プロスタグランジンF2α
WordNet
- first in order of importance; "the alpha male in the group of chimpanzees"; "the alpha star in a constellation is the brightest or main star"
- the 1st letter of the Greek alphabet
- the beginning of a series or sequence; "the Alpha and Omega, the first and the last, the beginning and the end"--Revelations
- early testing stage of a software or hardware product; "alpha version"
- any high mountain
PrepTutorEJDIC
- アルファ(ギリシア語アルファベットの第1字A,α;英語のA,aに相当) / アルファ星(星座の主星)
- parental guidance(映画の観客指定で)親の認可[映画]
- 高山,高峰
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/11/11 09:48:08」(JST)
[Wiki en表示]
This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.
Dinoprost Tromethamine
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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 |
Legal status |
?
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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 |
4444062 N |
KEGG |
D01352 N |
ChEMBL |
CHEMBL815 N |
Chemical data |
Formula |
C20H34O5 |
Mol. 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
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InChI
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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 N
Key:PXGPLTODNUVGFL-YNNPMVKQSA-N N
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N (what is this?) (verify) |
Prostaglandin F2α (PGF2α 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 PGF2α is dependent on the number of receptors on the corpus luteum membrane.
The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.[1]
Contents
- 1 Mechanism of action
- 2 Synthesis
- 3 Analogs
- 4 References
Mechanism of action
Further information: Prostaglandin F2α receptor
PGF2α acts by binding to the prostaglandin F2α receptor.
Synthesis
In 2012 a concise and highly stereoselective total synthesis of PGF2α 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 F2α:
- 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.
Autacoids, unsaturated fatty acids: Eicosanoids
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Precursor |
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Prostanoids |
Prostaglandins (PG) and
analogues |
Precursor |
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Active |
D/J |
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E/F |
- E2 (Dinoprostone): Enprostil
- Sulprostone
- E1 (Alprostadil): Misoprostol
- Gemeprost
- F2α (Dinoprost): Bimatoprost
- Carboprost
- Latanoprost
- Tafluprost
- Travoprost
- Unoprostone
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I |
- I2 (Prostacyclin/Epoprostenol): Beraprost
- Iloprost
- Treprostinil
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Thromboxanes (TX) |
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Leukotrienes (LT) |
Precursor |
- Arachidonic acid 5-hydroperoxide
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Initial |
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SRS-A |
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Nonclassic |
- Lipoxins (A4, B4)
- Virodhamine
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By function |
- vasoconstriction
- vasodilation
- platelets: induce
- inhibit
- leukocytes: induce
- inhibit
- labor stimulation:
- PGE2 (Dinoprostone)
- PGF2α (Dinoprost)
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- Biochemical families
- carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- glycerides
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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Uterotonics/labor inducers/oxytocics (G02A)
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Cervical ripening |
Ergot alkaloids
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- Ergometrine# (+oxytocin)
- Methylergometrine
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Prostaglandins and
analogues
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- E: Misoprostol/E1#
- Gemeprost/E1
- Dinoprostone/E2
- Sulprostone/E2
- F: Dinoprost/F2α
- Carboprost/F2α
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Contraction induction |
- Oxytocin#
- Carbetocin
- Demoxytocin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Severity of oxidative stress and inflammatory activation in end-stage heart failure patients are unaltered after 1month of left ventricular mechanical assistance.
- Caruso R, Verde A, Campolo J, Milazzo F, Russo C, Boroni C, Parolini M, Trunfio S, Paino R, Martinelli L, Frigerio M, Parodi O.SourceCNR Clinical Physiology Institute, Cardiovascular Department, Niguarda Cà Granda Hospital, Piazzale Ospedale Maggiore, 3-20162 Milan, Italy.
- Cytokine.Cytokine.2012 Jul;59(1):138-44. Epub 2012 May 9.
- This study investigates the impact of early left ventricular (LV)-mechanical unloading on systemic oxidative stress and inflammation in terminal heart failure patients and their impact both on multi organ failure and on intensive care unit (ICU) stay. Circulating levels of urinary 15-isoprostane-F(2
- PMID 22579113
- Compared to dinoprost tromethamine, cloprostenol sodium increased rates of estrus detection, conception and pregnancy in lactating dairy cows on a large commercial dairy.
- Pursley JR, Martins JP, Wright C, Stewart ND.SourceDepartment of Animal Science, Michigan State University, East Lansing, Michigan, USA.
- Theriogenology.Theriogenology.2012 May 22. [Epub ahead of print]
- Using two PGF(2α) treatments 14 days apart as a way to enhance estrus detection rate following the 2nd treatment is a reproductive management tool that continues to be used on large dairy farms. In one study, in cows with a functional CL and a dominant follicle, treatment with cloprostenol vs. dino
- PMID 22626771
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, 2010-04-00
- … 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
- Molecular Mechanisms Underlying PGF2.ALPHA.-induced Hypertrophy of Vascular Smooth Muscle Cells
- FAN Chunyuan,KATSUYAMA Masato,WEI Haiyan,XIA Qingjie,LIU Wentao,YABE-NISHIMURA Chihiro
- 薬学雑誌 130(2), 211-214, 2010
- … The present review focuses primarily on the studies we made in recent years to improve the understanding of the molecular mechanisms of PGF2α-induced hypertrophy of Vascular Smooth Muscle Cells (VSMC). … In this review, we will summarize the recent findings in the context of the PGF2α signaling pathway in three parts: PGF2α binding to its receptor, transactivation of EGF receptor, two independent signaling transduction pathways increasing the expression of NOX1 gene. …
- NAID 130000171290
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Related Pictures
★リンクテーブル★
[★]
- 英
- prostaglandin F2 alpha, prostaglandin F2alpha, prostaglandin F2α, PGF2 alpha, PGF2alpha, PGF2α
- 同
- ジノプロスト dinoprost
- 商
- グランディノン、プロスタルモン・F、プロスタグランジンF2α
- 関
- プロスタグランジンF2 prostaglandin F2。プロスタグランジン
[★]
プロスタグランジンF2
- 関
- dinoprost、PGF2 alpha、PGF2alpha、prostaglandin F2 alpha、prostaglandin F2alpha
[★]
- 同
- プロスタグランジン
[★]
α、アルファ
- 関
- alfa
[★]
- 関
- prostaglandin F
[★]
プロスタグランジンF2