WordNet

a potent substance that acts like a hormone and is found in many bodily tissues (and especially in semen); produced in response to trauma and may affect blood pressure and metabolism and smooth muscle activity

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/12 08:36:28」(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.

Analogues

The following medications are analogues 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.
^ 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.
^ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.

UpToDate Contents

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1. 経腟分娩後の出血管理 management of postpartum hemorrhage at vaginal delivery
2. 思春期における原発性月経困難症 primary dysmenorrhea in adolescents
3. 陣痛誘発前に未成熟な頸管を熟化させる手技 techniques for ripening the unfavorable cervix prior to induction
4. 産褥性子宮内反症 puerperal uterine inversion
5. 成人女性における原発性月経困難症：臨床的特徴および診断 primary dysmenorrhea in adult women clinical features and diagnosis

English Journal

Altered secretion of selected arachidonic acid metabolites during subclinical endometritis relative to estrous cycle stage and grade of fibrosis in mares.

Gajos K1, Kozdrowski R2, Nowak M3, Siemieniuch MJ4.
Theriogenology.Theriogenology.2015 Aug;84(3):457-66. doi: 10.1016/j.theriogenology.2015.03.038. Epub 2015 Apr 8.
Mares that fail to become pregnant after repeated breeding, without showing typical signs of clinical endometritis, should be suspected of subclinical endometritis (SE). Contact with infectious agents results in altered synthesis and secretion of inflammatory mediators, including cytokines and arach
PMID 25963128

Dysregulated post-transcriptional control of COX-2 gene expression in gestational diabetic endothelial cells.

Di Francesco L1, Dovizio M1, Trenti A2, Marcantoni E1, Moore A3, O Gaora P4, McCarthy C4, Tacconelli S1, Bruno A1, Alberti S1, Gizzo S5, Nardelli GB5, Orso G6, Belton O4, Trevisi L2, Dixon DA3, Patrignani P1.
British journal of pharmacology.Br J Pharmacol.2015 Jul 3. doi: 10.1111/bph.13241. [Epub ahead of print]
BACKGROUND AND PURPOSE: Hyperglycemic memory describes the progression of diabetic complications during subsequent periods of improved glycemia.We addressed the hypothesis that transient hyperglycemia causes aberrant cyclooxygenase(COX)-2 expression in human umbilical vein endothelial cells(HUVEC) i
PMID 26140661

Rare SNP rs12731181 in the miR-590-3p Target Site of the Prostaglandin F2α Receptor Gene Confers Risk for Essential Hypertension in the Han Chinese Population.

Xiao B1, Gu SM1, Li MJ1, Li J1, Tao B1, Wang Y1, Wang Y1, Zuo S1, Shen Y1, Yu Y1, Chen D1, Chen G1, Kong D1, Tang J1, Liu Q1, Chen DR1, Liu Y1, Alberti S1, Dovizio M1, Landolfi R1, Mucci L1, Miao PZ1, Gao P1, Zhu DL1, Wang J1, Li B1, Patrignani P1, Yu Y2.
Arteriosclerosis, thrombosis, and vascular biology.Arterioscler Thromb Vasc Biol.2015 Jul;35(7):1687-95. doi: 10.1161/ATVBAHA.115.305445. Epub 2015 May 14.
OBJECTIVE: To investigate whether rs12731181 (A→G) interrupted miR-590-3p-mediated suppression of the prostaglandin F2α receptor (FP) and whether it is associated with essential hypertension in the Chinese population.APPROACH AND RESULTS: We found that miR-590-3p regulates human FP gene expressio
PMID 25977569

Japanese Journal

緑内障点眼薬の薬物相互作用の解明と点眼薬物療法の費用最小化分析の確立

医療薬学 40(10), 543-557, 2014
NAID 130005103176

ウマ子宮内膜のprostaglandin F2alpha (PGF)分泌調節における自己増幅機構の存在

日本繁殖生物学会　講演要旨集 106(0), P-86-P-86, 2013
NAID 130005051219

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

Acta Medica Okayama 64(2), 143-147, 2010-04
NAID 120002311883

「プロスタグランジンF2α」

Dinoprost
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
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 Number	551-11-1 38562-01-5
ATC code	G02AD01 (WHO)
PubChem	CID 5280363
IUPHAR/BPS	1884
DrugBank	DB01160
ChemSpider	4444062
KEGG	D01352
ChEMBL	CHEMBL815
Chemical data
Formula	C20H34O5
Molar 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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