medroxyprogesterone caproate

{{Short description|Chemical compound}}

{{Distinguish|Hydroxyprogesterone caproate|Medroxyprogesterone acetate}}

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| 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

| image = Medroxyprogesterone caproate.svg

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| routes_of_administration = Intramuscular injection

| class = Progestogen; Progestin; Progestogen ester

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| CAS_number = 6678-23-5

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| PubChem = 62997

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| ChemSpiderID = 56699

| UNII = GNC5BCM98A

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| synonyms = MPC; Medroxyprogesterone capronate; Medroxyprogesterone hexanoate; 6α-Methyl-17α-hydroxyprogesterone hexanoate; 6α-Methyl-17α-hydroxypregn-4-ene-3,20-dione hexanoate

| C=28 | H=42 | O=4

| 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

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = RDNJGIAWTAMGGM-UPIZIACDSA-N

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Medroxyprogesterone caproate (MPC) is a progestin and a progestogen ester which was synthesized in 1958 but was never marketed.{{cite journal| vauthors = Babcock JC, Gutsell ES, Herr ME, Hogg JA, Stucki JC, Barnes LE, Dulin WE |title=6α-Methyl-17α-hydroxyprogesterone 17-acylates; a new class of potent progestins|journal=Journal of the American Chemical Society|volume=80|issue=11|year=1958|pages=2904–2905|issn=0002-7863|doi=10.1021/ja01544a079|bibcode=1958JAChS..80.2904B }}{{cite journal| vauthors = Barton DH, Taylor WC |title=510. Photochemical transformations. Part IV. The photochemistry of prednisone acetate|journal=Journal of the Chemical Society (Resumed)|year=1958|pages=2500–2510|issn=0368-1769|doi=10.1039/jr9580002500}} It has been confused with hydroxyprogesterone caproate (OHPC) and medroxyprogesterone acetate (MPA) in a number of publications.{{cite journal | vauthors = Pasqualini JR, Paris J, Sitruk-Ware R, Chetrite G, Botella J | title = Progestins and breast cancer | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 65 | issue = 1–6 | pages = 225–235 | date = April 1998 | pmid = 9699877 | doi = 10.1016/S0960-0760(98)00028-4 | s2cid = 28416130 }}{{cite journal | vauthors = Pasqualini JR, Ebert C | title = Biological effects of progestins in breast cancer | journal = Gynecological Endocrinology | volume = 13 | issue = Suppl 4 | pages = 11–19 | date = June 1999 | pmid = 12227897 | doi = 10.1080/gye.13.s4.11.19 }}{{cite journal | vauthors = Pasqualini JR, Chetrite GS | title = Biological responses of progestogen metabolites in normal and cancerous human breast | journal = Hormone Molecular Biology and Clinical Investigation | volume = 3 | issue = 3 | pages = 427–435 | date = December 2010 | pmid = 25961215 | doi = 10.1515/HMBCI.2010.066 | s2cid = 41680565 | doi-access = free }}{{cite journal | vauthors = Lantta M, Kahanpää K, Kärkkäinen J, Lehtovirta P, Wahlström T, Widholm O | title = Estradiol and progesterone receptors in two cases of endometrial stromal sarcoma | journal = Gynecologic Oncology | volume = 18 | issue = 2 | pages = 233–239 | date = June 1984 | pmid = 6735266 | doi = 10.1016/0090-8258(84)90031-3 }}{{cite book| vauthors = Gusberg SB, Shingleton HM, Deppe G |title=Female genital cancer|url=https://books.google.com/books?id=DKNrAAAAMAAJ|year=1988|publisher=Churchill Livingstone|isbn=978-0-443-08525-3|page=374}}{{cite book|title=Proceedings|url=https://books.google.com/books?id=yJQRAQAAMAAJ|year=1970|publisher=American Cancer Society and National Cancer Institute of the U.S. Public Health Service, Federal Security Agency.|page=376}}{{cite book| vauthors = Nichols DH, Evrard JR |title=Ambulatory Gynecology|url=https://books.google.com/books?id=zMZsAAAAMAAJ|year=1985|publisher=Harper & Row|isbn=978-0-06-141815-0|page=518}}{{cite book| vauthors = Goodman LS, Gilman A |title=Goodman & Gilman's the Pharmacological Basis of Therapeutics|url=https://books.google.com/books?id=09h_hZiYXgUC|year=1996|publisher=McGraw-Hill, Health Professions Division|isbn=978-0-07-026266-9|pages=1427,1823,1858}}{{cite book|title=Endokrinologie|url=https://books.google.com/books?id=8ZW3AAAAIAAJ|year=1969|publisher=Johann Ambrosius Barth Verlag.|page=431}}{{cite journal | vauthors = McKinnon AO, Tarrida Del Marmol Figueroa S, Nobelius AM, Hyland JH, Vasey JR | title = Failure of medroxyprogesterone caproate to maintain pregnancy in ovariectomised mares. | journal = Equine Vet J | date = 1993 | volume = 25 | issue = 2 | pages = 158–160 | doi = 10.1111/j.2042-3306.1993.tb02928.x | pmid = 8467776 }} In addition to MPA and OHPC, analogues of MPC include chlormadinone caproate, gestonorone caproate, megestrol caproate, and methenmadinone caproate.