Prostaglandin E2

Prostaglandin E2
This article is about the pharmaceutical agent 'dinoprostone'. For the drug 'dinoprost', see Prostaglandin F2alpha.
Prostaglandin E2
Systematic (IUPAC) name
(5Z,11α,13E,15S)-7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)- 5-oxo-cyclopentyl] hept-5-enoic acid
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a682512
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 363-24-6 YesY
ATC code G02AD02
PubChem CID 9691
DrugBank APRD00927
ChEMBL CHEMBL548 N
Synonyms (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid
Chemical data
Formula C20H32O5 
Mol. mass 352.465 g/mol
 N(what is this?)  (verify)

The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone. It has important effects in labour (softens cervix and causes uterine contraction) and also stimulates osteoblasts to release factors that stimulate 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.), Propess (by Ferring Pharmaceuticals) and Glandin (by Nabiqasim Pharmaceuticals Pakistan) as a vaginal suppository, to prepare the cervix for labour; it is used to induce labour.

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 inhibit platelet aggregation, where PGI2 does.

It works by binding and activating the prostaglandin E2 receptor.

It was discovered by Bunting, Gryglewski, Moncada and Vane in 1976.

Precautions : uterine scar tissues; asthma; low blood pressure; heart disease; adrenal problems; anemia; diabetes; glaucoma; icterus; multiparity (5 pregnancies); heart, lung or liver disease.

References

Pharmacology 2007. Rang, Ritter, Dale, Flower. Churchill Livingstone Elsevier.
Judiths Hopfer Deglin and April Hazard Vallerand (2006), Davis Drug Guide for Nurses,F.A Davis, Philadelphia, Pennsylvania, U.S.A Copyright, 1427 pages.

External links

v · Autacoids, unsaturated fatty acids: Eicosanoids
Precursor
Prostanoids
Precursor
Active
D/J
E/F
I
A2 · B2
Leukotrienes (LT)
Precursor
Initial
A4 · B4
SRS-A
C4 · D4 · E4
Nonclassic
By function

bronchoconstriction (PGF2α, TXA2, LTC4, LTD4, LTE4)

vasoconstriction (PGF2α, TXA2, TXB2) · vasodilation (PGE2, PGI2, LTC4, LTD4, LTE4)

platelets: induce (TXA2) inhibit (PGD2, PGI2) · leukocytes: induce (TXA2, LTB4) inhibit (PGD2, PGE2)

fever stimulation: (PGE2)

labor stimulation: (PGE2 (Dinoprostone), PGF2α (Dinoprost))

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i
v · d · eUterotonics/labor inducers/oxytocics (G02A)
Cervical ripening
Ergot alkaloids
Ergometrine# (+oxytocin) • Methylergometrine

E: Misoprostol/E1# • Gemeprost/E1 • Dinoprostone/E2 • Sulprostone/E2

F: Dinoprost/F2α • Carboprost/F2α
Contraction induction
Oxytocin# • Carbetocin • Demoxytocin • WAY-267,464

M: OBS

phys/devp/memb

mthr/fetu/infc, epon

proc, drug(2A/G2C)
v · d · eTocolytics/labor repressants (G02CA)
β2-agonists
Oxytocin antagonist
NSAID
Calcium channel blocker
Myosin inhibitor

M: OBS

phys/devp/memb

mthr/fetu/infc, epon

proc, drug(2A/G2C)

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