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Prostaglandin E2

CAS No.
363-24-6
Chemical Name:
Prostaglandin E2
Synonyms
PROSTAGLANDIN;DINOPROSTONE;PGE2;dinoproston;Propess;Cervidil;Prepidil;Dinoprostol;Prostaglandin E2 (PGE2);l-pge2
CBNumber:
CB8461799
Molecular Formula:
C20H32O5
Molecular Weight:
352.47
MDL Number:
MFCD00077861
MOL File:
363-24-6.mol
MSDS File:
SDS
Last updated:2024-03-27 14:23:05

Prostaglandin E2 Properties

Melting point 66-68 °C
alpha -85.5 º (c=1, C2H5OH)
Boiling point 406.07°C (rough estimate)
Density 1.0601 (rough estimate)
refractive index 1.6120 (estimate)
storage temp. -20°C
solubility ethanol: 1 mg/mL
form powder
pka pKa 4.77± 0.09(H2O,t=25±0.1,I=0.1(NaCl)) (Uncertain)
color Clear yellow to amber
Water Solubility insoluble
Merck 14,7877
BRN 4709356
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey XEYBRNLFEZDVAW-ARSRFYASSA-N
CAS DataBase Reference 363-24-6(CAS DataBase Reference)
FDA UNII K7Q1JQR04M
NCI Dictionary of Cancer Terms prostaglandin
ATC code G02AD02

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H360FD
Precautionary statements  P202-P264-P270-P280-P301+P312-P308+P313
Hazard Codes  T
Risk Statements  60-22-61
Safety Statements  53-22-26-36/37/39-45
WGK Germany  3
RTECS  UK8000000
8-10
HS Code  29375000
NFPA 704
0
2 0

Prostaglandin E2 price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 538904 Prostaglandin E? 363-24-6 1mg $214 2024-03-01 Buy
Sigma-Aldrich 1213103 Dinoprostone United States Pharmacopeia (USP) Reference Standard 363-24-6 125mg $4250 2024-03-01 Buy
Sigma-Aldrich BP902 Dinoprostone British Pharmacopoeia (BP) Reference Standard 363-24-6 100MG $142 2022-05-15 Buy
TCI Chemical P1884 Prostaglandin E2 >98.0%(HPLC) 363-24-6 1mg $75 2024-03-01 Buy
TCI Chemical P1884 Prostaglandin E2 >98.0%(HPLC) 363-24-6 10mg $445 2024-03-01 Buy
Product number Packaging Price Buy
538904 1mg $214 Buy
1213103 125mg $4250 Buy
BP902 100MG $142 Buy
P1884 1mg $75 Buy
P1884 10mg $445 Buy

Prostaglandin E2 Chemical Properties,Uses,Production

Description

Prostaglandin E2 (363-24-6; PGE2) is an endogenous prostaglandin derived from the action of cyclooxygenase on arachidonic acid. PGE2 has diverse biological actions in the areas of inflammation, cancer, immune modulation, fertility, smooth muscle relaxation and hematopoietic stem cell homeostasis. Prostaglandin E2 acts through four distinct receptors: EP1, EP2, EP3, EP4.

Chemical Properties

White to pale yellowish-cream powder. Melting point 64-66°C, specific rotation -61°(26°C, c=1, THF). Easily hydrolyzed at pH<4 or pH>8. Soluble in chloroform, ethyl acetate, methanol, absolute ethanol and other organic solvents, slightly soluble in water.

Originator

Prostin E2,Upjohn,UK,1972

Uses

The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

Uses

For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.

Definition

ChEBI: Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostagland ns.

Manufacturing Process

Hexamethyldisilazane (1 ml) and trimethylchlorosilane (0.2 ml) are added with stirring to a solution of PGA2 (250 mg) in 4 ml of tetrahydrofuran at 0°C under nitrogen. This mixture is maintained at 5°C for 15 hours. The mixture is then evaporated under reduced pressure. Toluene is added and evaporated twice. Then the residue is dissolved in 6 ml of methanol, and the solution is cooled to -20°C. Hydrogen peroxide (0.45 ml; 30% aqueous) is added. Then, 1N sodium hydroxide solution (0.9 ml) is added dropwise with stirring at - 20°C. After 2 hours at -20°C, an additional 0.3 ml of the sodium hydroxide solution is added with stirring at -20°C. After another hour in the range -10°C to -20°C, an additional 0.1 ml of the sodium hydroxide solution is added. Then, 1.5 ml of 1 N hydrochloric acid is added, and the mixture is evaporated under reduced pressure. The residue is extracted with ethyl acetate, and the extract is washed successively with 1 N hydrochloric acid and
ine, dried with anhydrous sodium sulfate and evaporated. The residue is dissolved in 5 ml of diethyl ether. To this solution is added 0.5 ml of methanol and 0.1 ml of water. Amalgamated aluminum made from 0.5 g of aluminum metal is then added in small portions during 3 hours at 25°C. Then, ethyl acetate and 3 N hydrochloric acid are added, and the ethyl acetate layer is separated and washed successively with 1 N hydrochloric acid and
ine, dried with anhydrous sodium sulfate, and evaporated. The residue is chromatographed on 50 g of acid-washed silica gel, eluting first with 400 ml of a gradient of 50- 100% ethyl acetate in Skellysolve B, and then with 100 ml of 5% methanol in ethyl acetate, collecting 25 ml fractions. Fractions 9 and 10 are combined and evaporated to give 18 mg of 11β-PGE2. Fractions 17-25 are combined and evaporated to give 39 mg of PGE2.

brand name

Cervidil (Controlled Therapeutics); Prepidil (Pharmacia & Upjohn); Prostin E2 (Pharmacia & Upjohn);Minprostin;Prostaglandin;Prostarmon e;Prostin vr pediatric.

Therapeutic Function

Oxytocic, Abortifacient

World Health Organization (WHO)

Dinoprostone, prostaglandin E2, was introduced into medicine in 1971 and is primarily used for cervical ripening during the induction of labour. It is available in various formulations for oral, parenteral and vaginal administration. Tablets, ampoules and vaginal dosage forms (tablets, pessaries, gel) remain registered in many countries.

General Description

PGE2 Dinoprostone (Prostin E2;Cervidil) is a naturally occurring prostaglandin that is administeredin a single dose of 10 mg by controlled-release(0.3 mg/hr) vaginal insert to induce cervical ripening. Use ofthis agent will potentiate the effects of oxytocin.

Biological Activity

Endogenous prostaglandin and primary product of arachidonic acid/cyclooxygenase pathway. Binds with high affinity to EP 1 , EP 2 , EP 3 and EP 4 receptors (K d values range between ~ 1-10 nM). Influences a wide range of processes including inflammation, smooth muscle relaxation, fertility and gastric mucosal integrity. Regulates vertebrate hematopoietic stem cell (HSC) homeostasis.

Biochem/physiol Actions

Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.

Safety Profile

Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Human reproductive effects by intravenous, intraplacental, and intravaginal routes: changes in the uterus, cervix and vagina; termination of pregnancy; and changes in ferthty. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

in vitro

pge2 can stimulate the gastric nonparietal secretion [3] and has been shown to regulate the function of many cell types including dendritic cells, macrophages, t and b lymphocytes leading to both pro- and anti-inflammatory effects [2].

in vivo

pge2 regulates many physiological systems including the gastrointestinal and immune systems. in the gastrointestinal tract, pge2 plays a protective role in maintaining the integrity of the gastric mucosa. pge2 has also been shown to play a role in the maintenance of blood pressure, particularly in the setting of salt overload [2].

storage

-20°C

References

1) Healy (1990) Progesterone receptor antagonist and prostaglandins in human fertility regulation: a clinical review; Reprod. Fertil. Dev. 2 477
2) Greenhough et al. (2009) The COX-2/PGE2 pathway: key roles in the hallmarks of cancer and adaptation to the tumour microenvironment; Carcinogenesis, 30 377
3) Kalinski (2012) Regulation of Immune Responses by Prostaglandin E2; J. Immunol., 188 21
4) North et al. (2007) Prostaglandin E2 regulates vertebrate haematopoietic stem cell homeostasis; Nature, 447 1007
5) Hoggatt et al. (2013) Differential stem- and progenitor-cell trafficking by prostaglandin E2; Nature, 495 365
6) Coleman et al. (1994) Classification of prostanoid receptors: Properties, distribution and structure of the receptors and their subtypes; Pharmacol. Rev. 46 205

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View Lastest Price from Prostaglandin E2 manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Dinoprostone pictures 2024-03-27 Dinoprostone
363-24-6
US $350.00-250.00 / Gram 1Gram USP 1kg Hangzhou Hyper Chemicals Limited
Prostaglandin E2 pictures 2023-11-27 Prostaglandin E2
363-24-6
US $15.00 / gram 10gram 99% 50000 kilograms Wuhan Senwayer Century Chemical Co.,Ltd
Prostaglandin E2 pictures 2023-01-29 Prostaglandin E2
363-24-6
US $75.00-63.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
  • Dinoprostone pictures
  • Dinoprostone
    363-24-6
  • US $350.00-250.00 / Gram
  • USP
  • Hangzhou Hyper Chemicals Limited
  • Prostaglandin E2 pictures
  • Prostaglandin E2
    363-24-6
  • US $15.00 / gram
  • 99%
  • Wuhan Senwayer Century Chemical Co.,Ltd
  • Prostaglandin E2 pictures
  • Prostaglandin E2
    363-24-6
  • US $75.00-63.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.

Prostaglandin E2 Spectrum

7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicaci l-5-heptenoicaci l-7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoicacid l-pge2 l-prostaglandine2 prostin prostine2 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid (5Z,11A,13E,15S)-11,15-DIHYDROXY-9-OXO-PROSTA-5,13-DIEN-1OIC ACID [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROSTA-5,13-DIEN-1-OIC ACID [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROSTA-5,13-DIENOIC ACID PROSTAGLANDIN E2 PROSTAGLANDINS E2 (15s)-prostaglandine2 (5z,11-alpha,13e,15s)-11,15-dihydroxy-9-oxo-prosta-13-dien-1-oicacid 11,15-dihydroxy-9-oxo-,(5z,11-alpha,13e,15s)-prosta-13-dien-1-oicacid PROSTAGLANDIN E2 CELL CULTURE TESTED PROSTAGLANDIN E2 GAMMA-IRRADIATED*CELL C ULTURE TEST PROSTAGLANDIN,PGE2 9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID 7-(3-HydroxyProsta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid [5Z,11R,13E,15S,(-)]-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid Prostaglandin E2,98% [5Z,11ALPHA,13E,15S]-11,15-DIHYDROXY-9-OXOPROS Prostaglandin E2,(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, PGE2 Dinoprostone (50 mg) (COLD SHIPMENT REQUIRED) cGMP Dinoprostone Prostaglandin E2 Lipid Maps MS Standard (5Z,11α,13E,15S)- CervidilProstaglandin E2 (5z,11α,13e,15s)-11,15-dihydroxy-9-oxoprosta-5,13-dienoic acid (E)-7-[(1S,2S,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic acid 11α,15α-Dihydroxy-9-ketoprosta-5,13-dienoic acid 11α,15α-Dihydroxy-9-oxo-5-cis,13-trans-prostadienoic acid 5-Heptenoic acid, 7-[3a-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]- (7CI) Cerviprost Enzaprost E Minprositin E2 Minprostin E2 NSC 165560 NSC 196514 Prostarmon E Prostenon Prostenone Prostin (prostaglandin) U 12062 PGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid Dinoprostone, PGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid (5Z,11α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid Dinoprostone PGE2 (Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid Prosta-5,13-dien-1-oicacid, 11,15-dihydroxy-9-oxo-, (5Z,11a,13E,15S)- Dinoprostone (125 mg) (COLD SHIPMENT REQUIRED) Prostaglandin E2-biotinamide prostaglandin,PG PROSTAGLANDIN E2, >=93% (HPLC), SYNT Prostaglandin E2 MaxSpecStandard Dinoprostone/Prostaglandin E2