Prostacyclin
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| Prostacyclin
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| Systematic (IUPAC) name | |
| 5-[7-hydroxy-8- (3-hydroxyoct-1-enyl) -4-oxabicyclo[3.3.0]oct-3-ylidene] pentanoic acid | |
| Identifiers | |
| CAS number | |
| ATC code | B01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C20H32O5 |
| Mol. mass | 352.465 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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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.
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:
- 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.
- 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
Medications used in the management of pulmonary arterial hypertension (B01, C02) | |
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| Prostacyclin analogues | Beraprost, Epoprostenol, Iloprost, Treprostinil |
| Endothelin receptor antagonists | Ambrisentan, Bosentan, Sitaxsentan |
| PDE5 inhibitors | Sildenafil, Tadalafil |
| Adjunctive therapy | Calcium channel blockers, Diuretics, Digoxin, Oxygen therapy, Warfarin |
Eicosanoids: prostaglandins | |
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| Endogenous/series 2 | D2 - E2 (Dinoprostone) - F2 (Dinoprost) - H2 - I2 (Prostacyclin) |
| Prostaglandin analogues | E: Alprostadil - Enprostil - Misoprostol
F: Bimatoprost - Carboprost - Latanoprost - Travoprost I: Beraprost - Iloprost - Treprostinil |
WikiDoc Research Resources for Prostacyclin | |
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| Articles on Prostacyclin | Most recent articles on Prostacyclin • Most cited articles on Prostacyclin • Review articles on Prostacyclin • Articles on Prostacyclin in N Eng J Med, Lancet, BMJ |
| Media (Slides, Video, Images, MP3) on Prostacyclin | Powerpoint slides on Prostacyclin • Images of Prostacyclin • Photos of Prostacyclin • Podcasts & MP3s on Prostacyclin • Videos on Prostacyclin |
| Evidence Based Medicine Regarding Prostacyclin | Cochrane Collaboration on Prostacyclin • Bandolier on Prostacyclin • TRIP on Prostacyclin |
| Cost Effectiveness of Prostacyclin | Cost Effectiveness of Prostacyclin |
| Clinical Trials Involving Prostacyclin | Ongoing Trials on Prostacyclin at Clinical Trials.gov • Trial results on Prostacyclin • Clinical Trials on Prostacyclin at Google |
| Guidelines / Policies / Government Resources (FDA/CDC) Regarding Prostacyclin | US National Guidelines Clearinghouse on Prostacyclin • NICE Guidance on Prostacyclin • NHS PRODIGY Guidance • FDA on Prostacyclin • CDC on Prostacyclin |
| Textbook Information on Prostacyclin | Books and Textbook Information on Prostacyclin |
| Pharmacology Resources on Prostacyclin | Dosing of Prostacyclin • Drug interactions with Prostacyclin • Side effects of Prostacyclin • Allergic reactions to Prostacyclin • Overdose information on Prostacyclin • Carcinogenicity information on Prostacyclin • Prostacyclin in pregnancy • Pharmacokinetics of Prostacyclin • |
| Genetics, Pharmacogenomics, and Proteinomics of Prostacyclin | Genetics of Prostacyclin • Pharmacogenomics of Prostacyclin • Proteomics of Prostacyclin |
| Newstories on Prostacyclin | Prostacyclin in the news • Be alerted to news on Prostacyclin • News trends on Prostacyclin |
| Commentary on Prostacyclin | Blogs on Prostacyclin |
| Patient Resources on Prostacyclin | Patient resources on Prostacyclin • Discussion groups on Prostacyclin • Patient Handouts on Prostacyclin • Directions to Hospitals Treating Prostacyclin • Risk calculators and risk factors for Prostacyclin |
| Healthcare Provider Resources on Prostacyclin | Symptoms of Prostacyclin • Causes & Risk Factors for Prostacyclin • Diagnostic studies for Prostacyclin • Treatment of Prostacyclin |
| Continuing Medical Education (CME) Programs on Prostacyclin | CME Programs on Prostacyclin |
| International Resources on Prostacyclin | Prostacyclin en Espanol • Prostacyclin en Francais |
| Business Resources on Prostacyclin | Prostacyclin in the Marketplace • Patents on Prostacyclin |
| Informatics Resources on Prostacyclin | List of terms related to Prostacyclin |
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
