17-phenyl trinor Prostaglandin F2α serinol amide

17-phenyl trinor Prostaglandin F_2α serinol amide

Cayman Chemical Item Number 10004237

17-phenyl trinor PGF_2α-SA; 17-phenyl trinor PGF_2α serinol amide; Bimatoprost serinol amide

Description

2-Arachidonyl glycerol (2-AG) exhibits cannabinoid agonist activity at the CB₁ receptor,¹ is an important endogenous monoglyceride species,² and is thus considered to be the natural ligand for the CB₁ receptor. 2-AG can also be metabolized by COX-2 to form prostaglandin 2-glyceryl esters.³ These 2-glyceryl esters rapidly equilibrate to form 90:10 mixtures favoring the more stable 1-glyceryl ester. 17-phenyl trinor Prostaglandin F_2α serinol amide (17-phenyl trinor PGF_2α serinol amide) is a stable analog of PGF_2α 2-glyceryl ester incorporating an activity-enhancing 17-phenyl substitution. The biological activity of 17-phenyl trinor PGF_2α serinol amide has not yet been determined.

1 Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB₁ receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem 122 890-895 (1997).

2 Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).

3 Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. J Biol Chem 277(47) 44877-44885 (2002).

Synonyms

17-phenyl trinor PGF2α-SA
17-phenyl trinor PGF2α serinol amide
Bimatoprost serinol amide

Formal Name

N-[(2-hydroxy-1-hydroxymethyl)ethyl]-9α,11α,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-amide

Molecular Formula

C₂₆H₃₉NO₆

Formula Weight

461.6

Formulation

A solution in ethanol

Purity

>98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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O[C@H](/C=C/[C@@H]1C(C/C=C\CCCC(N([H])C(CO)CO)=O)[C@@H](O)C[C@H]1O)CCC2=CC=CC=C2

Size

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Subtotal

1 mg 
$54.00

$0.00

5 mg 
$243.00

$0.00

10 mg 
$432.00

$0.00

50 mg 
$1,890.00

$0.00

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17-phenyl trinor Prostaglandin F_2α serinol amide