Prostaglandin E2
From DrugPedia: A Wikipedia for Drug discovery
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| Prostaglandin E2
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| Systematic (IUPAC) name | |
| (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C20H32O5 |
| Mol. mass | 352.47 |
| SMILES | & |
| Synonyms | Dinoprostone |
| Physical data | |
| Melt. point | 67(EXP) °C |
| Solubility in water | 58.1(EST) mg/mL |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
The most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa. In medicine, dinoprostone, is a naturally occurring prostaglandin E2 (PGE2). It has important effects in labour and also stimulates osteoblasts to release factors which stimulates bone resorption by osteoclasts. PGE2 is also the prostaglandin that ultimately induces fever.
It is sold under the trade name of Cervidil (by Forest Laboratories, Inc.), Prostin E2 (by Pfizer Inc.) and Propess (by Ferring Pharmaceuticals), as a vaginal suppository, to prepare the cervix for labour; it is used to induce labour.
The chemical name is (5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid.
Like other prostaglandins, dinoprostone can be used as an abortifacient. It is a direct vasodilator, relaxing smooth muscles, and it inhibits the release of noradrenaline from sympathetic nerve terminals. It does not activate platelets, where PGI2 does.
It works by binding and activating the prostaglandin E2 receptor.
It was discovered by Bunting, Gryglewski, Moncada and Vane in 1976.
Contents |
[edit] General Properties
*Molecular Weight
352.47
*Molecular Formula
C20H32O5
*IUPAC NAME
(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
*Canonical Smiles
CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
*Isomeric Smiles
CCCCC[C@@H](C=C[C@H]1[C@@H](CC(=O)[C@@H]1CC=C/CCCC(=O)O)O)O
[edit] PhysioChemical Properties
*Melting Point
67(EXP)
*LogP
2.82(EXP)
*Water Solubility
58.1(EST)
[edit] References
Pharmacology 2007. Rang, Dale, Ritter, Flower. Churchill Livingstone Elsevier.
[edit] External Links
- [1]Pubchem
- [2]KEGG Compound
- [3]KEGG Drug
- [4]Human Metabolome DataBase
- [5]Drugbank
- Dinoprostone - medlineplus.org
- Cervidil - Forest Laboratories, Inc. (the distributor of Cervidil).
- Prostin E2 - pfizer.com
- Cervidil/Prostin E2 - RxList.com
- What is Cervidil? - birthingnaturally.net.
- Cervidil/Prostin E2 - drugs.com
