Norethisterone

Norethisterone

Systematic (IUPAC) name
(17β)-17-ethynyl-17-hydroxyestr-4-en-3-one; (8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a604034
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Bioavailability	64%
Protein binding	>95%
Half-life	7 hours
Identifiers
CAS number	68-22-4 Y
ATC code	G03AC01 G03DC02
PubChem	CID 6230
DrugBank	DB00717
ChemSpider	5994 Y
UNII	T18F433X4S Y
KEGG	D00182 Y
ChEBI	CHEBI:7627 Y
ChEMBL	CHEMBL1162 Y
Chemical data
Formula	C20H26O2
Mol. mass	298.419 g/mol
SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
InChI InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1 Y Key:VIKNJXKGJWUCNN-XGXHKTLJSA-N Y
Y (what is this?)  (verify)

Norethisterone (or norethindrone) (or 19-nor-17α-ethynyltestosterone) is a molecule used in some combined oral contraceptive pills, progestogen only pills and is also available as a stand-alone drug. It is a progestogen and can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with oestrogen), or to postpone a period. It is also commonly used to help prevent uterine hemorrhage in complicated non-surgical or pre-surgical gynecologic cases. Norethindrone was the first orally highly active progestin to be synthesized. It was synthesized for the first time by chemists Luis Miramontes, Carl Djerassi, and George Rosenkranz at Syntex in Mexico City in 1951. It was the progestin used in one of the first three oral contraceptives. Its related ester, norethisterone acetate, is used for the same indications.

Chemistry