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Substance Name: Glyburide [USAN:USP]
RN: 10238-21-8
UNII: SX6K58TVWC
InChIKey: ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Note

  • An antidiabetic sulfonylurea derivative with actions similar to those of chlorpropamide.

Molecular Formula

  • C23-H28-Cl-N3-O5-S

Molecular Weight

  • 494.0092
 

Classification Codes

  • Antidiabetic
  • Drug / Therapeutic Agent
  • Human Data
  • Hypoglycemic Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Glibenclamide [INN]
  • Glyburide
  • Glyburide [USAN:USP]

MeSH Heading

  • Glyburide

Synonyms

  • 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea
  • 1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea
  • 5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide
  • Adiab
  • Apo-Glibenclamide
  • Azuglucon
  • Bastiverit
  • Benclamin
  • Benzamide, 5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxy-
  • Betanase
  • Betanese 5
  • BRN 2230085
  • Calabren
  • Cytagon
  • Daonil
  • Debtan
  • Diabeta
  • Dibelet
  • Duraglucon
  • EINECS 233-570-6
  • Euclamin
  • Euglucan
  • Euglucon
  • Euglucon 5
  • Euglykon
  • GBN 5
  • Gen-Glybe
  • Gewaglucon
  • Gilemal
  • Glamide
  • Gliban
  • Gliben
  • Glibenbeta
  • Glibenclamid AL
  • Glibenclamid Basics
  • Glibenclamid Fabra
  • Glibenclamid Genericon
  • Glibenclamid Heumann
  • Glibenclamid Riker M.
  • Glibenclamid-Cophar
  • Glibenclamid-Ratiopharm
  • Glibenclamida
  • Glibenclamida [INN-Spanish]
  • Glibenclamide
  • Glibenclamidum
  • Glibenclamidum [INN-Latin]
  • Glibenil
  • Glibens
  • Glibesyn
  • Glibet
  • Glibetic
  • Glibil
  • Gliboral
  • Glicem
  • Glidiabet
  • Glimel
  • Glimide
  • Glisulin
  • Glitisol
  • Glubate
  • Gluben
  • Glucobene
  • Glucohexal
  • Glucolon
  • Glucomid
  • Glucoremed
  • Glucoven
  • Glyben
  • Glybenclamide
  • Glybenzcyclamide
  • Glyburide
  • Glyburide (micronized)
  • Glycomin
  • Glynase
  • HB 419
  • Hemi-Daonil
  • Hexaglucon
  • Humedia
  • Lederglib
  • Libanil
  • Lisaglucon
  • Maninil
  • Med-Glionil
  • Melix
  • Micronase
  • Micronized glyburide
  • Miglucan
  • N-(4-(2-(5-Chloro-2-methoxybenzamido)ethyl)phenylsulfonyl)-N'-cyclohexylurea
  • N-(4-(beta-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff
  • Nadib
  • Neogluconin
  • Norglicem 5
  • Normoglucon
  • Novo-Glyburide
  • Orabetic
  • Pira
  • Praeciglucon
  • Prodiabet
  • Renabetic
  • RP-1127
  • Semi-daonil
  • Semi-Euglucon
  • Semi-Gliben-Puren N
  • Sugril
  • Suraben
  • Tiabet
  • U 26452
  • U-26,452
  • UNII-SX6K58TVWC
  • UR 606
  • Urea, 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexyl-
  • Yuglucon

Systematic Names

  • Benzamide, 5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxy-
  • Glibenclamide
  • Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl-

Registry Numbers

CAS Registry Number

  • 10238-21-8

FDA UNII

  • SX6K58TVWC

System Generated Number

  • 0010238218

Structure Descriptors

InChI

1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)

InChIKey

ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Smiles

c1(Cl)cc(c(OC)cc1)C(NCCc1ccc(cc1)S(NC(NC1CCCCC1)=O)(=O)=O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 10gm/kg (10000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
guinea pig LD50 oral > 15gm/kg (15000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
man TDLo oral 209mg/kg/4Y-I (209mg/kg) LIVER: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "JAUNDICE, CHOLESTATIC"		 Western Journal of Medicine. Vol. 168, Pg. 274, 1998.
mouse LD50 intraperitoneal 2700mg/kg (2700mg/kg)   Pharmaceutical Chemistry Journal Vol. 29, Pg. 265, 1995.
mouse LD50 oral 3250mg/kg (3250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1640, 1966.
mouse LD50 subcutaneous > 20gm/kg (20000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
rabbit LD oral > 20gm/kg (20000mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
rat LD50 intraperitoneal 3750mg/kg (3750mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
rat LD50 oral > 20gm/kg (20000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
rat LD50 subcutaneous > 20gm/kg (20000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
women TDLo oral 147ug/kg (0.147mg/kg) ENDOCRINE: HYPOGLYCEMIA

BEHAVIORAL: COMA		 Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 142, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 169 deg C   EXP
log P (octanol-water) 4.790 (none)   EST
Water Solubility 4 mg/L 27 EXP
Atmospheric OH Rate Constant 4.00E-11 cm3/molecule-sec 25 EST

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