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Medroxyprogesterone caproate

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Chemical compound Not to be confused with Hydroxyprogesterone caproate or Medroxyprogesterone acetate. Pharmaceutical compound
Medroxyprogesterone caproate
Clinical data
Other namesMPC; Medroxyprogesterone capronate; Medroxyprogesterone hexanoate; 6α-Methyl-17α-hydroxyprogesterone hexanoate; 6α-Methyl-17α-hydroxypregn-4-ene-3,20-dione hexanoate
Routes of
administration		Intramuscular injection
Drug classProgestogen; Progestin; Progestogen ester
Identifiers
IUPAC name
  • phenanthren-17-yl] hexanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H42O4
Molar mass442.640 g·mol
3D model (JSmol)
SMILES
  • CCCCCC(=O)O1(CC21(CC32C(C4=CC(=O)CC34C)C)C)C(=O)C
InChI
  • InChI=1S/C28H42O4/c1-6-7-8-9-25(31)32-28(19(3)29)15-12-23-21-16-18(2)24-17-20(30)10-13-26(24,4)22(21)11-14-27(23,28)5/h17-18,21-23H,6-16H2,1-5H3/t18-,21+,22-,23-,26+,27-,28-/m0/s1
  • Key:RDNJGIAWTAMGGM-UPIZIACDSA-N

Medroxyprogesterone caproate (MPC) is a progestin and a progestogen ester which was synthesized in 1958 but was never marketed. It has been confused with hydroxyprogesterone caproate (OHPC) and medroxyprogesterone acetate (MPA) in a number of publications. In addition to MPA and OHPC, analogues of MPC include chlormadinone caproate, gestonorone caproate, megestrol caproate, and methenmadinone caproate.

See also

References

  1. Babcock JC, Gutsell ES, Herr ME, Hogg JA, Stucki JC, Barnes LE, Dulin WE (1958). "6α-Methyl-17α-hydroxyprogesterone 17-acylates; a new class of potent progestins". Journal of the American Chemical Society. 80 (11): 2904–2905. doi:10.1021/ja01544a079. ISSN 0002-7863.
  2. Barton DH, Taylor WC (1958). "510. Photochemical transformations. Part IV. The photochemistry of prednisone acetate". Journal of the Chemical Society (Resumed): 2500–2510. doi:10.1039/jr9580002500. ISSN 0368-1769.
  3. Pasqualini JR, Paris J, Sitruk-Ware R, Chetrite G, Botella J (April 1998). "Progestins and breast cancer". The Journal of Steroid Biochemistry and Molecular Biology. 65 (1–6): 225–235. doi:10.1016/S0960-0760(98)00028-4. PMID 9699877. S2CID 28416130.
  4. Pasqualini JR, Ebert C (June 1999). "Biological effects of progestins in breast cancer". Gynecological Endocrinology. 13 (Suppl 4): 11–19. doi:10.1080/gye.13.s4.11.19. PMID 12227897.
  5. Pasqualini JR, Chetrite GS (December 2010). "Biological responses of progestogen metabolites in normal and cancerous human breast". Hormone Molecular Biology and Clinical Investigation. 3 (3): 427–435. doi:10.1515/HMBCI.2010.066. PMID 25961215. S2CID 41680565.
  6. Lantta M, Kahanpää K, Kärkkäinen J, Lehtovirta P, Wahlström T, Widholm O (June 1984). "Estradiol and progesterone receptors in two cases of endometrial stromal sarcoma". Gynecologic Oncology. 18 (2): 233–239. doi:10.1016/0090-8258(84)90031-3. PMID 6735266.
  7. Gusberg SB, Shingleton HM, Deppe G (1988). Female genital cancer. Churchill Livingstone. p. 374. ISBN 978-0-443-08525-3.
  8. Proceedings. American Cancer Society and National Cancer Institute of the U.S. Public Health Service, Federal Security Agency. 1970. p. 376.
  9. Nichols DH, Evrard JR (1985). Ambulatory Gynecology. Harper & Row. p. 518. ISBN 978-0-06-141815-0.
  10. Goodman LS, Gilman A (1996). Goodman & Gilman's the Pharmacological Basis of Therapeutics. McGraw-Hill, Health Professions Division. pp. 1427, 1823, 1858. ISBN 978-0-07-026266-9.
  11. Endokrinologie. Johann Ambrosius Barth Verlag. 1969. p. 431.
  12. McKinnon AO, Tarrida Del Marmol Figueroa S, Nobelius AM, Hyland JH, Vasey JR (1993). "Failure of medroxyprogesterone caproate to maintain pregnancy in ovariectomised mares". Equine Vet J. 25 (2): 158–160. doi:10.1111/j.2042-3306.1993.tb02928.x. PMID 8467776.
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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