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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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PHARMACEUTICALS","customerCountry":"INDIA","quantity":"210.00","actualQuantity":"210","unit":"KGS","unitRateFc":"350","totalValueFC":"74878.4","currency":"USD","unitRateINR":"29610","date":"03-Aug-2024","totalValueINR":"6218100","totalValueInUsd":"74878.4","indian_port":"Ahmedabad Air","hs_no":"29333990","bill_no":"4853208","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA MATTEOTTI 24928062 CAMERI (NO)SDNF IT","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"}]
    01-Jan-2021
    03-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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