プロスタグランジンF2α
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
Wikipedia preview
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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This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.
Dinoprost
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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
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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 Y 38562-01-5 |
ATC code |
G02AD01 (WHO) |
PubChem |
CID 5280363 |
IUPHAR/BPS |
1884 |
DrugBank |
DB01160 Y |
ChemSpider |
4444062 N |
KEGG |
D01352 N |
ChEMBL |
CHEMBL815 N |
Chemical data |
Formula |
C20H34O5 |
Molar mass |
354.48 g/mol |
SMILES
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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
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Key:PXGPLTODNUVGFL-YNNPMVKQSA-N N
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NY (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 Analogues
- 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.
Analogues
The following medications are analogues 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.
- ^ 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.
Eicosanoids
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Precursor |
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Prostanoids |
Prostaglandins (PG) |
Precursor |
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Active |
D/J |
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E/F |
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I |
- I2 (Prostacyclin/Epoprostenol):
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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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Eoxins (EX) |
Precursor |
- Arachidonic acid 15-hydroperoxide
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Eoxins |
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Nonclassic |
- Lipoxins (LX) (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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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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Prostanoid signaling
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Receptor
(ligands) |
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Enzyme
(inhibitors) |
COX (PTGS) |
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PGD2 synthase |
- Retinoids
- Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
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PGE synthase |
HQL-79
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PGF synthase |
Bimatoprost
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PGI2 synthase |
Tranylcypromine
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TXA synthase |
- Camonagrel
- Dazmegrel
- Dazoxiben
- Furegrelate
- Isbogrel
- Midazogrel
- Nafagrel
- Nicogrelate
- Ozagrel
- Picotamide
- Pirmagrel
- Ridogrel
- Rolafagrel
- Samixogrel
- Terbogrel
- U63557A
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Others |
- Precursors: Linoleic acid
- γ-Linolenic acid (gamolenic acid)
- Dihomo-γ-linolenic acid
- Diacylglycerol
- Arachidonic acid
- Prostaglandin G2
- Prostaglandin H2
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See also: Leukotrienergics
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UpToDate Contents
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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
- 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
- The effect of leg hyperthermia using far infrared rays in bedridden subjects with type 2 diabetes mellitus
Related Links
- This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.
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★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
[★]
プロスタグランジン prostaglandins PG
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プロスタグランジン