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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014855
Secondary Accession Numbers
  • HMDB14855
Metabolite Identification
Common NameNorethindrone
DescriptionNorethindrone, also known as 19-norethisterone or camila, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, norethindrone is considered to be a steroid lipid molecule. Norethindrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Norethindrone is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
Data?1582753228
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
NorethisteronChEBI
NorethisteronumChEBI
NoretisteronaChEBI
NoridayChEBI
NorlutenChEBI
NorlutinChEBI
Primolut-NChEBI
UtovlanChEBI
NorethisteroneKegg
(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
ConceplanHMDB
Nor QDHMDB
Norethindrone, (1 beta)-isomerHMDB
NorcoluteHMDB
MonogestHMDB
NorQDHMDB
NorethindroneChEBI
Chemical FormulaC20H26O2
Average Molecular Weight298.4192
Monoisotopic Molecular Weight298.193280076
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
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 KeyVIKNJXKGJWUCNN-XGXHKTLJSA-N
Chemical Taxonomy
Description 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
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0067 g/LNot Available
LogP3.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available174.376http://allccs.zhulab.cn/database/detail?ID=AllCCS00001173
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP2.72ALOGPS
logP3.22ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.42 m³·mol⁻¹ChemAxon
Polarizability34.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.00431661259
DarkChem[M-H]-169.75931661259
DeepCCS[M-2H]-207.58130932474
DeepCCS[M+Na]+181.79730932474
AllCCS[M+H]+175.832859911
AllCCS[M+H-H2O]+172.732859911
AllCCS[M+NH4]+178.732859911
AllCCS[M+Na]+179.532859911
AllCCS[M-H]-182.232859911
AllCCS[M+Na-2H]-182.232859911
AllCCS[M+HCOO]-182.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Norethindrone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]3732.9Standard polar33892256
Norethindrone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2625.2Standard non polar33892256
Norethindrone[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2691.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norethindrone,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C2782.7Semi standard non polar33892256
Norethindrone,1TMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C2645.4Semi standard non polar33892256
Norethindrone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C2746.8Semi standard non polar33892256
Norethindrone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C2814.7Standard non polar33892256
Norethindrone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C3117.4Standard polar33892256
Norethindrone,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C3046.0Semi standard non polar33892256
Norethindrone,1TBDMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C2926.7Semi standard non polar33892256
Norethindrone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C3263.0Semi standard non polar33892256
Norethindrone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C3286.2Standard non polar33892256
Norethindrone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C3312.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norethindrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00w9-0690000000-7050c3192b843aecc4822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norethindrone GC-MS (1 TMS) - 70eV, Positivesplash10-052f-1369000000-cfce41c0dca4a0c3cd9c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norethindrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01rt-4950000000-fcbe8bf03b1aa103152b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-qTof , Positive-QTOFsplash10-0002-0391000000-ae51cc90bb8f2161f1492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-qTof , Positive-QTOFsplash10-0j59-2494000000-76c71f96c07e87ef89622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOFsplash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOFsplash10-0a5c-3900000000-4b2a5d95e4b6d50f16fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOFsplash10-00ea-0790000000-60d1a1a37c0ba98d6a4a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOFsplash10-00e9-0890000000-5d3b8210450a1c43b1192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone , positive-QTOFsplash10-0002-0391000000-ae51cc90bb8f2161f1492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone , positive-QTOFsplash10-0ar0-3920000000-e31fa7c9e871f2e398462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 30V, Positive-QTOFsplash10-001j-0930000000-9c2fc72a1b360913fb562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 40V, Positive-QTOFsplash10-005c-0910000000-ef775abfdf43d67a42252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 80V, Positive-QTOFsplash10-0a5c-3900000000-11a6390c5bc5438291352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 20V, Positive-QTOFsplash10-0002-0391000000-7b2e411df9eccc111c8e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 10V, Positive-QTOFsplash10-0002-0091000000-3a83c5fc59fdaea612312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 55V, Positive-QTOFsplash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 35V, Positive-QTOFsplash10-00ea-0790000000-1844e6f664d23868bbab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 50V, Positive-QTOFsplash10-004l-0900000000-623cab7c657eda4d2f5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 15V, Positive-QTOFsplash10-0002-0090000000-412f7f0b9259fe7593722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 55V, Positive-QTOFsplash10-00e9-0890000000-d8c560fa1ac40e4ba22f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norethindrone 45V, Positive-QTOFsplash10-0a59-2910000000-7b16e32a71f6c1df6d1e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 10V, Positive-QTOFsplash10-0002-0090000000-ec79e2d15a020c198dde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 20V, Positive-QTOFsplash10-001m-0290000000-b8f5efd6d7713f50f65c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 40V, Positive-QTOFsplash10-0l5l-2980000000-14cb82df2a3c251f955e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 10V, Negative-QTOFsplash10-0002-0090000000-eab48ea9142da299d9232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 20V, Negative-QTOFsplash10-0002-0090000000-64471e6cc8b0f3e495b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norethindrone 40V, Negative-QTOFsplash10-00l6-0090000000-ccad820f0e5b5559e8e82016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00717 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00717 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00717
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5994
KEGG Compound IDC05028
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorethisterone
METLIN IDNot Available
PubChem Compound6230
PDB IDNot Available
ChEBI ID7627
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed:23351426 ]
  2. Karkar A: Pregnancy and contraceptive issues in renal transplant recipients. Saudi J Kidney Dis Transpl. 2008 Mar;19(2):165-73. [PubMed: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. [PubMed:19323063 ]
  4. Rabe T, Grunwald K, Runnebaum B: [Future prospects in contraception]. Arch Gynecol Obstet. 1995;257(1-4):541-7. [PubMed:8579440 ]
  5. Tscherne G: [Benefits and risks of hormonal contraception]. Gynakol Geburtshilfliche Rundsch. 1992;32(3):174-6. [PubMed:1467664 ]
  6. Spornitz UM: The functional morphology of the human endometrium and decidua. Adv Anat Embryol Cell Biol. 1992;124:1-99. [PubMed:1561944 ]
  7. Kovacs G: Progestogen-only pills and bleeding disturbances. Hum Reprod. 1996 Oct;11 Suppl 2:20-3. [PubMed:8982741 ]
  8. Lauritzen C: [Prevention of conception in adolescence]. Ther Umsch. 1994 May;51(5):314-24. [PubMed:8016756 ]
  9. Authors unspecified: Emergency contraception hot line launched. Reprod Freedom News. 1996 Feb 23;5(4):7. [PubMed:12290778 ]
  10. Authors unspecified: Maximizing the use of the progestin minipill. Contracept Technol Update. 1999 Feb;20(2):19-21. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:14644823 ]
  14. Authors unspecified: Is Cerazette the minipill of choice? Drug Ther Bull. 2003 Sep;41(9):68-9. [PubMed:14531209 ]
  15. Benagiano G, Bastianelli C, Farris M: Contraception today. Ann N Y Acad Sci. 2006 Dec;1092:1-32. [PubMed: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. [PubMed:8473408 ]
  17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  18. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  19. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  20. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  21. (). FDA label . .
  22. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:7711211 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. [PubMed:15290871 ]