88852-12-4

Basic information

• Product Name: Limaprost
• Synonyms: 17S,20-Dimethyl-trans-D2-PGE1 compd. with a-cyclodextrin;2,4,7,9,12,14,17,19,22,24,27,29-Dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane, a-cyclodextrin deriv.;2-Heptenoic acid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl]-, (2E)-, compd. with a-cyclodextrin (9CI);a-Cyclodextrin, compd. with (2E)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl]-2-heptenoic acid (9CI);a-Cyclodextrin, compd. with (2E,11a,13E,15S,17S)-11,15-dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic acid;Limaprost a-cyclodextrin clathrate;limaprost alfadex;OP 1206-a-cyclodextrin
• CAS NO: 88852-12-4
• Molecular Formula: C36H60O30.C22H36O5
• Molecular Weight: 1353.36
• Mol File: 88852-12-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Limaprost(CAS DataBase Reference)
• NIST Chemistry Reference: Limaprost(88852-12-4)
• EPA Substance Registry System: Limaprost(88852-12-4)

Safety Data

• Hazardous Substances Data: 88852-12-4(Hazardous Substances Data)

Usage

Description

Limaprost is an orally-active antithrombotic and vasodilator that is structurally related to alprostadil. It is known for its ability to inhibit platelet aggregation, increase platelet cAMP, and mildly suppress platelet adhesiveness. In patients with pulmonary emphysema, tuberculosis, and chronic lung disease, treatment with limaprost has been reported to produce significant cardiac improvements.

Uses

Used in Pharmaceutical Industry:
Limaprost is used as an antithrombotic and vasodilator for the treatment of patients with pulmonary emphysema, tuberculosis, and chronic lung disease. It helps in improving cardiac function and reducing platelet aggregation, which can contribute to the prevention of blood clots.
Used in Prostaglandin Synthesis:
Limaprost Alfadex is used in the synthesis of prostaglandins and their derivatives, which have various applications in medicine, including the treatment of various cardiovascular and respiratory conditions.
Brand Names:
Opalmon, Prorenal

InChI:InChI=1/C36H60O30.C22H36O5/c37-1-7-25-13(43)19(49)31(55-7)62-26-8(2-38)57-33(21(51)15(26)45)64-28-10(4-40)59-35(23(53)17(28)47)66-30-12(6-42)60-36(24(54)18(30)48)65-29-11(5-41)58-34(22(52)16(29)46)63-27-9(3-39)56-32(61-25)20(50)14(27)44;1-3-4-9-16(2)14-17(23)12-13-19-18(20(24)15-21(19)25)10-7-5-6-8-11-22(26)27/h7-54H,1-6H2;8,11-13,16-19,21,23,25H,3-7,9-10,14-15H2,1-2H3,(H,26,27)/b;11-8+,13-12+/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,36-;16-,17+,18+,19+,21+/m10/s1

Upstream product

• 144877-58-7 (E)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentyl}-hept-2-enoic acid allyl ester 
• 149585-88-6 C₂₉H₅₆O₄Si₂ 
• 58707-52-1 (3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol 

Downstream Products

• 853998-94-4 (2E)-7-{(1R,2S)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxo-3-cyclopenten-1-yl}-2-heptenoic acid 
• 75554-85-7 C₂₂H₃₆O₅ 

Relevant articles and documents

Before preparing a Lima intermediate row element, method for preparing the same and before the Lima row element through its method of preparation

An intermediate of formula (V) used for preparing limaprost of formula (I), preparation method thereof, and preparation method of limaprost therefrom. The present preparation method of limaprost from the intermediate of formula (V) includes: reduction of the compound of formula (V), followed by protection, deprotection and oxidation of hydroxyl group to provide the compound of formula (II), then deprotecion of hydroxyl group and/or carboxyl group of the compound of formula (II) to provide limaprost of formula (I).

Synthesis of Allyl Ester of Prostaglandin E and the Conversion of the Allyl Ester Moiety into Carboxylic Acid by Chemical Method. A Highly Practical Synthesis of Natural PGE1 and Limaprost

Synthesis of prostaglandin E allyl ester via two-component coupling process and the conversion of the allyl ester moiety into free carboxylic acid by the reaction with HCO2H-Et3N in the presence of a palladium catalyst has been described.