| Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type. It is used as a method of birth control and as a part of menopausal hormone therapy. It is also used to treat endometriosis, abnormal uterine bleeding, paraphilia, and certain types of cancer. The medication is available both alone and in combination with an estrogen. It is taken by mouth, used under the tongue, or by injection into a muscle or fat.
Common side effects include menstrual disturbances such as absence of periods, abdominal pain, and headaches. More serious side effects include bone loss, blood clots, allergic reactions, and liver problems. Use is not recommended during pregnancy as it may harm the baby. MPA is an artificial progestogen, and as such activates the progesterone receptor, the biological target of progesterone. It also has androgenic activity and weak glucocorticoid activity. Due to its progestogenic activity, MPA decreases the body's release of gonadotropins and can suppress sex hormone levels. It works as a form of birth control by preventing ovulation.
MPA was discovered in 1956 and was introduced for medical use in the United States in 1959. It is on the World Health Organization's List of Essential Medicines. MPA is the most widely used progestin in menopausal hormone therapy and in progestogen-only birth control. DMPA is approved for use as a form of long-acting birth control in more than 100 countries. In 2022, it was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions. |
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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 |
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| C1[C@]2([C@]3([C@@]([C@@]4(C(=CC(CC4)=O)[C@H](C3)C)C)(CC[C@@]2([C@@](C1)(OC(C)=O)C(=O)C)C)[H])[H])[H] |
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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progestin
A synthetic progestogen.
androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
inhibitor
A substance that diminishes the rate of a chemical reaction.
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female contraceptive drug
A chemical substance or agent with contraceptive activity in females.
synthetic oral contraceptive
An oral contraceptive which owes its effectiveness to synthetic preparation.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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View more via ChEBI Ontology
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(6α)-6-methyl-3,20-dioxopregn-4-en-17-yl acetate
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(6α)-17-(Acetyloxy)-6-methylpreg-4-ene-3,20-dione
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ChemIDplus
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17-Acetoxy-6α-methylprogesterone
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ChemIDplus
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17α-Hydroxy-6α-methylprogesterone acetate
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ChemIDplus
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6-alpha-Methyl-17-alpha-acetoxyprogesterone
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KEGG COMPOUND
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6-alpha-Methyl-17-alpha-hydroxyprogesterone acetate
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KEGG COMPOUND
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6α-Methyl-17-acetoxy progesterone
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ChemIDplus
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6α-Methyl-17α-hydroxyprogesterone acetate
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ChemIDplus
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6α-Methyl-4-pregnene-3,20-dion-17α-ol acetate
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ChemIDplus
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CBP-1011
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ChEBI
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depot medroxyprogesterone acetate
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ChEBI
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DMPA
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ChEBI
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MAP
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ChEBI
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Medroxyacetate progesterone
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ChemIDplus
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Medroxyprogesterone 17-acetate
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ChemIDplus
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Medroxyprogesterone acetate
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KEGG COMPOUND
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Methylacetoxyprogesterone
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ChemIDplus
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Metigestrona
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ChemIDplus
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MPA
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ChEBI
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2066112
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Beilstein Registry Number
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Beilstein
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71-58-9
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CAS Registry Number
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ChemIDplus
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