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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:19 UTC
HMDB IDHMDB14855
Secondary Accession NumbersNone
Metabolite Identification
Common NameNorethindrone
DescriptionA synthetic progestational hormone with actions similar to those of progesterone but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception. [PubChem]
Structure
Thumb
Synonyms
ValueSource
(17alpha)-17-Ethynyl-17-hydroxyestra-4,8(14),9-trien-3-oneChEBI
17-alpha-Ethynyl-17-hydroxy-4-estren-3-oneChEBI
17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-oneChEBI
17-alpha-Ethynyl-19-nortestosteroneChEBI
17-alpha-Ethynyl-4-estren-17-ol-3-oneChEBI
17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-oneChEBI
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-oneChEBI
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-oneChEBI
17alpha-Ethinyl-19-nortestosteroneChEBI
17alpha-Ethinylestra-4-en-17beta-ol-3-oneChEBI
17alpha-Ethynyl-17-hydroxy-4-estren-3-oneChEBI
17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-oneChEBI
17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-oneChEBI
17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-oneChEBI
17alpha-Ethynyl-19-nortestosteroneChEBI
17alpha-Ethynyl-4-estren-17-ol-3-oneChEBI
17beta-Hydroxy-19-norpregn-4-en-20-yn-3-oneChEBI
19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-oneChEBI
19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-oneChEBI
19-Nor-17-alpha-ethynyltestosteroneChEBI
19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-oneChEBI
19-Nor-17alpha-ethynylandrosten-17beta-ol-3-oneChEBI
19-Nor-17alpha-ethynyltestosteroneChEBI
19-Nor-ethindroneChEBI
19-NorethisteroneChEBI
4-Estren-17alpha-ethynyl-17beta-ol-3-oneChEBI
CamilaChEBI
ConludagChEBI
MicronorChEBI
MicronovumChEBI
Mini-peChEBI
Mini-pillChEBI
NorcolutChEBI
NorethindroneChEBI
NorethisteronChEBI
NorethisteronumChEBI
NoretisteronaChEBI
NoridayChEBI
NorlutenChEBI
NorlutinChEBI
Primolut-NChEBI
UtovlanChEBI
(17a)-17-Ethynyl-17-hydroxyestra-4,8(14),9-trien-3-oneGenerator
(17α)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-oneGenerator
17-a-Ethynyl-17-hydroxy-4-estren-3-oneGenerator
17-α-ethynyl-17-hydroxy-4-estren-3-oneGenerator
17-a-Ethynyl-19-norandrost-4-en-17-b-ol-3-oneGenerator
17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-oneGenerator
17-a-Ethynyl-19-nortestosteroneGenerator
17-α-ethynyl-19-nortestosteroneGenerator
17-a-Ethynyl-4-estren-17-ol-3-oneGenerator
17-α-ethynyl-4-estren-17-ol-3-oneGenerator
17-b-Hydroxy-19-norpregn-4-en-20-yn-3-oneGenerator
17-β-hydroxy-19-norpregn-4-en-20-yn-3-oneGenerator
17-Hydroxy-19-nor-17-a-pregn-4-en-20-yn-3-oneGenerator
17-Hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-oneGenerator
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-oneGenerator
17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-oneGenerator
17a-Ethinyl-19-nortestosteroneGenerator
17α-ethinyl-19-nortestosteroneGenerator
17a-Ethinylestra-4-en-17b-ol-3-oneGenerator
17α-ethinylestra-4-en-17β-ol-3-oneGenerator
17a-Ethynyl-17-hydroxy-4-estren-3-oneGenerator
17α-ethynyl-17-hydroxy-4-estren-3-oneGenerator
17a-Ethynyl-17b-hydroxy-19-norandrost-4-en-3-oneGenerator
17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-oneGenerator
17a-Ethynyl-19-nor-4-androsten-17b-ol-3-oneGenerator
17α-ethynyl-19-nor-4-androsten-17β-ol-3-oneGenerator
17a-Ethynyl-19-norandrost-4-en-17b-ol-3-oneGenerator
17α-ethynyl-19-norandrost-4-en-17β-ol-3-oneGenerator
17a-Ethynyl-19-nortestosteroneGenerator
17α-ethynyl-19-nortestosteroneGenerator
17a-Ethynyl-4-estren-17-ol-3-oneGenerator
17α-ethynyl-4-estren-17-ol-3-oneGenerator
17b-Hydroxy-19-norpregn-4-en-20-yn-3-oneGenerator
17β-hydroxy-19-norpregn-4-en-20-yn-3-oneGenerator
19-Nor-17-a-ethynyl-17-b-hydroxy-4-androsten-3-oneGenerator
19-Nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-oneGenerator
19-Nor-17-a-ethynylandrosten-17-b-ol-3-oneGenerator
19-Nor-17-α-ethynylandrosten-17-β-ol-3-oneGenerator
19-Nor-17-a-ethynyltestosteroneGenerator
19-Nor-17-α-ethynyltestosteroneGenerator
19-Nor-17a-ethynyl-17b-hydroxy-4-androsten-3-oneGenerator
19-Nor-17α-ethynyl-17β-hydroxy-4-androsten-3-oneGenerator
19-Nor-17a-ethynylandrosten-17b-ol-3-oneGenerator
19-Nor-17α-ethynylandrosten-17β-ol-3-oneGenerator
19-Nor-17a-ethynyltestosteroneGenerator
19-Nor-17α-ethynyltestosteroneGenerator
4-Estren-17a-ethynyl-17b-ol-3-oneGenerator
4-Estren-17α-ethynyl-17β-ol-3-oneGenerator
(17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-oneHMDB
17-alpha-Ethynyl-17-beta-hydroxy-4-estren-3-oneHMDB
17-Ethinyl-19-nor-testosteroneHMDB
17-Ethynyl-17-hydroxyestr-4-en-3-one (acd/name 4.0)HMDB
17-Ethynyl-17beta-hydroxyestr-4-en-3-oneHMDB
17-Ethynyl-19-nortestosteroneHMDB
17-Hydroxy-(17alpha)-19-norpregn-4-en-20-yn-3-oneHMDB
17-Hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-oneHMDB
17alpha-Ethinyl-17alpha-ethinyl-19-nortestosteroneHMDB
17alpha-Ethynyl-17-hydroxy-estr-4-en-3-oneHMDB
17alpha-Ethynyl-17-hydroxyest-4-en-3-oneHMDB
17alpha-Ethynyl-17beta-hydroxyestr-4-en-3-oneHMDB
17alpha-Ethynyl-3-oxo-4-estren-17beta-olHMDB
17alpha-Pregn-4-en-20-yn-3-oneHMDB
17beta-Hydroxy-17alpha-ethynylestr-4-en-3-oneHMDB
19-Nor-17-ethinyltestosteroneHMDB
19-NorethinyltestosteroneHMDB
AnhydrohydroxynorprogesteroneHMDB
AnovuleHMDB
ConludafHMDB
ENTHMDB
Ethinyl-19-nortestosteroneHMDB
EthinylnortestosteroneHMDB
EthynylnortestosteroneHMDB
GestestHMDB
MenzolHMDB
MicronettHMDB
MinovlarHMDB
NETHMDB
Nor-q.d.HMDB
Nor-QDHMDB
NoralutinHMDB
NoresthisteroneHMDB
NorethyndronHMDB
NorethynodroneHMDB
NorforHMDB
NorgestinHMDB
NorlutateHMDB
NorlutonHMDB
NormapauseHMDB
NorpregneninloneHMDB
NorpregneninoloneHMDB
Primolut NHMDB
ProluteasiHMDB
UtovlarHMDB
Chemical FormulaC20H26O2
Average Molecular Weight298.4192
Monoisotopic Molecular Weight298.193280076
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namenorethindrone
CAS Registry Number68-22-4
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
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
InChI KeyInChIKey=VIKNJXKGJWUCNN-XGXHKTLJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Cell signaling
  • Contraceptives, Oral, Synthetic
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Progestins
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.68e-03 g/LNot Available
LogP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0067 mg/mLALOGPS
logP2.72ALOGPS
logP3.22ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.42 m3·mol-1ChemAxon
Polarizability34.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-01rt-4950000000-fcbe8bf03b1aa103152bView in MoNA
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00717
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00717
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00717
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5994
KEGG Compound IDC05028
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorethindrone
NuGOwiki LinkHMDB14855
Metagene LinkHMDB14855
METLIN IDNot Available
PubChem Compound6230
PDB IDNDR
ChEBI ID7627
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Knox SA, Viney RC, Gu Y, Hole AR, Fiebig DG, Street DJ, Haas MR, Weisberg E, Bateson D: The effect of adverse information and positive promotion on women's preferences for prescribed contraceptive products. Soc Sci Med. 2013 Apr;83:70-80. doi: 10.1016/j.socscimed.2012.12.025. Epub 2013 Jan 5. [23351426 ]
  2. Karkar A: Pregnancy and contraceptive issues in renal transplant recipients. Saudi J Kidney Dis Transpl. 2008 Mar;19(2):165-73. [18310862 ]
  3. Debski R, Kotarski J, Paszkowski T, Pawelczyk L, Skrzypulec V, Tomaszewski J: [The statement of Polish Gynecological Society experts on oral use of contraceptive 75 microg desogestrel minipill in different clinical cases--state of art in 2008]. Ginekol Pol. 2009 Jan;80(1):63-75. [19323063 ]
  4. Rabe T, Grunwald K, Runnebaum B: [Future prospects in contraception]. Arch Gynecol Obstet. 1995;257(1-4):541-7. [8579440 ]
  5. Tscherne G: [Benefits and risks of hormonal contraception]. Gynakol Geburtshilfliche Rundsch. 1992;32(3):174-6. [1467664 ]
  6. Spornitz UM: The functional morphology of the human endometrium and decidua. Adv Anat Embryol Cell Biol. 1992;124:1-99. [1561944 ]
  7. Kovacs G: Progestogen-only pills and bleeding disturbances. Hum Reprod. 1996 Oct;11 Suppl 2:20-3. [8982741 ]
  8. Lauritzen C: [Prevention of conception in adolescence]. Ther Umsch. 1994 May;51(5):314-24. [8016756 ]
  9. Emergency contraception hot line launched. Reprod Freedom News. 1996 Feb 23;5(4):7. [12290778 ]
  10. Maximizing the use of the progestin minipill. Contracept Technol Update. 1999 Feb;20(2):19-21. [12294591 ]
  11. Dorea JG, Miazaki ES: The effects of oral contraceptive use on iron and copper concentrations in breast milk. Fertil Steril. 1999 Aug;72(2):297-301. [10438999 ]
  12. Benagiano G, Bastianelli C, Farris M: Hormonal contraception: state of the art and future perspectives. Minerva Ginecol. 2007 Jun;59(3):241-70. [17576403 ]
  13. Benagiano G, Primiero FM: Seventy-five microgram desogestrel minipill, a new perspective in estrogen-free contraception. Ann N Y Acad Sci. 2003 Nov;997:163-73. [14644823 ]
  14. Is Cerazette the minipill of choice? Drug Ther Bull. 2003 Sep;41(9):68-9. [14531209 ]
  15. Benagiano G, Bastianelli C, Farris M: Contraception today. Ann N Y Acad Sci. 2006 Dec;1092:1-32. [17308130 ]
  16. Helleday J, Siwers B, Ritzen EM, Carlstrom K: Subnormal androgen and elevated progesterone levels in women treated for congenital virilizing 21-hydroxylase deficiency. J Clin Endocrinol Metab. 1993 Apr;76(4):933-6. [8473408 ]
  17. FDA label

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:
PGR
Uniprot ID:
P06401
Molecular weight:
98980.0
References
  1. Mendoza-Rodriguez CA, Camacho-Arroyo I, Garcia GA, Cerbon MA: Variations of progesterone receptor and c-fos gene expression in the rat uterus after treatment with norethisterone and its A-ring reduced metabolites. Contraception. 1999 May;59(5):339-43. [10494488 ]
  2. Madauss KP, Deng SJ, Austin RJ, Lambert MH, McLay I, Pritchard J, Short SA, Stewart EL, Uings IJ, Williams SP: Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. [15189034 ]
  3. Garcia-Becerra R, Cooney AJ, Borja-Cacho E, Lemus AE, Perez-Palacios G, Larrea F: Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins. J Steroid Biochem Mol Biol. 2004 Jun;91(1-2):21-7. [15261304 ]
  4. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [16084894 ]
  5. Pasapera AM, Cerbon MA, Castro I, Gutierrez R, Camacho-Arroyo I, Garcia GA, Perez-Palacios G: Norethisterone metabolites modulate the uteroglobin and progesterone receptor gene expression in prepubertal rabbits. Biol Reprod. 1995 Feb;52(2):426-32. [7711211 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [15290871 ]