| Identification | More | [Name]
Prostaglandin F2a | [CAS]
551-11-1 | [Synonyms]
9ALPHA,11ALPHA,15S-TRIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID
DINOPROST
PGF2ALPHA
PROSTAGLANDIN F2ALPHA
(5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-3,13-dien-1-oicacid
2beta(s*,e),3alpha,5alpha))-alpha(z
5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-7-(l-5-heptenoicaci
7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoicaci
7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoicaci(1r-(1
7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoicacid
7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoicacid
9,11,15-trihydroxy-,(5z,9alpha,11alpha,13e,15s)-prosta-13-dien-1-oicacid
9,11,15-trihydroxyprosta-5,13-dien-1-oicacid
amoglandin
cyclosin
dinolytic
enzaprost
enzaprostf
glandin
l-pgf2-alpha | [EINECS(EC#)]
215-355-9 | [Molecular Formula]
C20H34O5 | [MDL Number]
MFCD00135231 | [Molecular Weight]
354.48 | [MOL File]
551-11-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
25-35° | [alpha ]
D25 +23.5° (c = 1 in tetrahydrofuran) | [Boiling point ]
407.69°C (rough estimate) | [density ]
1.0458 (rough estimate) | [refractive index ]
1.6120 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:100.0(Max Conc. mg/mL);282.1(Max Conc. mM)
Water:100.0(Max Conc. mg/mL);282.1(Max Conc. mM) | [form ]
Low melting white solid or colorless oil. | [pka]
pKa 4.90(H2O,t=25±2,I=0.0，c<0.01,N2) (Uncertain) | [color ]
White to light brown | [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+ | [InChIKey]
PXGPLTODNUVGFL-JPYXJAOSNA-N | [SMILES]
C([C@H]1[C@H](C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC)O)/C=C\CCCC(=O)O |&1:1,2,4,6,9,r| | [CAS DataBase Reference]
551-11-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 4 Oral
Repr. 1B | [Safety Profile]
Poison by subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Human and experimental teratogenic and experimental reproductive effects. Human reproductive effects by subcutaneous, intravenous, intramuscular, intraperitoneal, intravaginal, and intraplacental routes: postpartum depression and other maternal effects, abortion, and changes in measures of ferulity. Human teratogenic effects by intraplacental route: extra embryonic structures. Human systemic effects by intravenous route: hypermoulity, diarrhea, nausea or vomiting. Human mutation data reported. When heated to decomposition it emits acrid smoke and fumes | [Hazardous Substances Data]
551-11-1(Hazardous Substances Data) | [Toxicity]
LD50 in rabbits (mg/kg): 2.5-5.0 i.v.; 2.5-5.0 i.m. (Fujita) |
| Hazard Information | Back Directory | [Description]
Prostaglandin F2α (551-11-1) is present in numerous species and has a widespread distribution. It can cause smooth muscle contraction in the vascular, bronchial, intestinal, and myometrial regions, and has potent luteolytic activity. PGF2α exerts its physiological effects through receptor mediation, with maximal ovine myometrial contraction being achieved at 125 nM PGF2α in vitro, and its receptor-mediated activity is most potent at 50-100 nM. Studies have also shown that PGF2α inhibits nitric oxide production in uterine tissue, enhances uterine contractility, and exhibits potent luteolytic activity. Furthermore, PGF2α functions as an activator of PGF2αR. | [History]
Prostaglandins (PGs) are a class of important endogenous products with a wide range of physiological activities. PGs were first discovered and named by American scholar Von Eluer in 1930. In 1962, Bergstorm extracted two pure PGs (PGF1 and PGF2) and determined their chemical structures. In 1969, Willis first proposed that PGs are an inflammatory mediator in the body. Subsequently, various physiological and pharmacological activities of PGs have been intensively studied. | [Uses]
One of the most biologically studied of the primary prostaglandins. Closely related to Prostaglandin E2 (PGE2) in that both
prostaglandins are biosynthesized from the same precursors and that PGF2 is the synthetic reduction product of PGE2. Phospholipase | [Definition]
ChEBI: Prostaglandin F2α is a prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor. | [Pharmacokinetics]
Dinoprost is a natural prostaglandin F2α (PGF2α), which can directly act on the myometrium, stimulate the pregnant uterus to contract the uterine muscle, and can soften and dilate the cervix, so it can be used for induced abortion and late labor induction. However, due to the instability of dinoprost at room temperature, inconvenient storage and transportation, complex synthesis process and high cost, the application of dinoprost is difficult to popularize. | [storage]
Store at -20°C | [Mode of action]
Prostaglandin F2α (PGF2α) stimulates myometrial activity, relaxes the cervix, inhibits corpus luteal steroidogenesis, and induces luteolysis by direct action on the corpus luteum. In pregnancy, PGF2α is medically used to sustain contracture and provoke myometrial ischemia to accelerate labor and prevent significant blood loss in labor. | [References]
[1] CRAIG G M. Prostaglandins in reproductive physiology.[J]. Postgraduate Medical Journal, 1975, 51 592: 74-84. DOI: 10.1136/pgmj.51.592.74
[2] P. FALARDEAU D G A Martineau. [Prostaglandins and thromboxanes].[J]. La semaine des hopitaux?: organe fonde par l’Association d’enseignement medical des hopitaux de Paris, 1984, 2 1: 1117-1136. DOI: 10.1016/c2013-0-04149-7
[3] K WATANABE. Stereospecific conversion of prostaglandin D2 to (5Z,13E)-(15S)-9 alpha-11 beta,15-trihydroxyprosta-5,13-dien-1-oic acid (9 alpha,11 beta-prostaglandin F2) and of prostaglandin H2 to prostaglandin F2 alpha by bovine lung prostaglandin F synthase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1986, 83 6: 1583-1587. DOI: 10.1073/pnas.83.6.1583
[4] D J CRANKSHAW V G. Pharmacological characterization in vitro of prostanoid receptors in the myometrium of nonpregnant ewes.[J]. Journal of reproduction and fertility, 1995, 103 1: 55-61. DOI: 10.1530/jrf.0.1030055
[5] D S SKIBA. Anti-atherosclerotic effect of the angiotensin 1–7 mimetic AVE0991 is mediated by inhibition of perivascular and plaque inflammation in early atherosclerosis[J]. British Journal of Pharmacology, 2016, 174 22: 4055-4069. DOI: 10.1111/bph.13685
[6] Y SAKAIRI. 5,6-EET inhibits ion transport in collecting duct by stimulating endogenous prostaglandin synthesis.[J]. American Journal of Physiology, 1995, 268 5 Pt 2: F931-9. DOI: 10.1152/ajprenal.1995.268.5.f931 |
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Energy Chemical
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www.energy-chemical.com |
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