Medroxyprogesterone acetate

Medroxyprogesterone acetate

Clinical data
Trade names	Provera, Depo-Provera, Depo-SubQ Provera 104, Curretab, Cycrin, Farlutal, Gestapuran, Perlutex, Veramix, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604039
Pregnancy category	US: X (Contraindicated)
Routes of administration	by mouth, intramuscular, subcutaneous
ATC code	G03AC06 (WHO) G03DA02 (WHO), L02AB02 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	99%
Protein binding	88% (to albumin)
Biological half-life	By mouth: 12–33 hours I.M.: ~50 days S.C.: ~40 days
Identifiers
IUPAC name [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
Synonyms	NSC-26386
CAS Number	71-58-9
PubChem (CID)	6279
IUPHAR/BPS	2879
DrugBank	DB00603
ChemSpider	6043
UNII	C2QI4IOI2G
KEGG	C08150 Y
ChEBI	CHEBI:6716
ChEMBL	CHEMBL717 Y
ECHA InfoCard	100.000.689
Chemical and physical data
Formula	C24H34O4
Molar mass	386.52 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C
InChI 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 Key:PSGAAPLEWMOORI-PEINSRQWSA-N

Medroxyprogesterone acetate by injection
Background
Type	Hormonal
First use	?
Failure rates (first year)
Perfect use	0.2%
Typical use	6%
Usage
Duration effect	3 months (12–14 weeks)
Reversibility	3–18 months
User reminders	Maximum interval is just under 3 months
Advantages and disadvantages
STI protection	No
Period disadvantages	Especially in first injection may be frequent spotting
Period advantages	Usually no periods from 2nd injection
Benefits	Especially good if poor pill compliance. Reduced endometrial cancer risk.
Risks	Reduced bone density, which may reverse after discontinuation
Medical notes
For those intending to start family, suggest switch 6 months prior to alternative method (e.g. POP) allowing more reliable return fertility.

Medroxyprogesterone acetate (MPA), sold under the brand name Depo-Provera among others, is a manufactured hormone of the progestin type. It is used as birth control and as part of hormone replacement therapy for menopausal symptoms. It is also used to treat endometriosis, abnormal uterine bleeding, abnormal sexuality in males, and certain types of cancer. It is used by mouth or injection into a muscle or under the skin

Common side effects include no periods, abdominal pain, headaches, and anxiety. Other serious side effects include bone loss, blood clots, allergic reactions, depression, and liver problems. Use is not recommended during pregnancy as it may harm the baby. It works by decreasing the body's release of gonadotropins.

Medroxyprogesterone acetate was patented and came into medical use in 1958. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.59 to 1.57 USD per vial. In the United Kingdom this dose costs the NHS about 6.01 pounds. In the United States it costs less than 25 USD a dose as of 2015.