Medroxyprogesterone

Medroxyprogesterone
Clinical data
Other names	MP; Methylhydroxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione
Drug class	Progestin; Progestogen
ATC code	None;
Legal status
Legal status	US: WARNING;
Identifiers
	IUPAC name (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	520-85-4;
PubChem CID	10631;
ChemSpider	10185;
UNII	HSU1C9YRES;
CompTox Dashboard (EPA)	DTXSID0036508 ;
ECHA InfoCard	100.007.545
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)C)CC[C@H]3[C@@H]1C[C@@H]2C)C)(C)CC4;
	InChI InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1; Key:FRQMUZJSZHZSGN-HBNHAYAOSA-N;

Medroxyprogesterone (MP), is a progestin which is not used medically.^[2]^[3]^[4]^[5] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.^[6] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,^[6] and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.^[7]

Pharmacology

Pharmacodynamics

Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen.^[8] Medroxyprogesterone is also notable in that it is a minor metabolite of MPA.^[9] In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.^[10]

MP and related steroids at the PR (nM)^[8]
Compound	K_i	EC₅₀Tooltip Half-maximal effective concentration^a	EC₅₀^b
Progesterone	4.3	0.9	25
Medroxyprogesterone	241	47	32
Medroxyprogesterone acetate	1.2	0.6	0.15
Values are nM. ^a = Coactivator recruitment. ^b = Reporter cell line.

Chemistry

Medroxyprogesterone, also known as 6α-methyl-17α-hydroxyprogesterone or as 6α-methyl-17α-hydroxypregn-4-en-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone.^[2]^[3] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.^[2]^[3] The generic name of medroxyprogesterone is a contraction of 6α-methyl-17α-hydroxyprogesterone. It is closely related to medrogestone as well as other unesterified 17α-hydroxyprogesterone derivatives such as chlormadinone, cyproterone, and megestrol.^[2]^[3]

Society and culture

Generic names

Medroxyprogesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.^[2]^[3]^[5]

Brand Name

Meprate 10 Tablets (practo)

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ ^a ^b ^c ^d ^e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 657–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c ^d ^e Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 638–. ISBN 978-3-88763-075-1.
^ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.
^ ^a ^b "Medroxyprogesterone".
^ ^a ^b "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.
^ Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Annals of Surgery. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.
^ ^a ^b Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762. S2CID 24703323.
^ Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". Journal of Steroid Biochemistry. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.
^ Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, et al. (November 2018). "Do progestins contribute to (anti-)androgenic activities in aquatic environments?". Environmental Pollution. 242 (Pt A): 417–425. Bibcode:2018EPoll.242..417S. doi:10.1016/j.envpol.2018.06.104. PMID 29990947. S2CID 51622914.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[Elks2014-2] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 657–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-3] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 638–. ISBN 978-3-88763-075-1.

[MortonHall1999-4] Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.

[Drugs.com-5] "Medroxyprogesterone".

[Merck-6] "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.

[pmid1119869-7] Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Annals of Surgery. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.

[pmid16784762-8] Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762. S2CID 24703323.

[pmid1271819-9] Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". Journal of Steroid Biochemistry. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.

[10] Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, et al. (November 2018). "Do progestins contribute to (anti-)androgenic activities in aquatic environments?". Environmental Pollution. 242 (Pt A): 417–425. Bibcode:2018EPoll.242..417S. doi:10.1016/j.envpol.2018.06.104. PMID 29990947. S2CID 51622914.

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