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Substance Name: Distigmine bromide [INN:BAN:JAN]
RN: 15876-67-2
UNII: 750F36OP6J
InChIKey: GJHSNEVFXQVOHR-UHFFFAOYSA-L

Note

  • Parasympathomimetic, reversible cholinesterase inhibitor, similar to neostigmine used for postoperative intestinal and bladder atony, also in myasthenia gravis.

Molecular Formulas

  • C22-H32-Br2-N4-O4
  • C22-H32-N4-O4.2Br

Molecular Weight

  • 576.327
 

Classification Codes

  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Neurotransmitter Agents
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Names and Synonyms

Name of Substance

  • Distigmine
  • Distigmine bromide [INN:BAN:JAN]

Synonyms

  • 3,3'-(1,6-Hexanediylbis((methylimino)carbonyl)oxy)bis(1-methylpyridinium) dibromide
  • 3-Hydroxy-1-methylpyridinium bromide hexamethylenebis(methylcarbamate)
  • BC 51
  • Bromure de distigmine
  • Bromure de distigmine [INN-French]
  • Bromuro de distigmina
  • Bromuro de distigmina [INN-Spanish]
  • Distigmine bromide
  • Distigmini bromidum
  • Distigmini bromidum [INN-Latin]
  • EINECS 240-013-0
  • Hexamarium
  • Ubretid
  • Ubritil
  • UNII-750F36OP6J

Systematic Names

  • 3-Hydroxy-1-methylpyridinium bromide hexamethylenebis-(N-methylcarbamate)
  • Distigmine bromide
  • Pyridinium, 3,3'-(1,6-hexanediylbis((methylimino)carbonyl)oxy)bis-1-methyl-, dibromide
  • Pyridinium, 3-hydroxy-1-methyl-, bromide, hexamethylenebis(methylcarbamate)

Registry Numbers

CAS Registry Number

  • 15876-67-2

FDA UNII

  • 750F36OP6J

System Generated Number

  • 0015876672

Molecular Formulas

Molecular Formulas

  • C22-H32-Br2-N4-O4
  • C22-H32-N4-O4.2Br

Molecular Formula Fragments

  • Br
  • C22-H32-N4-O4
  • COMPONENT

Structure Descriptors

InChI

1S/C22H32N4O4.2BrH/c1-23-13-9-11-19(17-23)29-21(27)25(3)15-7-5-6-8-16-26(4)22(28)30-20-12-10-14-24(2)18-20;;/h9-14,17-18H,5-8,15-16H2,1-4H3;2*1H/q+2;;/p-2

InChIKey

GJHSNEVFXQVOHR-UHFFFAOYSA-L

Smiles

c1(OC(N(CCCCCCN(C(Oc2c[n+](ccc2)C)=O)C)C)=O)c[n+](ccc1)C.[BrH-].[BrH-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 310ug/kg (0.31mg/kg)   Drugs in Japan Vol. 6, Pg. 349, 1982.
mouse LD50 intravenous 300ug/kg (0.3mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
mouse LD50 oral 10500ug/kg (10.5mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
mouse LD50 subcutaneous 900ug/kg (0.9mg/kg)   Drugs in Japan Vol. 6, Pg. 349, 1982.
rat LD50 intraperitoneal 740ug/kg (0.74mg/kg)   Drugs in Japan Vol. 6, Pg. 349, 1982.
rat LD50 intravenous 740ug/kg (0.74mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
rat LD50 oral 10mg/kg (10mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 68, 1969.
rat LD50 subcutaneous 1080ug/kg (1.08mg/kg)   Drugs in Japan Vol. 6, Pg. 349, 1982.
women TDLo oral 700ug/kg/7D-I (0.7mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE
British Journal of Clinical Practice. Vol. 48, Pg. 103, 1994.
women TDLo oral 900ug/kg/3D (0.9mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: OTHER CHANGES

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Japanese Journal of Toxicology. Vol. 4, Pg. 383, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.430 (none)   EST
Atmospheric OH Rate Constant 5.14E-11 cm3/molecule-sec 25 EST

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