Basic information
- Name:
Flumazenil
- CAS No.:
78755-81-4
- Molecular Structure:
- Formula:
- C15H14FN3O3
- Synonyms:
- Anexate;Flumazepil;Flumazenil [USAN:BAN:INN];Romazicon;Flumazenilum [Latin];Flumazenil (JAN/USP);Romazicon (TN);4H-Imidazo[1,5-a][1,4]benzodiazepine-3- carboxylic acid,8-fluoro-5,6-dihydro-5- methyl-6-oxo-,ethyl ester;Flumazenilo;Lanexat;Ethyl 8-fluoro-5-methyl-5,6-dihydro-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate;4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester;Ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate;
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Chemistry
IUPAC Name: Ethyl 8-fluoro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate
Synonyms of of Flumazenil (CAS NO.78755-81-4): 4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester ; 4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester ; 8-Fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester ; 8-Fluoro-5-méthyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazépine-3-carboxylate d'éthyle
Molecular Structure : 
Molecular Formula: C15H14FN3O3
Molecular Weight: 303.29
CAS NO: 78755-81-4
Mol File: 78755-81-4.mol
H bond acceptors: 6
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 64.43 Å2
Index of Refraction: 1.633
Molar Refractivity: 77.58 cm3
Molar Volume: 217 cm3
Surface Tension: 48.4 dyne/cm
Density: 1.39 g/cm3
Flash Point: 273.1 °C
Enthalpy of Vaporization: 80.27 kJ/mol
Boiling Point: 528 °C at 760 mmHg
Vapour Pressure: 3.1E-11 mmHg at 25°C
Appearance: Colourless crystals
Melting point: 201-203°C
Storage temp: 2-8°C
Water Solubility : 128 mg/L
SMILES: Fc2cc1C(=O)N(C)Cc3c(ncn3c1cc2)C(=O)OCC
InChI: InChI=1/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-UHFFFAOYAD
Std. InChI: 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
Std. InChIKey: OFBIFZUFASYYRE-UHFFFAOYSA-N
Product Categories of Flumazenil (CAS NO.78755-81-4): Active Pharmaceutical Ingredients;GABA/Glycine receptor
Uses
Uses of Flumazenil (CAS NO.78755-81-4):
Flumazenil (CAS NO.78755-81-4) is used to against the sedative effect and disorientation after use of overdose of benzodiazepine drugs leather, and has anticonvulsant activity and antiepileptic effect. It can also be used after the recovery period and encephalopathy due to cirrhosis of the liver due to alcoholism, unexplained loss of consciousness diagnostic medicine. Besides it is also used to identify the benzodiazepine class and other drug intoxication or brain damage. It is still used as central nervous system stimulant.
Production
Raw materials Hydrogen peroxide-->Ethyl cyanoacetate-->N,N-Dimethylaniline-->Anthranilic acid-->Sodium tert-butoxide-->Sarcosine-->6-Fluoroisatoic anhydride-->5-Fluoroisatin
4 - Fluoro--2 - (N-carboxy amino) benzoic acid and N-Methyl glycine cyclization to generate compounds (Ⅲ), and then cyclization with 2 - Cyano-ethyl acetate , received Flumazenil (CAS NO.78755-81-4).
Toxicity Data With Reference
| 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: CARDIOMYOPATHY INCLUDING INFARCTION CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) 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: TREMOR BEHAVIORAL: REGIDITY | 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: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: REGIDITY | 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: EXCITEMENT BEHAVIORAL: AGGRESSION | Lancet. Vol. 339, Pg. 488, 1992. |
Safety Profile
Hazard Codes 
Xi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-27-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany 2
RTECS NI2922170
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