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Medroxyprogesterone caproate

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withHydroxyprogesterone caproate orMedroxyprogesterone 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
  • [(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
PubChemCID
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 aprogestin and aprogestogen ester which wassynthesized in 1958 but was never marketed.[1][2] It has been confused withhydroxyprogesterone caproate (OHPC) andmedroxyprogesterone 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 includechlormadinone caproate,gestonorone caproate,megestrol caproate, andmethenmadinone caproate.

See also

[edit]

References

[edit]
  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.
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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