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Benorilate

Names

[ CAS No. ]:
5003-48-5

[ Name ]:
Benorilate

[Synonym ]:
Fenasprate
4'-(Acetamido)phenyl-2-acetoxybenzoate
Fenasparate
(1E)-N-{4-[(2-Acetoxybenzoyl)oxy]phenyl}ethanimidic acid
4-Acetamidophenyl 2-acetoxybenzoate
p-Acetamidophenyl acetylsalicylate
Benzoic acid, 2-(acetyloxy)-, 4-[[(1E)-1-hydroxyethylidene]amino]phenyl ester
Benorilate
EINECS 225-674-5
4-(acetylamino)phenyl 2-(acetyloxy)benzoate
Benorylate
MFCD00864257
Aspirin acetaminophen ester
(4-acetamidophenyl) 2-acetyloxybenzoate
Benzoic acid, 2-(acetyloxy)-, 4-(acetylamino)phenyl ester
Salicylic Acid Acetate Ester with 4-Hydroxyacetanilide
4-Acetamidophenyl salicylate acetate
Salipran

Biological Activity

[Description]:

Benorylate (Benoral) is the esterification product of paracetamol and acetylsalicylic acid. It has anti-inflammatory, analgesic and antipyretic properties. Benorylate could also inhibit prostaglandin (PG) synthesis.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor
Research Areas >> Inflammation/Immunology

[Target]

Prostaglandin[4].


[In Vitro]

Benorilate is an esterified aspirin preparation whose antirheumatic properties are reported to be as good as those of aspirin[1]. Benorylate causes a large decrease in the liver’s conversion rate of lactate into glucose, an important component of glucose homeostasis. Benorylate also impairs the urea synthesis rate from ammonia, another important function of the liver[2].

[In Vivo]

Benorylate is probably absorbed as the intact molecule which accounts for its good gastric tolerance[3]. Benorylate could inhibit PG synthesis in laboratory animals and in human tissue[4].

[References]

[1]. Croft DN, et al. Gastric bleeding and benorylate, a new aspirin. Br Med J. 1972 Sep 2;3(5826):545-7.

[2]. Castell JV, et al. Effects of benorylate and impacina on the metabolism of cultured hepatocytes. Xenobiotica. 1985 Aug-Sep;15(8-9):743-9.

[3]. Wright V, et al. A review of benorylate - a new antirheumatic drug. Scand J Rheumatol Suppl. 1975;13:5-8.

[4]. A. Bennett , et al. Inhibition of Prostaglandin Synthesis by Benorylate. Rheumatology, Volume XII, Issue suppl, 1 January 1973, Pages 101-105.


[Related Small Molecules]

Dinoprostone | Prostaglandin E1 | E7046 | ONO-AE3-208 | PF 04418948 | Fevipiprant | grapiprant | TG6-10-1 | Taprenepag | GW 627368 | MRE-269 | Ramatroban | AH 6809 | Laropiprant | AZD1981

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
511.5±60.0 °C at 760 mmHg

[ Melting Point ]:
177-181ºC

[ Molecular Formula ]:
C17H15NO5

[ Molecular Weight ]:
313.305

[ Flash Point ]:
263.1±32.9 °C

[ Exact Mass ]:
313.095032

[ PSA ]:
81.70000

[ LogP ]:
2.22

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.566

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VO0720000
CHEMICAL NAME :
Salicylic acid, acetate, ester with 4'-hydroxyacetanilide
CAS REGISTRY NUMBER :
5003-48-5
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C17-H15-N-O5
MOLECULAR WEIGHT :
313.33
WISWESSER LINE NOTATION :
1VOR BVOR DMV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1280 mg/kg/8D-I
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Lungs, Thorax, or Respiration - respiratory stimulation Nutritional and Gross Metabolic - dehydration
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 288,1344,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0080609
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1830 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3431293
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1551 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 28,1692,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1255 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3431293 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3960 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
SEIJBO Senten Ijo. Congenital Anomalies. (Nippon Senten Ijo Gakkai, c/o Kinki Daigaku Igakubu Kaibagaku Kyoshitsu, 380 Nishiyama, Sayama-cho, Mirami-Kawachi-gun, Osaka-fu, Japan) V.1-26, 1960-86. For publisher information, see CGANE7. Volume(issue)/page/year: 20,143,1980

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2924299090

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%