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Identification
NameNorethisterone
Accession NumberDB00717  (APRD00679)
TypeSmall Molecule
GroupsApproved
Description

Norethisterone (INN, BAN), also known as Norethindrone (USAN), is a 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.

Structure
Thumb
Synonyms
(17alpha)-17-Ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one
17-alpha-Ethynyl-17-hydroxy-4-estren-3-one
17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one
17-alpha-Ethynyl-19-nortestosterone
17-alpha-Ethynyl-4-estren-17-ol-3-one
17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one
17alpha-Ethinyl-19-nortestosterone
17alpha-Ethinylestra-4-en-17beta-ol-3-one
17alpha-Ethynyl-17-hydroxy-4-estren-3-one
17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one
17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one
17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one
17alpha-Ethynyl-19-nortestosterone
17alpha-Ethynyl-4-estren-17-ol-3-one
17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
17α-ethinyl-19-nortestosterone
19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one
19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one
19-Nor-17-alpha-ethynyltestosterone
19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
19-Nor-17alpha-ethynylandrosten-17beta-ol-3-one
19-Nor-17alpha-ethynyltestosterone
19-nor-17α-ethynyltestosterone
19-Nor-ethindrone
19-Norethisterone
4-Estren-17alpha-ethynyl-17beta-ol-3-one
Norethindrone
Norethisteron
Norethisteronum
Noretisterona
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jencyclatablet0.35 mgoralLupin Pharma Canada Limited2015-09-14Not applicableCanada
Jolivettetablet.35 mg/1oralActavis Pharma, Inc.2003-03-01Not applicableUs
Micronortablet.35 mg/1oralPhysicians Total Care, Inc.2003-09-17Not applicableUs
Micronor Tablets 28-daytablet0.35 mgoralJanssen Inc1972-12-31Not applicableCanada
Movissetablet0.35 mgoralMylan Pharmaceuticals Ulc2015-06-30Not applicableCanada
Nor Qdtablet.35 mg/1oralWatson Pharma, Inc.1973-01-02Not applicableUs
Nora Betablet.35 mg/1oralWatson Pharma, Inc.2005-05-12Not applicableUs
Norlutatetablet5 mgoralErfa Canada 2012 Inc1961-12-31Not applicableCanada
Ortho Micronortablet.35 mg/1oralJanssen Pharmaceuticals, Inc.1973-01-02Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aygestintablet5 mg/1oralTeva Women's Health, Inc.2003-06-12Not applicableUs
Camilatablet.35 mg/1oralTeva Pharmaceuticals USA Inc2002-10-30Not applicableUs
Camilatablet.35 mg/1oralPhysicians Total Care, Inc.2003-06-19Not applicableUs
DeblitanekitNorthstar Rx LLC2014-06-01Not applicableUs
Errintablet.35 mg/1oralBarr Laboratories Inc.2003-01-08Not applicableUs
Heathertablet.35 mg/1oralA S Medication Solutions2010-04-23Not applicableUs
Heathertablet.35 mg/1oralGlenmark Pharmaceuticals Inc., Usa2010-04-23Not applicableUs
Jencyclatablet.35 mg/1oralLupin Pharmaceuticals, Inc.2013-05-08Not applicableUs
Jencyclatablet.35 mg/1oralLUPIN LIMITED2013-05-08Not applicableUs
Lyzatablet.35 mg/1oralAfaxys Inc.2013-06-24Not applicableUs
Norethindronetablet.35 mg/1oralLupin Pharmaceuticals, Inc.2011-11-10Not applicableUs
NorethindronekitNorthstar Rx LLC2013-09-10Not applicableUs
Norethindronetablet.35 mg/1oralCentral Texas Community Health Centers2013-07-12Not applicableUs
NorethindronekitNorthstar Rx LLC2013-09-07Not applicableUs
Norethindronetablet.35 mg/1oralGlenmark Pharmaceuticals Inc., Usa2010-11-03Not applicableUs
Norethindronetablet.35 mg/1oralMylan Pharmaceuticals Inc.2013-07-12Not applicableUs
Norethindronetablet.35 mg/1oralMylan Pharmaceuticals Inc.2013-06-24Not applicableUs
Norethindrone Acetatetablet5 mg/1oralKAISER FOUNDATION HOSPITALS2015-02-19Not applicableUs
Norethindrone Acetatetablet5 mg/1oralAmneal Pharmaceuticals of New York, LLC2009-07-01Not applicableUs
Norethindrone Acetatetablet5 mg/1oralAurobindo Pharma Limited2016-01-08Not applicableUs
Norethindrone Acetatetablet5 mg/1oralAv Pak2014-11-17Not applicableUs
Norethindrone Acetatetablet5 mg/1oralBarr Laboratories Inc.2001-06-29Not applicableUs
Norethindrone Acetatetablet5 mg/1oralGlenmark Pharmaceuticals Inc., Usa2010-07-21Not applicableUs
Norethindrone Acetatetablet5 mg/1oralAv Kare, Inc.2013-06-18Not applicableUs
Norlyroctablet, film coated.35 mg/1oralOhm Laboratories Inc.2014-04-15Not applicableUs
SharobelkitNorthstar Rx LLC2014-06-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ConludagNot Available
MicronovumNot Available
Mini-PENot Available
Mini-pillNot Available
NorcolutNot Available
NoridayNot Available
NorlutenNot Available
NorlutinNot Available
Primolut-NNot Available
UtovlanNot Available
Brand mixtures
NameLabellerIngredients
ActivellaNovo Nordisk
ActivelleNovo Nordisk Canada Inc
Activelle LdNovo Nordisk Canada Inc
Alyacen 1/35Glenmark Pharmaceuticals Inc., Usa
Alyacen 7/7/7Glenmark Pharmaceuticals Inc., Usa
AranelleBarr Laboratories Inc.
BalzivaBarr Laboratories Inc.
Blisovi 24 FeLupin Pharmaceuticals, Inc.
Blisovi Fe 1.5/30Lupin Pharmaceuticals, Inc.
Blisovi Fe 1/20Lupin Pharmaceuticals, Inc.
BreviconActavis Pharma, Inc.
Brevicon 0.5/35 21 TabSyntex Inc.
Brevicon 0.5/35 28 TabSyntex Inc.
Brevicon 0.5/35 Tablets (21-day Pack)Pfizer Canada Inc
Brevicon 0.5/35 Tablets (28-day Pack)Pfizer Canada Inc
Brevicon 1/35 21 TabSyntex Inc.
Brevicon 1/35 28 TabSyntex Inc.
Brevicon 1/35 Tablets (21-day Pack)Pfizer Canada Inc
Brevicon 1/35 Tablets (28-day Pack)Pfizer Canada Inc
BriellynGlenmark Pharmaceuticals Inc., Usa
CombipatchNovartis Pharmaceuticals Corporation
Combipatch (estradiol/norethindrone Acetate Transdermal System)NOVEN THERAPEUTICS, LLC
Cyclafem 1/35Qualitest Pharmaceuticals
Cyclafem 7/7/7Qualitest Pharmaceuticals
Dasetta 1/35Northstar Rx LLC
Dasetta 7/7/7Northstar Rx LLC
Estalis 140/50 McgNovartis Pharmaceuticals Canada Inc
Estalis 250/50 McgNovartis Pharmaceuticals Canada Inc
Estalis SequiNovartis Pharmaceuticals Canada Inc
EstracombNovartis Pharmaceuticals Canada Inc
Estradiol / Norethindrone AcetateBreckenridge Pharmaceutical, Inc.
Femcon FeWarner Chilcott (US), LLC
FemhrtWarner Chilcott (US), LLC
FyavolvLupin Pharmaceuticals, Inc.
GeneressActavis Specialty Pharmaceuticals Co
GildagiaQualitest Pharmaceuticals
Gildess 1.5/30Qualitest Pharmaceuticals
Gildess 1/20Qualitest Pharmaceuticals
Jevantique LoActavis Pharma, Inc.
JinteliTeva Pharmaceuticals USA Inc
Junel 1.5/30Barr Laboratories Inc.
Junel 1/20Barr Laboratories Inc.
Junel Fe 1.5/30Barr Laboratories Inc.
Junel Fe 1/20Barr Laboratories Inc.
Junel Fe 24Teva Pharmaceuticals USA Inc
Kaitlib FeLupin Pharmaceuticals, Inc.
LeenaActavis Pharma, Inc.
Lo Loestrin FeWarner Chilcott (US), LLC
Lo Minastrin FeWarner Chilcott (US), LLC
Loestrin 1.5/30Warner Chilcott Canada Co
Loestrin 1.5/30 21 DayTeva Women's Health, Inc.
Loestrin 1/20 21 DayTeva Women's Health, Inc.
Loestrin 21 1.5/30 21 DayTeva Women's Health, Inc.
Loestrin 21 1/20 21 DayTeva Women's Health, Inc.
Loestrin 24 FeWarner Chilcott (US), LLC
LoloWarner Chilcott Canada Co
Lomedia 24 FeAmneal Pharmaceuticals of New York, LLC
LopreezaAmneal Pharmaceuticals of New York, LLC
Lupaneta PackAbb Vie Inc.
MicrogestinActavis Pharma, Inc.
MimveyTeva Pharmaceuticals USA Inc
Mimvey LoTeva Pharmaceuticals USA Inc
Minastrin 24 FeWarner Chilcott (US), LLC
Minestrin 1/20Warner Chilcott Canada Co
ModiconJanssen Pharmaceuticals, Inc.
NeconRebel Distributors Corp
Necon 1/35Watson Pharma, Inc.
Necon 777Actavis Pharma, Inc.
Necon 777 777Dispensing Solutions, Inc.
Norethindrone Acetate and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Norethindrone and Ethinyl Estradiol and Ferrous FumarateLupin Pharmaceuticals, Inc.
NorinylActavis Pharma, Inc.
Norinyl 1/50 -(21-day Regimen)Pfizer Canada Inc
Norinyl 1/50 -(28-day Regimen)Pfizer Canada Inc
Norinyl 1/50 21 TabSyntex Inc.
Norinyl 1/50 28 TabSyntex Inc.
Nortrel (21 Day Regimen)Barr Laboratories Inc.
Nortrel (28 Day Regimen)Barr Laboratories Inc.
Nortrel 7/7/7 (28 Day Regimen)Barr Laboratories Inc.
Ortho 0.5/35 Tablets (21 Day)Janssen Inc
Ortho 0.5/35 Tablets (28 Day)Janssen Inc
Ortho 1/35 Tablets (21 Day)Janssen Inc
Ortho 1/35 Tablets (28 Day)Janssen Inc
Ortho 10/11 Tablets (21 Day)Janssen Inc
Ortho 10/11 Tablets (28 Day)Janssen Inc
Ortho 7/7/7 Tablets (21 Day)Janssen Inc
Ortho 7/7/7 Tablets (28 Day)Janssen Inc
Ortho Novum 135Janssen Pharmaceuticals, Inc.
Ortho-novum 1/50 Tablets (21 Day)Janssen Inc
Ortho-novum 1/50 Tablets (28 Day)Janssen Inc
Ortho-novum 777A S Medication Solutions Llc
Ovcon 35Warner Chilcott (US), LLC
Pirmella 1/35Lupin Pharmaceuticals, Inc.
Pirmella 7/7/7Lupin Pharmaceuticals, Inc.
Select 1/35 (21-day)Pfizer Canada Inc
Select 1/35 (28-day)Pfizer Canada Inc
Synphasic 21 TabletsPfizer Canada Inc
Synphasic 28 TabletsPfizer Canada Inc
Synphasic-28 TabletsSyntex Inc.
Tarina Fe 1/20Afaxys Inc.
Tilia FeRebel Distributors Corp
Tri-legest Fe 28 DayBarr Laboratories Inc.
Tri-norinylActavis Pharma, Inc.
VyfemlaLupin Pharmaceuticals, Inc.
WeraNorthstar Rx LLC
Wymzya FeLupin Pharmaceuticals, Inc.
ZenchentWatson Pharma, Inc.
Zenchent FeWatson Pharma, Inc.
ZeosaTeva Pharmaceuticals USA Inc
Salts
Name/CASStructureProperties
Norethisterone acetate
51-98-9
Thumb
  • InChI Key: IMONTRJLAWHYGT-ZCPXKWAGSA-N
  • Monoisotopic Mass: 340.203844762
  • Average Mass: 340.4559
DBSALT000129
Categories
UNIIT18F433X4S
CAS number68-22-4
WeightAverage: 298.4192
Monoisotopic: 298.193280076
Chemical FormulaC20H26O2
InChI KeyVIKNJXKGJWUCNN-XGXHKTLJSA-N
InChI
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
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
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]
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
Pharmacology
IndicationFor the treatment of secondary amenorrhea, endometriosis, and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer.
PharmacodynamicsNorethindrone is a synthetic oral progestin. It is used for contraception or to treat such conditions as secondary amenorrhea, abnormal uterine bleeding, and endometriosis. As an oral contraceptive, norethindrone is available as either a single agent or in combination with an estrogen. Norethindrone acetate induces secretory changes in an estrogen-primed endometrium. On a weight basis, it is twice as potent as norethindrone.
Mechanism of actionProgestins diffuse freely into target cells and bind to the progesterone receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge.
Related Articles
AbsorptionNorethindrone acetate is completely and rapidly deacetylated to norethindrone (NET) after oral administration, and the disposition of norethindrone acetate is indistinguishable from that of orally administered norethindrone. Norethindrone is rapidly absorbed from norethindrone acetate, in which maximum plasma concentration occur 2 hours post-dose (Tmax). When a single dose is given to healthy women, the Cmax is 26.19 ± 6.19 hours. The AUC (0-inf) is 166.90 ± 56.28 ng/mL*h. Absolute oral bioavailability is approximately 64%. The effect of food on the pharmacokinetics of norethindrone acetate is unknown.
Volume of distribution
  • 4 L/kg
Protein bindingNorethindrone is 36% bound to sex hormone-binding globulin and 61% bound to albumin.
Metabolism

Hepatic. Norethindrone is extensively metabolized, primarily via reduction. It also undergoes sulfate and glucuronide conjugation. The majority of metabolites in the circulation are sulfates, with glucuronides accounting for most of the urinary metabolites.

Route of eliminationNorethindrone is excreted in both urine and feces, primarily as metabolites.
Half life8.51 ± 2.19 (when a single dose is given to healthy women)
Clearance
  • 0.4 L/hr/kg [plasma clearance]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9413
Caco-2 permeable+0.8572
P-glycoprotein substrateSubstrate0.6346
P-glycoprotein inhibitor IInhibitor0.5079
P-glycoprotein inhibitor IINon-inhibitor0.9087
Renal organic cation transporterNon-inhibitor0.7603
CYP450 2C9 substrateNon-substrate0.7759
CYP450 2D6 substrateNon-substrate0.9237
CYP450 3A4 substrateSubstrate0.7415
CYP450 1A2 substrateNon-inhibitor0.844
CYP450 2C9 inhibitorNon-inhibitor0.8688
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8333
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7876
Ames testNon AMES toxic0.9319
CarcinogenicityNon-carcinogens0.9417
BiodegradationNot ready biodegradable0.9512
Rat acute toxicity1.8788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8777
hERG inhibition (predictor II)Non-inhibitor0.7744
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
  • Barr laboratories inc
  • Glenmark generics ltd
  • Ortho mcneil janssen pharmaceuticals inc
  • Watson laboratories inc
  • Duramed research inc
  • Glenmark generics ltd india
  • Warner Chilcott
Packagers
Dosage forms
FormRouteStrength
Patch, extended releasetransdermal
Kitoral
Patchtransdermal
Tablet (chewable)oral
Tabletoral
Kit
Tabletoral0.35 mg
Tablet, film coatedoral
Kit
Tabletoral.35 mg/1
Tabletoral5 mg/1
Tabletoral5 mg
Tablet, film coatedoral.35 mg/1
Prices
Unit descriptionCostUnit
Ovcon-35 (28) 28 0.4-35 mg-mcg tablet Disp Pack89.09USD disp
Ovcon-50 28 50-1 mcg-mg tablet Disp Pack89.09USD disp
Loestrin 1.5/30 (21) 21 1.5-30 mg-mcg tablet Disp Pack79.32USD disp
Loestrin 1/20 (21) 21 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1/20 28 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1.5/30 28 1.5-30 mg-mcg tablet Disp Pack77.1USD disp
Loestrin 24 Fe 28 1-20 mg-mcg tablet Disp Pack75.15USD disp
Nor-QD 28 0.35 mg tablet Disp Pack65.87USD disp
Tri-Norinyl (28) 28 0.5/1/0.5-35 mg-mcg tablet Disp Pack62.63USD disp
Ortho-Novum 10/11 (28) 28 35 mcg tablet Disp Pack60.25USD disp
Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack59.99USD disp
Norinyl 1+35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Ortho-Novum 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Brevicon (28) 28 0.5-35 mg-mcg tablet Disp Pack53.0USD disp
Norinyl 1+50 (28) 28 1-50 mg-mcg tablet 1 Disp Pack = 28 Pills52.99USD disp
Necon 10/11 (28) 28 35 mcg tablet Disp Pack35.99USD disp
Ortho-Novum 7/7/7 (28) 28 0.5/0.75/1-35 mg-mcg tablet Disp Pack33.99USD disp
Necon 0.5/35 (28) 28 0.5-35 mg-mcg tablet Disp Pack32.99USD disp
Necon 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack31.99USD disp
Loestrin fe 1-20 tablet5.23USD tablet
Loestrin 21 1.5-30 tablet3.66USD tablet
Loestrin 21 1-20 tablet3.66USD tablet
Aygestin 5 mg tablet3.27USD tablet
Ovcon-35 28 tablet3.06USD tablet
Loestrin fe 1.5-30 tablet2.75USD tablet
Norethindrone Acetate 5 mg tablet2.75USD tablet
Norethindrone 5 mg tablet2.65USD tablet
Ovcon-50 28 tablet2.62USD tablet
Micronor tablet2.44USD tablet
Nor-q-d tablet2.24USD tablet
Necon 1-35-28 tablet2.11USD tablet
Modicon 28 tablet2.07USD tablet
Tri-norinyl 28 tablet2.01USD tablet
Ortho-novum 1-35-28 tablet1.9USD tablet
Brevicon 28 tablet1.8USD tablet
Norinyl 1+35-28 tablet1.73USD tablet
Norinyl 1+50-28 tablet1.73USD tablet
Demulen 1-50-21 tablet1.67USD tablet
Ortho-novum 7-7-7-21 tablet1.4USD tablet
Errin 0.35 mg tablet1.34USD tablet
Ortho-novum 7/7/7-28 tablet1.33USD tablet
Camila tablet1.32USD tablet
Jolivette tablet1.32USD tablet
Nora-be tablet1.32USD tablet
Norethindrone 0.35 mg tablet1.32USD tablet
Demulen 1-50-28 tablet1.29USD tablet
Ortho micronor tablet1.23USD tablet
Necon 0.5-35-28 tablet1.15USD tablet
Necon 7-7-7-28 tablet1.15USD tablet
Necon 1-50-28 tablet1.05USD tablet
Ortho-novum 7-7-7-28 tablet1.02USD tablet
Micronor (28 Day) 0.35 mg Tablet0.66USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6036976 No1996-12-132016-12-13Us
US6652880 No2000-03-292020-03-29Us
US6667050 No1999-04-062019-04-06Us
US7704984 No2009-02-022029-02-02Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point203.5 °CPhysProp
water solubility7.04 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.97HANSCH,C ET AL. (1995)
logS-4.57ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.00668 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
Mass Spec (NIST)Download (11.3 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-01rt-4950000000-fcbe8bf03b1aa103152bView in MoNA
1D NMR1H NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General References
  1. FDA label
External Links
ATC CodesG03AA05G03AB04G03AC01G03DC02G03FA01G03FB05
AHFS Codes
  • 68:12.00
PDB EntriesNot Available
FDA labelDownload (322 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Norethindrone.
AcenocoumarolNorethindrone may decrease the anticoagulant activities of Acenocoumarol.
AcetaminophenThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Acetaminophen.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norethindrone.
AcitretinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Acitretin.
AlitretinoinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Alitretinoin.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Norethindrone.
AmobarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Amobarbital.
Anthrax immune globulinNorethindrone may increase the thrombogenic activities of Anthrax immune globulin.
AprepitantThe serum concentration of Norethindrone can be decreased when it is combined with Aprepitant.
ArtemetherThe serum concentration of Norethindrone can be decreased when it is combined with Artemether.
AtazanavirThe serum concentration of Norethindrone can be increased when it is combined with Atazanavir.
BatimastatThe serum concentration of Norethindrone can be decreased when it is combined with Batimastat.
BexaroteneThe serum concentration of Norethindrone can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Norethindrone can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Norethindrone can be decreased when it is combined with Bosentan.
ButabarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Butabarbital.
ButalbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Butalbital.
ButethalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Norethindrone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CaffeineThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Caffeine.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Norethindrone.
CapromabNorethindrone may decrease effectiveness of Capromab as a diagnostic agent.
CarbamazepineThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Carbamazepine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norethindrone.
CholestyramineThe serum concentration of Norethindrone can be decreased when it is combined with Cholestyramine.
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Norethindrone.
ClobazamThe serum concentration of Norethindrone can be decreased when it is combined with Clobazam.
CobicistatThe serum concentration of Norethindrone can be increased when it is combined with Cobicistat.
ColesevelamThe serum concentration of Norethindrone can be decreased when it is combined with Colesevelam.
ColestipolThe serum concentration of Norethindrone can be decreased when it is combined with Colestipol.
DabrafenibThe serum concentration of Norethindrone can be decreased when it is combined with Dabrafenib.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Norethindrone.
DarunavirThe serum concentration of Norethindrone can be decreased when it is combined with Darunavir.
DeferasiroxThe serum concentration of Norethindrone can be decreased when it is combined with Deferasirox.
DicoumarolNorethindrone may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Norethindrone.
EfavirenzThe serum concentration of Norethindrone can be decreased when it is combined with Efavirenz.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Norethindrone.
Eslicarbazepine acetateThe serum concentration of Norethindrone can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Norethindrone.
ExenatideThe serum concentration of Norethindrone can be decreased when it is combined with Exenatide.
FelbamateThe serum concentration of Norethindrone can be decreased when it is combined with Felbamate.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Norethindrone.
FloxuridineThe metabolism of Norethindrone can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Norethindrone can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Norethindrone.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Norethindrone.
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Norethindrone resulting in a loss in efficacy.
FosaprepitantThe serum concentration of Norethindrone can be decreased when it is combined with Fosaprepitant.
FosphenytoinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Fosphenytoin.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Norethindrone.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Norethindrone.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Norethindrone.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Norethindrone.
GriseofulvinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Griseofulvin.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Norethindrone.
HeptabarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Norethindrone.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Norethindrone.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Norethindrone.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Norethindrone.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Norethindrone.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Norethindrone.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Norethindrone.
IsoflurophateThe serum concentration of Norethindrone can be decreased when it is combined with Isoflurophate.
IsotretinoinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Isotretinoin.
LamotrigineThe serum concentration of Norethindrone can be decreased when it is combined with Lamotrigine.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Norethindrone.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Norethindrone.
LopinavirThe serum concentration of Norethindrone can be decreased when it is combined with Lopinavir.
LumacaftorThe serum concentration of Norethindrone can be decreased when it is combined with Lumacaftor.
LumefantrineThe serum concentration of Norethindrone can be decreased when it is combined with Lumefantrine.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Norethindrone.
MethohexitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Methohexital.
MetreleptinThe serum concentration of Norethindrone can be decreased when it is combined with Metreleptin.
MifepristoneThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Mifepristone.
MitotaneThe serum concentration of Norethindrone can be decreased when it is combined with Mitotane.
Mycophenolate mofetilThe serum concentration of Norethindrone can be decreased when it is combined with Mycophenolate mofetil.
Mycophenolic acidThe serum concentration of Norethindrone can be decreased when it is combined with Mycophenolic acid.
NelfinavirThe serum concentration of Norethindrone can be decreased when it is combined with Nelfinavir.
NevirapineThe serum concentration of Norethindrone can be decreased when it is combined with Nevirapine.
OxcarbazepineThe serum concentration of Norethindrone can be decreased when it is combined with Oxcarbazepine.
PentobarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Pentobarbital.
PerampanelThe serum concentration of Norethindrone can be decreased when it is combined with Perampanel.
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Norethindrone.
PhenobarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Phenobarbital.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Norethindrone.
PhenytoinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Phenytoin.
PrimidoneThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Primidone.
PrucaloprideThe serum concentration of Norethindrone can be decreased when it is combined with Prucalopride.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Norethindrone.
RifabutinThe serum concentration of Norethindrone can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Norethindrone can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Norethindrone can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Norethindrone can be decreased when it is combined with Ritonavir.
RufinamideThe serum concentration of Norethindrone can be decreased when it is combined with Rufinamide.
SaquinavirThe serum concentration of Norethindrone can be decreased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Norethindrone.
SecobarbitalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Secobarbital.
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Norethindrone.
SiltuximabThe serum concentration of Norethindrone can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Norethindrone can be decreased when it is combined with Simeprevir.
St. John's WortThe therapeutic efficacy of Norethindrone can be decreased when used in combination with St. John's Wort.
SugammadexThe serum concentration of Norethindrone can be decreased when it is combined with Sugammadex.
SulfisoxazoleThe metabolism of Norethindrone can be decreased when combined with Sulfisoxazole.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Norethindrone.
TelaprevirThe serum concentration of Norethindrone can be decreased when it is combined with Telaprevir.
ThalidomideNorethindrone may increase the thrombogenic activities of Thalidomide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Norethindrone.
TipranavirThe serum concentration of Norethindrone can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Norethindrone can be decreased when it is combined with Tocilizumab.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Norethindrone.
TopiramateThe serum concentration of Norethindrone can be decreased when it is combined with Topiramate.
Tranexamic AcidNorethindrone may increase the thrombogenic activities of Tranexamic Acid.
TreprostinilThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Norethindrone.
TretinoinThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Tretinoin.
UlipristalThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Ulipristal.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Norethindrone.
Vitamin CThe serum concentration of Norethindrone can be increased when it is combined with Vitamin C.
VoriconazoleThe serum concentration of Norethindrone can be increased when it is combined with Voriconazole.
WarfarinNorethindrone may decrease the anticoagulant activities of Warfarin.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial ...
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Steroid hydroxylase 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:
55930.545 Da
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 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. FDA label
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Androgen binding
Specific Function:
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular Weight:
43778.755 Da
References
  1. FDA label

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 27, 2016 02:18