NDR

(14beta,17alpha)-17-ethynyl-17-hydroxyestr-4-en-3-one


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Chemical Component Summary

Name(14beta,17alpha)-17-ethynyl-17-hydroxyestr-4-en-3-one
Identifiers(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
FormulaC20 H26 O2
Molecular Weight298.419
TypeNON-POLYMER
Isomeric SMILESC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChIInChI=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
InChIKeyVIKNJXKGJWUCNN-XGXHKTLJSA-N

Chemical Details

Formal Charge0
Atom Count48
Chiral Atom Count6
Bond Count51
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00717 
NameNorethisterone
Groups approved
DescriptionNorethisterone, also known as norethindrone, is a synthetic progestational hormone belonging to the 19-nortestosterone-derived class of progestins.[A10367] It is further classified as a second-generation progestin, along with [levonorgestrel] and its derivatives, and is the active form of several other progestins including [norethynodrel] and [lynestrenol].[A10367] Norethisterone mimics the actions of endogenous [progesterone], albeit with a greater potency,[A188075] and is used on its own or in combination with estrogen derivatives in a variety of applications including contraception and hormone replacement therapy.[L9527,L10301,L10304,L10307] First derived in 1951 in Mexico City, norethisterone was originally intended for use as a remedy for irregular menstruation and endometriosis, and was not marketed for use as an oral contraceptive until 1962.[L10439]
Synonyms
  • 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one
  • Noretisterona
  • 19-nor-17α-ethynylandrosten-17β-ol-3-one
  • 17-α-ethynyl-17-hydroxy-4-estren-3-one
  • 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one
Brand Names
  • Larin Fe 1.5/30
  • Gildess 1/20
  • Hailey Fe 1.5/30
  • Oriahnn
  • Microgestin 24 Fe
IndicationNorethisterone is indicated as an oral contraceptive when given as monotherapy[L9527] or in combination with an estrogen component, such as [ethinylestradiol] or [estradiol].[L10313,L10307] In combination with an estrogen component, oral norethisterone is also indicated as a hormone replacement therapy in the treatment of postmenopausal osteoporosis and moderate-to-severe vasomotor symptoms arising from menopause.[L10304] When applied via transdermal patch, the combination of norethisterone and estradiol is indicated for the treatment of hypoestrogenism, vulvovaginal atrophy, and moderate-severe vasomotor symptoms.[L10301] Norethisterone, taken in combination with intramuscular [leuprolide], is also indicated for the symptomatic treatment of endometriosis-related pain.[L10310]
Categories
  • Adrenal Cortex Hormones
  • Anti-Gonadotropin-Releasing Hormones
  • Combination Contraceptives (with Estrogen and derivatives)
  • Contraceptive Agents, Female
  • Contraceptive Agents, Hormonal
ATC-Code
  • H01CC53
  • H01CC54
  • G03AA05
  • G03DC02
  • G03AB04
CAS number68-22-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Progesterone receptorMTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...unknownagonist
Androgen receptorMEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...unknownagonist
Glucocorticoid receptorMDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...unknownagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Aldo-keto reductase family 1 member C4MDPKYQRVELNDGHFMPVLGFGTYAPPEVPRNRAVEVTKLAIEAGFRHID...unknownsubstrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1162
PubChem 6230
ChEMBL CHEMBL1162
ChEBI CHEBI:7627
CCDC/CSD NETIND, NETIND01