13,14-dihydro-16,16-difluoro Prostaglandin E1

13,14-dihydro-16,16-difluoro Prostaglandin E₁

Cayman Chemical Item Number 9000405

15-hydroxy Lubiprostone (CAS 475992-30-4)

13,14-dihydro-16,16-difluoro Prostaglandin E1 (CAS 475992-30-4)

Description

Prostaglandin E₁ (PGE₁) is produced by the metabolism of dihomo-γ-linolenic acid (DGLA) by the cyclooxygenase pathway. PGE₁ inhibits platelet aggregation (IC₅₀ = 40 nM)^1,2 and increases vasodilation. 13,14-dihydro-16,16-difluoro PGE₁ is an analog of PGE₁. 13,14-dihydro PGE₁ is a biologically active metabolite of PGE₁, inhibiting platelet aggregation with comparable potency to the parent compound.^3,2 The addition of two electron-withdrawing fluorine atoms, which should stabilize the molecule against hydrolytic cleavage, may be expected to delay degradation in vivo.⁴

1 Kobzar, G., Mardla, V., Järving, I., et al. Antiaggregating potency of E-type prostaglandins in human and rabbit platelets. Proc Est Acad Sci Chem 40 179-180 (1991).

2 Westwick, J. The effect of pulmonary metabolites of prostaglandins E₁, E₂ and F_2α on ADP-induced aggregation of human and rabbit platelets. Br J Pharmacol 58 297P-298P (1976).

3 Peskar, B.A., Cawello, W., Rogatti, W., et al. On the metabolism of prostaglandin E₁ administered intravenously to human volunteers. J Physiol Pharmacol 42 327-331 (1991).

4 Hatano, Y., Kohli, J.D., Goldberg, L.I., et al. Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclin. Proc Natl Acad Sci USA 77(11) 6846-6850 (1980).

Synonyms

15-hydroxy Lubiprostone

Formal Name

9-oxo-11α,15S-dihydroxy-16,16-difluoro-prostan-1-oic acid

CAS Number

475992-30-4

Molecular Formula

C₂₀H₃₄F₂O₅

Formula Weight

392.5

Formulation

A solution in methyl acetate

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Wet ice in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

O=C1[C@H](CCCCCCC(O)=O)[C@@H](CC[C@@H](O)C(F)(F)CCCC)[C@H](O)C1

Background Reading

Hatano, Y., Kohli, J.D., Goldberg, L.I., et al. Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclin. Proc Natl Acad Sci USA 77(11) 6846-6850 (1980).

Kobzar, G., Mardla, V., Järving, I., et al. Antiaggregating potency of E-type prostaglandins in human and rabbit platelets. Proc Est Acad Sci Chem 40 179-180 (1991).

Peskar, B.A., Cawello, W., Rogatti, W., et al. On the metabolism of prostaglandin E₁ administered intravenously to human volunteers. J Physiol Pharmacol 42 327-331 (1991).

Westwick, J. The effect of pulmonary metabolites of prostaglandins E₁, E₂ and F_2α on ADP-induced aggregation of human and rabbit platelets. Br J Pharmacol 58 297P-298P (1976).

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