16,16-dimethyl Prostaglandin E2

Cayman Chemical Item Number 14750

16,16-dimethyl PGE2 (CAS 39746-25-3)

16,16-dimethyl Prostaglandin E2 (CAS 39746-25-3)

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Description

16,16-dimethyl PGE2 is a competitive inhibitor of 15-hydroxy PGDH, but it is not a substrate for the enzyme.1 Because of its resistance to metabolism by 15-hydroxy PGDH, it has a prolonged half-life in vivo. 16,16-dimethyl PGE2 acts as an agonist on most EP receptor subtypes, and has been used experimentally to induce cervical ripening, uterine contraction, and prevent ulceration of the gastric mucosa in rats and dogs.2,3 The Kd for activation of isolated EP2 receptors is about 1 nM.3

1 Ohno, H., Morikawa, Y., and Hirata, F. Studies on 15-hydroxyprostaglandin dehydrogenase with various prostaglandin analogues. J Biochem 84 1485-1494 (1978).

2 Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70 359-370 (1976).

3 Coleman, R.A., Smith, W.L., and Narumiya, S. Classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol Rev 46 205-229 (1994).

Synonyms
  • 16,16-dimethyl PGE2
Formal Name 9-​oxo-​11α,​15R-​dihydroxy-​16,​16-​dimethyl-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 39746-25-3
Molecular Formula C22H36O5
Formula Weight 380.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O=C1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/[C@@H]​(O)​C(C)​(C)​CCCC)​[C@H]​(O)​C1
InCHI Code
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​1S/C22H36O5/c1-4-5-14-22(2,3)​20(25)​13-12-17-16(18(23)​15-19(17)​24)​10-8-6-7-9-11-21(26)​27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)​/b8-6-,13-12+/t16-,17-,19-,20-/m1/s1
InCHI Key
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QAOBBBBDJSWHMU-WMBBNPMCSA-N

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16,16-dimethyl Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $69.00 $0.00
5 mg $328.00 $0.00
10 mg $621.00 $0.00
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Pricing updated 2014-04-20. Prices are subject to change without notice.

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