5094-14-4

Basic information

• Product Name: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1
• Synonyms: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1;9,15-DIOXO-11ALPHA-HYDROXY-PROSTAN-1-OIC ACID;CDUVSQMTLOYKTR-ZHALLVOQSA-N;13,14-dihydro-15-keto PGE1;9,15-dioxo-11α-hydroxy-prostan-1-oic acid
• CAS NO: 5094-14-4
• Molecular Formula: C20H34O5
• Molecular Weight: 354.48
• Mol File: 5094-14-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 537.2°C at 760 mmHg
• Flash Point: 292.7°C
• Appearance: /
• Density: 1.072g/cm³
• Vapor Pressure: 8.82E-14mmHg at 25°C
• Refractive Index: 1.492
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), THF (Slightly)
• PKA: 4.77±0.10(Predicted)
• CAS DataBase Reference: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1(CAS DataBase Reference)
• NIST Chemistry Reference: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1(5094-14-4)
• EPA Substance Registry System: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1(5094-14-4)

Safety Data

• Hazardous Substances Data: 5094-14-4(Hazardous Substances Data)

Usage

Description

13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1 is a metabolite of Prostaglandin E1 (PGE1) with significantly reduced biological activity compared to its parent compound. It is characterized by its weak inhibitory effect on ADP-induced platelet aggregation in human platelet-rich plasma and washed platelets, with IC50 values of 54 and 200 μM, respectively, as opposed to PGE1's IC50 of 40 nM. Steady state plasma concentrations of 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1 are approximately 10 pg/ml.

Uses

Used in Pharmaceutical Industry:
13,14-DIHYDRO-15-KETO PROSTAGLANDIN E1 is used as an active ingredient in compositions for the treatment of external secretion disorders. It has been demonstrated to induce arterial thromboresistance in experimental animals and humans, albeit at concentrations several magnitudes higher than those of Prostaglandin E1. This makes it a valuable component in formulations aimed at addressing specific medical conditions related to blood flow and platelet aggregation.

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/h16-17,19,23H,2-14H2,1H3,(H,24,25)/t16-,17-,19-/m1/s1

Upstream product

• 191919-02-5 13,14-dihydro-15-keto-prostaglandin F_2α 

Relevant articles and documents

Characterization of aldo-keto reductase 1C subfamily members encoded in two rat genes (akr1c19 and RGD1564865). Relationship to 9-hydroxyprostaglandin dehydrogenase

Rat genes, akr1c19 and RGD1564865, encode members (R1C19 and 20HSDL, respectively) of the aldo-keto reductase (AKR) 1C subfamily, whose functions, however, remain unknown. Here, we show that recombinant R1C19 and 20HSDL exhibit NAD+-dependent dehydrogenase activity for prostaglandins (PGs) with 9α-hydroxy group (PGF2α, its 13,14-dihydro- and 15-keto derivatives, 9α,11β-PGF2 and PGD2). 20HSDL oxidized the PGs with much lower Km (0.3–14 μM) and higher kcat/Km values (0.064–2.6 min?1μM?1) than those of R1C19. They also differed in other properties: R1C19, but not 20HSDL, oxidized some 17β-hydroxysteroids (5β-androstane-3α,17β-diol and 5β-androstan-17β-ol-3-one). 20HSDL was specifically inhibited by zomepirac, but not by R1C19-selective inhibitors (hexestrol, flavonoids, ibuprofen and flufenamic acid), although the two enzymes were sensitive to indomethacin and cis-unsaturated fatty acids. The mRNA for 20HSDL was expressed abundantly in rat kidney and at low levels in the liver, testis, brain, heart and colon, in contrast to ubiquitous expression of R1C19 mRNA. The comparison of enzymic features of R1C19 and 20HSDL with rat PG dehydrogenases and other AKRs suggests not only a close relationship of 20HSDL with 9-hydroxy-PG dehydrogenase in rat kidney, but also roles of R1C19 and rat AKRs (1C16 and 1C24) in the metabolism of PGF2α, PGD2 and 9α,11β-PGF2 in other tissues.