MEDROXYPROGESTERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H32O3
Molecular Weight	344.4877
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1C[C@H]2[C@@H]3CC[C@](O)(C(C)=O)[C@@]3(C)CC[C@@H]2[C@@]4(C)CCC(=O)C=C14

InChI

InChIKey=FRQMUZJSZHZSGN-HBNHAYAOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C22H32O3
Molecular Weight	344.4877
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/011839s079s080lbl.pdf

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 Target	Pharmacology	Condition	Potency
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8852830	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Secondary amenorrhea 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/011839s079s080lbl.pdf	Primary	Approved 8583	PROVERA Approved Use Medroxyprogesterone Acetate Tablets USP are a progestin indicated for the treatment of secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as fibroids or uterine cancer. Medroxyprogesterone Acetate Tablets USP are also indicated to reduce the incidence of endometrial hyperplasia in nonhysterectomized postmenopausal women receiving daily oral conjugated estrogens 0.625 mg tablets. Launch Date 1959
Abnormal uterine bleeding 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/011839s079s080lbl.pdf	Primary	Approved 8583	PROVERA Approved Use Medroxyprogesterone Acetate Tablets USP are a progestin indicated for the treatment of secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as fibroids or uterine cancer. Medroxyprogesterone Acetate Tablets USP are also indicated to reduce the incidence of endometrial hyperplasia in nonhysterectomized postmenopausal women receiving daily oral conjugated estrogens 0.625 mg tablets. Launch Date 1959
Endometrial cancer 44 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/011839s079s080lbl.pdf	Preventing	Approved 8583	PROVERA Approved Use Medroxyprogesterone Acetate Tablets USP are a progestin indicated for the treatment of secondary amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as fibroids or uterine cancer. Medroxyprogesterone Acetate Tablets USP are also indicated to reduce the incidence of endometrial hyperplasia in nonhysterectomized postmenopausal women receiving daily oral conjugated estrogens 0.625 mg tablets. Launch Date 1959

C_max

Value	Dose	Co-administered	Analyte	Population
0.71 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MEDROXYPROGESTERONE ACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
6.01 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MEDROXYPROGESTERONE ACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MEDROXYPROGESTERONE ACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MEDROXYPROGESTERONE ACETATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Doses

Dose	Population	Adverse events
150 mg 3 times / month multiple, intramuscular Recommended Dose: 150 mg, 3 times / month Route: intramuscular Route: multiple Dose: 150 mg, 3 times / month Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf	healthy, 15 - 51 Health Status: healthy Age Group: 15 - 51 Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf	Disc. AE: Bleeding, Amenorrhea... AEs leading to discontinuation/dose reduction: Bleeding (8.2%) Amenorrhea (2.1%) Weight gain (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15107205	healthy, 45-66 Health Status: healthy Age Group: 45-66 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/15107205	Disc. AE: Bleeding, Uterine fibroids... AEs leading to discontinuation/dose reduction: Bleeding (3.8%) Uterine fibroids (2.3%) Gallstones (0.76%) Endometrial polyp (0.76%) Sources: https://pubmed.ncbi.nlm.nih.gov/15107205
2.5 mg 1 times / day multiple, oral Studied dose Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16875644	healthy, 45-79 Health Status: healthy Age Group: 45-79 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/16875644	Disc. AE: Bleeding vaginal... AEs leading to discontinuation/dose reduction: Bleeding vaginal (9%) Sources: https://pubmed.ncbi.nlm.nih.gov/16875644
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	healthy, 50 -79 Health Status: healthy Age Group: 50 -79 Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	Disc. AE: Myocardial infarction, Stroke... AEs leading to discontinuation/dose reduction: Myocardial infarction Stroke Breast cancer invasive NOS Embolism pulmonary Deep vein thrombosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20733445/	unhealthy, >18 Health Status: unhealthy Age Group: >18 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20733445/	Disc. AE: Dizziness, Fluid retention... AEs leading to discontinuation/dose reduction: Dizziness (1.2%) Fluid retention (1.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/20733445/
2.5 mg 1 times / day multiple, oral Studied dose Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	healthy, >65 Health Status: healthy Age Group: >65 Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	Disc. AE: Dementia... AEs leading to discontinuation/dose reduction: Dementia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	unhealthy Health Status: unhealthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf	Disc. AE: Cardiovascular disorder... AEs leading to discontinuation/dose reduction: Cardiovascular disorder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011839s071lbl.pdf
150 mg 3 times / month multiple, intramuscular Recommended Dose: 150 mg, 3 times / month Route: intramuscular Route: multiple Dose: 150 mg, 3 times / month Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf	healthy Health Status: healthy Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf	Disc. AE: Bone density abnormal... AEs leading to discontinuation/dose reduction: Bone density abnormal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C8 1057	CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1119 CYP2E1 729 CYP3A5 446

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	moderate [IC50 16.1 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	slight [IC50 >100 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	slight [IC50 >100 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	slight [IC50 >100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	slight [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	weak [IC50 31.5 uM]
CYP2E1 1146	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/16645869/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/11301566/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 389	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP1A2 1197	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2A6 626	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2B6 776	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2C18 149	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2C19 1119	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2C8 810	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2C9 1193	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2D6 1388	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP2E1 729	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297	no
CYP3A5 446	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297; https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf#page=1	no
CYP3A4 1946	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/6/8/3297; https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf#page=1	yes	likely (co-administration study) Comment: Drugs or herbal products that induce certain enzymes, including CYP3A4, may decrease the effectiveness of contraceptive drug products. Sources: https://clincancerres.aacrjournals.org/content/6/8/3297; https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020246s035lbl.pdf#page=1

PubMed

Title	Date	PubMed
Effect of hormone replacement therapy on uterine fibroids in postmenopausal women--a 3-year study.	2002-09-30	12270580
Influence of estradiol and gestagens on oxidative stress in the rat uterus.	2002-09	12217744
Chronic respiratory failure: an unusual cause and treatment.	2002-09	12200531
HRT: forever or never?	2002-08-30	12199410
Contraceptive efficacy and patient acceptance of Lunelle.	2002-08	12242850
Effects of tibolone and continuous combined hormone replacement therapy on bleeding rates, quality of life and tolerability in postmenopausal women.	2002-08	12197367
Pharmacologic doses of medroxyprogesterone may cause bone loss through glucocorticoid activity: an hypothesis.	2002-08	12181616
Effect of methyl testosterone administration on plasma viscosity in postmenopausal women.	2002-08	12153599
Six months of hormone replacement therapy does not influence muscle strength in postmenopausal women.	2002-07-25	12161047
[One case of locally advanced breast cancer in which multidisciplinary treatment, chiefly, therapy with preoperative intraarterial infusion of docetaxel (TXT), was successful].	2002-07	12146005
Medroxyprogesterone-induced endocrine alterations after menopause.	2002-06-26	12082365
Comparison of physical and emotional side effects of progesterone or medroxyprogesterone in early postmenopausal women.	2002-06-26	12082361
Contraceptive applications of estrogen.	2002-06-20	12071380
Intramuscular depot medroxyprogesterone versus oral megestrol for the control of postmenopausal hot flashes in breast cancer patients: a randomized study.	2002-06	12123333
New developments in contraception.	2002-06	12106759
[Positive effects of estrogens on cardiovascular health].	2002-05-02	12082786
Effect of postmenopausal hormone therapy on cardiovascular risk.	2002-05	12183856
[Comparative study on two different dosages of conjugated equine estrogen continuously combined with medroxyprogesterone in prevention of postmenopausal osteoporosis].	2002-05	12133397
Hormone replacement therapy: estrogen and progestin effects on plasma C-reactive protein concentrations.	2002-05	12015523
Effect of medroxyprogesterone on pulmonary arterial pressure, exhaled nitric oxide, ECG and arterial blood gases.	2002-05	11982742
Monthly injection provides new contraceptive choice.	2002-04-05	11930928
Use of medroxyprogesterone acetate in the treatment of Müllerian adenosarcoma: a case report.	2002-04	11925144
Pharmacological characterization of the ATP-dependent low K(m) guanosine 3',5'-cyclic monophosphate (cGMP) transporter in human erythrocytes.	2002-03-01	11911846
Estrogen status correlates with the calcium content of coronary atherosclerotic plaques in women.	2002-03	11889163
Effects of hormone replacement therapy and methylenetetrahydrofolate reductase polymorphism on plasma folate and homocysteine levels in postmenopausal Japanese women.	2002-03	11872199
High-risk teen compliance with prescription contraception: an analysis of Ohio Medicaid claims.	2002-02	11888805
Intrauterine 10 microg and 20 microg levonorgestrel systems in postmenopausal women receiving oral oestrogen replacement therapy: clinical, endometrial and metabolic response.	2002-02	11888095
[A case of long surviving advanced recurrent breast cancer with multiple bone metastases responding to treatment with 5'-DFUR combined with MPA].	2002-02	11865641
Estrogen therapy for unstable angina: another bump for the bandwagon.	2002-01-16	11788213
Effects of acute hormone therapy on recurrent ischemia in postmenopausal women with unstable angina.	2002-01-16	11788212
Effects of hormonal replacement therapy on oxidative stress and total antioxidant capacity in postmenopausal hemodialysis patients.	2002-01	11921698
Interactions between antiepileptic drugs and hormonal contraception.	2002	11945109
Effects of hormone replacement therapy on plasma homocysteine and C-reactive protein levels.	2002	11803230
Medroxyprogesterone in postmenopausal females with partial upper airway obstruction during sleep.	2001-12	11829107
A comparison of continuous combined hormone replacement therapy, HMG-CoA reductase inhibitor and combined treatment for the management of hypercholesterolemia in postmenopausal women.	2001-12	11794823
[Results of treatment based on endocrine therapy for bone metastasis from breast cancer].	2001-12	11791380
An open trial of mirtazapine in menopausal women with depression unresponsive to estrogen replacement therapy.	2001-12	11788110
Transdermal hormone replacement therapy in postmenopausal women with uterine leiomyomas.	2001-12	11755553
Urinary tract infections in postmenopausal women: effect of hormone therapy and risk factors.	2001-12	11755552
Hormone replacement therapy and endothelial function: the exception that proves the rule?	2001-12	11742856
Hormone replacement therapy and endothelial function. Results of a randomized controlled trial in healthy postmenopausal women.	2001-12	11730815
Current options for injectable contraception in the United States.	2001-12	11727175
The influence of apo E phenotypes on the plasma triglycerides response to hormonal replacement therapy during the menopause.	2001-11-30	11716996
Quinacrine non-surgical female sterilization in Bangladesh.	2001-11	11777487
[Clinical analysis of pulmonary lymphangioleiomyomatosis].	2001-10-25	11825531
New options in contraception for adolescents.	2001-10	12112958
Anaylsis of birefringence during wound healing and remodeling following alkali burns in rabbit cornea.	2001-10	11825023
How to use progestin in hormone replacement therapy: an animal experiment.	2001-02	11780201
[Pulmonary lymphangioleiomyomatosis: presentation and results of treatment].	2001	12134438
Autophagy and nuclear changes in FM3A breast tumor cells after epirubicin, medroxyprogesterone and tamoxifen treatment in vitro.	2001	11872957

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

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:16:53 GMT 2025` Edited by `admin` on `Wed Apr 02 09:16:53 GMT 2025`
Record UNII	HSU1C9YRES
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEDROXYPROGESTERONE

Official Name

English

FARLUTAL INYECTABLE

Preferred Name

English

MEDROXYPROGESTERONE [VANDF]

Common Name

English

Medroxyprogesterone [WHO-DD]

Common Name

English

MEDROXYPROGESTERONE ACETATE IMPURITY B [WHO-IP]

Common Name

English

MEDROXYPROGESTERONE [WHO-IP]

Common Name

English

NSC-27408

Code

English

medroxyprogesterone [INN]

Common Name

English

MEDROXYPROGESTERONE [MI]

Common Name

English

17-HYDROXY-6.ALPHA.-METHYLPREGN-4-ENE-3,20-DIONE

Systematic Name

English

MEDROXYPROGESTERONE ACETATE RELATED COMPOUND B [USP-RS]

Common Name

English

G03AC06

Code

English

MEDROXYPROGESTERONE ACETATE IMPURITY B [EP IMPURITY]

Common Name

English

MEDROXYPROGESTERONE [HSDB]

Common Name

English

MEDROXYPROGESTERONE ACETATE RELATED COMPOUND B

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C776