Prostaglandin E2

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Prostaglandin E2
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	5280360
DrugBank	DB00917
Chemical data
Formula	C20H32O5
Mol. mass	352.47
SMILES	eMolecules & PubChem
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.	?
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.

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

PhysioChemical Properties

*Melting Point

67(EXP)

*LogP

2.82(EXP)

*Water Solubility

58.1(EST)

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