NOG

13-BETA-ETHYL-17-ALPHA-ETHYNYL-17-BETA-HYDROXYGON-4-EN-3-ONE

Created:	2002-04-29
Last modified:	2021-03-01

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2 entries where NOG is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	51
Chiral Atom Count	6
Bond Count	54
Aromatic Bond Count	0

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Chemical Component Summary
Name	13-BETA-ETHYL-17-ALPHA-ETHYNYL-17-BETA-HYDROXYGON-4-EN-3-ONE
Synonyms	NORGESTREL
Systematic Name (OpenEye OEToolkits)	(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Formula	C₂₁ H₂₈ O₂
Molecular Weight	312.446
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C4C=C3C(C2CCC1(C(CCC1(C#C)O)C2CC3)CC)CC4
SMILES	CACTVS	3.341	CC[C]12CC[CH]3[CH](CCC4=CC(=O)CC[CH]34)[CH]1CC[C]2(O)C#C
SMILES	OpenEye OEToolkits	1.5.0	CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Canonical SMILES	CACTVS	3.341	CC[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	1.5.0	CC[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/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChIKey	InChI	1.03	WWYNJERNGUHSAO-XUDSTZEESA-N

Drug Info: DrugBank

DrugBank ID	DB00367 ?
Name	Levonorgestrel
Groups	approved investigational
Description	Levonorgestrel (LNG) is a synthetic progestogen similar to [Progesterone] used in contraception and hormone therapy.[A181988,T659] Also known as Plan B, it is used as a single agent in emergency contraception, and as a hormonal contraceptive released from an intrauterine device, commonly referred to as an IUD. Some of these devices are known as Jaydess, Kyleena, and Mirena. A subdermal implant of levonorgestrel that slowly releases the hormone over a long-term period is also available.[L7823] In addition to the above uses, levonorgestrel is used as a component of long-term combination contraceptives.[A181991,L7760,L7778] Globally, levonorgestrel is the most commonly used emergency contraceptive. It was initially granted FDA approval in 1982 and was the first emergency contraceptive containing only progesterone, showing high levels of efficacy and a lack of estrogenic adverse effects when compared to older emergency contraceptive regimens.[A181976,A181994,L7760]
Synonyms	13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one 18-Methyl-17-alpha-ethynyl-19-nortestosterone 17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one 17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol 13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one Levonorgestrel 17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one Levonorgestrelum d(-)-Norgestrel Lèvonorgestrel 18-Methylnorethisterone 17-Ethynyl-18-methyl-19-nortestosterone (-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one 17alpha-Ethynyl-18-homo-19-nortestosterone 13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one 17-alpha-Ethynyl-13-ethyl-19-nortestosterone
Brand Names	Opcicon One-Step Quaterna Triquilar 21 Morning After Pill Simpesse My Choice TM Contingency Levonorgestrel and Ethinyl Estradiol Joyeaux Levonorgestrel Emergency Contraceptive Julie Contingency One Portia Triquilar 28 Plan B One-Step Setlakin Triphasil 21 PostDay One-Step Backup Plan Backup Plan Onestep Tyblume Daysee Kurvelo Amethia Myzilra Aviane 21 Rivelsa Alysena 28 Laylaa 28 Alesse 28 Ithappenz Morning After Audrina 28 Levlite Camrese Levonorgetsrel and Ethinyl Estradiol SheWise Athentia Next Chateal EQ Liletta Chateal Lutera 28 Ovima 21 Delyla Esme 28 Aftera Lybrel LEADER Emergency Contraceptive Levonorgestrel Plan B Triphasil-21 Minivlar 30 BionaFem Aubra EQ EContra One-Step Norlevo Altavera Teva-levonorgestrel Marlissa Morning After Falmina Aubra Her Style React Esme 21 Quasense Lutera Jaimiess AfterPlan Aviane 28 Day Levora Emergency Contraceptive camrese Lo Levonorgestrel Tablet, 1.5 mg EContra EZ Norplant System Kit 36mg/implant Jolessa Seasonique Portia 21 Lillow Indayo Introvale Ashlyna Preventeza Levonorgestrel and Ethinyl Estradiol and Ethinyl Estradiol Levonorgestrel and Ethinyl Estradoil Preven Tablets Jaydess Min-ovral 21 New Day Vienva Kyleena Take Action Larissia Basic Care Levonorgestrel Mirena Triphasil 28 Tab Preven Emergency Contraceptive Amethyst Fayosim Levonest Lutera 21 Levonorgestrel Alysena 21 Ayuna Enpresse Econ Morning After Min-ovral 21 Tab Vienva TM Stix Restart Orsythia Skyla Sronyx Laylaa 21 Afirmelle Triphasil 21 Tab Next Choice One Dose Amethia Lo Twirla Falessa Levonorgestrel Tablets, 0.75mg Min-ovral 28 Quartette Aviane AfterPill Climara Pro Portia 28 Nordette After Banger Fem Choice morning after Seasonale Audrina 21 Next Choice Optionelle Alesse 21 Balcoltra Triphasil 28 Option 2 Her style Aviane 28 Lessina Min-ovral 28 Tab LoSeasonique Fallback Solo Empowered Choice Dolishale My Way Lo Simpesse Trivora Iclevia Ovima 28 LoJaimiess Curae
Indication	Emergency contraception Levonorgestrel, in the single-agent emergency contraceptive form, is indicated for the prevention of pregnancy after the confirmed or suspected failure of contraception methods or following unprotected intercourse. It is distributed by prescription for patients under 17, and over the counter for those above this age.[L7760] This levonorgestrel-only form of contraception is not indicated for regular contraception and must be taken as soon as possible within 72 hours after intercourse.[A181976,L7760] It has shown a lower efficacy when it is used off label within 96 hours.[T659] Long-term contraception or nonemergency contraception In addition to the above indication in emergency contraception, levonorgestrel is combined with other contraceptives in contraceptive formulations designed for regular use, for example with ethinyl estradiol.[L7766] It is used in various hormone-releasing intrauterine devices for long-term contraception ranging for a duration of 3-5 years.[L7778,L7781,L7787] Product labeling for Mirena specifically mentions that it is recommended in women who have had at least 1 child and can be indicated for the prevention of pregnancy for up to 8 years.[L7778,L42950] A subdermal implant is also available for the prevention of pregnancy for up to 5 years.[L7823] Hormone therapy and off-label uses Levonorgestrel is prescribed in combination with estradiol as hormone therapy during menopause to manage vasomotor symptoms and to prevent osteoporosis.[L7805]Off-label, levonorgestrel may be used to treat menorrhagia, endometrial hyperplasia, and endometriosis.[T659]
Categories	Adrenal Cortex Hormones Combination Contraceptives (with Estrogen and derivatives) Contraceptive Agents, Female Contraceptive Agents, Hormonal Contraceptives, Oral Contraceptives, Oral, Synthetic Contraceptives, Postcoital Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 Substrates Fused-Ring Compounds Genito Urinary System and Sex Hormones Hormonal Contraceptives for Systemic Use Hyperglycemia-Associated Agents Inhibit Ovum Fertilization Norpregnanes Norpregnenes Norsteroids Progestin Contraceptives Progestin-containing Intrauterine Device Progestins Progestogens and Estrogens, Sequential Preparations Reproductive Control Agents Sex Hormones and Modulators of the Genital System Steroids
ATC-Code	G03AB03 G03AD01 G03AC03 G03FB09 G03AA07 G03FA11
CAS number	797-63-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Progesterone receptor	MTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...	unknown	modulator
3-oxo-5-alpha-steroid 4-dehydrogenase 1	MATATGVAEERLLAALAYLQCAVGCAVFARNRQTNSVYGRHALPSHRLRV...	unknown	inhibitor
Estrogen receptor alpha	MTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...	unknown	other/unknown
Androgen receptor	MEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...	unknown	binder
Sex hormone-binding globulin	MESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...	unknown	inhibitor,binder
Glucocorticoid receptor	MDSKESLTPGREENPSSVLAQERGDVMDFYKTLRGGATVKVSASSPSLAV...	unknown	binder
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
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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