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Substance Name: Glycopyrrolate [USAN:USP]
RN: 596-51-0
InChIKey: VPNYRYCIDCJBOM-UHFFFAOYSA-M

Note

  • A muscarinic antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics.

Molecular Formula

  • C19-H28-N-O3.Br

Molecular Weight

  • 398.3382
 

Classification Codes

  • Adjuvants, Anesthesia
  • Anticholinergic
  • Central Nervous System Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Muscarinic Antagonists
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Glycopyrrolate
  • Glycopyrrolate [USAN:USP]

MeSH Heading

  • Glycopyrrolate

Synonyms

  • 1,1-Dimethyl-3-hydroxypyrrolidinium bromide alpha-cyclopentylmandelate
  • 1-Methyl-3-pyrrolidyl alpha-phenylcyclopentaneglycolate methobromide
  • 3-Hydroxy-1,1-dimethylpyrrolidinium bromide alpha-cyclopentylmandelate
  • AHR 504
  • AHR-504
  • Asecryl
  • Bromure de glycopyrronium
  • Bromure de glycopyrronium [INN-French]
  • Bromuro de glicopirronio
  • Bromuro de glicopirronio [INN-Spanish]
  • Copyrrolate
  • Cuvposa
  • EINECS 209-887-0
  • Gastrodyn
  • Glycopyrrolate
  • Glycopyrrolate bromide
  • Glycopyrronii bromidum
  • Glycopyrronii bromidum [INN-Latin]
  • Glycopyrronium bromide
  • Nodapton
  • NSC 250836
  • NSC 251251
  • NSC 251252
  • NVA 237
  • Robinul
  • Robinul Forte
  • Seebri
  • Seebri Neohaler
  • Tarodyl
  • Tarodyn

Systematic Names

  • Glycopyrronium bromide
  • Pyrrolidinium, 1,1-dimethyl-3-hydroxy-, bromide, alpha-cyclopentylmandelate
  • Pyrrolidinium, 3-((cyclopentylhydroxyphenylacetyl)oxy)-1,1-dimethyl-, bromide
  • Pyrrolidinium, 3-hydroxy-1,1-dimethyl-, bromide, alpha-cyclopentylmandelate (8CI)

Registry Numbers

CAS Registry Number

  • 596-51-0

System Generated Number

  • 0000596510

Molecular Formulas

Molecular Formula

  • C19-H28-N-O3.Br

Molecular Formula Fragments

  • Br
  • C19-H28-N-O3
  • COMPONENT

Structure Descriptors

InChI

1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1

InChIKey

VPNYRYCIDCJBOM-UHFFFAOYSA-M

Smiles

[Br-].C[N+]1(C)CCC(C1)OC(=O)C(O)(C2CCCC2)c3ccccc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 90mg/kg (90mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 523, 1960.
mouse LD50 intravenous 15mg/kg (15mg/kg)   "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 55, 1969.
mouse LD50 oral 570mg/kg (570mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 523, 1960.
mouse LD50 subcutaneous 122mg/kg (122mg/kg)   Yakkyoku. Pharmacy. Vol. 26, Pg. 741, 1975.
rabbit LD50 intravenous 29100ug/kg (29.1mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 627, 1973.
rabbit LD50 oral 2360mg/kg (2360mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 627, 1973.
rat LD50 intraperitoneal 196mg/kg (196mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toxicology and Applied Pharmacology. Vol. 17, Pg. 361, 1970.
rat LD50 oral 709mg/kg (709mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 93, 1971.
rat LD50 subcutaneous 833mg/kg (833mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 627, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 192.5 deg C   EXP
log P (octanol-water) -0.990 (none)   EST
Atmospheric OH Rate Constant 3.53E-11 cm3/molecule-sec 25 EST

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