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