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

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	(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 13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one 17alpha-Ethynyl-18-homo-19-nortestosterone Levonorgestrelum 17-Ethynyl-18-methyl-19-nortestosterone 17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one 17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one (-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one 17-alpha-Ethynyl-13-ethyl-19-nortestosterone 17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol 13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one d(-)-Norgestrel Lèvonorgestrel 18-Methylnorethisterone 18-Methyl-17-alpha-ethynyl-19-nortestosterone Levonorgestrel 13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
Brand Names	Curae Lo Simpesse Optionelle Vienva Quasense Morning After Liletta React Preven Tablets Emergency Contraceptive Triquilar 21 Teva-levonorgestrel Norlevo Lybrel Levonorgestrel and Ethinyl Estradiol and Ethinyl Estradiol Triquilar 28 My Way Indayo Orsythia Tyblume Alesse 21 Kurvelo Minivlar 30 Alysena 28 Chateal EQ Backup Plan Portia Opcicon One-Step Preventeza Min-ovral 28 Tab Aviane 28 Day Ithappenz Morning After Levlite Climara Pro Min-ovral 21 Julie LoSeasonique Rivelsa After Banger Lessina Plan B My Choice TM Lutera Afirmelle Take Action Aubra Triphasil-21 Jaydess Triphasil 21 Introvale Triphasil 28 Tab Ovima 28 Levonorgestrel Tablets, 0.75mg Camrese Laylaa 28 Amazon Basic Care Levonorgestrel LEADER Emergency Contraceptive Levonorgestrel Levora Lutera 28 Nordette Seasonale Lillow Triphasil 28 Falessa New Day Levonorgestrel and Ethinyl Estradoil Levonorgestrel and Ethinyl Estradiol Balcoltra Preven Emergency Contraceptive Portia 21 Aviane 21 Seasonique Backup Plan Onestep PostDay One-Step Amethia Lo Next Choice One Dose Laylaa 21 Jaimiess Empowered Choice Econ Morning After Aviane Kyleena Setlakin Audrina 28 Norplant System Kit 36mg/implant Joyeaux Simpesse Vienva Tm Chateal EContra EZ Audrina 21 Minzoya SheWise Aftera Marlissa Twirla Fallback Solo Iclevia AfterPill Lutera 21 Enpresse Levonorgetsrel and Ethinyl Estradiol Min-ovral 21 Tab Esme 21 Triphasil 21 Tab Alysena 21 AfterPlan Sronyx Jolessa Her style Next Choice Daysee Fem Choice morning after Option 2 Delyla Levonorgestrel Ayuna camrese Lo Contingency Plan B One-Step Alesse 28 Trivora Levonorgestrel Emergency Contraceptive Mystep Quaterna Levonorgestrel Tablet, 1.5 mg Aubra EQ Dolishale Levonest Skyla Myzilra Min-ovral 28 Amethia Stix Restart Amethyst Fayosim BionaFem Contingency One Athentia Next LoJaimiess Larissia Falmina Quartette Altavera Aviane 28 Portia 28 Ashlyna EContra One-Step Esme 28 Her Style Ovima 21 Basic Care Levonorgestrel Vienva TM Morning After Pill Mirena
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

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	modulator
3-oxo-5-alpha-steroid 4-dehydrogenase 1	MATATGVAEERLLAALAYLQCAVGCAVFARNRQTNSVYGRHALPSHRLRV...	unknown	inhibitor
Estrogen receptor	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