Medrogestone

Medrogestone
Clinical data
Trade names	Colprone, others
Other names	Metrogestone; Medrogesterone; AY-62022, NSC-123018, R-13615; 6,17α-Dimethyl-6-dehydroprogesterone; 6,17α-Dimethyl-4,6-pregnadiene-3,20-dione
Pregnancy; category	X;
Routes of; administration	By mouth
Drug class	Progestogen; Progestin
ATC code	G03DB03 (WHO) ; G03FB07 (WHO) (with estrogen);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Nearly 100%
Protein binding	95%: Albumin (90%), CBGTooltip corticosteroid-binding globulin (3%), SHBGTooltip sex hormone-binding globulin (2%)
Metabolism	Hepatic (hydroxylation)
Elimination half-life	35–36 hours
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-acetyl-6,10,13,17-tetramethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	977-79-7;
PubChem CID	9949848;
DrugBank	DB09124;
ChemSpider	8125459;
UNII	077DN93G5B;
KEGG	D04885;
CompTox Dashboard (EPA)	DTXSID70878637 ;
ECHA InfoCard	100.012.323
Chemical and physical data
Formula	C23H32O2
Molar mass	340.507 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](C(=O)C)(CC[C@@H]12)C)C)[C@@]3(C)CC4)C;
	InChI InChI=1S/C23H32O2/c1-14-12-17-18(21(3)9-6-16(25)13-20(14)21)7-11-23(5)19(17)8-10-22(23,4)15(2)24/h12-13,17-19H,6-11H2,1-5H3/t17-,18+,19+,21-,22-,23+/m1/s1; Key:HCFSGRMEEXUOSS-JXEXPEPMSA-N;

Medrogestone, sold under the brand name Colprone among others, is a progestin medication which has been used in menopausal hormone therapy and in the treatment of gynecological disorders.^[6]^[2] It is available both alone and in combination with an estrogen.^[7] It is taken by mouth.^[2]^[8]

Medrogestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[2] It has weak antiandrogenic, glucocorticoid, and antimineralocorticoid activity and no other important hormonal activity.^[2]^[1]^[9]^[10] Due to its progestogenic activity, medrogestone has antigonadotropic effects.^[1]^[2]

Medrogestone was described as early as 1963 and was introduced for medical use by at least 1966.^[11]^[12]^[9] It has mostly been discontinued and remains available only in a few countries.^[13]^[7]

^ ^a ^b ^c ^d Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins" (PDF). Maturitas. 46 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641.^{[permanent dead link]}
^ ^a ^b ^c ^d ^e ^f ^g Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
^ Stanczyk FZ (2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716. S2CID 27018468. Medrogestone The pharmacokinetics of medrogestone (5 mg dose) was studied in 12 Chinese young males who received a single oral dose of this drug [20]. The mean ± standard deviation Cmax was 8.21 ± 2.78 ng/ml and Tmax was 2.57 ± 1.02; the half-life of elimination was 34.9 ± 17.0 hours.
^ Lobo R, Crosignani P, Paoletti R, Bruschi F (6 December 2012). Women's Health and Menopause: New Strategies — Improved Quality of Life. Springer Science & Business Media. pp. 142–. ISBN 978-1-4615-1061-1.
^ Stanczyk FZ, Hapgood JP, Winer S, Mishell DR (April 2013). "Progestogens used in postmenopausal hormone therapy: differences in their pharmacological properties, intracellular actions, and clinical effects". Endocrine Reviews. 34 (2): 171–208. doi:10.1210/er.2012-1008. PMC 3610676. PMID 23238854.
^ Cite error: The named reference MortonHall1999 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ Cutler WB, Garcia CR (1993). Menopause: A Guide for Women and Those who Love Them. Norton. pp. 134–. ISBN 978-0-393-30995-9.
^ ^a ^b Cite error: The named reference ReveszChappel1966 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid4105445 was invoked but never defined (see the help page).
^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Cite error: The named reference DeghenghiLefebvre1963 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[SchindlerCampagnoli2003-1] Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (December 2003). "Classification and pharmacology of progestins" (PDF). Maturitas. 46 (Suppl 1): S7–S16. doi:10.1016/j.maturitas.2003.09.014. PMID 14670641.^{[permanent dead link]}

[pmid16112947-2] ^ ^a ^b ^c ^d ^e ^f ^g Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.

[Stanczyk2002-3] Stanczyk FZ (2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–24. doi:10.1023/A:1020072325818. PMID 12215716. S2CID 27018468. Medrogestone The pharmacokinetics of medrogestone (5 mg dose) was studied in 12 Chinese young males who received a single oral dose of this drug [20]. The mean ± standard deviation Cmax was 8.21 ± 2.78 ng/ml and Tmax was 2.57 ± 1.02; the half-life of elimination was 34.9 ± 17.0 hours.

[LoboCrosignani2012-4] Lobo R, Crosignani P, Paoletti R, Bruschi F (6 December 2012). Women's Health and Menopause: New Strategies — Improved Quality of Life. Springer Science & Business Media. pp. 142–. ISBN 978-1-4615-1061-1.

[StanczykHapgood2013-5] Stanczyk FZ, Hapgood JP, Winer S, Mishell DR (April 2013). "Progestogens used in postmenopausal hormone therapy: differences in their pharmacological properties, intracellular actions, and clinical effects". Endocrine Reviews. 34 (2): 171–208. doi:10.1210/er.2012-1008. PMC 3610676. PMID 23238854.

[MortonHall1999-6] Cite error: The named reference MortonHall1999 was invoked but never defined (see the help page).

[Drugs.com-7] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[CutlerGarcia1993-8] Cutler WB, Garcia CR (1993). Menopause: A Guide for Women and Those who Love Them. Norton. pp. 134–. ISBN 978-0-393-30995-9.

[ReveszChappel1966-9] Cite error: The named reference ReveszChappel1966 was invoked but never defined (see the help page).

[pmid4105445-10] Cite error: The named reference pmid4105445 was invoked but never defined (see the help page).

[Elks2014-11] Cite error: The named reference Elks2014 was invoked but never defined (see the help page).

[DeghenghiLefebvre1963-12] Cite error: The named reference DeghenghiLefebvre1963 was invoked but never defined (see the help page).

[IndexNominum2000-13] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

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Medrogestone

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