Medroxyprogesterone caproate

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.

Not to be confused with Hydroxyprogesterone caproate or Medroxyprogesterone acetate.

Medroxyprogesterone caproate

Clinical data
Other names	MPC; 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
IUPAC name [(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	6678-23-5
PubChem CID	62997
ChemSpider	56699
UNII	GNC5BCM98A
CompTox Dashboard (EPA)	DTXSID00216902
Chemical and physical data
Formula	C28H42O4
Molar mass	442.640 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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 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

See also

• List of progestogen esters § Esters of 17α-hydroxyprogesterone derivatives

References

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.
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.
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.