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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/07 22:45:53」(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

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 思春期における原発性月経困難症 primary dysmenorrhea in adolescents
2. アナフィラキシーの臨床診断を裏付ける臨床検査 laboratory tests to support the clinical diagnosis of anaphylaxis
3. 心不全における酸化ストレスの役割 role of oxidative stress in heart failure
4. 肥満細胞活性化障害 mast cell activation disorders
5. 分娩の生理学 physiology of parturition

English Journal

Comparison of two intravaginal progesterone releasing devices (PRID-Delta vs CIDR) in dairy cows: Blood progesterone profile and field fertility.

van Werven T, Waldeck F, Souza AH, Floch S, Englebienne M.SourceUniversity Farm Animal Practice, Dorpsstraat 221a, 3481 EH Harmelen, The Netherlands; Department of Farm Animal Health, Faculty of Veterinary Medicine, Utrecht University, Yalelaan 7, 3584 CL Utrecht, The Netherlands.
Animal reproduction science.Anim Reprod Sci.2013 May;138(3-4):143-9. doi: 10.1016/j.anireprosci.2013.02.010. Epub 2013 Feb 22.
Objectives were to compare circulating progesterone (P4) profile and pregnancies per AI (P/AI) of two commercial intravaginal P4 devices (PRID-Delta(®) vs CIDR(®)). In Experiment 1, ovariectomized dairy cows (PRID-Delta, n=6 vs CIDR, n=6) were sampled throughout 7 days to measure circulating P4. I
PMID 23523234

Acid-Base Parameters and Steroid Concentrations in Pre-Ovulatory Follicles and Plasma of Lactating Dairy Cows with Spontaneous and Synchronized Oestrus or Follicular Cyst.

Hussein H, Boryczko Z, Bostedt H.SourceTheriogenology Department, Faculty of Veterinary Medicine, Assiut University, Assiut, Egypt.
Reproduction in domestic animals = Zuchthygiene.Reprod Domest Anim.2013 Apr 15. doi: 10.1111/rda.12171. [Epub ahead of print]
The study aimed to compare the acid-base balance and steroid concentrations between follicular fluids (FF) of pre-ovulatory follicles derived from a spontaneous oestrus (SO), synchronized or induced oestrus (IO) and follicular cysts (CYS) and between FF and blood in dairy cows. Forty-two dairy cows
PMID 23581396

Improved oxidative stress and cardio-metabolic status in obese prepubertal children with liver steatosis treated with lifestyle combined with Vitamin E.

D'Adamo E, Marcovecchio ML, Giannini C, de Giorgis T, Chiavaroli V, Chiarelli F, Mohn A.SourceDepartment of Pediatrics, University of Chieti, Chieti, Italy. ebe.dadamo@yahoo.com
Free radical research.Free Radic Res.2013 Mar;47(3):146-53. doi: 10.3109/10715762.2012.755262. Epub 2013 Jan 9.
In obese adults with non alcoholic fatty liver disease (NAFLD), treatment with Vitamin E has resulted in an improvement in liver histology, whereas variable and limited results are available in children. Our aim was to assess whether lifestyle combined with supplementation with Vitamin E might reduc
PMID 23205728

Japanese Journal

Preovulatory Follicular and Subsequent Luteal Size Influence Pregnancy Success in Water Buffaloes

RAHMAN Md Saidur,SHOHAG Abu Said,KAMAL Md Mostofa,BARI Farida Yeasmin,SHAMSUDDIN Mohammed
Journal of Reproduction and Development advpub(0), 1112060421, 2012
… The buffaloes were synchronized with two injections of a synthetic analogue of PGF2α administered 11 days apart. …
NAID 130001388617

Comparison of Plasma Concentrations of Estradiol-17β and Progesterone, and Conception in Dairy Cows with Cystic Ovarian Diseases between Ovsynch and Ovsynch plus CIDR Timed AI Protocols

KAWATE Noritoshi,WATANABE Kensuke,UENAKA Kazuhiro,TAKAHASHI Masahiro,INABA Toshio,TAMADA Hiromichi
The Journal of reproduction and development 57(2), 267-272, 2011-04-01
… They were treated with either the Ovsynch (GnRH on Day 0, PGF2α on Day 7 and GnRH on Day 9, with AI on Day 10; …
NAID 10028275486

Related Pictures

★リンクテーブル★

リンク元	「プロスタグランジンF2」
拡張検索	「PGF2 alpha」「PGF2alpha」「PGF2α」
関連記事	「PG」「PGF」

「プロスタグランジンF2」

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
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 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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