QuickView for Medroxyprogesterone (compound)

Summary
General Info

PubChem

PubChem Compound 10631

Name:	Medroxyprogesterone
PubChem Compound ID:	10631
Description:	(6 alpha)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione. A synthetic progestational hormone used in veterinary practice as an estrus regulator.
Molecular formula:	C₂₂H₃₂O₃
Molecular weight:	344.488 g/mol
Synonyms:	Medroxyprogesteron; MLS000069571; Medroxyprogesteronum [INN-Latin]; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6alpha)- (9CI); Curretab; Pregn-4-ene-3,20-dione, 17-hydroxy-6.alpha.-methyl-; NSC 27408; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6-alpha)- (9CI); Pregn-4-ene-3,20-dione, 17-hydroxy-6-alpha-methyl-; U 8840. show more » Medroxyprogesteron; MLS000069571; Medroxyprogesteronum [INN-Latin]; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6alpha)- (9CI); Curretab; Pregn-4-ene-3,20-dione, 17-hydroxy-6.alpha.-methyl-; NSC 27408; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6-alpha)- (9CI); Pregn-4-ene-3,20-dione, 17-hydroxy-6-alpha-methyl-; U 8840; 17-Hydroxy-6alpha-methyl-pregn-4-ene-3,20-dione; Medroxiprogesterona [INN-Spanish]; 17-Hydroxy-6.alpha.-methylprogesterone; 17alpha-Hydroxy-6alpha-methylprogesterone; NSC27408; Medroxyprogesterone; Pregn-4-ene-3,20-dione, 17-hydroxy-6-methyl-, (6.alpha.)-; BRN 2510965; 17-Hydroxy-6alpha-methylprogesterone; 6alpha-Methyl-17alpha-hydroxyprogesterone; 6.alpha.-Methyl-17.alpha.-hydroxyprogesterone; 6-alpha-Methyl-17-alpha-hydroxyprogesterone; HSDB 3114; C07119; Farlutal; EINECS 208-298-6; 4-08-00-02211 (Beilstein Handbook Reference); Amen; 17.alpha.-Hydroxy-6.alpha.-methylprogesterone; 520-85-4; SMR000058769; Medrossiprogesterone [DCIT]; Medroxiprogesteronum; 6alpha-Methyl-4-pregnen-17alpha-ol-3,20-dione show less «

DrugBank

Identification

Name:	Medroxyprogesterone
Name (isomeric):	DB00603
Drug Type:	small molecule
Description:	(6 alpha)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione. A synthetic progestational hormone used in veterinary practice as an estrus regulator.
Synonyms:	Medroxyprogesteron; Medroxyprogesteronum [INN-Latin]; Medroxiprogesterona [INN-Spanish]; Medroxyprogesteron acetate; Hydroxymethylprogesterone; CBP-1011; Medroprogesterone Acetate; Medroxiprogesteronum; Medrossiprogesterone [Dcit]; MAP
Brand:	Nadigest, Prodasone, Repromap, Depo-Promone, Lunelle, Progevera, Sirprogen, Gestapuran, Lutopolar, Asconale, Ralovera, Aragest 5, Oragest, Depo-Progestin, Clinofem, Lutoral, Colirest, Med-Pro, Farlutin, MPA Gyn 5, Sodelut G, Repromix, Depot-Medroxyprogesterone acetate, Depo-Clinovir, Nidaxin, Perlutex, Hysron, Provera, Indivina, Meprate, Depo-Prodasone, Hematrol, Progestalfa, DMPA, Proverone, Farlutal, Perlutex Leo, Aragest, Metigestrona, Clinovir, G-Farlutal, Novo-Medrone, Veramix
Brand name mixture:	Lunelle(Medroxyprogesterone + Estradiol)
Category:	Progestins, Contraceptives, Oral, Synthetic, Contraceptives
CAS number:	520-85-4

Pharmacology

Indication:	Used as a contraceptive and to treat secondary amenorrhea, abnormal uterine bleeding, pain associated with endometriosis, endometrial and renal cell carcinomas, paraphilia in males, GnRH-dependent forms of precocious puberty, as well as to prevent endometrial changes associated with estrogens.
Pharmacology:	Medroxyprogesterone is a synthetic progestin more potent than progesterone.
Mechanism of Action:	Progestins diffuse freely into target cells in the female reproductive tract, mammary gland, hypothalamus, and the pituitary and bind to the progesterone receptor. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge.
Absorption:	Rapidly absorbed from GI tract
Protein binding:	90%
Biotransformation:	Hepatic
Route of elimination:	Following oral dosing, MPA is extensively metabolized in the liver via hydroxylation, with subsequent conjugation and elimination in the urine. Most MPA metabolites are excreted in the urine as glucuronide conjugates with only minor amounts excreted as sulfates.
Half Life:	50 days
Clearance:	64110 +/- 42662 mL/min [postmenopausal women under fasting conditions with a single Dose of 2 × 10 mg] 74123 +/- 35126 mL/min [postmenopausal women under fasting conditions with a single Dose of 8 × 2.5 mg] 41963 +/- 38402 mL/min [postmenopausal women following daily administration of one PROVERA 10 mg tablet for 7 days]
Toxicity:	Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take with food.

Drug interaction:

Talbutal	The enzyme inducer, talbutal, decreases the effect of the hormone agent, medroxyprogesterone.
Dicumarol	Medroxyprogesterone may increase the anticoagulant effect of dicumarol.
Griseofulvin	The enzyme inducer, griseofulvin, may decrease the effect of the hormone, medroxyprogesterone.
Primidone	The enzyme inducer, primidone, may decrease the effect of the hormone, medroxyprogesterone.
Secobarbital	The enzyme inducer, secobarbital, decreases the effect of the hormone agent, medroxyprogesterone.

Talbutal	The enzyme inducer, talbutal, decreases the effect of the hormone agent, medroxyprogesterone.
Dicumarol	Medroxyprogesterone may increase the anticoagulant effect of dicumarol.
Griseofulvin	The enzyme inducer, griseofulvin, may decrease the effect of the hormone, medroxyprogesterone.
Primidone	The enzyme inducer, primidone, may decrease the effect of the hormone, medroxyprogesterone.
Secobarbital	The enzyme inducer, secobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
Butethal	The enzyme inducer, butethal, decreases the effect of the hormone agent, medroxyprogesterone.
Mephenytoin	The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, medroxyprogesterone.
Butalbital	The enzyme inducer, butalbital, decreases the effect of the hormone agent, medroxyprogesterone.
Thiopental	Thiopental may decrease the effect of Medroxyprogesterone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Methylphenobarbital	The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Warfarin	Medroxyprogesterone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if medroxyprogesterone is initiated, discontinued or dose changed.
Bosentan	Bosentan may decrease the contraceptive effect of medroxyprogesterone. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
Hexobarbital	The enzyme inducer, hexobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Bexarotene	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of medroxyprogesterone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Acenocoumarol	Medroxyprogesterone may increase the anticoagulant effect of acenocoumarol.
Ethotoin	The enzyme inducer, ethotoin, decreases the effect of the hormone agent, medroxyprogesterone.
Pentobarbital	The enzyme inducer, pentobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Phenobarbital	The enzyme inducer, phenobarbital, may decrease the effect of the hormone, medroxyprogesterone.
Amobarbital	The enzyme inducer, amobarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Anisindione	Medroxyprogesterone may increase the anticoagulant effect of anisindione.
Fosphenytoin	The enzyme inducer, fosphenytoin, may decrease the effect of the hormone, medroxyprogesterone.
Heptabarbital	The enzyme inducer, heptabarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Artemether	Artemether may decrease the effectiveness of medroxyprogesterone by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Phenytoin	The enzyme inducer, phenytoin, may decrease the effect of medroxyprogesterone.
Methohexital	The enzyme inducer, methohexital, decreases the effect of the hormone agent, medroxyprogesterone.
Butabarbital	The enzyme inducer, butabarbital, decreases the effect of the hormone agent, medroxyprogesterone.
Aprobarbital	The enzyme inducer, aprobarbital, decreases the effect of the hormone agent, medroxyprogesterone.

show less «

Targets

Progesterone receptor

Estrogen receptor

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C8

3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type II

Cytochrome P450 2C9