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