Prostaglandin F2α Ethanolamide-d4

Prostaglandin F_2α Ethanolamide-d₄

Cayman Chemical Item Number 316013

PGF_2α-EA-d₄; Dinoprost Ethanolamide-d₄

Description

Prostaglandin F_2α ethanolamide (PGF_2α-EA-d₄) contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of PGF_2α-EA by GC- or LC-mass spectrometry. PGF_2α-EA is produced by cyclooxygenase 2 (COX-2) metabolism of the endogenous cannabinoid arachidonoyl ethanolamide (AEA) found in brain, liver, and other mammalian tissues.¹ AEA can be metabolized by fatty acid amide hydrolase (FAAH) to give free arachidonic acid, which is the well known and conventional substrate for COX enzymes. However, it has also been reported that AEA can be used directly by COX-2 to produce ethanolamide congeners of the classical prostaglandins, including PGE₂.² PGF_2α-EA has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of living mice. PGF_2α-EA is a potent dilator (EC₅₀ = 58 nM) of the cat iris sphincter, which is a model system for testing potential intraocular hypotensive agents.³

1 Bachur, N.R., Masek, K., Melmon, K.L., et al. Fatty acid amides of ethanolamine in mammalian tissues. J Biol Chem 240 1019-1024 (1965).

2 Yu, M., Ives, D., and Ramesha, C.S. Synthesis of prostaglandin E₂ ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272 21181-21186 (1997).

3 Woodward, D.F., Tang-Liu, D.D., Madhu, C., et al. Prostaglandin F_2α (PGF_2α) 1-ethanolamide: A pharmacologically unique local hormone biosynthesized from anandamide. 27 (2000).

Synonyms

PGF2α-EA-d4
Dinoprost Ethanolamide-d4

Formal Name

N-(2-hydroxyethyl)-9α,11α,15S-trihydroxy-prosta-5Z,13E-dien-1-amide-3,3,4,4-d4

Molecular Formula

C₂₂H₃₅D₄NO₅

Formula Weight

401.6

Formulation

A solution in methyl acetate

Purity

≥99% deuterated forms (d1-d4)

Stability

2 years

Storage

-20°C

Shipping

Wet ice in continental US; may vary elsewhere

SMILES

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CCCCCC(O)/C=C/C1C(O)CC(O)C1C/C=C\CCCC(=O)NCCO

Background Reading

Bachur, N.R., Masek, K., Melmon, K.L., et al. Fatty acid amides of ethanolamine in mammalian tissues. J Biol Chem 240 1019-1024 (1965).

Yu, M., Ives, D., and Ramesha, C.S. Synthesis of prostaglandin E₂ ethanolamide from anandamide by cyclooxygenase-2. J Biol Chem 272 21181-21186 (1997).

Woodward, D.F., Tang-Liu, D.D., Madhu, C., et al. Prostaglandin F_2α (PGF_2α) 1-ethanolamide: A pharmacologically unique local hormone biosynthesized from anandamide. 27 (2000).

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25 µg 
$50.00

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50 µg 
$95.00

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100 µg 
$180.00

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1 mg 
$1,400.00

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Prostaglandin F_2α Ethanolamide-d₄