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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H34O4
Molecular Weight 386.5244
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEDROXYPROGESTERONE ACETATE

SMILES

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C[C@H](C)C4=CC(=O)CC[C@]34C

InChI

InChIKey=PSGAAPLEWMOORI-PEINSRQWSA-N
InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1

HIDE SMILES / InChI

Description

Medroxyprogesterone acetate (INN, USAN, BAN), also known as 17α-hydroxy-6α-methylprogesterone acetate, and commonly abbreviated as MPA, is a steroidal progestin, a synthetic variant of the human hormone progesterone. Medroxyprogesterone acetate (MPA) administered orally or parenterally in the recommended doses to women with adequate endogenous estrogen, transforms proliferative into secretory endometrium. Androgenic and anabolic effects have been noted, but the drug is apparently devoid of significant estrogenic activity. While parenterally administered MPA inhibits gonadotropin production, which in turn prevents follicular maturation and ovulation, available data indicate that this does not occur when the usually recommended oral dosage is given as single daily doses. MPA is a more potent derivative of its parent compound medroxyprogesterone (MP). While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, what is normally being administered is MPA and not MP. 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. 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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVERA
Primary
PROVERA
Preventing
PROVERA

Cmax

ValueDoseCo-administeredAnalytePopulation
0.71 ng/mL
10 mg 1 times / day steady-state, oral
MEDROXYPROGESTERONE ACETATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.01 ng × h/mL
10 mg 1 times / day steady-state, oral
MEDROXYPROGESTERONE ACETATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.6 h
10 mg 1 times / day steady-state, oral
MEDROXYPROGESTERONE ACETATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
10 mg 1 times / day steady-state, oral
MEDROXYPROGESTERONE ACETATE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Secondary Amenorrhea: PROVERA (medroxyprogesterone acetate ) tablets may be given in dosages of 5 or 10 mg daily for 5 to 10 days. Abnormal Uterine Bleeding Due to Hormonal Imbalance in the Absence of Organic Pathology: Beginning on the calculated 16th or 21st day of the menstrual cycle, 5 or 10 mg of PROVERA may be given daily for 5 to 10 days. Reduction of Endometrial Hyperplasia in Postmenopausal Women: Receiving Daily 0.625 mg Conjugated Estrogens
Route of Administration: Oral
In Vitro Use Guide
Freshly isolated PBMCs (peripheral blood mononuclear cells) from normal blood donors were treated with physiologic MPA (medroxyprogesterone acetate) concentrations ranging from 0.003 to 5 ng/ml and infected with GFP-tagged R5-tropic or X4-tropic HIV-1 pseudoviruses by spinoculation. The infection was limited to a single cycle. Cells were stained with CD3, CD8 and CD14