Identification
NameLevonorgestrel
Accession NumberDB00367  (APRD00754, DB00506, APRD00106)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral.

Structure
Thumb
Synonyms
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one
17-alpha-Ethynyl-13-ethyl-19-nortestosterone
17-Ethynyl-18-methyl-19-nortestosterone
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
17alpha-Ethynyl-18-homo-19-nortestosterone
18-Methyl-17-alpha-ethynyl-19-nortestosterone
18-Methylnorethisterone
d(-)-Norgestrel
Jadelle
Levonelle
Levonorgestrel
Lévonorgestrel
Levonorgestrelum
Levonova
Microlut
Microluton
Microval
Mirena
NorLevo
Plan b
Postinor
External IDs Wy 5104
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
JaydessInsert, extended release13.5 mgIntrauterineBayer2013-10-30Not applicableCanada
KyleenaIntrauterine device19.5 mg/1IntrauterineBayer2016-09-19Not applicableUs
KyleenaInsert, extended release19.5 mgIntrauterineBayer2017-01-10Not applicableCanada
LilettaIntrauterine device52 mg/1IntrauterineActavis Pharma Company2015-02-26Not applicableUs
LilettaIntrauterine device52 mg/1IntrauterineAllergan2016-05-31Not applicableUs
MirenaInsert, extended release52 mgIntrauterineBayer2001-02-22Not applicableCanada
MirenaIntrauterine device52 mg/1IntrauterineBayer2009-10-01Not applicableUs
MirenaIntrauterine device52 mg/1IntrauterineBayer2009-10-01Not applicableUs
Norplant System Kit 36mg/implantImplant36 mgSubcutaneousWyeth Ayerst Canada Inc.1994-03-212002-09-24Canada
Plan BTablet.75 mg/1OralPhysicians Total Care, Inc.2003-08-14Not applicableUs
Plan B One-stepTablet1.5 mg/1OralRebel Distributors2009-07-10Not applicableUs
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2009-07-282016-09-30Us
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2009-09-142016-04-30Us
SkylaIntrauterine device13.5 mg/1IntrauterineBayer2013-01-11Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevonorgestrelTablet1.5 mg/1OralWatson Pharma, Inc.2012-07-162017-01-28Us
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-22Not applicableUs
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-15Not applicableUs
LevonorgestrelTablet1.5 mg/1OralPharmacist Pharmaceutical, LLC2013-06-11Not applicableUs
Levonorgestrel Emergency ContraceptiveTablet.75 mg/1OralPerrigo New York Inc.2011-03-102017-01-18Us
My WayTablet1.5 mg/1OralGavis Pharmaceuticals, LLC.2013-02-22Not applicableUs
Next ChoiceTablet.75 mg/1OralDispensing Solutions, Inc.2009-09-04Not applicableUs
Next ChoiceTablet.75 mg/1OralWatson Pharma, Inc.2009-09-042017-01-28Us
Next ChoiceTablet.75 mg/1OralPreferreed Pharmaceuticals Inc.2012-02-14Not applicableUs
Next ChoiceTablet.75 mg/1OralRebel Distributors2009-07-21Not applicableUs
Next ChoiceTablet.75 mg/1OralWatson Pharma, Inc.2009-07-21Not applicableUs
Next ChoiceTablet.75 mg/1OralH.J. Harkins Company2009-09-04Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AfteraTablet1.5 mg/1OralTeva Women's Health2014-10-20Not applicableUs
AfterpillTablet1.5 mg/1OralSyzygy Healthcare Solutions, LLC2013-02-15Not applicableUs
Athentia NextTablet1.5 mg/1OralAurohealth LLC2015-12-08Not applicableUs
Backup PlanTablet0.75 mgOralApotex CorporationNot applicableNot applicableCanada
Backup Plan OnestepTablet1.5 mgOralApotex Corporation2016-06-07Not applicableCanada
ContingencyTablet0.75 mgOralJai Pharma LimitedNot applicableNot applicableCanada
Contingency OneTablet1.5 mgOralMylan Pharmaceuticals2015-08-31Not applicableCanada
Econtra EzTablet1.5 mg/1OralAfaxys Inc.2015-01-01Not applicableUs
Fallback SoloTablet1.5 mg/1OralLupin Pharmaceuticals2014-07-22Not applicableUs
Fallback SoloTablet1.5 mg/1OralLupin Pharmaceuticals2014-07-22Not applicableUs
Her StyleTablet1.5 mg/1OralNorth Star Rx Llc2016-11-01Not applicableUs
LevonorgestrelTablet1.5 mg/1OralGlenmark Pharmaceuticals Inc.,Usa2016-03-25Not applicableUs
LevonorgestrelTablet1.5 mg/1OralLotus Pharmaceutical Co., Ltd. Nantou Plant2015-09-01Not applicableUs
LevonorgestrelTablet1.5 mg/1OralPharmacist Pharmaceutical, LLC2014-03-12Not applicableUs
Levonorgestrel Tablets, 0.75mgTablet0.75 mgOralLupin PharmaceuticalsNot applicableNot applicableCanada
Morning AfterTablet1.5 mg/1.5mgOralRapha Pharmaceuticals, Inc.2015-07-01Not applicableUs
My Choice TmTablet1.5 mg/1OralSun Pharmaceutical Industries Limited2017-05-12Not applicableUs
My WayTablet1.5 mg/1OralLupin Pharmaceuticals2017-04-25Not applicableUs
My WayTablet1.5 mg/1OralLupin Pharmaceuticals2013-02-15Not applicableUs
Next ChoiceTablet0.75 mgOralActavis Pharma Company2011-05-13Not applicableCanada
Next Choice One DoseTablet1.5 mg/1OralActavis Pharma Company2014-05-12Not applicableUs
NorlevoTablet1.5 mgOralLaboratoire HRA PharmaNot applicableNot applicableCanada
NorlevoTablet0.75 mgOralLaboratoire HRA Pharma2009-05-152017-01-31Canada
Opcicon One-stepTablet1.5 mg/1OralSun Pharmaceutical Industries Limited2014-09-12Not applicableUs
Option 2Tablet0.75 mgOralPerrigo International2013-09-25Not applicableCanada
Option 2Tablet1.5 mg/1OralL. Perrigo Company2016-01-29Not applicableUs
Plan BTablet0.75 mgOralTeva Branded Pharmaceutical Products, R&D Inc.2000-02-24Not applicableCanada
Plan BTablet1.5 mgOralTeva Branded Pharmaceutical Products, R&D Inc.2015-07-23Not applicableCanada
Plan B One-stepTablet1.5 mg/1OralCentral Texas Community Health Centers2013-12-12Not applicableUs
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2013-07-082016-09-30Us
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2013-11-012017-06-30Us
Plan B One-stepTablet1.5 mg/1OralA S Medication Solutions2013-12-18Not applicableUs
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2013-12-12Not applicableUs
Plan B One-stepTablet1.5 mg/1OralTeva Women's Health2013-08-26Not applicableUs
Plan B One-stepTablet1.5 mg/1OralA S Medication Solutions2013-12-12Not applicableUs
ReactTablet1.5 mg/1OralWockhardt2016-04-13Not applicableUs
Take ActionTablet1.5 mg/1OralTeva Women's Health2014-02-17Not applicableUs
Teva-levonorgestrelTablet0.75 mgOralTevaNot applicableNot applicableCanada
Unapproved/Other Products Not Available
International Brands
NameCompany
JadelleBayer
LevonelleBayer
MedonorMedopharm
MicrolutBayer
MicrovalWyeth
NeogestSchering
NorgestonBayer
NorplantBayer
PostinorGedeon Richter
Brand mixtures
NameLabellerIngredients
AfirmelleAurobindo Pharma
Alesse 21Pfizer
Alesse 28Pfizer
AltaveraSandoz
Alysena 21Apotex Corporation
Alysena 28Apotex Corporation
AmethiaMayne Pharma
AmethystWatson Pharma, Inc.
AubraAfaxys Inc.
AvianePhysicians Total Care, Inc.
Aviane 21Teva
Aviane 28Teva
Aviane 28 DayRebel Distributors
AyunaAurobindo Pharma
CamreseTeva
Camrese LoTeva
ChatealAfaxys Inc.
Climara ProPhysicians Total Care, Inc.
DayseeLupin Pharmaceuticals
DelylaOhm Laboratories, Inc.
EnpresseRebel Distributors
FalessaAvion Pharmaceuticals, Llc
FalminaNorth Star Rx Llc
IndayoMylan Pharmaceuticals
IntrovaleSandoz
JolessaPhysicians Total Care, Inc.
KurveloLupin Pharmaceuticals
LarissiaAmneal Pharmaceuticals
LessinaTeva
LevonestNorth Star Rx Llc
Levonorgestrel and Ethinyl EstradiolMylan Pharmaceuticals
Levonorgestrel and Ethinyl Estradiol and Ethinyl EstradiolLupin Pharmaceuticals
Levonorgestrel and Ethinyl Estradiol Tablets, 0.1 Mg/0.02 mgLupin Pharmaceuticals
LevoraRebel Distributors
LillowAmneal Pharmaceuticals
Lo SimpesseAurobindo Pharma
LuteraWatson Pharma, Inc.
Lutera 21Cobalt Laboratories
Lutera 28Cobalt Laboratories
MarlissaGlenmark Pharmaceuticals Inc.,Usa
Min-ovral 21Pfizer
Min-ovral 21 TabWyeth Ltd.
Min-ovral 28Pfizer
Min-ovral 28 TabWyeth Ltd.
MyzilraQualitest
OrsythiaQualitest
Ovima 21Apotex Corporation
Ovima 28Apotex Corporation
PortiaTeva
Portia 21Teva
Portia 28Teva
Preven Emergency ContraceptiveGynÉtics Ltd/LtÉe
Preven TabletsShire Pharma Canada Ulc
QuasenseWatson Pharma, Inc.
SeasonaleTeva Women's Health
SeasoniqueTeva Women's Health
SetlakinNorth Star Rx Llc
SimpesseAurobindo Pharma
SronyxWatson Pharma, Inc.
Triphasil 21Wyeth Ltd.
Triphasil 21 TabWyeth Ltd.
Triphasil 28Wyeth Ltd.
Triphasil 28 TabWyeth Ltd.
Triquilar 21Bayer
Triquilar 28Bayer
TrivoraMayne Pharma
Vienva TmSandoz
Categories
UNII5W7SIA7YZW
CAS number797-63-7
WeightAverage: 312.4458
Monoisotopic: 312.20893014
Chemical FormulaC21H28O2
InChI KeyWWYNJERNGUHSAO-XUDSTZEESA-N
InChI
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Pharmacology
Indication

For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.

Structured Indications
Pharmacodynamics

Levonorgestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Levonorgestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.

Mechanism of action

Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

TargetKindPharmacological actionActionsOrganismUniProt ID
Progesterone receptorProteinyes
binder
HumanP06401 details
3-oxo-5-alpha-steroid 4-dehydrogenase 1Proteinyes
inhibitor
HumanP18405 details
Estrogen receptorProteinyes
other
HumanP03372 details
Androgen receptorProteinunknown
agonist
HumanP10275 details
Related Articles
Absorption

Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.

Volume of distribution
  • 260 L [Healthy Female Volunteers under Fasting Conditions]
  • 1.8 L/kg
Protein binding

55%

Metabolism

Hepatic

Route of elimination

About 45% of levonorgestrel and its metabolites are excreted in the urine and about 32% are excreted in feces, mostly as glucuronide conjugates.

Half lifeNot Available
Clearance
  • 7.7 +/- 2.7 L/h [Healthy Female Volunteers under Fasting Conditions]
Toxicity

LD50 >5000 mg/kg (orally in rats)

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Levonorgestrel.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Levonorgestrel.Approved, Investigational
AcenocoumarolLevonorgestrel may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Levonorgestrel.Withdrawn
AcitretinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Adapalene.Approved
AicarThe therapeutic efficacy of Aicar can be decreased when used in combination with Levonorgestrel.Experimental
AlitretinoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Levonorgestrel.Approved
AmiodaroneThe metabolism of Levonorgestrel can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Amobarbital.Approved, Illicit
AncrodThe therapeutic efficacy of Ancrod can be decreased when used in combination with Levonorgestrel.Investigational
Antithrombin III humanThe therapeutic efficacy of Antithrombin III human can be decreased when used in combination with Levonorgestrel.Approved
ApixabanThe therapeutic efficacy of Apixaban can be decreased when used in combination with Levonorgestrel.Approved
AprepitantThe serum concentration of Levonorgestrel can be decreased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe therapeutic efficacy of Ardeparin can be decreased when used in combination with Levonorgestrel.Approved, Withdrawn
ArgatrobanThe therapeutic efficacy of Argatroban can be decreased when used in combination with Levonorgestrel.Approved, Investigational
ArtemetherThe serum concentration of Levonorgestrel can be decreased when it is combined with Artemether.Approved
AtazanavirThe serum concentration of Levonorgestrel can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Levonorgestrel can be decreased when combined with Atomoxetine.Approved
BarbexacloneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Barbital.Illicit
BecaplerminThe therapeutic efficacy of Becaplermin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
BexaroteneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Bexarotene.Approved, Investigational
BexaroteneThe serum concentration of Levonorgestrel can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe therapeutic efficacy of Bivalirudin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
BoceprevirThe serum concentration of Levonorgestrel can be increased when it is combined with Boceprevir.Approved, Investigational
BortezomibThe metabolism of Levonorgestrel can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Levonorgestrel can be decreased when it is combined with Bosentan.Approved, Investigational
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Levonorgestrel.Withdrawn
C1 Esterase Inhibitor (Human)Levonorgestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Levonorgestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Levonorgestrel.Approved
CarbamazepineThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Carbamazepine.Approved, Investigational
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Levonorgestrel.Experimental
CeritinibThe serum concentration of Levonorgestrel can be increased when it is combined with Ceritinib.Approved
CertoparinThe therapeutic efficacy of Certoparin can be decreased when used in combination with Levonorgestrel.Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Levonorgestrel.Approved
CholestyramineThe serum concentration of Levonorgestrel can be decreased when it is combined with Cholestyramine.Approved
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Levonorgestrel.Experimental
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Levonorgestrel.Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Levonorgestrel can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Levonorgestrel can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Levonorgestrel can be decreased when it is combined with Clobazam.Approved, Illicit
ClotrimazoleThe metabolism of Levonorgestrel can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Levonorgestrel can be increased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Levonorgestrel can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Levonorgestrel can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Levonorgestrel can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Levonorgestrel can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Levonorgestrel can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe therapeutic efficacy of Dabigatran etexilate can be decreased when used in combination with Levonorgestrel.Approved
DabrafenibThe serum concentration of Levonorgestrel can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Levonorgestrel.Approved
DarunavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Levonorgestrel can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Levonorgestrel can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Levonorgestrel can be decreased when combined with Delavirdine.Approved
DesirudinThe therapeutic efficacy of Desirudin can be decreased when used in combination with Levonorgestrel.Approved
DexamethasoneThe serum concentration of Levonorgestrel can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextranThe therapeutic efficacy of Dextran can be decreased when used in combination with Levonorgestrel.Approved, Vet Approved
Dextran 40The therapeutic efficacy of Dextran 40 can be decreased when used in combination with Levonorgestrel.Approved
DicoumarolLevonorgestrel may decrease the anticoagulant activities of Dicoumarol.Approved
DihydroergotamineThe metabolism of Levonorgestrel can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Levonorgestrel can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Levonorgestrel can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Levonorgestrel can be decreased when combined with Dronedarone.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Levonorgestrel.Approved
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Levonorgestrel.Approved, Vet Approved
EdoxabanThe therapeutic efficacy of Edoxaban can be decreased when used in combination with Levonorgestrel.Approved
EfavirenzThe serum concentration of Levonorgestrel can be decreased when it is combined with Efavirenz.Approved, Investigational
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Levonorgestrel.Approved
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Levonorgestrel.Approved
EnzalutamideThe serum concentration of Levonorgestrel can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Levonorgestrel can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Levonorgestrel can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateLevonorgestrel may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtravirineThe serum concentration of Levonorgestrel can be decreased when it is combined with Etravirine.Approved
ExenatideThe serum concentration of Levonorgestrel can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Levonorgestrel can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Levonorgestrel.Approved
FluconazoleThe metabolism of Levonorgestrel can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Levonorgestrel can be decreased when combined with Fluvoxamine.Approved, Investigational
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Levonorgestrel.Approved, Investigational
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Levonorgestrel resulting in a loss in efficacy.Approved
FosaprepitantThe serum concentration of Levonorgestrel can be decreased when it is combined with Fosaprepitant.Approved
FosphenytoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Levonorgestrel can be increased when it is combined with Fusidic Acid.Approved
GabexateThe therapeutic efficacy of Gabexate can be decreased when used in combination with Levonorgestrel.Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Levonorgestrel.Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Levonorgestrel.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Levonorgestrel.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Levonorgestrel.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Levonorgestrel.Approved
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Levonorgestrel.Approved
GriseofulvinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Griseofulvin.Approved, Vet Approved
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Hexobarbital.Approved
IdelalisibThe serum concentration of Levonorgestrel can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Levonorgestrel can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Levonorgestrel can be decreased when combined with Indinavir.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Levonorgestrel.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Levonorgestrel.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Levonorgestrel.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Levonorgestrel.Approved
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Levonorgestrel.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Levonorgestrel.Approved
IsavuconazoniumThe metabolism of Levonorgestrel can be decreased when combined with Isavuconazonium.Approved, Investigational
IsotretinoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Isotretinoin.Approved
IsradipineThe metabolism of Levonorgestrel can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Levonorgestrel can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Levonorgestrel can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Levonorgestrel can be decreased when combined with Ketoconazole.Approved, Investigational
LamotrigineThe serum concentration of Levonorgestrel can be decreased when it is combined with Lamotrigine.Approved, Investigational
LepirudinThe therapeutic efficacy of Lepirudin can be decreased when used in combination with Levonorgestrel.Approved
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Levonorgestrel.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Levonorgestrel.Approved
LopinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Lopinavir.Approved
LovastatinThe metabolism of Levonorgestrel can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Levonorgestrel can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Levonorgestrel can be decreased when it is combined with Lumacaftor.Approved
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Levonorgestrel.Approved
MethohexitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Methylphenobarbital.Approved
MetreleptinThe serum concentration of Levonorgestrel can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe serum concentration of Levonorgestrel can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Levonorgestrel.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Levonorgestrel.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
MitotaneThe serum concentration of Levonorgestrel can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Levonorgestrel can be decreased when it is combined with Modafinil.Approved, Investigational
Mycophenolic acidThe serum concentration of Levonorgestrel can be decreased when it is combined with Mycophenolic acid.Approved
NadroparinThe therapeutic efficacy of Nadroparin can be decreased when used in combination with Levonorgestrel.Approved
NafamostatThe therapeutic efficacy of Nafamostat can be decreased when used in combination with Levonorgestrel.Approved, Investigational
NafcillinThe serum concentration of Levonorgestrel can be decreased when it is combined with Nafcillin.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
NefazodoneThe metabolism of Levonorgestrel can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Levonorgestrel can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Levonorgestrel can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Levonorgestrel can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Levonorgestrel can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Levonorgestrel can be increased when it is combined with Osimertinib.Approved
OxcarbazepineThe serum concentration of Levonorgestrel can be decreased when it is combined with Oxcarbazepine.Approved
PalbociclibThe serum concentration of Levonorgestrel can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Levonorgestrel 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 Levonorgestrel.Approved
PerampanelThe serum concentration of Levonorgestrel can be decreased when it is combined with Perampanel.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Levonorgestrel.Approved, Withdrawn
PhenindioneLevonorgestrel may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Levonorgestrel can be increased when combined with Phenobarbital.Approved
PhenprocoumonLevonorgestrel may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Levonorgestrel.Approved, Investigational
PosaconazoleThe metabolism of Levonorgestrel can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
PrimidoneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Primidone.Approved, Vet Approved
Protein S humanThe therapeutic efficacy of Protein S human can be decreased when used in combination with Levonorgestrel.Approved
PrucaloprideThe serum concentration of Levonorgestrel can be decreased when it is combined with Prucalopride.Approved
RanolazineThe metabolism of Levonorgestrel can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
ReviparinThe therapeutic efficacy of Reviparin can be decreased when used in combination with Levonorgestrel.Approved
RifabutinThe metabolism of Levonorgestrel can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Levonorgestrel can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Levonorgestrel can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Levonorgestrel can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe therapeutic efficacy of Rivaroxaban can be decreased when used in combination with Levonorgestrel.Approved
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Levonorgestrel.Approved, Investigational
SaquinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Levonorgestrel.Approved
SecobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Levonorgestrel.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Levonorgestrel can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Levonorgestrel can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Levonorgestrel can be increased when it is combined with Simeprevir.Approved
SitagliptinThe therapeutic efficacy of Sitagliptin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
St. John's WortThe serum concentration of Levonorgestrel can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Levonorgestrel can be increased when it is combined with Stiripentol.Approved
SugammadexThe serum concentration of Levonorgestrel can be decreased when it is combined with Sugammadex.Approved
SulfisoxazoleThe metabolism of Levonorgestrel can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Levonorgestrel.Approved, Investigational
TelaprevirThe serum concentration of Levonorgestrel can be decreased when it is combined with Telaprevir.Approved
TelithromycinThe metabolism of Levonorgestrel can be decreased when combined with Telithromycin.Approved
ThalidomideLevonorgestrel may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Thiopental.Approved, Vet Approved
TiclopidineThe metabolism of Levonorgestrel can be decreased when combined with Ticlopidine.Approved
TipranavirThe serum concentration of Levonorgestrel can be increased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Levonorgestrel can be decreased when it is combined with Tocilizumab.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Levonorgestrel.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Levonorgestrel.Approved
TopiramateThe serum concentration of Levonorgestrel can be decreased when it is combined with Topiramate.Approved
Tranexamic AcidLevonorgestrel may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Levonorgestrel.Withdrawn
UlipristalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Ulipristal.Approved
VenlafaxineThe metabolism of Levonorgestrel can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Levonorgestrel can be decreased when combined with Verapamil.Approved
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Levonorgestrel.Approved, Investigational
VoriconazoleThe serum concentration of Levonorgestrel can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinLevonorgestrel may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe therapeutic efficacy of Ximelagatran can be decreased when used in combination with Levonorgestrel.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Levonorgestrel can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take at the same time everyday.
  • Take with food.
References
Synthesis Reference

Yu-Sheng Chang, Shu-Ping Chen, “Levonorgestrel Crystallization.” U.S. Patent US20090069584, issued March 12, 2009.

US20090069584
General References
  1. Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [PubMed:10715364 ]
  2. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771 ]
External Links
ATC CodesG03FA11G03FB09G03AC03G03AB03G03AD01G03AA07
AHFS Codes
  • 68:12.00
PDB EntriesNot Available
FDA labelDownload (8.04 KB)
MSDSDownload (19.7 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableContraception / Postcoital Contraception2
1CompletedNot AvailableInfections, Human Immunodeficiency Virus and Hepatitis1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Mirabegron1
1CompletedDiagnosticEndometriosis1
1CompletedPreventionFemale Contraception1
1CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV) Infections / Pharmacokinetics1
1CompletedTreatmentDiabetes / Type 2 Diabetes Mellitus (T2D)1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHepatitis C, Chronic1
1CompletedTreatmentType 2 Diabetes Mellitus (T2D)1
1Not Yet RecruitingPreventionHIV Prevention1
1RecruitingHealth Services ResearchHIV Disease1
1RecruitingPreventionContraception1
1RecruitingTreatmentHealthy Volunteers1
1, 2Active Not RecruitingPreventionContraception / Hemostasis Parameter / Liver Metabolism1
1, 2Unknown StatusTreatmentHealthy Volunteers1
2CompletedBasic ScienceHemostasis / Oral Contraceptives (OC)1
2CompletedPreventionBreakthrough Bleeding1
2CompletedPreventionContraception2
2CompletedPreventionEndometrial Cancers1
2CompletedPreventionMigraines1
2CompletedTreatmentBone Mineral Density1
2CompletedTreatmentContraception1
2CompletedTreatmentContraception / HIV Disease1
2CompletedTreatmentDysmenorrhea1
2CompletedTreatmentEndometriosis1
2CompletedTreatmentOvulation1
2CompletedTreatmentOvulation Suppression1
2RecruitingTreatmentAnorexia Nervosa (AN) / Osteoporosis1
2RecruitingTreatmentComplex Endometrial Hyperplasia With Atypia / Grade 1 Endometrial Endometrioid Adenocarcinoma1
2RecruitingTreatmentContraception / HIV Disease1
2Unknown StatusPreventionCancer, Ovarian1
2, 3CompletedTreatmentPost coital contraception1
2, 3SuspendedTreatmentEndometriosis1
3Active Not RecruitingTreatmentContraception1
3CompletedEducational/Counseling/TrainingOral Contraceptives (OC)1
3CompletedPreventionContraception7
3CompletedPreventionHealthy Volunteers1
3CompletedTreatmentContraception1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeavy Menstrual Bleeding1
3CompletedTreatmentMenorrhagia2
3CompletedTreatmentPost coital contraception1
3RecruitingTreatmentContraception2
3Unknown StatusTreatmentOral Contraceptives (OC)1
3WithdrawnTreatmentOsteopenia1
4Active Not RecruitingNot AvailableContraception / HIV Disease1
4Active Not RecruitingBasic ScienceContraception1
4CompletedNot AvailableContraception1
4CompletedNot AvailableContraception / Epilepsies1
4CompletedNot AvailableEndometriosis1
4CompletedBasic ScienceBody Weights / Contraception1
4CompletedDiagnosticBody Weights / Contraceptive Usage1
4CompletedHealth Services ResearchPost Partum1
4CompletedPreventionContraception1
4CompletedPreventionPostpartum Contraception1
4CompletedTreatmentContraception3
4CompletedTreatmentContraception / Medicated Intrauterine Devices1
4CompletedTreatmentContraception / Menorrhagia1
4CompletedTreatmentContraceptive Usage1
4CompletedTreatmentHot Flashes1
4CompletedTreatmentInfertilities1
4CompletedTreatmentPost coital contraception1
4CompletedTreatmentUterine Hemorrhage1
4Not Yet RecruitingTreatmentBMI >30 kg/m21
4Not Yet RecruitingTreatmentEndometriosis1
4RecruitingBasic ScienceContraception1
4RecruitingPreventionContraception / Malposition of Intrauterine Contraceptive Device1
4RecruitingTreatmentContraception / HIV Disease1
4TerminatedTreatmentAbnormal Uterine Bleeding, Unspecified / Uterine Bleeding Heavy1
Not AvailableActive Not RecruitingNot AvailableBMI >30 kg/m21
Not AvailableActive Not RecruitingNot AvailableContraception / HIV Disease / Immune Cells (Mucosal and Systemic)1
Not AvailableActive Not RecruitingPreventionContraception1
Not AvailableCompletedNot AvailableContraception5
Not AvailableCompletedNot AvailableContraception / Endometrial Hyperplasia / Estrogen Replacement Therapy / Menorrhagia1
Not AvailableCompletedNot AvailableFemale Contraception1
Not AvailableCompletedNot AvailableIdiopathic Menorrhagia2
Not AvailableCompletedNot AvailableMenorrhagia2
Not AvailableCompletedNot AvailableNulliparous1
Not AvailableCompletedNot AvailablePregnancy2
Not AvailableCompletedNot AvailableQuality of Life1
Not AvailableCompletedBasic ScienceCoronary Heart Disease (CHD)1
Not AvailableCompletedPreventionPregnancy2
Not AvailableCompletedTreatmentInfertilities1
Not AvailableCompletedTreatmentMenopausal and Other Perimenopausal Disorders1
Not AvailableCompletedTreatmentTemporomandibular Joint Disorders1
Not AvailableRecruitingNot AvailableContraception1
Not AvailableRecruitingNot AvailableIntrauterine Devices, Medicated1
Not AvailableRecruitingNot AvailableMenorrhagia, Dysmenorrhea1
Not AvailableTerminatedNot AvailableInitiation of Depo-Provera (DMPA) / Initiation of Mirena (LNG-IUD) / Initiation of Oral Contraception (OC)1
Not AvailableUnknown StatusPreventionContraception1
Not AvailableUnknown StatusTreatmentFemale Contraception1
Pharmacoeconomics
Manufacturers
  • Wyeth pharmaceuticals inc
  • Population council
  • Population council center for biomedical research
  • Bayer healthcare pharmaceuticals inc
  • Watson laboratories inc
  • Duramed pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
PatchTransdermal
Insert, extended releaseIntrauterine13.5 mg
Insert, extended releaseIntrauterine19.5 mg
Intrauterine deviceIntrauterine19.5 mg/1
Kit
Insert, extended releaseIntrauterine52 mg
Intrauterine deviceIntrauterine52 mg/1
TabletOral1.5 mg/1.5mg
TabletOral.75 mg/1
ImplantSubcutaneous36 mg
KitOral
TabletOral0.75 mg
TabletOral1.5 mg
TabletOral1.5 mg/1
Intrauterine deviceIntrauterine13.5 mg/1
Prices
Unit descriptionCostUnit
Mirena system843.66USD each
Mirena System 52 mg Insert363.54USD insert
Nordette (28) 28 0.15-30 mg-mcg tablet Disp Pack79.32USD disp
Plan b one-step 1.5 mg tablet40.62USD tablet
Next choice 0.75 mg tablet36.56USD tablet
Levora 0.15/30 (28) 28 0.15-30 mg-mcg tablet Disp Pack32.99USD disp
Trivora (28) 28 tablet Box29.99USD box
Plan b 0.75 mg tablet15.65USD tablet
Nordette-28 tablet2.75USD tablet
Nordette-8 tablet2.39USD tablet
Levlen 28 tablet1.3USD tablet
Tri-levlen 28 tablet1.25USD tablet
Levora-28 tablet1.1USD tablet
Trivora-28 tablet0.98USD tablet
Acidophilus 10 bu/gm granules0.6USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5785053 No1995-12-052015-12-05Us
US5898032 No1997-06-232017-06-23Us
US6156742 No2000-12-052020-12-05Us
US6500814 No1998-09-032018-09-03Us
US7252839 No2003-11-132023-11-13Us
US7320969 No2004-01-302024-01-30Us
US7615545 No2003-06-152023-06-15Us
US7855190 No2008-12-052028-12-05Us
US7858605 No2003-06-232023-06-23Us
US8415332 No2009-03-112029-03-11Us
US8450299 No2005-10-072025-10-07Us
USRE39861 No1997-06-232017-06-23Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)240 °CPhysProp
water solubility2.05 mg/LNot Available
logP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00583 mg/mLALOGPS
logP3.25ALOGPS
logP3.66ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.03 m3·mol-1ChemAxon
Polarizability36.73 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9453
Caco-2 permeable+0.8094
P-glycoprotein substrateSubstrate0.6648
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.7697
CYP450 2C9 substrateNon-substrate0.7904
CYP450 2D6 substrateNon-substrate0.9165
CYP450 3A4 substrateSubstrate0.7239
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.7772
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.516
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9328
BiodegradationNot ready biodegradable0.9814
Rat acute toxicity1.8264 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8205
hERG inhibition (predictor II)Non-inhibitor0.7408
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0439000000-bcbc7c657a115dced40aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a5a-3920000000-edbd3785e7d20d9e81beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
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
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:6443 )
  • 3-oxo Delta(4)-steroid (CHEBI:6443 )
  • 17beta-hydroxy steroid (CHEBI:6443 )
  • Pregnane and derivatives [Fig] (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
binder
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. Maruo T, Ohara N, Matsuo H, Xu Q, Chen W, Sitruk-Ware R, Johansson ED: Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception. 2007 Jun;75(6 Suppl):S99-103. Epub 2007 Mar 21. [PubMed:17531625 ]
  2. 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 ]
  3. Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506 ]
  4. Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229 ]
  5. Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Electron carrier activity
Specific Function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular Weight:
29458.18 Da
References
  1. Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [PubMed:11521119 ]
  2. Rabe T, Kowald A, Ortmann J, Rehberger-Schneider S: Inhibition of skin 5 alpha-reductase by oral contraceptive progestins in vitro. Gynecol Endocrinol. 2000 Aug;14(4):223-30. [PubMed:11075290 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
other
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Vereide AB, Kaino T, Sager G, Arnes M, Orbo A: Effect of levonorgestrel IUD and oral medroxyprogesterone acetate on glandular and stromal progesterone receptors (PRA and PRB), and estrogen receptors (ER-alpha and ER-beta) in human endometrial hyperplasia. Gynecol Oncol. 2006 May;101(2):214-23. Epub 2005 Dec 1. [PubMed:16325240 ]
  2. 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 ]
  3. Abdel-Aleem H, Shaaban OM, Amin AF, Abdel-Aleem AM: Tamoxifen treatment of bleeding irregularities associated with Norplant use. Contraception. 2005 Dec;72(6):432-7. Epub 2005 Aug 9. [PubMed:16307966 ]
  4. Sun D, Yan C, Jacobson A, Jiang H, Carroll MA, Huang A: Contribution of epoxyeicosatrienoic acids to flow-induced dilation in arteries of male ERalpha knockout mice: role of aromatase. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1239-46. Epub 2007 Jul 18. [PubMed:17634204 ]
  5. Vijayanathan V, Venkiteswaran S, Nair SK, Verma A, Thomas TJ, Zhu BT, Thomas T: Physiologic levels of 2-methoxyestradiol interfere with nongenomic signaling of 17beta-estradiol in human breast cancer cells. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2038-48. [PubMed:16609013 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731 ]
  2. Freyberger A, Witters H, Weimer M, Lofink W, Berckmans P, Ahr HJ: Screening for (anti)androgenic properties using a standard operation protocol based on the human stably transfected androgen sensitive PALM cell line. First steps towards validation. Reprod Toxicol. 2010 Aug;30(1):9-17. doi: 10.1016/j.reprotox.2009.10.002. Epub 2009 Oct 27. [PubMed:19836445 ]
  3. Freyberger A, Weimer M, Tran HS, Ahr HJ: Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. [PubMed:19833195 ]
  4. Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361 ]

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
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 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 ]
Drug created on June 13, 2005 07:24 / Updated on May 28, 2017 03:57