Identification

Name
Norethisterone
Accession Number
DB00717  (APRD00679)
Type
Small Molecule
Groups
Approved
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 IDs
NSC-9564 / SC-4640
Product Ingredients
IngredientUNIICASInChI Key
Norethisterone acetate9S44LIC7OJ51-98-9IMONTRJLAWHYGT-ZCPXKWAGSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
JencyclaTablet0.35 mgOralSandoz Canada Incorporated2015-09-14Not applicableCanada
JolivetteTablet.35 mg/1OralActavis Pharma Company2003-03-01Not applicableUs52544 0892 28 nlmimage10 5f45afed
MicronorTablet.35 mg/1OralPhysicians Total Care, Inc.2003-09-17Not applicableUs
Micronor Tablets 28-dayTablet0.35 mgOralJanssen Pharmaceuticals1972-12-31Not applicableCanada
MovisseTablet0.35 mgOralMylan Pharmaceuticals2015-06-30Not applicableCanada
Nor QDTablet.35 mg/1OralWatson Pharma, Inc.1973-01-02Not applicableUs
Nora BETablet.35 mg/1OralWatson Pharma, Inc.2005-05-12Not applicableUs52544 0629 28 nlmimage10 0a49857c
Norethindrone Tablets, USPTablet0.35 mgOralGlenmark Pharmaceuticals, IncNot applicableNot applicableCanada
NorlutateTablet5 mgOralErfa Canada 2012 Inc1961-12-31Not applicableCanada
Ortho MicronorTablet.35 mg/1OralJanssen Pharmaceuticals1973-01-02Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AygestinTablet5 mg/1OralTeva Women's Health2003-06-12Not applicableUs51285 0424 10 nlmimage10 562f2b09
CamilaTablet.35 mg/1OralMayne Pharma2016-08-03Not applicableUs
CamilaTablet.35 mg/1OralPhysicians Total Care, Inc.2003-06-19Not applicableUs
CamilaTablet.35 mg/1OralTeva2002-10-302018-02-28Us00555 0715 58 nlmimage10 fb2f7deb
DeblitaneKitNorth Star Rx Llc2013-09-13Not applicableUs
ErrinTablet.35 mg/1OralMayne Pharma2016-08-03Not applicableUs
ErrinTablet.35 mg/1OralTeva2003-01-08Not applicableUs00555 0344 58 nlmimage10 20369034
HeatherTablet.35 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2010-04-23Not applicableUs68462 0303 29 nlmimage10 5745ab9d
HeatherTablet.35 mg/1OralA S Medication Solutions2010-04-232017-06-20Us
IncassiaTablet.35 mg/1OralAurobindo Pharma2016-09-23Not applicableUs
International/Other Brands
Conludag / Micronovum / Mini-PE / Mini-pill / Norcolut / Noriday / Norluten / Norlutin / Primolut-N / Utovlan
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ActivellaNorethisterone acetate (.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralGemini Pharmaceuticals, Inc.2016-05-12Not applicableUs
ActivellaNorethisterone acetate (.1 mg/1) + Estradiol (.5 mg/1)Tablet, film coatedOralNovo Nordisk2007-04-09Not applicableUs
ActivellaNorethisterone acetate (.1 mg/1) + Estradiol (.5 mg/1)Tablet, film coatedOralGemini Pharmaceuticals, Inc.2016-05-12Not applicableUs
ActivellaNorethisterone acetate (.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralNovo Nordisk2003-07-22Not applicableUs
ActivelleNorethisterone acetate (0.5 mg) + Estradiol (1.0 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada
Activelle LdNorethisterone acetate (0.1 mg) + Estradiol (0.5 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada
Alyacen 1/35Norethisterone + Ethinyl EstradiolKitA S Medication Solutions2012-01-192017-06-20Us
Alyacen 1/35Norethisterone + Ethinyl EstradiolKitGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUs
Alyacen 7/7/7Norethisterone + Ethinyl EstradiolKitA S Medication Solutions2012-01-192017-06-20Us
Alyacen 7/7/7Norethisterone + Ethinyl EstradiolKitGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUs
Categories
UNII
T18F433X4S
CAS number
68-22-4
Weight
Average: 298.4192
Monoisotopic: 298.193280076
Chemical Formula
C20H26O2
InChI Key
VIKNJXKGJWUCNN-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

Pharmacology

Indication

For 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.

Structured Indications
Pharmacodynamics

Norethindrone 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 action

Progestins 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.

TargetActionsOrganism
UProgesterone receptor
agonist
Human
Absorption

Norethindrone 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 binding

Norethindrone 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 elimination

Norethindrone is excreted in both urine and feces, primarily as metabolites.

Half life

8.51 ± 2.19 (when a single dose is given to healthy women)

Clearance
  • 0.4 L/hr/kg [plasma clearance]
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Norethisterone.Investigational
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Norethisterone.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Norethisterone.Approved, Investigational
AcebutololThe serum concentration of Acebutolol can be decreased when it is combined with Norethisterone.Approved
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Norethisterone.Approved
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Norethisterone.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Norethisterone.Withdrawn
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be decreased when it is combined with Norethisterone.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Norethisterone.Approved
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Norethisterone.Experimental
AldosteroneThe serum concentration of Aldosterone can be decreased when it is combined with Norethisterone.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be decreased when it is combined with Norethisterone.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Norethisterone.Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Norethisterone.Approved
AmbrisentanThe serum concentration of Ambrisentan can be decreased when it is combined with Norethisterone.Approved, Investigational
AmiodaroneThe metabolism of Norethisterone can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be decreased when it is combined with Norethisterone.Approved
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Norethisterone.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Norethisterone.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Norethisterone.Approved
AprepitantThe serum concentration of Norethisterone can be increased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Norethisterone.Approved, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Norethisterone.Approved, Investigational
Arsenic trioxideThe serum concentration of Arsenic trioxide can be decreased when it is combined with Norethisterone.Approved, Investigational
AtazanavirThe metabolism of Norethisterone can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Atenolol can be decreased when it is combined with Norethisterone.Approved
AtomoxetineThe metabolism of Norethisterone can be decreased when combined with Atomoxetine.Approved
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Norethisterone.Approved, Investigational
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Norethisterone.Investigational
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Norethisterone.Approved, Investigational
BelinostatThe serum concentration of Belinostat can be decreased when it is combined with Norethisterone.Approved, Investigational
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Norethisterone.Investigational
BetamethasoneThe serum concentration of Betamethasone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Norethisterone.Approved, Investigational
BoceprevirThe metabolism of Norethisterone can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Norethisterone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Norethisterone can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Norethisterone.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Norethisterone.Approved
BromocriptineThe serum concentration of Bromocriptine can be decreased when it is combined with Norethisterone.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Norethisterone.Withdrawn
CabazitaxelThe serum concentration of Cabazitaxel can be decreased when it is combined with Norethisterone.Approved
CaffeineThe serum concentration of Caffeine can be decreased when it is combined with Norethisterone.Approved
CamptothecinThe serum concentration of Camptothecin can be decreased when it is combined with Norethisterone.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be decreased when it is combined with Norethisterone.Approved
CarbamazepineThe metabolism of Norethisterone can be increased when combined with Carbamazepine.Approved, Investigational
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Norethisterone.Experimental
CarfilzomibThe serum concentration of Carfilzomib can be decreased when it is combined with Norethisterone.Approved
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Norethisterone.Experimental
CeritinibThe serum concentration of Norethisterone can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be decreased when it is combined with Norethisterone.Withdrawn
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Norethisterone.Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be decreased when it is combined with Norethisterone.Approved, Vet Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Norethisterone.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Norethisterone.Experimental
CimetidineThe serum concentration of Cimetidine can be decreased when it is combined with Norethisterone.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be decreased when it is combined with Norethisterone.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be decreased when it is combined with Norethisterone.Approved
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Norethisterone.Approved
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Norethisterone.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Norethisterone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Norethisterone can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Clobazam can be decreased when it is combined with Norethisterone.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be decreased when it is combined with Norethisterone.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be decreased when it is combined with Norethisterone.Approved
ClopidogrelThe serum concentration of Clopidogrel can be decreased when it is combined with Norethisterone.Approved, Nutraceutical
ClotrimazoleThe metabolism of Norethisterone can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Norethisterone.Approved
CobicistatThe metabolism of Norethisterone can be decreased when combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be decreased when it is combined with Norethisterone.Approved
ColchicineThe serum concentration of Colchicine can be decreased when it is combined with Norethisterone.Approved
ColesevelamThe serum concentration of Norethisterone can be decreased when it is combined with Colesevelam.Approved
Conestat alfaNorethisterone may increase the thrombogenic activities of Conestat alfa.Approved
ConivaptanThe serum concentration of Norethisterone can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Norethisterone.Approved
CopanlisibThe serum concentration of Copanlisib can be decreased when it is combined with Norethisterone.Approved
CrizotinibThe metabolism of Norethisterone can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Norethisterone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Norethisterone.Approved
DabrafenibThe serum concentration of Norethisterone can be decreased when it is combined with Dabrafenib.Approved
DactinomycinThe serum concentration of Dactinomycin can be decreased when it is combined with Norethisterone.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Norethisterone.Approved
DanaparoidThe therapeutic efficacy of Danaparoid can be decreased when used in combination with Norethisterone.Approved, Withdrawn
DapagliflozinThe serum concentration of Dapagliflozin can be decreased when it is combined with Norethisterone.Approved
DarexabanThe therapeutic efficacy of Darexaban can be decreased when used in combination with Norethisterone.Investigational
DarunavirThe serum concentration of Norethisterone can be decreased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Norethisterone can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Norethisterone.Approved
DebrisoquinThe serum concentration of Debrisoquin can be decreased when it is combined with Norethisterone.Approved
DeferasiroxThe serum concentration of Norethisterone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Norethisterone can be decreased when combined with Delavirdine.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Norethisterone.Investigational
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Norethisterone.Approved
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Norethisterone.Approved, Investigational, Vet Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Norethisterone.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Norethisterone.Approved
Dextran 70The therapeutic efficacy of Dextran 70 can be decreased when used in combination with Norethisterone.Approved
Dextran 75The therapeutic efficacy of Dextran 75 can be decreased when used in combination with Norethisterone.Approved
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Norethisterone.Approved, Illicit, Vet Approved
DicoumarolThe therapeutic efficacy of Dicoumarol can be decreased when used in combination with Norethisterone.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Norethisterone.Approved
DigitoxinThe serum concentration of Digitoxin can be decreased when it is combined with Norethisterone.Approved
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Norethisterone.Approved
DihydroergotamineThe metabolism of Norethisterone can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be decreased when it is combined with Norethisterone.Illicit
DiltiazemThe metabolism of Norethisterone can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Dipyridamole can be decreased when it is combined with Norethisterone.Approved
DocetaxelThe serum concentration of Docetaxel can be decreased when it is combined with Norethisterone.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be decreased when it is combined with Norethisterone.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Norethisterone.Approved, Investigational
DoxycyclineThe metabolism of Norethisterone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Norethisterone can be decreased when combined with Dronedarone.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Norethisterone.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Norethisterone.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Norethisterone.Approved
ElbasvirThe serum concentration of Elbasvir can be decreased when it is combined with Norethisterone.Approved
EletriptanThe serum concentration of Eletriptan can be decreased when it is combined with Norethisterone.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Norethisterone.Approved
EnasidenibThe serum concentration of Enasidenib can be decreased when it is combined with Norethisterone.Approved
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Norethisterone.Approved
EnzalutamideThe serum concentration of Norethisterone can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be decreased when it is combined with Norethisterone.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Norethisterone.Approved, Investigational
ErythromycinThe metabolism of Norethisterone can be decreased when combined with Erythromycin.Approved, Vet Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Norethisterone.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be decreased when it is combined with Norethisterone.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be decreased when it is combined with Norethisterone.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Norethisterone.Approved
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Norethisterone.Withdrawn
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Norethisterone.Approved
ExenatideThe therapeutic efficacy of Exenatide can be decreased when used in combination with Norethisterone.Approved, Investigational
EzetimibeThe serum concentration of Ezetimibe can be decreased when it is combined with Norethisterone.Approved
Ferulic acidThe therapeutic efficacy of Ferulic acid can be decreased when used in combination with Norethisterone.Experimental
FesoterodineThe serum concentration of Fesoterodine can be decreased when it is combined with Norethisterone.Approved
FexofenadineThe serum concentration of Fexofenadine can be decreased when it is combined with Norethisterone.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be decreased when it is combined with Norethisterone.Approved
FluconazoleThe metabolism of Norethisterone can be decreased when combined with Fluconazole.Approved
FluindioneThe therapeutic efficacy of Fluindione can be decreased when used in combination with Norethisterone.Investigational
Fluticasone furoateThe serum concentration of Fluticasone furoate can be decreased when it is combined with Norethisterone.Approved
FluvoxamineThe metabolism of Norethisterone can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxThe therapeutic efficacy of Fondaparinux can be decreased when used in combination with Norethisterone.Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Norethisterone.Approved, Investigational
FosamprenavirThe metabolism of Norethisterone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Norethisterone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Norethisterone can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Norethisterone can be increased when it is combined with Fusidic Acid.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Norethisterone.Investigational
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Norethisterone.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be decreased when it is combined with Norethisterone.Approved
GlecaprevirThe serum concentration of Glecaprevir can be decreased when it is combined with Norethisterone.Approved
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Norethisterone.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Norethisterone.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Norethisterone.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Norethisterone.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Norethisterone.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Norethisterone.Approved
GrazoprevirThe serum concentration of Grazoprevir can be decreased when it is combined with Norethisterone.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be decreased when it is combined with Norethisterone.Withdrawn
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Norethisterone.Investigational
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Norethisterone.Approved
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Norethisterone.Approved, Investigational
Human C1-esterase inhibitorNorethisterone may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be decreased when it is combined with Norethisterone.Approved
IdelalisibThe serum concentration of Norethisterone can be increased when it is combined with Idelalisib.Approved
IdraparinuxThe therapeutic efficacy of Idraparinux can be decreased when used in combination with Norethisterone.Investigational
ImatinibThe metabolism of Norethisterone can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Imipramine can be decreased when it is combined with Norethisterone.Approved
IndacaterolThe serum concentration of Indacaterol can be decreased when it is combined with Norethisterone.Approved
IndinavirThe metabolism of Norethisterone can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Indomethacin can be decreased when it is combined with Norethisterone.Approved, Investigational
Inotuzumab ozogamicinThe serum concentration of Inotuzumab ozogamicin can be decreased when it is combined with Norethisterone.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Norethisterone.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Norethisterone.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Norethisterone.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Norethisterone.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Norethisterone.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Norethisterone.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Norethisterone.Approved
IrinotecanThe serum concentration of Irinotecan can be decreased when it is combined with Norethisterone.Approved, Investigational
IsavuconazoniumThe metabolism of Norethisterone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Norethisterone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Norethisterone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Norethisterone can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Norethisterone.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be decreased when it is combined with Norethisterone.Approved
KetoconazoleThe metabolism of Norethisterone can be decreased when combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be decreased when it is combined with Norethisterone.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Norethisterone.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Norethisterone.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Norethisterone.Approved
LenalidomideThe serum concentration of Lenalidomide can be decreased when it is combined with Norethisterone.Approved
LenvatinibThe serum concentration of Lenvatinib can be decreased when it is combined with Norethisterone.Approved
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Norethisterone.Approved
LetaxabanThe therapeutic efficacy of Letaxaban can be decreased when used in combination with Norethisterone.Investigational
LevetiracetamThe serum concentration of Levetiracetam can be decreased when it is combined with Norethisterone.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be decreased when it is combined with Norethisterone.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be decreased when it is combined with Norethisterone.Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Norethisterone.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Norethisterone.Approved
LoperamideThe serum concentration of Loperamide can be decreased when it is combined with Norethisterone.Approved
LopinavirThe metabolism of Norethisterone can be decreased when combined with Lopinavir.Approved
LosartanThe serum concentration of Losartan can be decreased when it is combined with Norethisterone.Approved
LovastatinThe metabolism of Norethisterone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Norethisterone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Norethisterone can be increased when combined with Lumacaftor.Approved
MannitolThe serum concentration of Mannitol can be decreased when it is combined with Norethisterone.Approved, Investigational
MelagatranThe therapeutic efficacy of Melagatran can be decreased when used in combination with Norethisterone.Experimental
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Norethisterone.Approved
MethotrexateThe serum concentration of Methotrexate can be decreased when it is combined with Norethisterone.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be decreased when it is combined with Norethisterone.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be decreased when it is combined with Norethisterone.Approved, Illicit
MifepristoneThe serum concentration of Norethisterone can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Norethisterone.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Norethisterone.Approved
MirabegronThe serum concentration of Mirabegron can be decreased when it is combined with Norethisterone.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Norethisterone.Approved, Investigational
MitotaneThe serum concentration of Norethisterone can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be decreased when it is combined with Norethisterone.Approved, Investigational
MorphineThe serum concentration of Morphine can be decreased when it is combined with Norethisterone.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Norethisterone.Approved, Investigational
NadololThe serum concentration of Nadolol can be decreased when it is combined with Norethisterone.Approved
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Norethisterone.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Norethisterone.Approved, Investigational
NaloxoneThe serum concentration of Naloxone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Norethisterone.Approved, Investigational
NefazodoneThe metabolism of Norethisterone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Norethisterone can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Norethisterone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Norethisterone can be increased when combined with Nevirapine.Approved
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Norethisterone.Approved
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Norethisterone.Approved
NilotinibThe metabolism of Norethisterone can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Norethisterone.Approved
NizatidineThe serum concentration of Nizatidine can be decreased when it is combined with Norethisterone.Approved
OdanacatibThe serum concentration of Odanacatib can be decreased when it is combined with Norethisterone.Investigational
OlanzapineThe serum concentration of Olanzapine can be decreased when it is combined with Norethisterone.Approved, Investigational
OlaparibThe metabolism of Norethisterone can be decreased when combined with Olaparib.Approved
OmbitasvirThe serum concentration of Ombitasvir can be decreased when it is combined with Norethisterone.Approved
OsimertinibThe serum concentration of Norethisterone can be increased when it is combined with Osimertinib.Approved
OtamixabanThe therapeutic efficacy of Otamixaban can be decreased when used in combination with Norethisterone.Investigational
PaclitaxelThe serum concentration of Paclitaxel can be decreased when it is combined with Norethisterone.Approved, Vet Approved
PalbociclibThe serum concentration of Norethisterone can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Norethisterone.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Norethisterone.Approved
PentobarbitalThe metabolism of Norethisterone can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe therapeutic efficacy of Pentosan Polysulfate can be decreased when used in combination with Norethisterone.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Norethisterone.Approved, Withdrawn
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Norethisterone.Approved
PhenobarbitalThe metabolism of Norethisterone can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Norethisterone.Approved
PhenytoinThe metabolism of Norethisterone can be increased when combined with Phenytoin.Approved, Vet Approved
PibrentasvirThe serum concentration of Pibrentasvir can be decreased when it is combined with Norethisterone.Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Norethisterone.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be decreased when it is combined with Norethisterone.Approved
PomalidomideThe serum concentration of Pomalidomide can be decreased when it is combined with Norethisterone.Approved
PonatinibThe serum concentration of Ponatinib can be decreased when it is combined with Norethisterone.Approved
PosaconazoleThe metabolism of Norethisterone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Norethisterone.Approved, Investigational
PravastatinThe serum concentration of Pravastatin can be decreased when it is combined with Norethisterone.Approved
PrazosinThe serum concentration of Prazosin can be decreased when it is combined with Norethisterone.Approved
PrednisoloneThe serum concentration of Prednisolone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
PrimidoneThe metabolism of Norethisterone can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe serum concentration of Progesterone can be decreased when it is combined with Norethisterone.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be decreased when it is combined with Norethisterone.Approved, Investigational
Protein CThe therapeutic efficacy of Protein C can be decreased when used in combination with Norethisterone.Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Norethisterone.Approved
ProtocatechualdehydeThe therapeutic efficacy of Protocatechualdehyde can be decreased when used in combination with Norethisterone.Approved
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Norethisterone.Approved
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Norethisterone.Approved
QuinineThe serum concentration of Quinine can be decreased when it is combined with Norethisterone.Approved
RanitidineThe serum concentration of Ranitidine can be decreased when it is combined with Norethisterone.Approved
RanolazineThe metabolism of Norethisterone can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Norethisterone.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be decreased when it is combined with Norethisterone.Approved
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Norethisterone.Approved
RifabutinThe metabolism of Norethisterone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Norethisterone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Norethisterone can be increased when combined with Rifapentine.Approved
RisperidoneThe serum concentration of Risperidone can be decreased when it is combined with Norethisterone.Approved, Investigational
RitonavirThe metabolism of Norethisterone can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Norethisterone.Approved
RomidepsinThe serum concentration of Romidepsin can be decreased when it is combined with Norethisterone.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Norethisterone.Approved, Investigational
RufinamideThe serum concentration of Norethisterone can be decreased when it is combined with Rufinamide.Approved
Salicylic acidThe serum concentration of Salicylic acid can be decreased when it is combined with Norethisterone.Approved, Vet Approved
SaquinavirThe metabolism of Norethisterone can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Norethisterone.Approved
SelexipagThe serum concentration of Selexipag can be decreased when it is combined with Norethisterone.Approved
SildenafilThe metabolism of Norethisterone can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be decreased when it is combined with Norethisterone.Approved
SiltuximabThe serum concentration of Norethisterone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Norethisterone can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Sitagliptin can be decreased when it is combined with Norethisterone.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Norethisterone.Approved
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Norethisterone.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Norethisterone.Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be decreased when it is combined with Norethisterone.Approved
SphingosineThe serum concentration of Sphingosine can be decreased when it is combined with Norethisterone.Experimental
St. John's WortThe serum concentration of Norethisterone can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Norethisterone can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Norethisterone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Norethisterone.Approved, Investigational
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Norethisterone.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be decreased when it is combined with Norethisterone.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be decreased when it is combined with Norethisterone.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be decreased when it is combined with Norethisterone.Approved
TelaprevirThe metabolism of Norethisterone can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Norethisterone can be decreased when combined with Telithromycin.Approved
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Norethisterone.Approved
TicagrelorThe serum concentration of Ticagrelor can be decreased when it is combined with Norethisterone.Approved
TiclopidineThe metabolism of Norethisterone can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be decreased when it is combined with Norethisterone.Approved
TocilizumabThe serum concentration of Norethisterone can be decreased when it is combined with Tocilizumab.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Norethisterone.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Norethisterone.Approved
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Norethisterone.Approved
TopotecanThe serum concentration of Topotecan can be decreased when it is combined with Norethisterone.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Norethisterone.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be decreased when it is combined with Norethisterone.Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Norethisterone.Withdrawn
TroxerutinThe therapeutic efficacy of Troxerutin can be decreased when used in combination with Norethisterone.Investigational
UlipristalThe therapeutic efficacy of Norethisterone can be decreased when used in combination with Ulipristal.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be decreased when it is combined with Norethisterone.Approved
VecuroniumThe serum concentration of Vecuronium can be decreased when it is combined with Norethisterone.Approved
VelpatasvirThe serum concentration of Velpatasvir can be decreased when it is combined with Norethisterone.Approved
VenetoclaxThe serum concentration of Venetoclax can be decreased when it is combined with Norethisterone.Approved
VenlafaxineThe metabolism of Norethisterone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Norethisterone can be decreased when combined with Verapamil.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Norethisterone.Approved, Investigational
VinblastineThe serum concentration of Vinblastine can be decreased when it is combined with Norethisterone.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Norethisterone.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be decreased when it is combined with Norethisterone.Approved
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Norethisterone.Approved, Investigational
VoriconazoleThe metabolism of Norethisterone can be decreased when combined with Voriconazole.Approved, Investigational
VoxilaprevirThe serum concentration of Voxilaprevir can be decreased when it is combined with Norethisterone.Approved
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Norethisterone.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Norethisterone.Approved, Investigational, Withdrawn
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Norethisterone.Approved
ZiprasidoneThe metabolism of Norethisterone can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Take without regard to meals.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14855
KEGG Drug
D00182
KEGG Compound
C05028
ChemSpider
5994
BindingDB
50148732
ChEBI
7627
ChEMBL
CHEMBL1162
Therapeutic Targets Database
DAP001212
PharmGKB
PA450651
HET
NDR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Norethisterone
ATC Codes
G03FB05 — Norethisterone and estrogenG03AC01 — NorethisteroneG03FA01 — Norethisterone and estrogenG03DC02 — NorethisteroneG03AA05 — Norethisterone and ethinylestradiolG03AB04 — Norethisterone and ethinylestradiol
AHFS Codes
  • 68:12.00 — Contraceptives
  • 68:32.00 — Progestins
PDB Entries
1sqn / 2w8y
FDA label
Download (322 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableBioequivalence1
1CompletedNot AvailableHealthy Volunteers4
1CompletedOtherHealthy Female Volunteers / Type 2 Diabetes Mellitus1
1CompletedTreatmentHIV / AIDS / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentType 2 Diabetes Mellitus1
1RecruitingTreatmentArthritic Psoriasis / Inflammatory Bowel Diseases (IBD) / Psoriasis / Systemic Lupus Erythematosus (SLE)1
1RecruitingTreatmentRheumatoid Arthritis1
1RecruitingTreatmentTumors, Solid1
2CompletedTreatmentEndometrial Hyperplasia1
2CompletedTreatmentEndometriosis1
2RecruitingTreatmentEndometriosis1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS)1
2Unknown StatusTreatmentEndometrial Cancers / Endometrial Hyperplasia1
2, 3CompletedPreventionAlkylating Agents / Fertility Preservation / Malignant Lymphomas1
3CompletedPreventionContraceptive Usage1
3CompletedSupportive CareCancer, Breast / Menopausal Symptoms1
3CompletedTreatmentEndometriosis / Pelvic Pain1
3CompletedTreatmentHealthy Volunteers2
3CompletedTreatmentSexual Dysfunctions1
3CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
3CompletedTreatmentOne to five years postmenopausal1
3TerminatedPreventionContraception1
3Unknown StatusTreatmentDysmenorrhea / Endometriosis / Painful Intercourse1
4CompletedTreatmentMenopause1
4CompletedTreatmentPremature Ovarian Failure (POF)1
4RecruitingBasic ScienceContraception / Fertility1
4RecruitingTreatmentDysmenorrhea / Endometriosis / Interstitial Cystitis / Migraine Disorders / Pain, Chronic / Pelvic Pain / Visceral Pain1
4TerminatedPreventionMenopause1
4Unknown StatusTreatmentHeavy Menstrual Bleeding / Hypermenorrhea1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Pregnancy1
Not AvailableCompletedTreatmentEndometrial Hyperplasia1
Not AvailableCompletedTreatmentHypermenorrhea1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableRecruitingBasic ScienceCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentEtonogestrel Contraceptive Implant, Bothersome Bleeding1
Not AvailableTerminatedPreventionDisorders, Blood Coagulation / Women's Health1
Not AvailableUnknown StatusBasic ScienceOral Contraceptives (OC)1
Not AvailableWithdrawnPreventionEndometriotic Cysts1

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
Tablet, film coatedOral
Patch, extended releaseTransdermal
KitOral
PatchTransdermal
Tablet, chewableOral
Kit
TabletOral0.35 mg
Kit
TabletOral.35 mg/1
TabletOral5 mg/1
TabletOral
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)
US6036976No1996-12-132016-12-13Us
US6667050No1999-04-062019-04-06Us
US7704984No2009-02-022029-02-02Us
US6652880No2000-03-292020-03-29Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)203.5 °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-4.6ALOGPS
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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (11.3 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-01rt-4950000000-fcbe8bf03b1aa103152b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5c-3900000000-4b2a5d95e4b6d50f16fc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00ea-0790000000-60d1a1a37c0ba98d6a4a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00e9-0890000000-5d3b8210450a1c43b119
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0391000000-ae51cc90bb8f2161f149
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ar0-3920000000-e31fa7c9e871f2e39846
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-4-steroid / Cyclohexenone / Ynone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, tertiary alcohol, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:7627) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05028) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030097)

Targets

Details
1. Progesterone receptor
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 ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
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...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da

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
Uniprot Name
Multidrug resistance protein 1
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]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13