NDR

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

Created:	2004-03-24
Last modified:	2011-06-04

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Chemical Details
Formal Charge	0
Atom Count	48
Chiral Atom Count	6
Bond Count	51
Aromatic Bond Count	0

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Chemical Component Summary
Name	(14beta,17alpha)-17-ethynyl-17-hydroxyestr-4-en-3-one
Systematic Name (OpenEye OEToolkits)	(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
Formula	C₂₀ H₂₆ O₂
Molecular Weight	298.419
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	CACTVS	3.352	C[C]12CC[CH]3[CH](CCC4=CC(=O)CC[CH]34)[CH]1CC[C]2(O)C#C
SMILES	OpenEye OEToolkits	1.6.1	CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Canonical SMILES	CACTVS	3.352	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILES	OpenEye OEToolkits	1.6.1	C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChI	InChI	1.03	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
InChIKey	InChI	1.03	VIKNJXKGJWUCNN-XGXHKTLJSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00717
Name	Norethisterone
Groups	approved investigational
Description	Norethisterone, 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-ethynyltestosterone Norethindrone 17-α-ethynyl-17-hydroxy-4-estren-3-one 17α-ethinyl-19-nortestosterone Norethisterone acetate 17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-one 17-α-ethynyl-4-estren-17-ol-3-one 19-nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one 17α-ethynyl-4-estren-17-ol-3-one 17-hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one Noretisterona 17β-hydroxy-19-norpregn-4-en-20-yn-3-one Norethisterone 19-nor-17-α-ethynylandrosten-17-β-ol-3-one 17-α-ethynyl-19-nortestosterone Norethisteron 17α-ethynyl-19-nortestosterone 17-β-hydroxy-19-norpregn-4-en-20-yn-3-one 19-nor-17-α-ethynyltestosterone 19-nor-17α-ethynylandrosten-17β-ol-3-one (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one 19-norethisterone Norethisteronum 19-nor-ethindrone Noréthistérone 17α-ethynyl-19-norandrost-4-en-17β-ol-3-one 17α-ethinylestra-4-en-17β-ol-3-one 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one 17α-ethynyl-17-hydroxy-4-estren-3-one 17α-ethynyl-19-nor-4-androsten-17β-ol-3-one 4-estren-17α-ethynyl-17β-ol-3-one
Brand Names	Hailey 1.5/30 Jencycla Aurovela 24 Fe Finzala Wera Larin 1.5/30 Norethindrone and Ethinyl Estradiol and Ferrous Fumarate Norethindrone acetate and ethinyl estradiol, and ferrous fumarate Zenchent FE Junel Fe 1/20 Norethindrone and Ethinyl Estradiol, and Ferrous Fumarate MICROGESTIN Fe 1/20 Loestrin 21 Day Norlyda Nora BE Larin Fe 1/20 Ortho Micronor Femhrt Nortrel 21 Day Estracomb Nylia 7/7/7 Zeosa Dasetta 7/7/7 Aurovela 1/20 Feirza 1/20 Microgestin Fe 1.5/30 Mimvey Ortho 0.5/35 Tablets (28 Day) Layolis Fe Xarah Fe Errin Junel FE Minastrin 24 Fe Myfembree Ortho-novum Femlyv Necon (28 Day Regimen) Loestrin 24 Fe Norlutate Nortrel 28 Day Orquidea Necon 777 777 Microgestin 24 Fe Lomedia 24 Fe Lo Minastrin Fe Minestrin 1/20 Gallifrey Brevicon 0.5/35 Tablets (21-day Pack) Brevicon Affodel Ortho-Novum 777 Gemmily Norinyl 1/50 -(21-day Regimen) CombiPatch (estradiol/norethindrone acetate transdermal system) Tri-Norinyl Nortrel (21 Day Regimen) LOESTRIN Fe 1/20 Ryeqo Micronor Tablets 28-day Jevantique Movisse Zenchent 0.4/35 Gildess 1.5/30 TARINA Fe 1/20 Lyza Junel Fe 24 Emzahh Ortho-novum 1/50 Tablets (21 Day) Tulana Vyfemla Sharobel Lopreeza Merzee Ovcon 35 LOESTRIN 1.5/30 21 Day Larin 24 Fe Luizza 1.5/30 Norethindrone and ethinyl estradiol and ferrous fumarate Camila Estalis 250/50 Mcg Nora-BE Microgestin 1/20 Norethindrone Acetate and Ethinyl Estradiol Charlotte 24Fe Gildagia Norethindrone Acetate and Ethinyl Estradiol and Ferrous Fumarate Norethindrone Acetate and Ethinyl Estradiol, and Ferrous Fumarate Nylia 1/35 Xelria Fe Nexesta Fe Tarina Fe 1/20 EQ Micronor Select 1/35 (28-day) Galbriela Blisovi Fe 1/20 Cyclafem 1/35 Brevicon 1/35 21 Tab LOESTRIN 1/20 21 Day Junel 1.5/30 Select 1/35 (21-day) Ortho 10/11 Tablets (28 Day) Ortho Novum 1/35 Ortho 7/7/7 Tablets (21 Day) Norethindrone Acetate Junel Fe 1.5/30 Fyavolv Alyacen 7/7/7 Brevicon 0.5/35 28 Tab Cyonanz Maeve Loestrin 21 1/20 AUROVELA Fe Activelle Zenchent Necon LOESTRIN Fe 1.5/30 28 Day Necon 1/35 (28 Day Regimen) Norethindrone acetate Mimvey Lo Ortho 1/35 Tablets (21 Day) Estalis Sequi Microgestin Gildess Fe 1.5/30 Ortho-novum 10/11 GENERESS Fe Necon 1/35 WYMZYA Fe Meleya Ovcon 50 Norinyl 1/50 28 Tab Junel 21 Day Jevantique Lo Tilia Fe Aurovela 1.5/30 Nortrel 7/7/7 (28 Day Regimen) Deblitane Tri-Legest Fe 28 Day Rhuzdah Melodetta 24 Fe Taytulla Amabelz Necon 10/11 Cyclafem 7/7/7 Blisovi 24 Fe Dasetta 1/35 Gildess Fe 1/20 Briellyn Brevicon 0.5/35 Tablets (28-day Pack) Larin Fe 1.5/30 Brevicon 1/35 Tablets (21-day Pack) Estalis 140/50 Mcg LOESTRIN Fe 1.5/30 Lo Loestrin Fe Norinyl 1/50 21 Tab Microgestin 1.5/30 Aygestin Hailey 24 Fe FEMCON Fe Feirza 1.5/30 Tm Gildess 1/20 Jinteli Abigale Loestrin 21 1.5/30 Estradiol / Norethindrone Acetate Taysofy Gildess 24 Fe Alyacen 1/35 Necon 0.5/35 Etyqa Microgestin Fe 1/20 Loestrin 1.5/30 HAILEY Fe 1/20 Ortho-novum 1/50 Tablets (28 Day) Luizza 1/20 Lyleq Ortho 0.5/35 Tablets (21 Day) Estradiol and Norethindrone Acetate Activelle Ld Nor QD Leena Synphasic 28 Tablets Hailey Fe 1.5/30 Norethindrone and ethinyl estradiol Jolivette Oriahnn Ortho 1/35 Tablets (28 Day) Abigale Lo LOESTRIN Fe 1/20 28 Day Norlyroc Brevicon 1/35 Tablets (28-day Pack) Modicon ESTROSTEP Fe Norethindrone Larin 1/20 Incassia Ortho 7/7/7 Tablets (28 Day) Activella Philith Loestrin Fe 28 Day Brevicon 0.5/35 21 Tab Mibelas 24 Fe Heather Kaitlib Fe Wymzya Fe Junel Fe 28 Day CombiPatch Brevicon 1/35 28 Tab Synphasic-28 Tablets Balziva Ortho Novum 135 Synphasic 21 Tablets Tarina 24 Fe Lolo MICROGESTIN Fe 1.5/30 Blisovi Fe 1.5/30 Ortho 10/11 Tablets (21 Day) Microgestin Fe Norinyl 1/50 -(28-day Regimen) Aranelle Necon 777 Pirmella 7/7/7 Oshih Aurovela Fe 1/20 Norinyl Lupaneta Pack Pirmella 1/35 Generess
Indication	Norethisterone 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 Contraceptives, Oral Contraceptives, Oral, Hormonal Contraceptives, Oral, Synthetic Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2A6 Substrates Cytochrome P-450 CYP2C19 Inducers Cytochrome P-450 CYP2C19 Inducers (strength unknown) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Substrates Estren Derivatives Fused-Ring Compounds Genito Urinary System and Sex Hormones Hormonal Contraceptives for Systemic Use Hyperglycemia-Associated Agents Hypothalamic Hormones Norpregnenes Norsteroids P-glycoprotein inhibitors Pituitary and Hypothalamic Hormones and Analogues Progestin Contraceptives Progestins Progestogens and Estrogens, Sequential Preparations Reproductive Control Agents Sex Hormones and Modulators of the Genital System Steroids Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
ATC-Code	H01CC53 H01CC54 G03AA05 G03DC02 G03AB04 G03AC01 G03FA01 G03FB05
CAS number	68-22-4

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Progesterone receptor	MTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...	unknown	agonist
Androgen receptor	MEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...	unknown	agonist
Glucocorticoid receptor	MDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...	unknown	agonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Aldo-keto reductase family 1 member C4	MDPKYQRVELNDGHFMPVLGFGTYAPPEVPRNRAVEVTKLAIEAGFRHID...	unknown	substrate
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	MGWSCLVTGAGGLLGQRIVRLLVEEKELKEIRALDKAFRPELREEFSKLQ...	unknown	substrate
3-oxo-5-alpha-steroid 4-dehydrogenase	MATATGVAEERLLAALAYLQCAVGCAVFARNRQTNSVYGRHALPSHRLRV...	unknown	substrate
Aldo-keto reductase family 1 member D1	MDLSAASHRIPLSDGNSIPIIGLGTYSEPKSTPKGACATSVKVAIDTGYR...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inducer
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2A6	MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...	unknown	substrate
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
Sex hormone-binding globulin	MESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...	unknown	substrate
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
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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