PGF2alpha-EA
Basic information
- CAS
353787-70-9- Standard SMILES
CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NCCO)[C@@H](O)C[C@H]1O- InChIKey
XCVCLIRZZCGEMU-WLOFLUCMSA-N- Molecular formula
- C22H39NO5
- Average molar mass
- 397.5 g/mol
- Monoisotopic mass
- 397.28282334
Overview
Prostaglandin F2alpha 1-ethanolamide is an N-acylethanolamine compound formed by a condensation of prostaglandin F2alpha and ethanolamine. It is a prostaglandins Falpha and a N-acylethanolamine. It is functionally related to a prostaglandin F2alpha.
Names & identifiers
- Preferred name
- PGF2alpha-EA
- IUPAC
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide
- English name
- Dinoprost ethanolamide
- Molecular formula
- C22H39NO5
- Molecular weight
- 397.55
Names & synonyms
PGF2alpha-EAN-(9S,11R,15S-trihydroxy-5Z,13E-prostadienoyl)-ethanolamineRefChem:1094644353787-70-9(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamideProstaglandin F2|A ethanolamideDinoprost ethanolamideprostamide F2alphaprostaglandin F2alpha 1-ethanolamideProstaglandin F2alpha Ethanolamide Lipid Maps(R) MS Standard(5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxy-N-(2-hydroxyethyl)prosta-5,13-dien-1-amideProstaglandin F2alpha-EA
Show more names
ProstaglandinF2α ethanolamidePROSTAGLANDIN F2A ETHANOLAMIDEProstaglandin F2α EthanolamidePROSTAGLANDIN F2ALPHA ETHANOLAMIDEProstaglandin F2 Ethanolamide MaxSpecStandardProstaglandin F2α Ethanolamide MaxSpec? StandardProstaglandin F2α Ethanolamide Lipid Maps MS StandardProstaglandin F2α Ethanolamide Lipid Maps? MS Standard
Prostaglandin F2.alpha. EthanolamidePMF2alphaProstamide-F2alphaLMFA03010075orb1692224SCHEMBL7602862Prostaglandin F2?? EthanolamideCHEBI:53081
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 110 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 14
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 480
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physicochemical properties
- Flash point
- 14 °C · 14 °C
- storage temp.
- 20 °C · −20°C
- solubility
- 10 mg/ml; · DMF: Miscible; DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): 10 mg/ml
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
- 210 · P210-P305+P351+P338
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38
- Safety Statements
- 7 · 7-16-26-36
- RIDADR
- 1170 · UN 1170 3/PG 2
- WGK Germany
- 1 · 1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 1
- ridadr
- UN 1170 3/PG 2
- risk_code
- 11-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 7-16-26-36
- Hazard statements
- H225-H319
- Precautionary statements
- P210-P305+P351+P338
Chemistry & industry
Applications
DescriptionProstaglandin F2α ethanolamide (PGF2α-EA) is produced by COX-2 metabolism of the endogenous cannabinoid, arachidonoyl ethanolamide (AEA), found in brain, liver, and other mammalian tissues. AEA can be metabolized directly by the sequential action of COX-2 and specific PG synthases to produce ethanolamide congeners of the classical PGs. PGF2α-EA has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of living mice. PGF2α-EA is a potent dilator (EC50 = 58 nM) of the cat iris sphincter, which is a model system for testing potential intraocular hypotensive agents.
UsesProstaglandin F2α ethanolamide (Prostamide F2α) is an ethanolamide-like G protein-coupled receptor. Prostaglandin F2α is also a luteinizing hormone in sheep and may be a nociceptive mediator in the spinal cord[1][2][3].
Additional notes
DefinitionChEBI: Prostaglandin F2alpha 1-ethanolamide is an N-acylethanolamine compound formed by a condensation of prostaglandin F2alpha and ethanolamine. It is a N-acylethanolamine and a prostaglandins Falpha. It is functionally related to a prostaglandin F2alpha.
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