Alminoprofen

Names

[ Name ]:
Alminoprofen

[Synonym ]:
tetraethyldipyrromethane
1H-Pyrrole,2,2'-methylenebis[3,4-diethyl
3,3',4,4'-Tetraethyl-2,2'-dipyrrolylmethane
rac Alminoprofen
2-(p-methallylaminophenyl)-propionic acid
2,2'-methylenebis(3,4-diethylpyrrole)
(+/-)-2-{p-[(2-methylallyl)amino]phenyl}propionic acid

Biological Activity

[Description]:

Alminoprofen (EB-382) is a nonsteroidal anti-inflammatory drug (NSAID) of the phenylpropionic acid class. Alminoprofen possesses a dual anti-inflammatory action, by inhibiting both secretory phospholipase A2 (sPLA2) and COX-2[1].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

sPLA2

COX-2

[In Vitro]

Alminoprofen possesses a dual anti-inflammatory action, by inhibiting both sPLA2 but also COX-2. Alminoprofen (from 0 to 50 μM) induces a dose-related inhibitory response on thelevels of PGE2 formed by the CRL-1517 cell line[1].

[In Vivo]

Alminoprofen (100-300 mg/kg; p.o.) exerts an anti-inflammatory activity[1]. Animal Model: Groups of Wistar Rats (Oedema of the paw)[1] Dosage: 100 mg/kg Administration: P.o. Result: Exerted a statistically significant dose-dependent antagonist action lasting throughout the 2-hr observation period.

[References]

[1]. Raguenes-Nicol C, et al. Anti-inflammatory mechanism of alminoprofen: action on the phospholipid metabolism pathway. Biochem Pharmacol. 1999;57(4):433-443.

Chemical & Physical Properties

[ Density]:
1.107g/cm3

[ Boiling Point ]:
373.1ºC at 760 mmHg

[ Melting Point ]:
107°

[ Molecular Formula ]:
C₁₃H₁₇NO₂

[ Molecular Weight ]:
219.28000

[ Flash Point ]:
179.4ºC

[ Exact Mass ]:
219.12600

[ PSA ]:
49.33000

[ LogP ]:
2.93570

[ Index of Refraction ]:
1.571

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UF5552000

CHEMICAL NAME :: Propionic acid, 2-(4-(methallylamino)phenyl)-

CAS REGISTRY NUMBER :: 39718-89-3

LAST UPDATED :: 199709

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C13-H17-N-O2

MOLECULAR WEIGHT :: 219.31

WISWESSER LINE NOTATION :: QVY1&R DM1Y1&U1

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 :: 550 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,79,1990

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 700 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,79,1990

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 660 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,79,1990

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2400 mg/kg

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

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 14,207,1979

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 705 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,79,1990

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 980 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,79,1990

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1780 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 9,165,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12740 mg/kg/52W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14,2187,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10800 mg/kg/90D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Blood - changes in leukocyte (WBC) count

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14,3019,1986 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 910 mg/kg

SEX/DURATION :: female 17-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - other neonatal measures or effects

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14,3089,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2600 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - abortion

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14,3079,1986