Norelgestromin

Norelgestromin
Clinical data

Trade names	Evra, Ortho Evra
AHFS/Drugs.com	International Drug Names
MedlinePlus	a602006
Routes of administration	Transdermal patch
ATC code	G03AA13 (WHO) (only combinations with estrogens)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Synonyms	Norelgestromine; Levonorgestrel 3-oxime; 17β-Deacetylnorgestimate; 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime
CAS Number	53016-31-2^N
PubChem CID	62930
DrugBank	DB06713^Y
ChemSpider	56648^Y
UNII	R0TAY3X631
KEGG	D05205^Y
ChEBI	CHEBI:111762^N
ChEMBL	CHEMBL1200807^N
Chemical and physical data
Formula	C₂₁H₂₉NO₂
Molar mass	327.461 g/mol
3D model (JSmol)	Interactive image
SMILES ON=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
InChI InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1^Y Key:ISHXLNHNDMZNMC-XUDSTZEESA-N^Y
^NY (what is this?)

Norelgestromin, or norelgestromine, is a progestin which is used in the contraceptive patches Evra and Ortho Evra, in combination with the estrogen ethinylestradiol.

Norelgestromin is a progestogen. It is one of the active metabolites of norgestimate. Unlike many related progestins, norelgestromin has negligible androgenic activity.

Norelgestromin, also known as 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime or as 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime, is a synthetic estrane steroid and a derivative of testosterone. It is a racemic mixture of E and Z isomers, which have approximately the same activity. Norelgestromin is more specifically a derivative of norethisterone (17α-ethynyl-19-nortestosterone) and is a member of the gonane (18-methylestrane) subgroup of the 19-nortestosterone family of progestins. It is the C3 oxime derivative of levonorgestrel and the C17β deacetyl derivative of norgestimate and is also known as levonorgestrel 3-oxime and as 17β-deacetylnorgestimate.

Norelgestromin was introduced in 2002.

Norelgestromin is the generic name of the drug and its INN, USAN, and BAN.

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