Progesterone (medication)

Progesterone

Clinical data
Trade names	Prometrium, Utrogestan, Endometrin, Crinone, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604017
Pregnancy category	B (US)
Routes of administration	• By mouth (capsule) • Vaginal (gel, insert) • Topical (cream, gel) • I.M. injection (oil solution) • S.C. injection (aq. soln.)
ATC code	G03DA04 (WHO)
Pharmacokinetic data
Bioavailability	OMP: <10%
Protein binding	• Albumin: 80% • CBG: 18% • SHBG: <1% • Free: 1–2%
Metabolism	Mainly hepatic: • 5α- and 5β-reductase • 3α- and 3β-HSD • 20α- and 20β-HSD • Conjugation • 17α-Hydroxylase • 21-Hydroxylase • (e.g., CYP3A4)
Metabolites	• Dihydroprogesterones • • Pregnanediols • 20α-Hydroxyprogesterone • 17α-Hydroxyprogesterone • Pregnanetriols • 11-Deoxycorticosterone (And glucuronide/sulfate conjugates)
Biological half-life	• Oral: 16–18 hours • Vaginal: 25–50 hours • Topical: 30–40 hours • I.M.: 20–28 hours • S.C.: 13–18 hours
Excretion	Bile and urine
Identifiers
IUPAC name (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms	Pregn-4-ene-3,20-dione
CAS Number	57-83-0 Y
PubChem CID	5994
IUPHAR/BPS	2377
DrugBank	DB00396 Y
ChemSpider	5773 Y
UNII	4G7DS2Q64Y
KEGG	C00410 N
ChEBI	CHEBI:17026 Y
ChEMBL	CHEMBL103 Y
Chemical and physical data
Formula	C21H30O2
Molar mass	314.46 g/mol
3D model (Jmol)	Interactive image
Specific rotation	[α]D
Melting point	126 °C (259 °F)
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI InChI=InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 N Key:RJKFOVLPORLFTN-LEKSSAKUSA-N Y
NY (what is this?)

Progesterone is a medication and naturally occurring steroid hormone. It is a progestogen and neurosteroid and is used mainly in hormone replacement therapy (HRT) for menopause,hypogonadism, and transgender women. Progesterone can be taken by mouth, in through the vagina, and by injection into muscle or fat, among other routes. A progesterone vaginal ring form used for birth control also exists in some areas of the world.

Progesterone was first isolated in pure form in 1934. It first became available as a medication later that year. Oral micronized progesterone (OMP), which first allowed progesterone to be taken by mouth, was introduced in 1980. A large number of manufactured progestogens, or progestins, have been derived from progesterone and are used as medications as well. Examples include medroxyprogesterone acetate and norethisterone.

The use of progesterone and its analogues have many medical applications, both to address acute situations and to address the long-term decline of natural progesterone levels. Because of the poor bioavailability of progesterone when taken by mouth, many synthetic progestins have been designed with improved bioavailability by mouth and have been used long before progesterone formulations became available.

Progesterone is used in combination with estrogen as a component of HRT for menopausal symptoms.