Identification

Name
Medroxyprogesterone acetate
Accession Number
DB00603  (APRD00627)
Type
Small Molecule
Groups
Approved, Investigational
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. It is used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis as well as several other indications. 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.

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularPharmacia and Upjohn Company LLC1992-10-29Not applicableUs
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/1mLIntramuscularA-S Medication Solutions1992-10-29Not 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, suspension400 mg/1mLIntramuscularPhysicians Total Care, Inc.1995-01-13Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA-S Medication Solutions1992-10-29Not applicableUs
Depo-ProveraInjection, suspension400 mg/1mLIntramuscularPharmacia & Upjohn Inc1960-11-01Not applicableUs
Depo-ProveraInjection, suspension150 mg/1mLIntramuscularA S Medication Solutions1992-10-29Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-medroxyTablet100 mgOralApotex Corporation2005-08-04Not applicableCanada
Apo-medroxyTablet10 mgOralApotex Corporation2007-01-10Not applicableCanada
Apo-medroxy TabletsTablet2.5 mgOralApotex Corporation2002-04-22Not applicableCanada
Apo-medroxy TabletsTablet5 mgOralApotex Corporation2002-04-22Not applicableCanada
Dom-medroxyprogesteroneTablet10 mgOralDominion Pharmacal2003-05-132016-10-25Canada
Dom-medroxyprogesteroneTablet5 mgOralDominion Pharmacal2003-05-132016-10-25Canada
Dom-medroxyprogesteroneTablet2.5 mgOralDominion Pharmacal2003-05-132016-10-25Canada
Gen-medroxy Tablet 10mgTablet10 mgOralGenpharm Ulc1997-03-122010-08-04Canada
Gen-medroxy Tablet 2.5mgTablet2.5 mgOralGenpharm Ulc1997-03-122010-08-04Canada
Gen-medroxy Tablet 5mgTablet5 mgOralGenpharm Ulc1997-03-122010-08-04Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
PremphaseMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1) + Conjugated estrogens (0.625 mg/1)KitPhysicians Total Care, Inc.2005-07-08Not applicableUs
PremphaseMedroxyprogesterone acetate (5 mg/1) + Conjugated estrogens (0.625 mg/1) + Conjugated estrogens (0.625 mg/1)KitWyeth 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)KitWyeth Pharmaceuticals Inc.1995-12-012009-10-23Us
PremplusMedroxyprogesterone acetate (5.0 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizer2002-05-09Not applicableCanada
PremplusMedroxyprogesterone acetate (2.5 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizer2000-10-30Not applicableCanada
Premplus CycleMedroxyprogesterone acetate (10 mg) + Conjugated estrogens (0.625 mg)Kit; TabletOralPfizerNot applicableNot applicableCanada
PremproMedroxyprogesterone acetate (1.5 mg/1) + Conjugated estrogens (0.45 mg/1)Tablet, sugar coatedOralWyeth Pharmaceuticals Inc.2003-06-012009-10-23Us
PremproMedroxyprogesterone acetate (1.5 mg/1) + Conjugated estrogens (0.3 mg/1)Tablet, sugar coatedOralPhysicians Total Care, Inc.2004-04-08Not applicableUs
PremproMedroxyprogesterone acetate (2.5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralWyeth Pharmaceuticals Inc.1995-12-012009-10-23Us
PremproMedroxyprogesterone acetate (2.5 mg/1) + Conjugated estrogens (0.625 mg/1)Tablet, sugar coatedOralA-S Medication Solutions2009-09-21Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Lunelle Monthly ContraceptiveMedroxyprogesterone acetate (25 mg/0.5mL) + Estradiol cypionate (5 mg/0.5mL)Injection, suspensionIntramuscularPhysicians Total Care, Inc.2002-08-262004-10-31Us
International/Other Brands
Depo-subq provera 104
Categories
UNII
C2QI4IOI2G
CAS number
71-58-9
Weight
Average: 386.5244
Monoisotopic: 386.245709576
Chemical Formula
C24H34O4
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

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.

Associated Conditions
Associated Therapies
Pharmacodynamics

Medroxyprogesterone acetate 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.

TargetActionsOrganism
AProgesterone receptor
agonist
Human
AEstrogen receptor alpha
agonist
Human
Absorption

Rapidly absorbed from GI tract

Volume of distribution
Not Available
Protein binding

90%

Metabolism

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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Medroxyprogesterone acetate.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Medroxyprogesterone acetate.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be increased when combined with Medroxyprogesterone acetate.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Medroxyprogesterone acetate.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Medroxyprogesterone acetate.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Medroxyprogesterone acetate.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Medroxyprogesterone acetate.
6-Deoxyerythronolide BThe metabolism of Medroxyprogesterone acetate can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Medroxyprogesterone acetate.
AbacavirMedroxyprogesterone acetate may decrease the excretion rate of Abacavir which could result in a higher serum level.
Food Interactions
  • Take with food.

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. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. [PubMed:19434889]
  2. Lenco W, Mcknight M, Macdonald AS: Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits. Ann Surg. 1975 Jan;181(1):67-73. [PubMed:1119869]
External Links
KEGG Drug
D00951
KEGG Compound
C08150
PubChem Compound
6279
PubChem Substance
46508895
ChemSpider
6043
BindingDB
50067678
ChEBI
6716
ChEMBL
CHEMBL717
Therapeutic Targets Database
DAP001211
PharmGKB
PA450344
IUPHAR
2879
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
1Active Not RecruitingPreventionContraception1
1CompletedNot AvailableHealthy Volunteers1
1CompletedHealth Services ResearchOne to five years postmenopausal1
1CompletedPreventionContraception1
1CompletedPreventionHIV Prevention1
1CompletedTreatmentEstrogen Replacement Therapy1
1CompletedTreatmentOne to five years postmenopausal1
1TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1WithdrawnBasic ScienceDiabetes, Diabetes Mellitus Type 11
1, 2CompletedBasic ScienceTransplantation, Kidney1
1, 2CompletedTreatmentEndometriosis1
1, 2RecruitingTreatmentAdult Living Donor Kidney Transplant Recipients / Living Kidney Donors / Transplant, Kidney1
2Active Not RecruitingTreatmentAdvanced, Persistent, or Recurrent Endometrial Cancer1
2Active Not RecruitingTreatmentCrohn's Disease (CD)1
2Active Not RecruitingTreatmentGrade 1 Endometrial Endometrioid Adenocarcinoma / Grade 2 Endometrial Endometrioid Adenocarcinoma / Grade 3 Endometrial Endometrioid Adenocarcinoma / Uterine Corpus Adenosarcoma1
2CompletedPreventionEndometrial Cancers1
2CompletedPreventionEndometrial Safety / Vasomotor Symptoms1
2CompletedTreatmentClinically Diagnosed Endometriotic Patient Was Defined as a Woman Who Has Pelvic Pain and at Least One Evidence of PV or TVS1
2CompletedTreatmentEndometrial Adenocarcinomas / Endometrial Adenosquamous Carcinoma / Endometrial Cancers / Endometrial Endometrioid Adenocarcinoma, Variant With Squamous Differentiation / Recurrent Uterine Corpus Carcinoma / Stage I Uterine Corpus Cancer / Stage II Uterine Corpus Cancer / Stage III Uterine Corpus Cancer / Stage IV Uterine Corpus Cancer1
2CompletedTreatmentEpilepsies / Menopause1
2CompletedTreatmentEstrogen Receptor-negative Breast Cancer / Progesterone Receptor-negative Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentHigh Blood Pressure (Hypertension) / One to five years postmenopausal / Pre-Hypertension1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I / Tuberculosis1
2CompletedTreatmentMenopausal Hot Flushes / Menopause1
2TerminatedPreventionEndometrial Cancers1
2TerminatedTreatmentMenopause1
2, 3CompletedHealth Services ResearchCardiovascular Disease (CVD) / Coronary Arteriosclerosis / Coronary Heart Disease (CHD) / Heart Diseases1
2, 3CompletedTreatmentAlzheimer's Disease (AD)1
2, 3CompletedTreatmentHealthy Volunteers1
2, 3CompletedTreatmentSleep Apnea Syndrome1
2, 3Not Yet RecruitingTreatmentEndometrial Hyperplasia Without Atypia1
2, 3RecruitingTreatmentAtypical Endometrial Hyperplasia / Endometrial Cancers1
2, 3RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2, 3TerminatedTreatmentDelayed Graft Function1
3Active Not RecruitingTreatmentDysfunctional Uterine Bleeding1
3CompletedOtherPostmenopausal Women1
3CompletedPreventionBone destruction / Bone Diseases / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Ischemia / One to five years postmenopausal / Thrombosis1
3CompletedPreventionCancer, Breast / Endometrial Cancers1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Arteriosclerosis / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia / One to five years postmenopausal1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Ischemia / One to five years postmenopausal1
3CompletedSupportive CareCancer, Breast / Menopausal Hot Flushes / Menopausal Symptoms1
3CompletedSupportive CareMenopausal Hot Flushes1
3CompletedTreatmentAdenocarcinoma, Prostate1
3CompletedTreatmentHypermenorrhea1
3CompletedTreatmentBone destruction / Menopause1
3CompletedTreatmentMetastatic Renal Cell Carcinoma1
3CompletedTreatmentRejection, Transplant / Transplantation, Kidney1
3CompletedTreatmentRenal Cancers1
3CompletedTreatmentTurner's Syndrome1
3CompletedTreatmentBone destruction1
3RecruitingPreventionInfertilities1
3RecruitingTreatmentHeavy Menstrual Bleeding / Improve Quality of Life1
3RecruitingTreatmentHypermenorrhea1
3RecruitingTreatmentPrimary Ovarian Insufficiency1
3TerminatedTreatmentSystemic Lupus Erythematosus (SLE)1
4Active Not RecruitingHealth Services ResearchContraception1
4CompletedOtherRenal Failure1
4CompletedPreventionAdverse Effects / Transplantation, Kidney1
4CompletedPreventionCardiovascular Disease (CVD)1
4CompletedTreatmentApoptotic Signal Pathways in Endometrial Hyperplasia1
4CompletedTreatmentChronic Kidney Disease (CKD) / End Stage Renal Disease (ESRD) / Hemodialysis-dependent patients / Renal Replacement Therapies / Transplantation, Renal1
4CompletedTreatmentDysfunctional Uterine Bleeding1
4CompletedTreatmentEndometriosis1
4CompletedTreatmentInfertilities1
4CompletedTreatmentOvulatory Dysfunction1
4CompletedTreatmentRenal Transplanted Recipients1
4CompletedTreatmentTransplant, Kidney1
4RecruitingBasic ScienceHormonal Contraception1
4RecruitingTreatmentEBV / Transplant; Failure, Kidney1
4RecruitingTreatmentGastrointestinal Disorder, Functional / Kidney Transplant Rejection1
4TerminatedTreatmentDysfunctional Uterine Bleeding1
4TerminatedTreatmentTransplantation, Renal1
4Unknown StatusTreatmentEndometrial Hyperplasia1
Not AvailableActive Not RecruitingNot AvailableContraception / Human Immunodeficiency Virus (HIV) / Immune Cells (Mucosal and Systemic) / Microbiota1
Not AvailableCompletedNot AvailableContraception1
Not AvailableCompletedNot AvailableContraception / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedNot AvailableDementia Syndromes1
Not AvailableCompletedBasic ScienceCardiovascular Disease (CVD) / Cognitive Impairments / Endothelial Dysfunction / Executive Dysfunction1
Not AvailableCompletedPreventionContraception1
Not AvailableCompletedSupportive CareContraception / Postpartum Period1
Not AvailableCompletedTreatmentDeficiency, Vitamin D / Polycystic Ovarian Syndrome1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentHypermenorrhea / Uterine Hemorrhage1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableRecruitingNot AvailableContraception / Contraceptive implant therapy / Emergency Contraception / IUD1
Not AvailableRecruitingNot AvailableFemale Sexual Function1
Not AvailableTerminatedNot AvailableInitiation of Depo-Provera (DMPA) / Initiation of Mirena (LNG-IUD) / Initiation of Oral Contraception (OC)1
Not AvailableTerminatedBasic ScienceFibromyalgia1
Not AvailableTerminatedTreatmentInfertilities / Polycystic Ovaries Syndrome1
Not AvailableTerminatedTreatmentPolycystic Ovarian Syndrome1
Not AvailableTerminatedTreatmentTransplantation, Kidney1

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
TabletOral100 mg
Injection, suspensionIntramuscular400 mg/1mL
SuspensionIntramuscular150 mg
SuspensionIntramuscular50 mg
Injection, suspensionSubcutaneous104 mg/0.65mL
Injection, suspensionIntramuscular
InjectionIntramuscular150 mg/1mL
Injection, suspensionIntramuscular150 mg/1mL
Injection, suspension, extended releaseIntramuscular150 mg/1mL
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
Kit
Kit; tabletOral
Tablet, sugar coatedOral
TabletOral2.5 mg
TabletOral5 mg
TabletOral10 mg
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)
CA2409059No2006-04-182021-04-25Canada
US6495534No2000-05-152020-05-15Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)214.5 °CPhysProp
water solubility22.2mg/LNot Available
logP3.5Not Available
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

Taxonomy

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
Progestogin-skeleton / Steroid ester / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Oxosteroid / Delta-4-steroid / Cyclohexenone / Alpha-acyloxy ketone / Carboxylic acid ester
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:6716)

Targets

Details
1. Progesterone receptor
Kind
Protein
Organism
Human
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
Human
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]

Enzymes

Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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]
Kind
Protein
Organism
Human
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
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2018 04:36