Licofelone

Names

[ Name ]:
Licofelone

[Synonym ]:
Licofelone
ML-3000
[6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
[2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid
2-[2-(4-Chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid
1H-Pyrrolizine-5-acetic acid, 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-

Biological Activity

[Description]:

Licofelone (ML-3000) is a dual COX/5-lipoxygenase (5-LOX) inhibitor for the treatment of osteoarthritis. Licofelone (ML-3000) exerts anti-inflammatory and anti-proliferative effects. Licofelone (ML-3000) induces apoptosis, and decreases the production of proinflammatory leukotrienes and prostaglandins[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> COX

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

[References]

[1]. Tavolari S, et al. Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade. Carcinogenesis. 2008 Feb;29(2):371-80.

[2]. Alvaro-Gracia JM, et al. Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis. Rheumatology (Oxford). 2004 Feb;43 Suppl 1:i21-5.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
539.7±50.0 °C at 760 mmHg

[ Melting Point ]:
162-163ºC

[ Molecular Formula ]:
C₂₃H₂₂ClNO₂

[ Molecular Weight ]:
379.879

[ Flash Point ]:
280.2±30.1 °C

[ Exact Mass ]:
379.133911

[ PSA ]:
42.23000

[ LogP ]:
6.73

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.627

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY7759650

CHEMICAL NAME :: 1H-Pyrrolizine-5-acetic acid, 2,3-dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-

CAS REGISTRY NUMBER :: 156897-06-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C23-H22-Cl-N-O2

MOLECULAR WEIGHT :: 379.91

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >300 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: 45,159,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1100 mg/kg/11D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from duodenum

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,1329,1994

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds

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