Prostaglandin F2alpha

Prostaglandin F2alpha: This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.

Dinoprost Tromethamine

Systematic (IUPAC) name

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

Clinical data

AHFS/Drugs.com International Drug Names

Pregnancy cat. ?

Legal status ?

Routes Intravenous (to induce labor), intra-amniotic (to induce abortion)

Pharmacokinetic data

Half-life 3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma

Identifiers

CAS number 551-11-1^Y 38562-01-5

ATC code G02AD01

PubChem CID 5280363

IUPHAR ligand 1884

DrugBank DB01160

ChemSpider 4445570^N

KEGG D01352^N

ChEMBL CHEMBL815^N

Chemical data

Formula C₂₀H₃₄O₅

Mol. mass 354.48 g/mol

InChI

InChI=1S/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1^N
Key:IYGXEHDCSOYNKY-RZHHZEQLSA-N^N

N(what is this?) F2alpha (verify)

Prostaglandin F_2α (PGF_2α in prostanoid nomenclature) is pharmaceutically termed Dinoprost (INN) is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.

In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular phase. It acts on the corpus luteum to cause luteolysis, forming a corpus albicans and stopping the production of progesterone. Action of PGF_2α is dependent on the number of receptors on the corpus luteum membrane.

The PGF_2α isoform 8-iso-PGF_2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.^[1]

Mechanism of action

Further information: Prostaglandin F2α receptor

PGF_2α acts by binding to the prostaglandin F2α receptor.it is also commercially available as (Enzaprost)

References

^ Sharma, I.; Dhaliwal, L.; Saha, S.; Sangwan, S.; Dhawan, V. (2010). "Role of 8-iso-prostaglandin F2alpha and 25-hydroxycholesterol in the pathophysiology of endometriosis". Fertility and sterility 94 (1): 63–70. doi:10.1016/j.fertnstert.2009.01.141. PMID 19324352. edit

v · Autacoids, unsaturated fatty acids: Eicosanoids

Precursor
Arachidonic acid

Prostanoids

Prostaglandins (PG) and
analogues

Precursor

H₂

Active

D/J

D₂

E/F

E₂ (Dinoprostone): Enprostil · Sulprostone

E₁ (Alprostadil): Misoprostol · Gemeprost
F_2α (Dinoprost): Bimatoprost · Carboprost · Latanoprost · Tafluprost · Travoprost · Unoprostone

I

I₂ (Prostacyclin/Epoprostenol): Beraprost · Iloprost · Treprostinil

Thromboxanes (TX)

A₂ · B₂

Leukotrienes (LT)

Precursor

Arachidonic acid 5-hydroperoxide

Initial

A₄ · B₄

SRS-A

C₄ · D₄ · E₄

Nonclassic
Lipoxins (A₄, B₄) · Virodhamine

By function

bronchoconstriction (PGF_2α, TXA₂, LTC₄, LTD₄, LTE₄)

vasoconstriction (PGF_2α, 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), PGF_2α (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

Prostaglandins and
analogues

E: Misoprostol/E1^# • Gemeprost/E1 • Dinoprostone/E2 • Sulprostone/E2
F: Dinoprost/F2α • Carboprost/F2α

Contraction induction
Oxytocin^# • Carbetocin • Demoxytocin • WAY-267,464

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: OBS

phys/devp/memb

mthr/fetu/infc, epon

proc, drug(2A/G2C)

Categories:
Abortifacients
Prostaglandins
Medicine stubs

Dinoprost Tromethamine

Systematic (IUPAC) name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Routes	Intravenous (to induce labor), intra-amniotic (to induce abortion)
Pharmacokinetic data
Half-life	3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS number	551-11-1^Y 38562-01-5
ATC code	G02AD01
PubChem	CID 5280363
IUPHAR ligand	1884
DrugBank	DB01160
ChemSpider	4445570^N
KEGG	D01352^N
ChEMBL	CHEMBL815^N
Chemical data
Formula	C₂₀H₃₄O₅
Mol. mass	354.48 g/mol
InChI InChI=1S/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1^N Key:IYGXEHDCSOYNKY-RZHHZEQLSA-N^N
N(what is this?) F2alpha (verify)

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Prostaglandin F receptor — (FP) is a receptor for Prostaglandin F2α. It is encoded by the gene PTGFR.cite web | title = Entrez Gene: PTGFR prostaglandin F receptor (FP)| url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene Cmd=ShowDetailView TermToSearch=5737| accessdate … Wikipedia
Prostaglandin 2 alpha — Prostaglandin F2alpha causes luteolysis or regression of the corpus luteum if the animal is not pregnant.References*Bagnell, C. 2005. Animal Reproduction . Rutgers University Department of Animal Sciences … Wikipedia
Prostaglandin — A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. Every prostaglandin contains 20 carbon atoms, including a 5 carbon ring.They are… … Wikipedia
Prostaglandin-F synthase — In enzymology, a prostaglandin F synthase (EC number|1.1.1.188) is an enzyme that catalyzes the chemical reaction:(5Z,13E) (15S) 9alpha,11alpha,15 trihydroxyprosta 5,13 dienoate + NADP+ ightleftharpoons (5Z,13E) (15S) 9alpha,15 dihydroxy 11… … Wikipedia
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 cyclopent … Wikipedia
PTGFRN — Prostaglandin F2 receptor negative regulator, also known as PTGFRN, is a human gene.cite web | title = Entrez Gene: PTGFRN prostaglandin F2 receptor negative regulator| url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene Cmd=ShowDetailView… … Wikipedia
Sauna — For other uses, see Sauna (disambiguation). A traditional Finnish shore sauna view … Wikipedia
Luteolysis — is the structural and functional degradation of the corpus luteum that occurs at the end of the luteal phase in the absence of pregnancy. It is caused by the hormones prostaglandin F2alpha and oxytocin. Communication between the corpus luteum and … Wikipedia
Endometriosis — Classification and external resources ICD 10 N80 I … Wikipedia

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Prostaglandin F2alpha

Mechanism of action

References

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Prostaglandin F2alpha

Mechanism of action

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