13,14-dihydro-15(R,S)-hydroxy-16,16-difluoro Prostaglandin E₁-d₄ Exclusive

Cayman Chemical Item Number 9000406

15-hydroxy Lubiprostone

13,14-dihydro-15(R,S)-hydroxy-16,16-difluoro Prostaglandin E1-d4

See more	Prostaglandins (517)

Description

PGE₁ is produced by the metabolism of dihomo-γ-linolenic acid (DGLA) by the cyclooxygenase pathway. PGE₁ inhibits platelet aggregation (IC₅₀ = 40 nM) and increases vasodilation.^1,213,14-dihydro-16,16-difluoro 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 13,14-dihydro-15(R,S)-hydroxy-16,16-difluoro PGE₁-3,3’,4,4’-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 13,14-dihydro-15(R,S)-hydroxy-16,16-difluoro Prostaglandin E₁ by GC- or LC-mass spectrometry (MS).

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,15R,S-dihydroxy-16,16-difluoro-prostan-1-oic-3,3,4,4-d4 acid
Molecular Formula	C₂₀H₃₀D₄F₂O₅
Formula Weight	396.5
Formulation	A solution in methyl acetate
Purity	≥99% deuterated forms (d1-d4)
Stability	1 year
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard O=C1[C@H](CCCC([2H])([2H])C([2H])([2H])CC(O)=O)[C@@H](CCC(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).

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).

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).

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1 mg	See a distributor in your region for pricing

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

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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13,14-dihydro-15(R,S)-hydroxy-16,16-difluoro Prostaglandin E1-d4 Exclusive