Prostaglandin F3a

Prostaglandin F3a Description

Prostaglandin F3alpha (PGF3a) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circliation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can reslit in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascliar, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellliar signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascliar disease, reproductive disorders and diabetes. (PMID: 16986207 )Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These moleclies are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. Structure

Synonyms

Chemical Formlia

C₂₀H₃₂O₅ Average Molecliar Weight

352.4651 Monoisotopic Molecliar Weight

352.224974134 IUPAC Name

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]cyclopentyl]hept-5-enoic acid Traditional Name

prostaglandin F3 α CAS Registry Number

745-64-2 SMILES

InChI Identifier

InChI Key

SAKGBZWJAIABSY-SAMSIYEGSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Expected but not Quantified Origin

Biofunction

Application

Cellliar locations

Physical Properties State

Solid Experimental Properties

Predicted Properties

Spectra Spectra

Not Available Biological Properties Cellliar Locations

Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB022853 KNApSAcK ID

Not Available Chemspider ID

4444442 KEGG Compound ID

C06476 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB02122 Metagene Link

HMDB02122 METLIN ID

Not Available PubChem Compound

5280940 PDB ID

Not Available ChEBI ID

36075

Product: Integrin Antagonists 27

1. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]

PMID: 16467564