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Substance Name: Pyridostigmine bromide [USP:INN:BAN:JAN]
RN: 101-26-8
UNII: KVI301NA53
InChIKey: VNYBTNPBYXSMOO-UHFFFAOYSA-M

Note

  • 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.

Molecular Formula

  • C9-H13-N2-O2.Br

Molecular Weight

  • 261.1177
 

Classification Codes

  • Cholinergic
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Pyridostigmine bromide
  • Pyridostigmine bromide [USP:INN:BAN:JAN]

MeSH Heading

  • Pyridostigmine bromide

Synonyms

  • 1-Methyl-3-hydroxypyridinium bromide dimethylcarbamate
  • 3-(((Dimethylamino)carbonyl)oxy)-1-methylpyridinium bromide
  • 3-(Dimethylcarbamyloxy)-1-methylpyridinium bromide
  • 3-Hydroxy-1-methylpyridinium bromide dimethylcarbamate
  • 3-Hydroxy-1-methylpyridinium bromide dimethylcarbamate (ester)
  • Bromure de pyridostigmine
  • Bromure de pyridostigmine [INN-French]
  • Bromuro de piridostigmina
  • Bromuro de piridostigmina [INN-Spanish]
  • Carbamic acid, dimethyl-, ester with 3-hydroxy-1-methylpyridinium bromide
  • CCRIS 6798
  • Dimethylcarbamic acid ester of 3-hydroxy-1-methylpyridinium bromide
  • EINECS 202-929-9
  • HSDB 3924
  • Kalimin
  • Kalymin
  • Mestinon
  • Mestinon bromide
  • Piridostigmina bromuro
  • Piridostigmina bromuro [DCIT]
  • Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, bromide
  • Pyridinium, 3-hydroxyl-1-methyl-, bromide, dimethylcarbamate
  • Pyridostigmine bromide
  • Pyridostigmini bromidum
  • Pyridostigmini bromidum [INN-Latin]
  • Regonal
  • Regonol
  • Ro 1-5130
  • UNII-KVI301NA53

Systematic Names

  • Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, bromide
  • Pyridinium, 3-hydroxy-1-methyl-, bromide, dimethylcarbamate (ester)
  • Pyridostigmine bromide

Registry Numbers

CAS Registry Number

  • 101-26-8

FDA UNII

  • KVI301NA53

System Generated Number

  • 0000101268

Molecular Formulas

Molecular Formula

  • C9-H13-N2-O2.Br

Molecular Formula Fragments

  • Br
  • C9-H13-N2-O2
  • COMPONENT

Structure Descriptors

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

InChIKey

VNYBTNPBYXSMOO-UHFFFAOYSA-M

Smiles

c1(OC(N(C)C)=O)c[n+](ccc1)C.[BrH-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 9mg/kg (9mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Israel Journal of Medical Sciences. Vol. 27, Pg. 659, 1991.
mouse LD50 intraperitoneal 1mg/kg (1mg/kg)   Drugs in Japan Vol. 6, Pg. 354, 1982.
mouse LD50 intravenous 1500ug/kg (1.5mg/kg)   Medicinal Chemistry, A Series of Reviews. Vol. 3, Pg. 329, 1956.
mouse LD50 oral 16mg/kg (16mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gendai no Rinsho. Vol. 2, Pg. 828, 1968.
mouse LD50 subcutaneous 1500ug/kg (1.5mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gendai no Rinsho. Vol. 2, Pg. 828, 1968.
rat LD50 intramuscular 2790ug/kg (2.79mg/kg)   Drug and Chemical Toxicology. Vol. 7, Pg. 507, 1984.
rat LD50 intraperitoneal 2699ug/kg (2.699mg/kg)   Fundamental and Applied Toxicology. Vol. 4, Pg. S195, 1984.
rat LD50 oral 37500ug/kg (37.5mg/kg)   Drugs in Japan Vol. -, Pg. 1042, 1995.
rat LD50 subcutaneous 3100ug/kg (3.1mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 145, 1983.
women TDLo oral 7800ug/kg (7.8mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

PERIPHERAL NERVE AND SENSATION: FASCICULATIONS
Israel Journal of Medical Sciences. Vol. 27, Pg. 659, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 153 deg C   EXP
log P (octanol-water) -3.730 (none)   EST
Atmospheric OH Rate Constant 1.53E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.