11β-Prostaglandin F

Cayman Chemical Item Number 16520

9α,11β-PGF; 11β-PGF; 11-epi PGF (CAS 38432-87-0)

11β-Prostaglandin F2α (CAS 38432-87-0)

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Description

11β-Prostaglandin F (11β-PGF) is the primary plasma metabolite of PGD2 in vivo.1 Normal human urinary excretion of 11β-PGF is about 54 ng/mmol creatinine, which is increased nearly 3-fold upon allergen-induced bronchoconstriction in asthmatics.2 It is equipotent to PGF in inducing human bronchial smooth muscle contractions and inhibition of adipose differentiation.3,4 11β-PGF inhibits ADP or thrombin-induced human platelet aggregation at concentrations of 0.14 to 2.8 µM.5

1 Liston, T.E., and Roberts, L.J. Transformation of prostaglandin D2 to 9α,11β-(15S)-trihydroxy-prosta-(5Z,13E)-dien-1-oic acid (9α,11β-prostaglandin F2): A unique biologically active prostaglandin produced enzymatically in vivo in humans. Proc Natl Acad Sci USA 82 6030-6034 (1985).

2 O'Sullivan, S., Dahlén, B., Dahlén, S., et al. Increased urinary excretion of the prostaglandin D2 metabolite 9α,11β-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction. J Allergy Clin Immunol 98 421-432 (1996).

3 Coleman, R.A., and Sheldrick, R.L.G. Prostanoid-induced contraction of human bronchial smooth muscle is mediated by TP-receptors. Br J Pharmacol 96 688-692 (1989).

4 Lepak, N.M., and Serrero, G. Inhibition of adipose differentiation by 9α, 11β-prostaglandins F. Prostaglandins 46 511-517 (1993).

5 Pugliese, G., Spokas, E.G., Marcinkiewicz, E., et al. Hepatic transformation of prostaglandin D2 to a new prostanoid, 9α,11β-prostaglandin F2, that inhibits platelet aggregation and constricts blood vessels. J Biol Chem 260 14621-14625 (1985).

Synonyms
  • 9α,11β-PGF
  • 11β-PGF
  • 11-epi PGF
Formal Name 9α,​11β,​15S-​trihydroxy-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 38432-87-0
Molecular Formula C20H34O5
Formula Weight 354.5
Formulation A crystalline solid
Purity ≥99%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@H]​(/C=C/[C@@H]​(O)​CCCCC)​[C@@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(O)​C1
InCHI Code
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​1S/C20H34O5/c1-2-3-6-9-15(21)​12-13-17-16(18(22)​14-19(17)​23)​10-7-4-5-8-11-20(24)​25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)​/b7-4-,13-12+/t15-,16+,17+,18-,19-/m0/s1
InCHI Key
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PXGPLTODNUVGFL-ZWAKLXPCSA-N

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11β-Prostaglandin F2α is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $104.00 $0.00
5 mg $468.00 $0.00
10 mg $832.00 $0.00
25 mg $1,820.00 $0.00
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