15(R)-15-methyl Prostaglandin F

Cayman Chemical Item Number 16730

15(R)-15-methyl PGF (CAS 35864-81-4)

15(R)-15-methyl Prostaglandin F2α (CAS 35864-81-4)

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Description

15(R)-15-methyl PGF is a metabolically stable analog of PGF. 15(R)-15-methyl PGF is an inactive, prodrug PGF agonist designed for activation by gastric acid after oral administration. Acid-catalyzed epimerization of 15(R)-15-methyl PGF converts it into the active 15(S)-isomer.1,2 The 15(S)-isomer induces luteolysis when injected in rhesus monkeys at a dose of about 12 mg/animal, while the 15(R)-isomer does not.3

1 Plaisted, S.M., DeZwaan, J., and Snider, B.G. High-performance liquid chromatographic determination of acid-catalyzed degradation products of methyl carboprost in a polymeric controlled-release device. J Chromatogr 314 369-377 (1984).

2 Hamberg, M., Zhang, L., and Bergström, S. On the pH-dependent degradation of 15(S)-15 methyl-prostaglandin F (carboprost). Eur J Pharm Sci 3 27-38 (1995).

3 Wilks, J.W. Inhibition of the monkey corpus luteum with 15-methyl prostaglandins. Prostaglandins 20 793-805 (1980).

Synonyms
  • 15(R)-15-methyl PGF
Formal Name 9α,​11α,​15R-​trihydroxy-​15-​methyl-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 35864-81-4
Molecular Formula C21H36O5
Formula Weight 368.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1C(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/[C@]​(C)​(O)​CCCCC)​[C@H]​(O)​C1
InCHI Code
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​1S/C21H36O5/c1-3-4-9-13-21(2,26)​14-12-17-16(18(22)​15-19(17)​23)​10-7-5-6-8-11-20(24)​25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)​/b7-5-,14-12+/t16?,17-,18+,19-,21-/m1/s1
InCHI Key
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DLJKPYFALUEJCK-YLFQPMNTSA-N

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15(R)-15-methyl Prostaglandin F2α is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $46.00 $0.00
5 mg $207.00 $0.00
10 mg $368.00 $0.00
50 mg $1,610.00 $0.00
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Pricing updated 2014-04-20. Prices are subject to change without notice.

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Related Products

15(R)-15-methyl Prostaglandin F methyl ester
15(S)-15-methyl Prostaglandin F
15(S)-15-methyl Prostaglandin F methyl ester
Prostaglandin F
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