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Substance Name: Neostigmine methylsulfate [USP:JAN]
RN: 51-60-5
UNII: 98IMH7M386
InChIKey: OSZNNLWOYWAHSS-UHFFFAOYSA-M

Note

  • A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.

Molecular Formula

  • C12-H19-N2-O2.C-H3-O4-S

Molecular Weight

  • 334.3908
 

Classification Codes

  • Autonomic Agents
  • Cholinergic
  • Cholinesterase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Parasympathomimetics
  • Peripheral Nervous System Agents
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Neostigmine methylsulfate [USP:JAN]

MeSH Heading

  • Neostigmine

Synonyms

  • (3-(Dimethylcarbamoxy)phenyl)trimethylammonium methyl sulfate
  • (3-(Dimethylcarbamoyl)oxyphenyl)trimethylammonium methyl sulfate
  • (3-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester
  • (m-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate
  • 3-(Dimethylcarbamoxy)phenyl trimethylammonium methyl sulfate
  • Ammonium, (3-(dimethylcarbamoyloxy)phenyl)trimethyl-, methylsulfate
  • Ammonium, (m-hydroxyphenyl)trimethyl-, methyl sulfate, dimethylcarbamate
  • AR-32
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, methyl sulfate
  • Bloxiverz
  • Carbamic acid, dimethyl-, ester with (m-hydroxyphenyl)trimethylammonium methyl sulfate
  • Carbamic acid, N,N-dimethyl-, 3-(trimethylammonio)phenyl ester, methylsulfate
  • Carbamic acid, N,N-dimethyl-, 3-dimethylaminophenyl ester, methosulfate
  • CCRIS 3274
  • Dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfate
  • EINECS 200-109-5
  • Eustigmin methyl sulfate
  • Eustigmin methylsulfate
  • GD 65
  • Hodostin
  • Kirkstigmine methyl sulfate
  • Leostigmine methyl sulfate
  • Neoeserine methyl sulfate
  • Neostigmeth
  • Neostigmine methosulfate
  • Neostigmine methyl sulfate
  • Neostigmine methylsulfate
  • Neostigmine methylsulphate
  • Neostigmine monomethyl sulfate
  • Neostigmine monomethylsulfate
  • Neostigminmetilsulfat
  • Normastigmin
  • NSC 93753
  • Philostigmin methyl sulfate
  • Polstigmine
  • Proserine
  • Proserine methyl sulfate
  • Proserinum
  • Prostigmin
  • Prostigmine
  • SB-23
  • Stigmanol methyl sulfate
  • Stigmosan methyl sulfate
  • Synstigmine
  • Synthostigmine methyl sulfate
  • Syntostigmin
  • Syntostigmin (injection)
  • Syntostigmin (VAN)
  • Syntostigmin methyl sulfate
  • Syntostigmine methyl sulfate
  • TL-1394
  • UNII-98IMH7M386
  • Vagostigmine methyl sulfate

Systematic Names

  • Ammonium, (m-hydroxyphenyl)trimethyl-, methyl sulfate, dimethylcarbamate
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-, methyl sulfate
  • Neostigmine methylsulphate
  • Neostigmine metilsulfate

Registry Numbers

CAS Registry Number

  • 51-60-5

FDA UNII

  • 98IMH7M386

Other Registry Number

  • 59954-03-9

Related Registry Number

  • 59-99-4 (Parent)

System Generated Number

  • 0000051605

Molecular Formulas

Molecular Formula

  • C12-H19-N2-O2.C-H3-O4-S

Molecular Formula Fragments

  • C-H3-O4-S
  • C12-H19-N2-O2
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1

InChIKey

OSZNNLWOYWAHSS-UHFFFAOYSA-M

Smiles

COS(=O)(=O)[O-].CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 300ug/kg (0.3mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 545, 1959.
cat LDLo subcutaneous 50ug/kg (0.05mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC		 National Technical Information Service. Vol. PB158-508,
dog LDLo subcutaneous 50ug/kg (0.05mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 National Technical Information Service. Vol. PB158-508,
guinea pig LDLo subcutaneous 50ug/kg (0.05mg/kg) BEHAVIORAL: COMA

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 National Technical Information Service. Vol. PB158-508,
mouse LD50 intraperitoneal 230ug/kg (0.23mg/kg)   Archiv fuer Toxikologie. Vol. 29, Pg. 39, 1972.
mouse LD50 intravenous 160ug/kg (0.16mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 16, 1950.
mouse LD50 oral 7500ug/kg (7.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 16, 1950.
mouse LD50 subcutaneous 420ug/kg (0.42mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 16, 1950.
rabbit LD50 intramuscular 310ug/kg (0.31mg/kg) BEHAVIORAL: TREMOR Archives Internationales de Pharmacodynamie et de Therapie. Vol. 81, Pg. 276, 1950.
rabbit LD50 intravenous 250ug/kg (0.25mg/kg)   Drugs in Japan Vol. 6, Pg. 556, 1982.
rabbit LD50 subcutaneous 500ug/kg (0.5mg/kg)   Drugs in Japan Vol. 6, Pg. 556, 1982.
rat LD50 subcutaneous 334ug/kg (0.334mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 569, 1973.