Identification

Name
Medroxyprogesterone acetate
Accession Number
DB00603
Description

Medroxyprogesterone acetate (MPA) is a progesterone derivative that is more resistant to metabolism for improved pharmacokinetic properties.9 MPA can be use to treat secondary amenorrhea, endometrial hyperplasia, abnormal uterine bleeding, osteoporosis, vasomotor symptoms in menopause, vulvar and vaginal atrophy, prevent pregnancy, manage pain in endometriosis, prevent pregnancy, and is also used in palliative care for endometrial and renal carcinoma.10,11,12,13,14

Medroxyprogesterone acetate was granted FDA approval on 18 June 1959.10

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 386.5244
Monoisotopic: 386.245709576
Chemical Formula
C24H34O4
Synonyms
  • (6α)-17-(Acetyloxy)-6-methylpreg-4-ene-3,20-dione
  • 17-Acetoxy-6α-methylprogesterone
  • 17α-hydroxy-6α-methylprogesterone acetate
  • 6-alpha-Methyl-17-alpha-acetoxyprogesterone
  • 6-alpha-Methyl-17-alpha-hydroxyprogesterone acetate
  • 6α-Methyl-17-acetoxy progesterone
  • 6α-Methyl-17α-hydroxyprogesterone acetate
  • 6α-Methyl-4-pregnene-3,20-dion-17α-ol acetate
  • Medroxyacetate progesterone
  • Medroxyprogesterone 17-acetate
  • Methylacetoxyprogesterone
  • Metigestrona
  • MPA
External IDs
  • NSC-21171
  • NSC-26386

Pharmacology

Indication

Medroxyprogesterone acetate (MPA) oral tablets are indicated to treat secondary amenorrhea, reduce the incidence of endometrial hyperplasia in postmenopausal women, and to treat abnormal uterine bleeding due to hormonal imbalance, not organic pathology.10 Oral tablets containing MPA and conjugated estrogens are indicated to prevent postmenopausal osteoporosis and to treat moderate to severe menopausal symptoms such as vasomotor symptoms, vulvar atrophy, and vaginal atrophy.11 Subcutaneous MPA is indicated to prevent pregnancy and manage pain associated with endometriosis.12 Intramuscular MPA is indicated to prevent pregnancy,13 and at higher concentrations for palliative treatment of endometrial or renal carcinoma.14

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Medroxyprogesterone acetate (MPA) inhibits gonadotropin production, reduces nuclear estrogen receptors and DNA synthesis in epithelial cells of the endometrium, and induces p53 dependant apoptosis in cancer cell lines.11,6 MPA oral tablets have a half life of 40-60 hours and other formulations can have half lives that are considerably longer, so the duration of action is long.2,3 The therapeutic window is wide as patients may take doses ranging from 5mg orally daily to 1000mg as a depo injection weekly.10,11,12,13,14 Long term use of MPA is associated with a reduction in bone density and patients who taking MPA during adolescence may have lower peak bone mass than untreated patients, which can also increase the risk of osteoporosis and fractures in the future.10,11,12,13,14

Mechanism of action

Medroxyprogesterone acetate (MPA) inhibits the production of gonadotropin, preventing follicular maturation and ovulation, which is responsible for it’s ability to prevent pregnancy.11 This action also thins the endometrium.11 MPA reduces nuclear estrogen receptors and DNA synthesis in epithelial cells of the endometrium.11 MPA can also induce p53 dependant apoptosis in certain cancer cell lines,6 and inhibit GABA-A receptors.8

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
AEstrogen receptor alpha
agonist
Humans
UP-glycoprotein 1
inhibitor
Humans
UGABA(A) Receptor
inhibitor
Humans
Absorption

Absorption of oral medroxyprogesterone acetate (MPA) varies considerably between formulations.2 A 1000mg oral dose reaches an average Cmax of 145-315nmol/L while a 500mg oral dose reaches an average Cmax of 33-178nmol/L with a Tmax of 1-3 hours and a lag time of half an hour.2 The AUC of a 500mg oral dose of MPA was 543.4-1981.1nmol*L/h depending on formulation.2

Intramuscular MPA reaches a Cmax of 4.69±1.52nmol/L with a Tmax of 4.75±2.09 days and an AUC of 81.58±27.64days*nmol/L.3 Subcutaneous MPA reaches a Cmax of 3.83±1.56nmol/L with a T±max of 6.52±2.07 days and an AUC of 72.26±38.73days*nmol/L.3 However, the pharmacokinetics of MPA may also vary depending on injection site.4

Volume of distribution

The volume of distribution of medroxyprogesterone acetate is 20±3L.15

Protein binding

Medroxyprogesterone acetate is 86% protein bound in serum, mainly to albumin.1,10,11,12,13 No binding occurs with sex hormone binding globulin.1,10,11,12,13

Metabolism

Medroxyprogesterone acetate undergoes beta hydroxylation to form the metabolites 6-beta (M-2), 2-beta (M-4), and 1-beta-hydroxymedroxyprogesterone acetate (M-3).9 M-2 and M-4 are further metabolized to 2-beta,6-beta-dihydroxymedroxyprogesterone (M-1).9 M-3 is further metabolized to 1,2-dehydromedroxyprogesterone acetate (M-5).9

Hover over products below to view reaction partners

Route of elimination

The majority of medroxyprogesterone acetate (MPA) is eliminated in the urine as glucuronide conjugates and a minority of sulphate conjugates.10,11,12,13 Glucuronide conjugates are also detected in the feces.15 Determining the exact ratio of metabolites and parent compound eliminated in the urine and feces is difficult as the metabolite profile in the urine is not significantly different7 and radio labelling studies are not readily available.10,11,12,13,14

Half-life

Oral medroxyprogesterone acetate (MPA) has an absorption half life of 15-30min and a biological half life of 40-60 hours.2 Intramuscular MPA has an absorption half life of 0.86±0.30 days and an elimination half life of 24.03±21.74 days.3 Subcutaneous MPA has an absorption half life of 1.05±0.56 days and an elimination half life of 30.90±15.11 days.3

Clearance

The mean clearance of medroxyprogesterone acetate (MPA) is 1668±146L/day or 21.9±4.3L/kg/day.5 Due to the high inter patient variability in MPA pharmacokinetics, clearance has been reported to be 1600-4000L/day.15

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The oral LD50 in rats is >6400mg/kg and in mice is >16g/kg.16 The intraperitoneal LD50 in rats is >900mg/kg and in mice is >1500mg/kg.16 The subcutaneous LD50 in rats is >900mg/kg and in mice is>1500mg/kg.16

Patients experiencing and overdose or oral medroxyprogesterone acetate (MPA) may present with nausea, vomiting, breast tenderness, dizziness, abdominal pain, drowsiness, fatigue, and withdrawal bleeding.10,11 Treat patients by stopping MPA and beginning symptomatic treatment.10,11 Patients who have been given too much of a MPA depo injection should contact a healthcare professional, hospital emergency department, or local poison control immediately.15

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirMedroxyprogesterone acetate may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Medroxyprogesterone acetate can be increased when it is combined with Abametapir.
AbciximabMedroxyprogesterone acetate may decrease the anticoagulant activities of Abciximab.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Medroxyprogesterone acetate.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Medroxyprogesterone acetate.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Medroxyprogesterone acetate.
AceclofenacAceclofenac may decrease the excretion rate of Medroxyprogesterone acetate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Medroxyprogesterone acetate which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Medroxyprogesterone acetate.
AcetaminophenThe metabolism of Medroxyprogesterone acetate can be increased when combined with Acetaminophen.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid St. John's Wort. St. John's Wort may decrease the effectiveness of medroxyprogesterone acetate.
  • Take with food. Food increases the bioavailability of medroxyprogesterone acetate.

Products

Product Images
International/Other Brands
Depo-subq provera 104
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularPhysicians Total Care, Inc.1999-06-302011-06-30Us
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA S Medication Solutions1992-10-29Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularPharmacia and Upjohn Company LLC1992-10-29Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA-S Medication Solutions1992-10-292019-01-31Us
Depo-ProveraInjection, suspension400 mg/1mLIntramuscularPhysicians Total Care, Inc.1995-01-13Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularPhysicians Total Care, Inc.2000-01-242011-06-30Us
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularPharmacia and Upjohn Company LLC1992-10-29Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA-S Medication Solutions1992-10-29Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA S Medication Solutions1992-10-29Not applicableUs
Depo-ProveraInjection, suspension400 mg/1mLIntramuscularPharmacia & Upjohn Inc1960-11-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-medroxyTabletOralApotex Corporation2007-01-10Not applicableCanada
Apo-medroxyTabletOralApotex Corporation2005-08-04Not applicableCanada
Apo-medroxy TabletsTabletOralApotex Corporation2002-04-22Not applicableCanada
Apo-medroxy TabletsTabletOralApotex Corporation2002-04-22Not applicableCanada
Dom-medroxyprogesteroneTabletOralDominion Pharmacal2003-05-132016-10-25Canada
Dom-medroxyprogesteroneTabletOralDominion Pharmacal2003-05-132016-10-25Canada
Dom-medroxyprogesteroneTabletOralDominion Pharmacal2003-05-132016-10-25Canada
Gen-medroxy Tablet 10mgTabletOralGenpharm Ulc1997-03-122010-08-04Canada
Gen-medroxy Tablet 2.5mgTabletOralGenpharm Ulc1997-03-122010-08-04Canada
Gen-medroxy Tablet 5mgTabletOralGenpharm Ulc1997-03-122010-08-04Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
PremphaseMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1) + Conjugated estrogens (0.625 mg/1)KitOralPhysicians Total Care, Inc.2005-07-08Not applicableUs
PremphaseMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1) + Conjugated estrogens (0.625 mg/1)OralWyeth Pharmaceuticals Llc, a Subsidiary of Pfizer Inc.2012-03-01Not applicableUs
PremphaseMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1) + Conjugated estrogens (0.625 mg/1)KitOralWyeth Pharmaceuticals Inc.1995-12-012009-10-23Us
PremplusMedroxyprogesterone acetate (5 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizer Canada Ulc2002-05-092019-11-06Canada
PremplusMedroxyprogesterone acetate (2.5 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizer Canada Ulc2000-10-302019-11-06Canada
Premplus CycleMedroxyprogesterone acetate (10 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizer Canada UlcNot applicableNot applicableCanada
PremproMedroxyprogesterone acetate (2.5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralAvera McKennan Hospital2016-01-28Not applicableUs
PremproMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralWyeth Pharmaceuticals Inc.1995-12-012009-10-23Us
PremproMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralPhysicians Total Care, Inc.2006-02-242010-06-30Us
PremproMedroxyprogesterone acetate (2.5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralWyeth Pharmaceuticals Llc, a Subsidiary of Pfizer Inc.2009-09-21Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Lunelle Monthly ContraceptiveMedroxyprogesterone acetate (25 mg/0.5mL) + Estradiol cypionate (5 mg/0.5mL)Injection, suspensionIntramuscularPhysicians Total Care, Inc.2002-08-262004-10-31Us

Categories

ATC Codes
G03DA02 — MedroxyprogesteroneL02AB02 — MedroxyprogesteroneG03AC06 — Medroxyprogesterone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Steroid esters / 20-oxosteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Alpha-acyloxy ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:6716)

Chemical Identifiers

UNII
C2QI4IOI2G
CAS number
71-58-9
InChI Key
PSGAAPLEWMOORI-PEINSRQWSA-N
InChI
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
IUPAC Name
(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate
SMILES
[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C

References

Synthesis Reference

Klaus ANNEN, Thomas Linz, Karl-Heinz Neff, Rolf Bohlmann, Henry Laurent, "PROCESS FOR PREPARING 17ALPHA-ACETOXY-6-METHYLENEPREGN-4-ENE-3,20-DIONE, MEDROXYPROGESTERONE ACETATE AND MEGESTROL ACETATE." U.S. Patent US20090012321, issued January 08, 2009.

US20090012321
General References
  1. Akpoviroro JO, Mangalam M, Jenkins N, Fotherby K: Binding of the contraceptive steroids medroxyprogesterone acetate and ethynyloestradiol in blood of various species. J Steroid Biochem. 1981 May;14(5):493-8. doi: 10.1016/0022-4731(81)90362-9. [PubMed:6457935]
  2. Johansson ED, Johansen PB, Rasmussen SN: Medroxyprogesterone acetate pharmacokinetics following oral high-dose administration in humans: a bioavailability evaluation of a new MPA tablet formulation. Acta Pharmacol Toxicol (Copenh). 1986 May;58(5):311-7. doi: 10.1111/j.1600-0773.1986.tb00115.x. [PubMed:2943134]
  3. Sierra-Ramirez JA, Lara-Ricalde R, Lujan M, Velazquez-Ramirez N, Godinez-Victoria M, Hernadez-Munguia IA, Padilla A, Garza-Flores J: Comparative pharmacokinetics and pharmacodynamics after subcutaneous and intramuscular administration of medroxyprogesterone acetate (25 mg) and estradiol cypionate (5 mg). Contraception. 2011 Dec;84(6):565-70. doi: 10.1016/j.contraception.2011.03.014. Epub 2011 May 11. [PubMed:22078184]
  4. Halpern V, Combes SL, Dorflinger LJ, Weiner DH, Archer DF: Pharmacokinetics of subcutaneous depot medroxyprogesterone acetate injected in the upper arm. Contraception. 2014 Jan;89(1):31-5. doi: 10.1016/j.contraception.2013.07.002. Epub 2013 Jul 12. [PubMed:23993431]
  5. Gupta C, Osterman J, Santen R, Bardin CW: In vivo metabolism of progestins. V. The effect of protocol design on the estimated metabolic clearance rate and volume of distribution of medroxyprogesterone acetate in women. J Clin Endocrinol Metab. 1979 May;48(5):816-20. doi: 10.1210/jcem-48-5-816. [PubMed:429526]
  6. Altinoz MA, Bilir A, Ozar E, Onar FD, Sav A: Medroxyprogesterone acetate alone or synergistic with chemotherapy suppresses colony formation and DNA synthesis in C6 glioma in vitro. Int J Dev Neurosci. 2001 Oct;19(6):541-7. doi: 10.1016/s0736-5748(01)00045-4. [PubMed:11600316]
  7. Yovich JL, Willcox DL, Wilkinson SP, Poletti VM, Hahnel R: Medroxyprogesterone acetate does not perturb the profile of steroid metabolites in urine during pregnancy. J Endocrinol. 1985 Mar;104(3):453-9. doi: 10.1677/joe.0.1040453. [PubMed:3156203]
  8. Braden BB, Garcia AN, Mennenga SE, Prokai L, Villa SR, Acosta JI, Lefort N, Simard AR, Bimonte-Nelson HA: Cognitive-impairing effects of medroxyprogesterone acetate in the rat: independent and interactive effects across time. Psychopharmacology (Berl). 2011 Nov;218(2):405-18. doi: 10.1007/s00213-011-2322-4. Epub 2011 May 12. [PubMed:21562760]
  9. Zhang JW, Liu Y, Zhao JY, Wang LM, Ge GB, Gao Y, Li W, Liu HT, Liu HX, Zhang YY, Sun J, Yang L: Metabolic profiling and cytochrome P450 reaction phenotyping of medroxyprogesterone acetate. Drug Metab Dispos. 2008 Nov;36(11):2292-8. doi: 10.1124/dmd.108.022525. Epub 2008 Aug 25. [PubMed:18725509]
  10. FDA Approved Drug Products: Provera Medroxyprogesterone Acetate Oral Tablets [Link]
  11. FDA Approved Drug Products: Conjugated Estrogens and Medroxyprogesterone Acetate Oral Tablets [Link]
  12. FDA Approved Drug Products: Medroxyprogesterone Acetate Subcutaneous Injection [Link]
  13. FDA Approved Drug Products: Medroxyprogesterone Acetate Intramuscular Injection 150mg/mL [Link]
  14. FDA Approved Drug Products: Medroxyprogesterone Acetate Intramuscular Injection 400mg/mL [Link]
  15. Pfizer Canada: Depo-Provera Monograph [Link]
  16. Cayman Chemicals: Medroxyprogesterone Acetate MSDS [Link]
KEGG Drug
D00951
KEGG Compound
C08150
PubChem Compound
6279
PubChem Substance
46508895
ChemSpider
6043
BindingDB
50067678
RxNav
1000112
ChEBI
6716
ChEMBL
CHEMBL717
ZINC
ZINC000005029557
Therapeutic Targets Database
DAP001211
PharmGKB
PA450344
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Medroxyprogesterone
AHFS Codes
  • 68:32.00 — Progestins
FDA label
Download (1.2 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticBone Density / Contraception1
4CompletedHealth Services ResearchContraception1
4CompletedHealth Services ResearchContraception / Human Immunodeficiency Virus (HIV) Infections1
4CompletedOtherContraception / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionCardiovascular Heart Disease1
4CompletedTreatmentAbnormal Uterine Bleeding1
4CompletedTreatmentApoptotic Signal Pathways in Endometrial Hyperplasia1
4CompletedTreatmentContraception / Lactation / Postpartum Depression1
4CompletedTreatmentEndometrial Hyperplasia1
4CompletedTreatmentEndometriosis1

Pharmacoeconomics

Manufacturers
  • Sandoz canada inc
  • Teva parenteral medicines inc
  • Barr laboratories inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Usl pharma inc
  • Pharmacia and upjohn co
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Central Texas Community Health Centers
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Greenstone LLC
  • Group Health Cooperative
  • H and H Laboratories
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Co. Jelfa SA
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prescript Pharmaceuticals
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rite Aid Corp.
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • United Research Laboratories Inc.
  • USL Pharma Inc.
  • Veratex Corp.
  • Wyeth Pharmaceuticals
Dosage Forms
FormRouteStrength
Injection, suspensionIntramuscular400 mg/1mL
SuspensionIntramuscular
Injection, suspensionSubcutaneous104 mg/0.65mL
Tablet
Injection, suspensionIntramuscular
InjectionIntramuscular150 mg/1mL
Injection, suspensionIntramuscular150 mg/1mL
Injection, suspension, extended releaseIntramuscular150 mg/1mL
PowderNot applicable1 g/1g
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
KitOral
Kit; tabletOral
Tablet, sugar coatedOral
TabletOral
Prices
Unit descriptionCostUnit
Depo-Provera 400 mg/ml Suspension 2.5ml Vial201.13USD vial
Depo-subq provera 104 syringe108.17USD syringe
Depo-provera 400 mg/ml vial96.7USD ml
Depo-Provera 150 mg/ml Suspension 1ml Syringe94.58USD syringe
MedroxyPROGESTERone Acetate 150 mg/ml Suspension 1ml Syringe60.56USD syringe
MedroxyPROGESTERone Acetate 150 mg/ml Suspension 1ml Vial55.17USD vial
Depo-Provera 150 mg/ml31.02USD ml
Medroxyprogesterone Acetate 150 mg/ml23.05USD ml
Medroxyprogesterone ace powder18.97USD g
Depo-Provera 50 mg/ml6.01USD ml
Provera 10 mg tablet2.03USD tablet
Provera 5 mg tablet1.57USD tablet
Provera 100 mg Tablet1.41USD tablet
Provera 2.5 mg tablet1.15USD tablet
Apo-Medroxy 100 mg Tablet0.96USD tablet
Provera 10 mg Tablet0.73USD tablet
MedroxyPROGESTERone Acetate 10 mg tablet0.51USD tablet
MedroxyPROGESTERone Acetate 5 mg tablet0.48USD tablet
MedroxyPROGESTERone Acetate 2.5 mg tablet0.43USD tablet
Medroxyprogesterone 10 mg tablet0.4USD tablet
Provera 5 mg Tablet0.36USD tablet
Medroxyprogesterone 5 mg tablet0.33USD tablet
Apo-Medroxy 10 mg Tablet0.33USD tablet
Novo-Medrone 10 mg Tablet0.33USD tablet
Medroxyprogesterone 2.5 mg tablet0.32USD tablet
Provera 2.5 mg Tablet0.18USD tablet
Apo-Medroxy 5 mg Tablet0.16USD tablet
Novo-Medrone 5 mg Tablet0.16USD tablet
Apo-Medroxy 2.5 mg Tablet0.08USD tablet
Novo-Medrone 2.5 mg Tablet0.08USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2409059No2006-04-182021-04-25Canada
US6495534No2002-12-172020-05-15Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205-209FDA Approved Drug Products: Medroxyprogesterone Acetate Subcutaneous Injection
water solubility10mMChemspider
Predicted Properties
PropertyValueSource
Water Solubility0.00221 mg/mLALOGPS
logP3.42ALOGPS
logP4.13ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)17.82ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity107.81 m3·mol-1ChemAxon
Polarizability44.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9959
Blood Brain Barrier+0.9617
Caco-2 permeable+0.651
P-glycoprotein substrateSubstrate0.6107
P-glycoprotein inhibitor IInhibitor0.9149
P-glycoprotein inhibitor IIInhibitor0.7016
Renal organic cation transporterNon-inhibitor0.7753
CYP450 2C9 substrateNon-substrate0.8642
CYP450 2D6 substrateNon-substrate0.908
CYP450 3A4 substrateSubstrate0.7744
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.8907
CYP450 2D6 inhibitorNon-inhibitor0.9532
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8095
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.899
Ames testNon AMES toxic0.9775
CarcinogenicityNon-carcinogens0.9273
BiodegradationNot ready biodegradable0.9354
Rat acute toxicity1.8121 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9429
hERG inhibition (predictor II)Non-inhibitor0.7761
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002r-0449000000-c09cb0607e4a6118f05d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-3940000000-2c9513d9a6a2092f5759
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3930000000-453ace561b4dc5712e85
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-009i-2947000000-2c9190ea372fd54323e9
13C NMR Spectrum1D NMRNot Applicable

Targets

Details
1. Progesterone receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Risch HA, Bale AE, Beck PA, Zheng W: PGR +331 A/G and increased risk of epithelial ovarian cancer. Cancer Epidemiol Biomarkers Prev. 2006 Sep;15(9):1738-41. [PubMed:16985038]
  2. Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. [PubMed:17013809]
  3. Gizard F, Robillard R, Gross B, Barbier O, Revillion F, Peyrat JP, Torpier G, Hum DW, Staels B: TReP-132 is a novel progesterone receptor coactivator required for the inhibition of breast cancer cell growth and enhancement of differentiation by progesterone. Mol Cell Biol. 2006 Oct;26(20):7632-44. [PubMed:17015480]
  4. Wu HB, Fabian S, Jenab S, Quinones-Jenab V: Progesterone receptors activation after acute cocaine administration. Brain Res. 2006 Dec 18;1126(1):188-92. Epub 2006 Nov 15. [PubMed:17109827]
  5. Boonyaratanakornkit V, McGowan E, Sherman L, Mancini MA, Cheskis BJ, Edwards DP: The role of extranuclear signaling actions of progesterone receptor in mediating progesterone regulation of gene expression and the cell cycle. Mol Endocrinol. 2007 Feb;21(2):359-75. Epub 2006 Nov 30. [PubMed:17138644]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Jain JK, Li A, Yang W, Minoo P, Felix JC: Mifepristone alters expression of endometrial steroid receptors and their cofactors in new users of medroxyprogesterone acetate. Fertil Steril. 2007 Jan;87(1):8-23. Epub 2006 Nov 7. [PubMed:17094978]
  2. Kumar AS, Cureton E, Shim V, Sakata T, Moore DH, Benz CC, Esserman LJ, Hwang ES: Type and duration of exogenous hormone use affects breast cancer histology. Ann Surg Oncol. 2007 Feb;14(2):695-703. Epub 2006 Nov 14. [PubMed:17103262]
  3. Lessey BA, Palomino WA, Apparao KB, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006;4 Suppl 1:S9. [PubMed:17118173]
  4. Yuri T, Tsukamoto R, Uehara N, Matsuoka Y, Tsubura A: Effects of different durations of estrogen and progesterone treatment on development of N-methyl-N-nitrosourea-induced mammary carcinomas in female Lewis rats. In Vivo. 2006 Nov-Dec;20(6B):829-36. [PubMed:17203775]
  5. Ghebeh H, Tulbah A, Mohammed S, Elkum N, Bin Amer SM, Al-Tweigeri T, Dermime S: Expression of B7-H1 in breast cancer patients is strongly associated with high proliferative Ki-67-expressing tumor cells. Int J Cancer. 2007 Aug 15;121(4):751-8. [PubMed:17415709]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Altinoz MA, Bilir A, Ozar E, Onar FD, Sav A: Medroxyprogesterone acetate alone or synergistic with chemotherapy suppresses colony formation and DNA synthesis in C6 glioma in vitro. Int J Dev Neurosci. 2001 Oct;19(6):541-7. doi: 10.1016/s0736-5748(01)00045-4. [PubMed:11600316]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Braden BB, Garcia AN, Mennenga SE, Prokai L, Villa SR, Acosta JI, Lefort N, Simard AR, Bimonte-Nelson HA: Cognitive-impairing effects of medroxyprogesterone acetate in the rat: independent and interactive effects across time. Psychopharmacology (Berl). 2011 Nov;218(2):405-18. doi: 10.1007/s00213-011-2322-4. Epub 2011 May 12. [PubMed:21562760]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhang JW, Liu Y, Zhao JY, Wang LM, Ge GB, Gao Y, Li W, Liu HT, Liu HX, Zhang YY, Sun J, Yang L: Metabolic profiling and cytochrome P450 reaction phenotyping of medroxyprogesterone acetate. Drug Metab Dispos. 2008 Nov;36(11):2292-8. doi: 10.1124/dmd.108.022525. Epub 2008 Aug 25. [PubMed:18725509]
  2. Mimura N, Kobayashi K, Nakamura Y, Shimada N, Hosokawa M, Chiba K: Metabolism of medroxyprogesterone acetate (MPA) via CYP enzymes in vitro and effect of MPA on bleeding time in female rats in dependence on CYP activity in vivo. Life Sci. 2003 Nov 7;73(25):3201-12. doi: 10.1016/j.lfs.2003.05.004. [PubMed:14561525]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
  3. Zhang JW, Liu Y, Li W, Hao DC, Yang L: Inhibitory effect of medroxyprogesterone acetate on human liver cytochrome P450 enzymes. Eur J Clin Pharmacol. 2006 Jul;62(7):497-502. doi: 10.1007/s00228-006-0128-9. Epub 2006 Apr 28. [PubMed:16645869]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B2
Uniprot ID
P26439
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
Molecular Weight
42051.845 Da
References
  1. Lee TC, Miller WL, Auchus RJ: Medroxyprogesterone acetate and dexamethasone are competitive inhibitors of different human steroidogenic enzymes. J Clin Endocrinol Metab. 1999 Jun;84(6):2104-10. [PubMed:10372718]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhang JW, Liu Y, Li W, Hao DC, Yang L: Inhibitory effect of medroxyprogesterone acetate on human liver cytochrome P450 enzymes. Eur J Clin Pharmacol. 2006 Jul;62(7):497-502. doi: 10.1007/s00228-006-0128-9. Epub 2006 Apr 28. [PubMed:16645869]
  2. Laine K, Yasar U, Widen J, Tybring G: A screening study on the liability of eight different female sex steroids to inhibit CYP2C9, 2C19 and 3A4 activities in human liver microsomes. Pharmacol Toxicol. 2003 Aug;93(2):77-81. [PubMed:12899669]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Substrate
General Function
Testosterone 6-beta-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
Cyp3a1
Uniprot ID
P04800
Uniprot Name
Cytochrome P450 3A1
Molecular Weight
57917.375 Da
References
  1. Mimura N, Kobayashi K, Nakamura Y, Shimada N, Hosokawa M, Chiba K: Metabolism of medroxyprogesterone acetate (MPA) via CYP enzymes in vitro and effect of MPA on bleeding time in female rats in dependence on CYP activity in vivo. Life Sci. 2003 Nov 7;73(25):3201-12. doi: 10.1016/j.lfs.2003.05.004. [PubMed:14561525]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Akpoviroro JO, Mangalam M, Jenkins N, Fotherby K: Binding of the contraceptive steroids medroxyprogesterone acetate and ethynyloestradiol in blood of various species. J Steroid Biochem. 1981 May;14(5):493-8. doi: 10.1016/0022-4731(81)90362-9. [PubMed:6457935]
  2. FDA Approved Drug Products: Provera Medroxyprogesterone Acetate Oral Tablets [Link]
  3. FDA Approved Drug Products: Conjugated Estrogens and Medroxyprogesterone Acetate Oral Tablets [Link]
  4. FDA Approved Drug Products: Medroxyprogesterone Acetate Subcutaneous Injection [Link]
  5. FDA Approved Drug Products: Medroxyprogesterone Acetate Intramuscular Injection 150mg/mL [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Englund G, Hallberg P, Artursson P, Michaelsson K, Melhus H: Association between the number of coadministered P-glycoprotein inhibitors and serum digoxin levels in patients on therapeutic drug monitoring. BMC Med. 2004 Apr 2;2:8. doi: 10.1186/1741-7015-2-8. [PubMed:15061868]
  2. Zibera C, Gibelli N, Maestri L, Della Cuna GR: Medroxyprogesterone-acetate reverses the MDR phenotype of the CG5-doxorubicin resistant human breast cancer cell line. Anticancer Res. 1995 May-Jun;15(3):745-9. [PubMed:7645952]

Drug created on June 13, 2005 07:24 / Updated on August 09, 2020 06:16

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