551-11-1 Usage
Description
Prostaglandin F2α (PGF2α) is a naturally occurring prostaglandin that is widely distributed and found in many species. It is known for its ability to cause contraction of vascular, bronchial, intestinal, and myometrial smooth muscle, as well as its potent luteolytic activity. PGF2α exerts its receptor-mediated physiological activity at concentrations of 50-100 nM, with maximal ovine myometrial contraction achievable at 125 nM in vitro. It is closely related to Prostaglandin E2 (PGE2), as both are biosynthesized from the same precursors, and PGF2α is the synthetic reduction product of PGE2.
Uses
Used in Pharmaceutical Industry:
Prostaglandin F2α is used as a pharmaceutical agent for inducing labor in obstetrics. It is particularly effective due to its ability to cause contraction of myometrial smooth muscle, which helps initiate and maintain labor.
Used in Veterinary Medicine:
In veterinary medicine, PGF2α is used as a luteolytic agent to control the estrous cycle in animals, such as cows and sheep. Its potent luteolytic activity helps regulate reproductive processes and improve the efficiency of breeding programs.
Used in Research:
Prostaglandin F2α is also used in research settings to study the physiological effects of prostaglandins on various tissues and organs, including their role in inflammation, pain, and other biological processes. This helps scientists better understand the mechanisms of action and potential therapeutic applications of prostaglandins.
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.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 551-11-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 551-11:
(5*5)+(4*5)+(3*1)+(2*1)+(1*1)=51
51 % 10 = 1
So 551-11-1 is a valid CAS Registry Number.
InChI:InChI=1/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)/t15-,16+,17+,18-,19+/m0/s1
551-11-1Relevant articles and documents
Marnett,Bienkowski
, p. 4303,4304 - 4307 (1977)
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling
Kim, Taehyeong,Lee, Sung Il,Kim, Sejin,Shim, Su Yong,Ryu, Do Hyun
, (2019/09/17)
The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.
Synthesis of Alfaprostol and PGF2α through 1,4-Addition of an Alkyne to an Enal Intermediate as the Key Step
Baars, Hannah,Classen, Moritz J.,Aggarwal, Varinder K.
, p. 6008 - 6011 (2017/11/10)
The veterinary drug Alfaprostol and prostaglandin PGF2α have been synthesized in just nine steps. The strategy involved the conjugate addition of an alkyne to a bicyclic enal, available in three steps by a proline-catalyzed aldol reaction of succinaldehyde. In the case of Alfaprostol, this resulted in the shortest synthesis reported to date. For PGF2α, this approach improved our previous route by making the 1,4-addition and ozonolysis more operationally simple.