Medroxyprogesterone caproate

Last updated
Medroxyprogesterone caproate
Medroxyprogesterone caproate.svg
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 class Progestogen; Progestin; Progestogen ester
Identifiers
  • [(6S,8R,9S,10R,13S,14S,17R)-17-Acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C28H42O4
Molar mass 442.640 g·mol−1
3D model (JSmol)
  • CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C)C)C(=O)C
  • 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. [1] [2] It has been confused with hydroxyprogesterone caproate (OHPC) and medroxyprogesterone acetate (MPA) in a number of publications. [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] 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. Bibcode:1958JAChS..80.2904B. 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.
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