Medroxyprogesterone caproate

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;

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.

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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[BabcockGutsell1958-1] 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. doi:10.1021/ja01544a079. ISSN 0002-7863.

[BartonTaylor1958-2] 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.

[pmid9699877-3] 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.

[pmid12227897-4] 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.

[pmid25961215-5] 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.

[pmid6735266-6] 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.

[GusbergShingleton1988-7] Gusberg SB, Shingleton HM, Deppe G (1988). Female genital cancer. Churchill Livingstone. p. 374. ISBN 978-0-443-08525-3.

[ACSNCI1970-8] Proceedings. American Cancer Society and National Cancer Institute of the U.S. Public Health Service, Federal Security Agency. 1970. p. 376.

[NicholsEvrard1985-9] Nichols DH, Evrard JR (1985). Ambulatory Gynecology. Harper & Row. p. 518. ISBN 978-0-06-141815-0.

[GoodmanGilman1996-10] 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.

[JohannAmbrosiusBarthVerlag1969-11] Endokrinologie. Johann Ambrosius Barth Verlag. 1969. p. 431.

[NobeliusHyland1993-12] 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.

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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

Medroxyprogesterone caproate

See also

References