ContaminantDB: Medroxyprogesterone Acetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:13:46 UTC

Update Date

2026-03-27 00:47:19 UTC

Accession Number

CHEM003687

Identification

Common Name

Medroxyprogesterone Acetate

Class

Small Molecule

Description

Medroxyprogesterone acetate (INN, USAN, BAN), also known as 17‘±-hydroxy-6‘±-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.

Contaminant Sources

IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Antineoplastic Agent, Hormonal
Contraceptive Agent
Contraceptive Agent, Female
Contraceptive Agent, Male
Drug
Ester
Ether
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6alpha)-17-(Acetyloxy)-6-methylpreg-4-ene-3,20-dione	ChEBI
17-Acetoxy-6alpha-methylprogesterone	ChEBI
17alpha-Hydroxy-6alpha-methylprogesterone acetate	ChEBI
6-alpha-Methyl-17-alpha-acetoxyprogesterone	ChEBI
6-alpha-Methyl-17-alpha-hydroxyprogesterone acetate	ChEBI
6alpha-Methyl-17-acetoxy progesterone	ChEBI
6alpha-Methyl-17alpha-hydroxyprogesterone acetate	ChEBI
6alpha-Methyl-4-pregnene-3,20-dion-17alpha-ol acetate	ChEBI
CBP-1011	ChEBI
Depo-provera	ChEBI
Depot medroxyprogesterone acetate	ChEBI
DMPA	ChEBI
MAP	ChEBI
Medroxyacetate progesterone	ChEBI
Medroxyprogesterone 17-acetate	ChEBI
Methylacetoxyprogesterone	ChEBI
Metigestrona	ChEBI
MPA	ChEBI
Depo-subq provera 104	Kegg
Provera	Kegg
(6a)-17-(Acetyloxy)-6-methylpreg-4-ene-3,20-dione	Generator
(6Α)-17-(acetyloxy)-6-methylpreg-4-ene-3,20-dione	Generator
17-Acetoxy-6a-methylprogesterone	Generator
17-Acetoxy-6α-methylprogesterone	Generator
17a-Hydroxy-6a-methylprogesterone acetate	Generator
17a-Hydroxy-6a-methylprogesterone acetic acid	Generator
17alpha-Hydroxy-6alpha-methylprogesterone acetic acid	Generator
17Α-hydroxy-6α-methylprogesterone acetate	Generator
17Α-hydroxy-6α-methylprogesterone acetic acid	Generator
6-a-Methyl-17-a-acetoxyprogesterone	Generator
6-Α-methyl-17-α-acetoxyprogesterone	Generator
6-a-Methyl-17-a-hydroxyprogesterone acetate	Generator
6-a-Methyl-17-a-hydroxyprogesterone acetic acid	Generator
6-alpha-Methyl-17-alpha-hydroxyprogesterone acetic acid	Generator
6-Α-methyl-17-α-hydroxyprogesterone acetate	Generator
6-Α-methyl-17-α-hydroxyprogesterone acetic acid	Generator
6a-Methyl-17-acetoxy progesterone	Generator
6Α-methyl-17-acetoxy progesterone	Generator
6a-Methyl-17a-hydroxyprogesterone acetate	Generator
6a-Methyl-17a-hydroxyprogesterone acetic acid	Generator
6alpha-Methyl-17alpha-hydroxyprogesterone acetic acid	Generator
6Α-methyl-17α-hydroxyprogesterone acetate	Generator
6Α-methyl-17α-hydroxyprogesterone acetic acid	Generator
6a-Methyl-4-pregnene-3,20-dion-17a-ol acetate	Generator
6a-Methyl-4-pregnene-3,20-dion-17a-ol acetic acid	Generator
6alpha-Methyl-4-pregnene-3,20-dion-17alpha-ol acetic acid	Generator
6Α-methyl-4-pregnene-3,20-dion-17α-ol acetate	Generator
6Α-methyl-4-pregnene-3,20-dion-17α-ol acetic acid	Generator
Depot medroxyprogesterone acetic acid	Generator
Medroxyacetic acid progesterone	Generator
Medroxyprogesterone 17-acetic acid	Generator
Medroxyprogesterone acetic acid	Generator
6-alpha-Methyl-17alpha-hydroxyprogesterone acetate	MeSH
(6 alpha)-17-(Acetoxy)-6-methylpregn-4-ene-3,20-dione	MeSH
depo Medroxyprogesterone acetate	MeSH
depo-Medroxyprogesterone acetate	MeSH
Gestapuran	MeSH
6 alpha Methyl 17alpha hydroxyprogesterone acetate	MeSH
Curretab	MeSH
Cycrin	MeSH
depo Provera	MeSH
Medroxyprogesterone 17 acetate	MeSH
Medroxyprogesterone 17-acetate, (6 alpha,17 alpha)-isomer	MeSH
Veramix	MeSH
DepoProvera	MeSH
Farlutal	MeSH
Medroxyprogesterone 17-acetate, (6 beta)-isomer	MeSH
Perlutex	MeSH

Chemical Formula

C₂₄H₃₄O₄

Average Molecular Mass

386.524 g/mol

Monoisotopic Mass

386.246 g/mol

CAS Registry Number

71-58-9

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

Traditional Name

provera

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

InChI Identifier

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

InChI Key

PSGAAPLEWMOORI-PEINSRQWSA-N

Chemical Taxonomy

Description

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

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
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid ester (CHEBI:6716 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	214.5°C
Boiling Point	Not Available
Solubility	22.2mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	3.42	ALOGPS
logP	4.13	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	17.82	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.81 m³·mol⁻¹	ChemAxon
Polarizability	44.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lu-0594000000-78579410f8f6799b400b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4l-3940000000-cf90a6f216d592e2ad4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-1339100000-e2ebb13d416a5b485ad5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002r-0449000000-c09cb0607e4a6118f05d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00dj-3940000000-2c9513d9a6a2092f5759	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-3930000000-453ace561b4dc5712e85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-009i-2947000000-2c9190ea372fd54323e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-05f1f54a7d2de1236908	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p2-0049000000-ffc7818cd479acc19cab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uy0-0390000000-9ea2dbc66c9acf4b00ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-1009000000-0f7f31209fd83cf2cddf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2019000000-f92eb379c368e053c8ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-8049000000-31808bd6c16e7dab93e3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed from GI tract

Mechanism of Toxicity

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.

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include loss of bone mineral density, BMD changes in adult women, bleeding irregularities, cancer risks, and thromboembolic disorders.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00603

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Medroxyprogesterone_acetate

Chemspider ID

Not Available

ChEBI ID

6716

PubChem Compound ID

6279

Kegg Compound ID

C08150

YMDB ID

Not Available

ECMDB ID

Not Available

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.