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Substance Name: Flumazenil [USAN:USP:INN:BAN]
RN: 78755-81-4
UNII: 40P7XK9392
InChIKey: OFBIFZUFASYYRE-UHFFFAOYSA-N

Note

  • A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.

Molecular Formula

  • C15-H14-F-N3-O3

Molecular Weight

  • 303.2916
 

Classification Codes

  • Antagonist (to Benzodiazepine)
  • Antidotes
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Modulators
  • Human Data
  • Neurotransmitter Agents
  • Protective Agents
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Flumazenil
  • Flumazenil [USAN:USP:INN:BAN]

MeSH Heading

  • Flumazenil

Synonyms

  • 4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester
  • Anexate
  • BRN 4763661
  • Ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate
  • Ethyl 8-fluoro-5-methyl-5,6-dihydro-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate
  • Flumazenil
  • Flumazenilo
  • Flumazenilo [Spanish]
  • Flumazenilum
  • Flumazenilum [Latin]
  • Flumazepil
  • Flumazil
  • Lanexat
  • Ro 15-1788/000
  • Ro 151788
  • Ro-15-1788
  • Romazicon
  • UNII-40P7XK9392

Systematic Name

  • 4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester

Registry Numbers

CAS Registry Number

  • 78755-81-4

FDA UNII

  • 40P7XK9392

System Generated Number

  • 0078755814

Structure Descriptors

InChI

1S/C15H14FN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3

InChIKey

OFBIFZUFASYYRE-UHFFFAOYSA-N

Smiles

n12c3c(C(=O)N(Cc1c(nc2)C(=O)OCC)C)cc(cc3)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous > 30mg/kg (30mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
dog LDLo oral > 640mg/kg (640mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
man LDLo intravenous 5700ng/kg/C (0.0057mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: CHANGE IN RATE		 British Medical Journal. Vol. 304, Pg. 1415, 1992.
mouse LD50 intraperitoneal 4gm/kg (4000mg/kg)   Drugs of the Future. Vol. 7, Pg. 402, 1982.
mouse LD50 intravenous 143mg/kg (143mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY		 Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
mouse LD50 oral 1300mg/kg (1300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: TREMOR		 Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
mouse LDLo subcutaneous > 1gm/kg (1000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rabbit LD50 oral 2gm/kg (2000mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
rat LD50 intraperitoneal 1360mg/kg (1360mg/kg)   Drugs of the Future. Vol. 7, Pg. 402, 1982.
rat LD50 intravenous 85mg/kg (85mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY		 Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
rat LD50 oral 4200mg/kg (4200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: REGIDITY		 Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
women TDLo intravenous 4ug/kg (0.004mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Pediatric Emergency Care. Vol. 11, Pg. 186, 1995.
women TDLo oral 2mg/kg/2D-I (2mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: AGGRESSION

BEHAVIORAL: EXCITEMENT		 Lancet. Vol. 339, Pg. 488, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 201-203 deg C   EXP
log P (octanol-water) 1 (none)   EXP
Water Solubility 128 mg/L 25 EST
Vapor Pressure 8.30E-10 mm Hg 25 EST
Henry's Law Constant 9.89E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.63E-11 cm3/molecule-sec 25 EST

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