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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Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count6
Bond Count54
Aromatic Bond Count0
2D diagram of NOG
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Chemical Component Summary

Name13-BETA-ETHYL-17-ALPHA-ETHYNYL-17-BETA-HYDROXYGON-4-EN-3-ONE
SynonymsNORGESTREL
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
FormulaC21 H28 O2
Molecular Weight312.446
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C4C=C3C(C2CCC1(C(CCC1(C#C)O)C2CC3)CC)CC4
SMILESCACTVS3.341CC[C]12CC[CH]3[CH](CCC4=CC(=O)CC[CH]34)[CH]1CC[C]2(O)C#C
SMILESOpenEye OEToolkits1.5.0CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
Canonical SMILESCACTVS3.341 CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
Canonical SMILESOpenEye OEToolkits1.5.0 CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChIInChI1.03 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
InChIKeyInChI1.03 WWYNJERNGUHSAO-XUDSTZEESA-N

Drug Info: DrugBank

DrugBank IDDB00367 
NameLevonorgestrel
Groups
  • investigational
  • approved
DescriptionLevonorgestrel (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
  • 17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
  • d(-)-Norgestrel
  • 13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
  • Levonorgestrel
  • 17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
Brand Names
  • Enpresse
  • Jaydess
  • Seasonale
  • Aviane 21
  • Aviane 28 Day
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
ATC-Code
  • G03AB03
  • G03AD01
  • G03AC03
  • G03FB09
  • G03AA07
CAS number797-63-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Progesterone receptorMTELKAKGPRAPHVAGGPPSPEVGSPLLCRPAAGPFPGSQTSDTLPEVSA...unknownmodulator
3-oxo-5-alpha-steroid 4-dehydrogenase 1MATATGVAEERLLAALAYLQCAVGCAVFARNRQTNSVYGRHALPSHRLRV...unknowninhibitor
Estrogen receptorMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownother/unknown
Androgen receptorMEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...unknownbinder
Sex hormone-binding globulinMESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...unknowninhibitor,binder
View More
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

Related Resource References

Resource NameReference
PubChem 13109
ChEMBL CHEMBL1389
ChEBI CHEBI:6443
CCDC/CSD NORGES01, NORGES10