Prostacyclin

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Prostacyclin
Systematic (IUPAC) name
5-[7-hydroxy-8- (3-hydroxyoct-1-enyl) -4-oxabicyclo[3.3.0]oct-3-ylidene] pentanoic acid
Identifiers
CAS number 35121-78-9
ATC code B01AC09
PubChem 114805
DrugBank APRD00949
Chemical data
Formula C20H32O5 
Mol. mass 352.465 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

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Routes  ?

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See also: Epoprostenol

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

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Overview

Prostacyclin is a member of the family of lipid molecules known as eicosanoids. A synthetic form of prostacyclin, used as a medicine, is referred to as epoprostenol.

Production

It is produced in endothelial cells from prostaglandin H2 (PGH2) by the action of the enzyme prostacyclin synthase. Although prostacyclin is considered an independent mediator, it is called PGI2 (prostaglandin I2) in eicosanoid nomenclature, and is a member of the prostanoids (together with the prostaglandins and thromboxane).

The series-3 prostaglandin PGH3 also follows the prostacyclin synthase pathway, yielding another prostacyclin, PGI3.(Fischer, 1985)  The unqualified term 'prostacyclin' usually refers to PGI2. PGI2 is derived from the ω-6 arachidonic acid. PGI3 is derived from the ω-3 EPA.

Eicosanoid synthesis. (Prostacyclin near bottom center.)

Mode of action

Prostacyclin acts chiefly to prevent platelet formation and clumping involved in blood clotting. It is also an effective vasodilator. Prostacyclin's interactions in contrast to thromboxane, another eicosanoid, strongly suggest a mechanism of cardiovascular homeostasis between the two hormones in relation to vascular damage.

Pharmacology

Synthetic prostacyclin analogues (iloprost, cisaprost) are used intravenously, subcutaneously or by inhalation:

Its production is inhibited indirectly by NSAIDs, which inhibit the cyclooxygenase enzymes COX1 and COX2. These convert arachidonic acid to PGH2, the immediate precursor of prostacyclin.

References

  • Fischer S, Weber PC (1985). "Thromboxane (TX) A3 and prostaglandin (PG) I3 are formed in man after dietary eicosapentaenoic acid: identification and quantification by capillary gas chromatography-electron impact mass spectrometry". Biomed. Mass Spectrom. 12 (9): 470-6. PMID 2996649.

See also

Essential fatty acid


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