Limaprost

Names

[ Name ]:
Limaprost

[Synonym ]:
17S,20-Dimethyl-trans-delta2-PGE1
(E)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-1-nonenyl)-5-oxocyclopentyl)-2-heptenoic acid
(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)
Limaprost
(2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid
9-Oxo-11a,15a-dihydroxy-17S,20-dimethylprosta-trans-2,trans-13-dienoic Acid
17S,20-Dimethyl-trans-2,3-didehydro-PGE1
(2E,11a,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic Acid
17S-Methyl-w-homo-trans-D2-PGE1
ONO 1206
OP 1206

Biological Activity

[Description]:

Limaprost(OP1206) is a PGE1 analog and potent platelet adhesion inhibitor.Target: OthersLimaprost, an alprostadil (prostaglandin E1) analogue, is a vasodilator that increases blood flow and inhibits platelet aggregation. Limaprost is a n analog of PGE1 with structural modifications intended to give a prolonged half-life and greater potency. It is orally active in both guinea pigs and rats at doses of 100 mg/kg as an inhibitor of ADP and collagen induced platelet aggregation. It is 10-1,000 times more potent than PGE1 as a platelet adhesive inhibitor, measured in vitro. Intra-coronary injection (100 ng/kg) or intravenous injection (3 mg/kg) in anesthetized dogs causes vasodilation and increased coronary blood flow by 60-80%. Significant hypotensive effects were seen at 100 and 300 mg/kg orally in rats [1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> PGE synthase

Research Areas >> Inflammation/Immunology

[References]

[1]. Tsuboi, T., et al., Pharmacological evaluation of OP 1206, a prostaglandin E1 derivative, as an antianginal agent. Arch Int Pharmacodyn Ther, 1980. 247(1): p. 89-102.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
550.6±50.0 °C at 760 mmHg

[ Melting Point ]:
97-100°

[ Molecular Formula ]:
C₂₂H₃₆O₅

[ Molecular Weight ]:
380.518

[ Flash Point ]:
300.9±26.6 °C

[ Exact Mass ]:
380.256287

[ PSA ]:
94.83000

[ LogP ]:
3.15

[ Appearance of Characters ]:
crystalline

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.551

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMF: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UK8362500

CHEMICAL NAME :: Prost-2,13-dien-1-oic acid, 11,15-dihydroxy-17,20-dimethyl-9-oxo-, (2E,11-alpha,13E,15S,17S)-

CAS REGISTRY NUMBER :: 74397-12-9

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

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

REFERENCE :: BAXXDU British UK Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2041368

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 12 mg/kg

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

REFERENCE :: BAXXDU British UK Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2041368

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
25

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
UK8362500

Articles

OP-1206, a prostaglandin E1 derivative, attenuates the thermal hyperesthesia induced by constriction injury to the sciatic nerve in the rat.

Anesth. Analg. 80(3) , 515-20, (1995)

Nerve ischemia induces wallerian degeneration and peripheral neuropathy, the nerve constriction injury induces thermal hyperesthesia. Nerve ischemia is one possible mechanism in the development of the...

Inhibition of platelet aggregation by the cAMP-phosphodiesterase inhibitor, cilostamide, may not be associated with activation of cAMP-dependent protein kinase.

Cell. Signal. 4(4) , 453-63, (1992)

We examined the involvement of cAMP-dependent protein kinase (A kinase)2 in the inhibition by cilostamide, a specific inhibitor of the low Km cAMP-phosphodiesterase (PDE), on 9,11-epithio-11,12-methan...

Correlation between methotrexate-induced intestinal damage and decrease in polyamine content.

Life Sci. 72(6) , 669-76, (2002)

A synthetic analog of prostaglandin E(1), OP-1206 [17S, 20-dimethyl-trans-Delta(2)-prostaglandin E(1)] protects the small intestine from the methotrexate (MTX)-induced damage. The purpose of this stud...