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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/02 15:22:33」(JST)

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Prostaglandin F_2α (PGF_2α in prostanoid nomenclature), 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

PGF_2α acts by binding to the prostaglandin F2α receptor.

Synthesis

In 2012 a concise and highly stereoselective total synthesis of PGF_2α was described.^[2] The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng,^[3] and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.

Analogs

The following medications are analogs of prostaglandin F_2α:

Latanoprost
Bimatoprost
Travoprost
Carboprost

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
^ Coulthard, G.; Erb, W.; Aggarwal, V. K. (2012). "Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps". Nature 489 (7415): 278–281. doi:10.1038/nature11411. PMID 22895192. edit
^ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.

UpToDate Contents

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1. 人工妊娠中絶に対するミソプロストール単独投与 misoprostol as a single agent for medical termination of pregnancy
2. 全身性肥満細胞症の治療および予後 treatment and prognosis of systemic mastocytosis

English Journal

Protective role of curcumin in oxidative stress of breast cells.

Calaf GM, Echiburu-Chau C, Roy D, Chai Y, Wen G, Balajee AS.SourceInstituto de Alta Investigacion, Universidad de Tarapaca, Calle Antofagasta 1520, Arica, Chile. gmc24@columbia.edu
Oncology reports.Oncol Rep.2011 Oct;26(4):1029-35. doi: 10.3892/or.2011.1386. Epub 2011 Jul 11.
Curcumin (diferuloylmethane) is a well known antioxidant that exerts anti-proliferative and apoptotic effects. The effects of curcumin were evaluated in a breast cancer model that was developed with the immortalized breast epithelial cell line, MCF-10F after exposure to low doses of high LET (linear
PMID 21750867

Fertility Following CIDR Based Synchronization Regimens in Anoestrous Nili-Ravi Buffaloes.

Naseer Z, Ahmad E, Singh J, Ahmad N.SourceDepartment of Theriogenology, University of Veterinary and Animal Sciences, Lahore, Pakistan Western College of Veterinary Medicine, University of Saskatchewan, Saskatoon, SK, Canada.
Reproduction in domestic animals = Zuchthygiene.Reprod Domest Anim.2011 Oct;46(5):814-7. doi: 10.1111/j.1439-0531.2010.01746.x. Epub 2011 Jan 17.
The objective of this study was to compare oestrus expression and fertility rate in used and new controlled internal drug releasing (CIDR) device treated anoestrous buffaloes. Furthermore, to determine the timing of ovulation, and fertility rate in estradiol benzoate (EB) and GnRH-administered CIDR-
PMID 21241382

Japanese Journal

The effect of leg hyperthermia using far infrared rays in bedridden subjects with type 2 diabetes mellitus

Kawaura Akihiko,Tanida Noritoshi,Kamitani Masato,Akiyama Junichi,Mizutani Masatoshi,Tsugawa Naoko,Okano Toshio,Takeda Eiji
Acta Medica Okayama 64(2), 143-147, 2010-04
… Fasting plasma glucose, HbA1c, tumor necrosis factor (TNF)alpha, free fatty acid, leptin, adiponectin and plasma 8-epi-prostaglandin F2alpha (8-epi-PGF2alpha) levels as a marker of oxidative stress were measured on admission, just before and 2 weeks after local heating of the leg. … Results showed that plasma total 8-epi-PGF2alpha levels were decreased significantly while TNFalpha levels were increased significantly. …
NAID 120002311883

Effective Oxytocin Treatment on Placental Expulsion after Foaling in Heavy Draft Mares(Theriogenology)

ISHII Mitsuo,KOBAYASHI Syuichi,ACOSTA Tomas J.,MIKI Wataru,MATSUI Motozumi,YAMANOI Takahiro,MIYAKE Yoh-Ichi,MIYAMOTO Akio
The journal of veterinary medical science 71(3), 293-297, 2009-03-25
… The changes in the plasma concentrations of OT and the PGF2alpha metabolite (PGFM) were investigated, and the influence of OT administration was considered. …
NAID 110007131185

Related Pictures

★リンクテーブル★

リンク元	「プロスタグランジンF2α」「prostaglandin F2」

「プロスタグランジンF2α」

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
Routes of; administration	Intravenous (to induce labor), intra-amniotic (to induce abortion)
Pharmacokinetic data
Biological half-life	3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS Registry Number	551-11-1 38562-01-5
ATC code	G02AD01
PubChem	CID: 5280363
IUPHAR/BPS	1884
DrugBank	DB01160
ChemSpider	4444062
KEGG	D01352
ChEMBL	CHEMBL815
Chemical data
Formula	C20H34O5
Molecular mass	354.48 g/mol
	SMILES O=C(O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC ;
	InChI InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 ; Key:PXGPLTODNUVGFL-YNNPMVKQSA-N ;
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