13,14-dihydro-15-keto Prostaglandin E2

Cayman Chemical Item Number 14650

13,14-dihydro-15-keto PGE2 (CAS 363-23-5)

13,14-dihydro-15-keto Prostaglandin E2 (CAS 363-23-5)

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Description

13,14-dihydro-15-keto PGE2 is the primary metabolite of PGE2 in plasma.1 Endogenous or infused PGE2 is rapidly metabolized by the enzymes 15-hydroxy PGDH and 15-oxo-PG Δ13-reductase to form 13,14-dihydro-15-keto PGE2. 13,14-dihydro-15-keto PGE2 accumulates to detectable levels; plasma levels in humans are between 10-100 pg/ml.2,3 It undergoes further metabolism and chemical decomposition, giving it a relatively short half-life. In dogs, the plasma half-life of 13,14-dihydro-15-keto PGE2 is about 9 minutes.3 In humans the metabolite has a similar short half-life, making it a poor choice of analytes for assays designed to measure total PGE2 biosynthesis.4,5

1 Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. J Biol Chem 246 6713-6721 (1971).

2 Fitzpatrick, F.A., Aguirre, R., Pike, J.E., et al. The stability of 13,14-dihydro-15 keto-PGE2. Prostaglandins 19 917-931 (1980).

3 Bothwell, W., Verburg, M., Wynalda, M., et al. A radioimmunoassay for the unstable pulmonary metabolites of prostaglandin E1 and E2: An indirect index of their in vivo disposition and pharmacokinetics. J Pharmacol Exp Ther 220 229-235 (1982).

4 Leonhardt, A., Krauss, M., Gieler, U., et al. In vivo formation of prostaglandin E1 and prostaglandin E2 in atopic dermatitis. Br J Dermatol 136 337-340 (1997).

5 Granström, E., Hamberg, M., Hansson, G., et al. Chemical instability of 15-keto-13,14-dihydro-PGE2: The reason for low assay reliability. Prostaglandins 19 933-945 (1980).

Synonyms
  • 13,14-dihydro-15-keto PGE2
Formal Name 9,​15-​dioxo-​11α-​hydroxy-​prost-​5Z-​en-​1-​oic acid
CAS Number 363-23-5
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O=C1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(CCC(CCCCC)​=O)​[C@H]​(O)​C1
InCHI Code
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​1S/C20H32O5/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/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)​/b7-4-/t16-,17-,19-/m1/s1
InCHI Key
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CUJMXIQZWPZMNQ-XYYGWQPLSA-N

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13,14-dihydro-15-keto Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $59.00 $0.00
5 mg $266.00 $0.00
10 mg $472.00 $0.00
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