A prodrug PGF agonist that is converted to a luteolytic agent
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15(R)-15-methyl Prostaglandin F2α

Item No. 16730

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15R-trihydroxy-15-methyl-prosta-5Z,13E-dien-1-oic acid
CAS Number
35864-81-4
Synonyms
  • 15(R)-15-methyl PGF2α
Molecular Formula
C21H36O5
Formula Weight
368.5
Purity
≥95%
Formulation (Request formulation change)
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
10 mM Na2CO3: >6.5 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS pH 7.2: >10 mg/ml
SMILES
O[C@@H]1C(C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@](C)(O)CCCCC)[C@H](O)C1
InChi Code
InChI=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
DLJKPYFALUEJCK-YLFQPMNTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    15(R)-15-methyl PGF2α is a metabolically stable analog of PGF2α. 15(R)-15-methyl PGF2α is an inactive, prodrug PGF agonist designed for activation by gastric acid after oral administration. Acid-catalyzed epimerization of 15(R)-15-methyl PGF2α 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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.Y., and Bergström, S. On the pH-dependent degradation of 15(S)-15 methyl-prostaglandin F2α (Carboprost). Eur. J. Pharm. Sci. 3(1), 27-38 (1995).

    3. Wilks, J.W. Inhibition of the monkey corpus luteum with 15-methyl prostaglandins. Prostaglandins 20(5), 793-805 (1980).