Cinromide

Names

[ Name ]:
Cinromide

[Synonym ]:
MFCD00075351
cinromide
trans 3-bromo-N-ethylcinnamamide
Cinromide (usan/inn)
m-Bromo-N-ethylcinnamamide
trans-3-Brom-N-ethylzimtsaeureamid
(e)-3-(3-bromophenyl)-n-ethyl-2-propenamide

Biological Activity

[Description]:

Cinromide is a broad-spectrum anticonvulsant agent.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

Cinromide (10-100 μM) inhibits 5-HT-induced contractions in rat fundus strips by 46%. Cinromide (100 μM) inhibits monoamine oxidase prepared from both liver and brain of rats[1].

[In Vivo]

Cinromide shows electroshock convulsion and leptazol(pentetrazo1)-induced convulsion in mice, with ED50s of 60 ± 11 mg/kg, 90 ± 15 mg/kg and 80 ± 15 mg/kg, 300 ± 61 mg/kg for i.p. and oral administrion, respectively. Cinromide produces a dose-related antileptazol activity with an ED50 value of 58 ± 11 mg/kg by i.p. administration in rats. Furthermore, Cinromide (75 mg/kg) significantly elevates the amount of leptazol needed to induce clonic seizures in the intravenously infused leptazol-threshold test in rats. Cinromide (300 mg/kg, i.p) shows no sifnificant effect on the anaesthetized open-chested dogs after 4 h treatment, neither in conscious dogs after 5-h oral treatment with 300 and 600 mg/kg of Cinromide[1]. Cinromide (40 mg/kg, i.v.) depresses the response of the neuron to the unconditioned maxillary nerve stimulus, increasing the latency and decreasing the number of spikes, and depresses the response of the neuron to the unconditioned maxillary nerve stimulus, increasing the latency and decreasing the number of spikes. Cinromide (20, 40, 80 mg/kg, i.v.) increases the latency of the unconditioned response and segmental inhibition dose-dependently. Cinromide decreases periventricular inhibition and EEG[2].

[Animal admin]

Cinromide is dissolved in propylene glycol to produce a solution containing 50 mg/mL. It is slowly injected into the femoral vein over a 3-min period. Only one neuron in each cat is studied. To evaluate the dose-response relationship, the drug is given in three cumulative doses. The interval between drug injections is 15 min. Blood samples for drug level measurement are taken 10 min after each injection. Plasma levels of cinromide and its metabolites are determined by high-performance liquid chromotography[2].

[References]

[1]. Soroko FE, et al. Cinromide (3-bromo-N-ethylcinnanamide), novel anticonvulsant agent. J Pharm Pharmacol. 1981 Nov;33(11):741-3.

[2]. Fromm GH, et al. Effect of cinromide on inhibitory and excitatory mechanisms. Epilepsia. 1983 Aug;24(4):394-400.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.369g/cm3

[ Boiling Point ]:
417.5ºC at 760mmHg

[ Melting Point ]:
89-91ºC(lit.)

[ Molecular Formula ]:
C₁₁H₁₂BrNO

[ Molecular Weight ]:
254.12300

[ Flash Point ]:
206.3ºC

[ Exact Mass ]:
253.01000

[ PSA ]:
29.10000

[ LogP ]:
2.98930

[ Index of Refraction ]:
1.591

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UC6314000

CHEMICAL NAME :: 2-Propenamide, 3-(3-bromophenyl)-N-ethyl-, (E)-

CAS REGISTRY NUMBER :: 58473-74-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C11-H12-Br-N-O

MOLECULAR WEIGHT :: 254.15

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4437 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 33,741,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2277 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 33,741,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 660 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 33,741,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
UC6314000

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Prediction of steady-state behavior of metabolite from dosing of parent drug.

J. Pharm. Sci. 69(5) , 610-2, (1980)

Variability in the determination of fraction metabolized in a triangular metabolic problem and its resolution with stable isotope methodology.

J. Pharm. Sci. 73(2) , 285-7, (1984)

Simultaneous determination of the anticonvulsants, cinromide (3-bromo-n-ethylcinnamamide), 3-bromocinnamamide, and carbamazepine in plasma by high-performance liquid chromatography.

J. Chromatogr. A. 163(2) , 187-93, (1979)

A high-performance liquid chromatographic method is described for monitoring plasma concentrations of cinromide (3-bromo-N-ethylcinnamamide) and its de-ethylated metabolite. Carbamazepine levels can b...

Related Compounds

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