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Chemical compound
Medroxyprogesterone caproate
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
[(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 )
Formula C 28 H 42 O 4
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
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ Gusberg SB, Shingleton HM, Deppe G (1988).
Female genital cancer . Churchill Livingstone. p. 374.
ISBN
978-0-443-08525-3 .
^
Proceedings . American Cancer Society and National Cancer Institute of the U.S. Public Health Service, Federal Security Agency. 1970. p. 376.
^ Nichols DH, Evrard JR (1985).
Ambulatory Gynecology . Harper & Row. p. 518.
ISBN
978-0-06-141815-0 .
^ 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 .
^
Endokrinologie . Johann Ambrosius Barth Verlag. 1969. p. 431.
^ 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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