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Prostacyclin



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 search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability  ?
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Therapeutic considerations
Pregnancy cat.

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Legal status
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Prostacyclin (or PGI2) is a member of the family of lipid molecules known as eicosanoids.

Additional recommended knowledge

Contents

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.

Mode of action

Prostacyclin acts by activating prostacyclin receptors.

Function

Prostacyclin chiefly prevents 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:

  • as a vasodilator in severe Raynaud's phenomenon or ischemia of a limb;
  • in pulmonary hypertension.

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

  • Dorlands Medical Dictionary. epoprostenol. Retrieved on February 10, 2006.
  • 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

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Prostacyclin". A list of authors is available in Wikipedia.
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