Medroxyprogesterone caproate

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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 classProgestogen; 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
FormulaC28H42O4
Molar mass442.640 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[edit]

References[edit]

  1. ^ Babcock, John C.; Gutsell, Erwin S.; Herr, Milton E.; Hogg, John A.; Stucki, Jacob C.; Barnes, Lester E.; Dulin, William E. (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, D. H. R.; Taylor, W. C. (1958). "510. Photochemical transformations. Part IV. The photochemistry of prednisone acetate". Journal of the Chemical Society (Resumed): 2500. 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". J. Steroid Biochem. Mol. Biol. 65 (1–6): 225–35. 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". Gynecol. Endocrinol. 13 Suppl 4: 11–9. 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". Horm Mol Biol Clin Investig. 3 (3): 427–35. 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". Gynecol. Oncol. 18 (2): 233–9. doi:10.1016/0090-8258(84)90031-3. PMID 6735266.
  7. ^ Saul Bernard Gusberg; Hugh M. Shingleton; Gunter Deppe (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. ^ David H. Nichols; John R. Evrard (1985). Ambulatory Gynecology. Harper & Row. p. 518. ISBN 978-0-06-141815-0.
  10. ^ Louis Sanford Goodman; Alfred Goodman Gilman (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. Failure of medroxyprogesterone caproate to maintain pregnancy in ovariectomised mares. Equine Vet J 1993; 25:158–160.