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LIMAPROST

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LIMAPROST Basic information

Product Name:
LIMAPROST
Synonyms:
  • (2e,11-alpha,13e,15s,17s)-11,15-dihydroxy-17,20-dimethyl-9-oxoprost-2,13-die
  • ,13e,15s,17s)-
  • 11α,15s-dihydroxy-17s,20-dimethyl-9-oxo-prosta-2e,13e-dien-1-oic acid
  • 17S,20-Dimethyl-trans-D2-PGE1
  • 2-Heptenoic acid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl]-, (2E)- (9CI)
  • Prosta-2,13-dien-1-oic acid, 11,15-dihydroxy-17,20-dimethyl-9-oxo-, (2E,11a,13E,15S,17S)-
  • 17α,20-dimethyl-δ2-PGE1, 11α,15S-Dihydroxy-17S,20-dimethyl-9-oxo-prosta-2E,13E-dien-1-oic acid
  • (2E)-7-[(1R)-2β-[(1E,3S,5S)-3-Hydroxy-5-methyl-1-nonenyl]-3α-hydroxy-5-oxocyclopentan-1α-yl]-2-heptenoic acid
CAS:
74397-12-9
MF:
C22H36O5
MW:
380.52
Product Categories:
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
74397-12-9.mol
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LIMAPROST Chemical Properties

Melting point:
97-100°
Boiling point:
550.6±50.0 °C(Predicted)
Density 
1.118
storage temp. 
-20°C
solubility 
DMF: soluble
form 
crystalline
pka
4.78±0.10(Predicted)
color 
White to off-white
InChIKey
OJZYRQPMEIEQFC-UAWLTFRCSA-N
SMILES
C(O)(=O)/C=C/CCCC[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@@H](C)CCCC
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
36/37/39-45
RIDADR 
UN 2811 6.1/PG 2
WGK Germany 
3
RTECS 
UK8362500

MSDS

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LIMAPROST Usage And Synthesis

Chemical Properties

White crystals, melting point 97-100℃.

Uses

Limaprost is an analog of Prostaglandin E1 with structural modifications intended to give it a prolonged half-life and greater potency. Limaprost is used as an antianginal.

Definition

ChEBI: Limaprost is a long-chain fatty acid.

Biochem/physiol Actions

Limaprost exhibits cytoprotective, vasodilatory, and antiplatelet activity. Limaprost has the potential to treat lumbar spinal canal stenosis (LSCS) and several ischaemic symptoms of thromboangiitis obliterans (TAO).

in vivo

Limaprost (OP1206) given orally at more than 100 μg/kg relieves Argipressin-induced ST depression of rat electrocardiogram (ECG)[1].
Intra-coronary injection of Limaprost (OP1206; 1-100 ng/kg) in dogs results in a remarkable increase of coronary blood flow without any influence on heart rate, blood pressure, myocardial oxygen consumption and redox potential[1].
Resistance in both large and small vessels of dog coronary artery is decreased by intravenous injection of Limaprost (OP1206; 1-3 mg/kg)[1].
Platelet aggregation, adhesiveness, bleeding time, and thrombocytopenia induced by ADP and collagen infusion in guinea-pigs are inhibited by oral administration of Limaprost (OP1206) at the same doses or doses less than those relieving Argipressin-induced ST depression of ECG[1].

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