関: dinoprost、PGF2 alpha、PGF2alpha、prostaglandin F2 alpha、prostaglandin F2alpha

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
the 6th letter of the Roman alphabet (同)f

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/26 19:31:40」(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. 分娩第3期のマネージメントのための子宮収縮薬 uterotonic drugs for management of the third stage of labor
2. 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
3. 妊娠中絶：妊娠第二期 termination of pregnancy second trimester
4. 肥満細胞活性化障害 mast cell activation disorders
5. 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

English Journal

Pregnancy recognition signaling mechanisms in ruminants and pigs.

Bazer FW.AbstractMaternal recognition of pregnancy refers to the requirement for the conceptus (embryo and its associated extra-embryonic membranes) to produce a hormone that acts on the uterus and/or corpus luteum (CL) to ensure maintenance of a functional CL for production of progesterone; the hormone required for pregnancy in most mammals. The pregnancy recognition signal in primates is chorionic gonadotrophin which acts directly on the CL via luteinizing hormone receptors to ensure maintenance of functional CL during pregnancy. In ruminants, interferon tau (IFNT) is the pregnancy recognition signal. IFNT is secreted during the peri-implantation period of pregnancy and acts on uterine epithelia to silence expression of estrogen receptor alpha and oxytocin receptor which abrogates the oxytocin-dependent release of luteolytic pulses of prostaglandin F2-alpha (PGF) by uterine epithelia; therefore, the CL continues to produce progesterone required for pregnancy. Pig conceptuses secrete interferon delta and interferon gamma during the peri-implantation period of pregnancy, but there is no evidence that they are involved in pregnancy recognition signaling. Rather, pig conceptuses secrete abundant amounts of estrogens between Days 11 to 15 of pregnancy required for maternal recognition of pregnancy. Estrogen, likely in concert with prolactin, prevents secretion of PGF into the uterine venous drainage (endocrine secretion), but maintains secretion of PGF into the uterine lumen (exocrine secretion) where it is metabolized to a form that is not luteolytic. Since PGF is sequestered within the uterine lumen and unavailable to induce luteolysis, functional CL are maintained for production of progesterone. In addition to effects of chorionic gonadotrophin, IFNT and estrogens to signal pregnancy recognition, these hormones act on uterine epithelia to enhance expression of genes critical for growth and development of the conceptus.
Journal of animal science and biotechnology.J Anim Sci Biotechnol.2013 Jun 26;4(1):23. [Epub ahead of print]
Maternal recognition of pregnancy refers to the requirement for the conceptus (embryo and its associated extra-embryonic membranes) to produce a hormone that acts on the uterus and/or corpus luteum (CL) to ensure maintenance of a functional CL for production of progesterone; the hormone required for
PMID 23800120

Sex-specific differences in hyperoxic lung injury in mice: Implications for acute and chronic lung disease in humans.

Lingappan K, Jiang W, Wang L, Couroucli XI, Barrios R, Moorthy B.SourceDepartment of Pediatrics, Section of Neonatology, Texas Children's Hospital, Baylor College of Medicine, 1102 Bates Avenue, MC: FC530.01, Houston, TX 77030, USA. Electronic address: lingappa@bcm.edu.
Toxicology and applied pharmacology.Toxicol Appl Pharmacol.2013 Jun 21. pii: S0041-008X(13)00280-9. doi: 10.1016/j.taap.2013.06.007. [Epub ahead of print]
Sex-specific differences in pulmonary morbidity in humans are well documented. Hyperoxia contributes to lung injury in experimental animals and humans. The mechanisms responsible for sex differences in the susceptibility towards hyperoxic lung injury remain largely unknown. In this investigation, we
PMID 23792423

Endocrine delivery of interferon tau protects the corpus luteum from prostaglandin f2 alpha-induced luteolysis in ewes.

Antoniazzi AQ, Webb BT, Romero JJ, Ashley RL, Smirnova NP, Henkes LE, Bott RC, Oliveira JF, Niswender GD, Bazer FW, Hansen TR.SourceAnimal Reproduction and Biotechnology Laboratory, Department of Biomedical Sciences, College of Veterinary Medicine and Biomedical Sciences, Colorado State University, Fort Collins, Colorado.
Biology of reproduction.Biol Reprod.2013 Jun 13;88(6):144. doi: 10.1095/biolreprod.112.105684. Print 2013.
Paracrine release of ovine interferon tau (oIFNT) from the conceptus alters release of endometrial prostaglandin F2 alpha (PGF) and prevents luteolysis. Endocrine release of oIFNT into the uterine vein occurs by Day 15 of pregnancy and may impart resistance of the corpus luteum (CL) to PGF. It was h
PMID 23616594

Japanese Journal

Two-step inhibitory effect of kanzo on oxytocin-induced and prostaglandin F₂[α]-induced uterine myometrial contractions

Sumi Genichiro,Yasuda Katsuhiko,Kanamori Chiharu [他]
Journal of natural medicines 68(3), 550-560, 2014
NAID 40020091186

Exacerbation of Intracranial Aneurysm and Aortic Dissection in Hypertensive Rat Treated With the Prostaglandin F–Receptor Antagonist AS604872

Fukuda Miyuki,Aoki Tomohiro,Manabe Toshiaki,Maekawa Akiko,Shirakawa Takayuki,Kataoka Hiroharu,Takagi Yasushi,Miyamoto Susumu,Narumiya Shuh
Journal of Pharmacological Sciences, 2014
… Given the involvement of prostaglandin F2α and its receptor, FP, in extracellular matrix remodeling in a mouse model of pulmonary fibrosis, here we induced hypertension and IA in rats by salt loading and hemi-lateral ligation of renal and carotid arteries and examined effects of a selective FP antagonist, AS604872, on these vascular events. …
NAID 130004700281

Effects of Different Five-day Progesterone-based Fixed-time AI Protocols on Follicular/Luteal Dynamics and Fertility in Dairy Cows

GARCIA-ISPIERTO Irina,LÓPEZ-GATIUS Fernando
Journal of Reproduction and Development, 2014
… The protocols consisted of a progesterone intravaginal device fitted for five days, along with the administration of different combinations of gonadotropin releasing hormone, equine chorionic gonadotropin and a single or double dose (24 h apart) of prostaglandin F2α. …
NAID 130004687236

Related Pictures

★リンクテーブル★

リンク元	「プロスタグランジンF2α」「プロスタグランジンF2」
拡張検索	「prostaglandin F2 alpha」「prostaglandin F2alpha」「prostaglandin F2α」
関連記事	「prostaglandin」「F」「prostaglandins」

「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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