42935-17-1

Basic information

• Product Name: PROSTAGLANDIN H2
• Synonyms: ENDOPEROXIDE H2;9ALPHA,11ALPHA-EPIDIOXY-15S-HYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID;PROSTAGLANDIN R2;PROSTAGLANDIN H2;PGH2;[1-14C]Prostaglandin?H2;Prostaglandin?H2?(PGH2);7-[5-(3-hydroxyoct-1-enyl)-2,3-dioxabicyclo[2.2.1]hept-6-yl]hept-5-enoic acid
• CAS NO: 42935-17-1
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.47
• EINECS: 200-662-2
• Mol File: 42935-17-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 490.1°C at 760 mmHg
• Flash Point: -17 °C
• Appearance: /acetone solution
• Density: 1.129g/cm³
• Vapor Pressure: 1.16E-11mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: −70°C
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: PROSTAGLANDIN H2(CAS DataBase Reference)
• NIST Chemistry Reference: PROSTAGLANDIN H2(42935-17-1)
• EPA Substance Registry System: PROSTAGLANDIN H2(42935-17-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36-66-67
• Safety Statements: 9-16-26
• RIDADR: UN 1090 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 42935-17-1(Hazardous Substances Data)

Usage

Description

Prostaglandin H2 (PGH2) was first isolated from incubations of arachidonic acid with ovine seminal vesicle microsomes, and was described as a potent vasoconstrictor. PGH2 is the precursor for all 2-series PGs and thromboxanes (TXs), and is a TP receptor agonist which irreversibly aggregates human platelets at 50-100 ng/ml.

Uses

PGH2 (Prostaglandin H2) is a thromboxane A2 precursor and a platelet aggregator of vascular smooth muscle contraction.

InChI:InChI=1/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 51982-36-6 Prostaglandin G₂ 

Downstream Products

• 91712-41-3 levuglandin LGD₂ 
• 91712-44-6 levuglandin LGE₂ 
• 35121-78-9 Prostacyclin 
• 363-24-6 dinoprostone 
• 65026-04-2 prostaglandin D₂ 
• 551-11-1 dinoprost 

Relevant articles and documents

Human cyclooxygenase-2 is a sequence homodimer that functions as a conformational heterodimer

Prostaglandin endoperoxide H synthases 1 and 2, also known as cyclooxygenases (COXs) 1 and 2, convert arachidonic acid (AA) to prostaglandin endoperoxide H2. Prostaglandin endoperoxide H synthases are targets of nonspecific nonsteroidal anti-inflammatory drugs and COX-2-specific inhibitors called coxibs. PGHS-2 is a sequence homodimer. Each monomer has a peroxidase and a COX active site. We find that human PGHS-2 functions as a conformational heterodimer having a catalytic monomer (Ecat) and an allosteric monomer (Eallo). Heme binds tightly only to the peroxidase site of Ecat, whereas substrates, as well as certain inhibitors (e.g. celecoxib), bind the COX site of Ecat. Ecat is regulated by Eallo in a manner dependent on what ligand is bound to Eallo. Substrate and nonsubstrate fatty acids (FAs) and some COX inhibitors (e.g. naproxen) preferentially bind to the COX site of E allo. AA can bind to Ecat and Eallo, but the affinity of AA for Eallo is 25 times that for Ecat. Palmitic acid, an efficacious stimulator of human PGHS-2, binds only E allo in palmitic acid/murine PGHS-2 co-crystals. Nonsubstrate FAs can potentiate or attenuate actions of COX inhibitors depending on the FA and whether the inhibitor binds Ecat or Eallo. Our studies suggest that the concentration and composition of the free FA pool in the environment in which PGHS-2 functions in cells, the FA tone, is a key factor regulating PGHS-2 activity and its responses to COX inhibitors. We suggest that differences in FA tone occurring with different diets will likely affect both baseline prostanoid synthesis and responses to COX inhibitors.

COX-2-targeted imaging agents

The presently disclosed subject matter provides a method for synthesizing a radiological imaging agent by reacting a COX-2-selective ligand with a compound comprising a detectable group, wherein the COX-2-selective ligand is a derivative of a non-steroidal anti-inflammatory drug (NSAID) comprising an ester moiety or a secondary amide moiety. Also provided are compositions that are synthesized using the method, as well as methods of using the compositions of the presently disclosed subject matter.