NDR

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

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

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2 entries where NDR is found as a standalone ligand

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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
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	17α-ethynyl-17-hydroxy-4-estren-3-one 19-nor-17-α-ethynyltestosterone 17-α-ethynyl-4-estren-17-ol-3-one 19-nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one 17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-one 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one Norethisteronum 17-α-ethynyl-17-hydroxy-4-estren-3-one 17-α-ethynyl-19-nortestosterone Norethisterone 19-nor-17-α-ethynylandrosten-17-β-ol-3-one 19-nor-ethindrone Noréthistérone 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one 19-nor-17α-ethynyltestosterone 17-hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one 19-nor-17α-ethynylandrosten-17β-ol-3-one Noretisterona 17α-ethynyl-19-nor-4-androsten-17β-ol-3-one Norethindrone 17α-ethynyl-19-nortestosterone (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one 17α-ethynyl-19-norandrost-4-en-17β-ol-3-one 4-estren-17α-ethynyl-17β-ol-3-one Norethisterone acetate Norethisteron 17α-ethinylestra-4-en-17β-ol-3-one 17-β-hydroxy-19-norpregn-4-en-20-yn-3-one 17β-hydroxy-19-norpregn-4-en-20-yn-3-one 17α-ethynyl-4-estren-17-ol-3-one 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one 19-norethisterone 17α-ethinyl-19-nortestosterone 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one
Brand Names	Mimvey Lo Heather Estalis Sequi LOESTRIN Fe 1/20 28 Day Rhuzdah Brevicon 0.5/35 28 Tab Gildess 24 Fe Emzahh Junel Fe 1/20 Necon Affodel Nortrel (21 Day Regimen) Zenchent FE Activelle Ld Aygestin Ortho-novum 10/11 Norethindrone and Ethinyl Estradiol and Ferrous Fumarate Jinteli Nylia 7/7/7 Blisovi Fe 1.5/30 Ortho Novum 1/35 Gildess 1.5/30 Norinyl Amabelz Femhrt HAILEY Fe 1/20 Junel FE Necon 10/11 CombiPatch (estradiol/norethindrone acetate transdermal system) Zenchent 0.4/35 Ortho 0.5/35 Tablets (28 Day) Larin 1/20 LOESTRIN 1/20 21 Day Lyleq LOESTRIN Fe 1/20 Lolo Select 1/35 (28-day) Brevicon 0.5/35 Tablets (21-day Pack) Errin Norinyl 1/50 -(28-day Regimen) Micronor Tablets 28-day Tarina Fe 1/20 EQ Brevicon Nor QD Mibelas 24 Fe Blisovi 24 Fe Synphasic-28 Tablets Gildess Fe 1/20 Dasetta 7/7/7 Larin Fe 1/20 GENERESS Fe Estalis 250/50 Mcg Brevicon 1/35 28 Tab Wymzya Fe Blisovi Fe 1/20 Sharobel Norinyl 1/50 21 Tab Jolivette Ortho 7/7/7 Tablets (21 Day) Ortho 1/35 Tablets (28 Day) Norethindrone Acetate and Ethinyl Estradiol and Ferrous Fumarate Jencycla Jevantique Lo Norethindrone Ortho-novum Microgestin 24 Fe Ortho 10/11 Tablets (21 Day) Larin Fe 1.5/30 Ryeqo Fyavolv Junel 21 Day Pirmella 7/7/7 Necon 1/35 (28 Day Regimen) Brevicon 0.5/35 Tablets (28-day Pack) Ortho Novum 135 Tulana Aranelle Taysofy Norethindrone acetate CombiPatch Vyfemla Norethindrone and ethinyl estradiol and ferrous fumarate Norlyda Nortrel 21 Day Estracomb Alyacen 1/35 Activella Norinyl 1/50 -(21-day Regimen) Melodetta 24 Fe Larin 1.5/30 Briellyn Norlutate Brevicon 0.5/35 21 Tab TARINA Fe 1/20 Junel Fe 1.5/30 Necon (28 Day Regimen) Cyclafem 7/7/7 Estradiol and Norethindrone Acetate LOESTRIN Fe 1.5/30 Ortho 1/35 Tablets (21 Day) Etyqa LOESTRIN Fe 1.5/30 28 Day Dasetta 1/35 Myfembree Wera Zenchent Lupaneta Pack Estalis 140/50 Mcg Pirmella 1/35 Cyonanz Layolis Fe Leena Lyza Tri-Legest Fe 28 Day Microgestin Fe Junel Fe 28 Day Brevicon 1/35 Tablets (28-day Pack) Ortho 10/11 Tablets (28 Day) Aurovela Fe 1/20 Norethindrone acetate and ethinyl estradiol, and ferrous fumarate Junel Fe 24 Norinyl 1/50 28 Tab Lopreeza Norethindrone Acetate and Ethinyl Estradiol, and Ferrous Fumarate Jevantique Loestrin 1.5/30 Aurovela 1/20 Ortho-Novum 777 Microgestin Fe 1/20 Necon 0.5/35 Nora BE Deblitane Ortho-novum 1/50 Tablets (21 Day) Finzala Minastrin 24 Fe Nortrel 7/7/7 (28 Day Regimen) Necon 777 Aurovela 1.5/30 Norethindrone Acetate and Ethinyl Estradiol Select 1/35 (21-day) Synphasic 28 Tablets Hailey 24 Fe Hailey Fe 1.5/30 Modicon Lo Minastrin Fe Tri-Norinyl Necon 777 777 Aurovela 24 Fe ESTROSTEP Fe Estradiol / Norethindrone Acetate Femlyv MICROGESTIN Fe 1/20 Norethindrone Acetate Incassia Tarina 24 Fe Ovcon 35 Alyacen 7/7/7 Merzee Mimvey Zeosa Nora-BE Lomedia 24 Fe Microgestin 1.5/30 Ortho 7/7/7 Tablets (28 Day) Loestrin 21 1.5/30 Brevicon 1/35 Tablets (21-day Pack) Camila FEMCON Fe Microgestin 1/20 Minestrin 1/20 Norethindrone and Ethinyl Estradiol, and Ferrous Fumarate Larin 24 Fe Oriahnn Maeve Taytulla Balziva Norethindrone and ethinyl estradiol Brevicon 1/35 21 Tab Gallifrey Activelle Nortrel 28 Day Loestrin Fe 28 Day Movisse AUROVELA Fe Philith Loestrin 24 Fe Microgestin Necon 1/35 Loestrin 21 Day Oshih Lo Loestrin Fe Gildagia LOESTRIN 1.5/30 21 Day Nexesta Fe Hailey 1.5/30 Synphasic 21 Tablets Ortho Micronor MICROGESTIN Fe 1.5/30 Gildess 1/20 Generess Microgestin Fe 1.5/30 Nylia 1/35 Ortho-novum 1/50 Tablets (28 Day) Charlotte 24Fe Ovcon 50 Tilia Fe Gemmily Kaitlib Fe Ortho 0.5/35 Tablets (21 Day) WYMZYA Fe Loestrin 21 1/20 Micronor Gildess Fe 1.5/30 Cyclafem 1/35 Junel 1.5/30 Norlyroc
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