY OCCURS.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 842


Maternal Medication usually Compatible with Breast-Feeding: Pyridostigmine: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 141 (1994)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]
5.3 Absorption, Distribution and Excretion

ITS ONSET OF ACTION BY ORAL ROUTE IS ABOUT 320 MIN...ITS DURATION OF ACTION BY THE ORAL ROUTE IS USUALLY SOMEWHAT LONGER AND ABSORPTION IS LESS ERRATIC THAN NEOSTIGMINE, WHICH ARE ADVANTAGES.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 842


Plasma concn of pyridostigmine was determined in 2 nursing mothers who were receiving oral doses of pyridostigmine bromide, 120-300 mg daily. The drug was not detectable in infant plasma and there were no signs of drug effects in the infant.

Hardell LI et al; Pyridostigmine in human breast milk; Br J Clin Pharmacol 14 (Oct): 565-7 (1982)


5.4 Metabolism/Metabolites

PYRIDOSTIGMINE AND ITS QUATERNARY ALCOHOL ARE...THE PREDOMINANT ENTITIES FOUND IN URINE AFTER ADMIN OF THIS DRUG TO MAN.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 108


5.5 Biological Half-Life

After admin of pyridostigmine bromide (200 nmol/kg, iv) to human subjects, the disposition half-life was 0.6-1.78 min and terminal half-life was 14.81-37.01 min. Clearance was 9.3-26.5 ml/min/kg which was greater than the presumptive value for glomerular filtration rate and the vol of distribution was 246.5-833.9 ml/kg.

Calvey TN et al; Kinetics of intravenous pyridostigmine in man; Br J Clin Pharmacol 11 (4): 406-8 (1981)


5.6 Mechanism of Action

...PHARMACOLOGICAL EFFECTS OF ANTICHOLINESTERASE AGENTS ARE DUE PRIMARILY TO PREVENTION OF HYDROLYSIS OF /ACH/ ACETYLCHOLINE BY ACHE /ACETYLCHOLINESTERASE/ @ SITES OF CHOLINERGIC TRANSMISSION. TRANSMITTER THUS ACCUMULATES, AND THE ACTION OF ACH /ACETYLCHOLINE/ THAT IS LIBERATED BY CHOLINERGIC IMPULSES OR THAT LEAKS FROM THE NERVE ENDING IS ENHANCED.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 103


Following admin of pyridostigmine bromide to rats, erythrocyte acetylcholinesterase activity recovered only slowly due to the covalent nature of inhibition. The logarithm of the plasma concn of pyridostigmine bromide was linearly related to the increase in tibialis twitch tension due to facilitation of neuromuscular transmission.

Barber HE et al; The relationship between the pharmacokinetics, cholinesterase inhibition and facilitation of twitch tension of the quaternary ammonium anticholinesterase drugs, neostigmine, pyridostigmine, edrophonium and 3-hydroxyphenyltrimethylammonium; Br J Pharmacol 66 (4): 525-30 (1979)


Of 12 analogs of pyridostigmine prepared by reacting 2-substituted 3-pyridinols with the desired carbamoyl chloride 2-iodo-3-(dimethylcarbamoyloxy)pyridine methiodide was the most active inhibitor of acetylcholinesterase and butyrylcholinesterase. The progressive inhibition curves for AChE and BuChE are compared and related to ionic attraction and steric requirements of the inhibitors.

Millner OE Jr et al; Synthesis and enzymic evaluation of pyridostigmine analogs used to probe the active sites of acetylcholinesterase and butyrylcholinesterase; J Med Chem 17 (1): 13-8 (1974)


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01-Jan-2021
17-Oct-2024
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