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Identification
NameLevonorgestrel
Accession NumberDB00367  (APRD00106, APRD00754, DB00506)
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 Identifiers
  • Wy 5104
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jaydessinsert (extended-release)13.5 mgintrauterineBayer Inc2013-10-30Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Lilettaintrauterine device52 mg/1intrauterineActavis Pharma, Inc.2015-02-262016-02-05Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenaintrauterine device52 mg/1intrauterineBayer Health Care Pharmaceuticals Inc.2009-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenaintrauterine device52 mg/1intrauterineBayer Health Care Pharmaceuticals Inc.2009-10-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenainsert (extended-release)52 mgintrauterineBayer Inc2001-02-22Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Norplant System Kit 36mg/implantimplant36 mgsubcutaneousWyeth Ayerst Canada Inc.1994-03-212002-09-24Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Plan Btablet.75 mg/1oralPhysicians Total Care, Inc.2003-08-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralRebel Distributors Corp2009-07-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2009-09-142016-04-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2009-07-282016-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Skylaintrauterine device13.5 mg/1intrauterineBayer Health Care Pharmaceuticals Inc.2013-01-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Levonorgestreltablet1.5 mg/1oralWatson Pharma, Inc.2012-07-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mg/1oralNovel Laboratories, Inc.2013-02-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mg/1oralPharmacist Pharmaceutical, LLC2013-06-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mg/1oralNovel Laboratories, Inc.2013-02-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestrel Emergency Contraceptivetablet.75 mg/1oralPerrigo New York Inc2011-03-10Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
My Waytablet1.5 mg/1oralGavis Pharmaceuticals, LLC.2013-02-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralRebel Distributors Corp.2009-07-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralWatson Pharma, Inc.2009-07-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralWatson Pharma, Inc.2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralPreferred Pharmaceuticals, Inc2012-02-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralDispensing Solutions, Inc.2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mg/1oralH.J. Harkins Company, Inc.2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Afteratablet1.5 mg/1oralTeva Women's Health, Inc.2014-10-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Afterpilltablet1.5 mg/1oralSyzygy Healthcare Solutions, LLC2013-02-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Athentia Nexttablet1.5 mg/1oralAurohealth LLC2015-12-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Backup Plantablet0.75 mgoralApotex IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Backup Plan Onesteptablet1.5 mgoralApotex IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Contingencytablet0.75 mgoralJai Pharma LimitedNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Contingency Onetablet1.5 mgoralJai Pharma LimitedNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Econtra Eztablet1.5 mg/1oralAfaxys Inc.2015-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fallback Solotablet1.5 mg/1oralLupin Pharmaceuticals, Inc.2014-07-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mg/1oralLotus Pharmaceutical Co., Ltd. Nantou Plant2015-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mg/1oralPharmacist Pharmaceutical, LLC2014-03-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestrel Tablets, 0.75mgtablet0.75 mgoralLUPIN LIMITEDNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Morning Aftertablet1.5 mg/1.5mgoralRapha Pharmaceuticals, Inc.2015-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
My Waytablet1.5 mg/1oralGAVIS Pharmaceuticals, LLC2013-02-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet0.75 mgoralActavis Pharma Company2011-05-13Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Next Choice One Dosetablet1.5 mg/1oralWatson Pharma, Inc.2014-05-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Norlevotablet0.75 mgoralLaboratoire HRA Pharma2009-05-15Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Norlevotablet1.5 mgoralLaboratoire HRA PharmaNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Opcicon One-steptablet1.5 mg/1oralSun Pharmaceutical Industries Limited2014-09-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Option 2tablet0.75 mgoralPerrigo International2013-09-25Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Plan Btablet0.75 mgoralTeva Branded Pharmaceutical Products R&D Inc2000-02-24Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Plan Btablet1.5 mgoralTeva Branded Pharmaceutical Products R&D Inc2015-07-23Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2013-08-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2013-12-12Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2013-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mg/1oralTeva Women's Health, Inc.2013-07-082016-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Take Actiontablet1.5 mg/1oralTeva Women's Health, Inc.2014-02-17Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Teva-levonorgestreltablet0.75 mgoralTeva Canada LimitedNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International Brands
NameCompany
JadelleBayer
LevonelleBayer
MedonorMedopharm
MicrolutBayer
MicrovalWyeth
NeogestSchering
NorgestonBayer
NorplantBayer
PostinorGedeon Richter
Brand mixtures
NameLabellerIngredients
Alesse 21Pfizer Canada Inc
Alesse 28Pfizer Canada Inc
AltaveraSandoz Inc
Alysena 21Apotex Inc
Alysena 28Apotex Inc
AmethystWatson Pharma, Inc.
AubraAfaxys Inc.
AvianeBarr Laboratories Inc.
Aviane 21Teva Canada Limited
Aviane 28Teva Canada Limited
Aviane 28 DayRebel Distributors Corp
ChatealAfaxys Inc.
Climara ProBayer Health Care Pharmaceuticals Inc.
DayseeLupin Pharmaceuticals, Inc.
DelylaOhm Laboratories Inc.
EnpresseBarr Laboratories Inc.
Esme 21Jai Pharma Limited
Esme 28Jai Pharma Limited
FalessaAvion Pharmaceuticals, Llc
FalminaNorthstar Rx LLC
IndayoJai Pharma Limited
IntrovaleSandoz Inc
JolessaPhysicians Total Care, Inc.
KurveloLupin Pharmaceuticals, Inc.
LessinaBarr Laboratories Inc.
LevonestNorthstar Rx LLC
Levonorgestrel and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Levonorgestrel and Ethinyl Estradiol and Ethinyl EstradiolLupin Pharmaceuticals, Inc.
Levonorgestrel and Ethinyl Estradiol Tablets, 0.1 Mg/0.02 mgLUPIN LIMITED
LevoraRebel Distributors Corp
LuteraWatson Pharma, Inc.
Lutera 21Cobalt Pharmaceuticals Company
Lutera 28Cobalt Pharmaceuticals Company
MarlissaGlenmark Pharmaceuticals Inc., Usa
Min-ovral 21Pfizer Canada Inc
Min-ovral 21 TabWyeth Ltd.
Min-ovral 28Pfizer Canada Inc
Min-ovral 28 TabWyeth Ltd.
MyzilraQualitest Pharmaceuticals
OrsythiaQualitest Pharmaceuticals
Ovima 21Apotex Inc
Ovima 28Apotex Inc
PortiaBarr Laboratories Inc.
Portia 21Teva Canada Limited
Portia 28Teva Canada Limited
Preven Emergency ContraceptiveGynÉtics Ltd/LtÉe
Preven TabletsShire Pharma Canada Ulc
QuasenseWatson Pharma, Inc.
SeasonaleTeva Women's Health Inc
SetlakinNorthstar Rx LLC
SronyxWatson Pharma, Inc.
Vienva TmSandoz Inc
SaltsNot Available
Categories
CAS number797-63-7
WeightAverage: 312.4458
Monoisotopic: 312.20893014
Chemical FormulaC21H28O2
InChI KeyInChIKey=WWYNJERNGUHSAO-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]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:6443 )
  • 3-oxo Delta(4)-steroid (CHEBI:6443 )
  • 17beta-hydroxy steroid (CHEBI:6443 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153 )
  • Pregnane and derivatives [Fig] (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119 )
Pharmacology
IndicationFor the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
PharmacodynamicsLevonorgestrel 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 actionBinds 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.
AbsorptionLevonorgestrel 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 binding55%
Metabolism

Hepatic

Route of eliminationAbout 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]
ToxicityLD50 >5000 mg/kg (orally in rats)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9453
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 )
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-release)intrauterine13.5 mg
Kit
Insert (extended-release)intrauterine52 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
CountryPatent NumberApprovedExpires (estimated)
United States57850531995-12-052015-12-05
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point240 °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
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR13C NMR SpectrumNot Available
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
  2. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. Pubmed
  3. FDA label.
External Links
ATC CodesG03AC03G03AD01
AHFS Codes
  • 68:12.00
PDB EntriesNot Available
FDA labelDownload (8.04 KB)
MSDSDownload (19.7 KB)
Interactions
Drug Interactions
Drug
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Levonorgestrel.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Levonorgestrel.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Levonorgestrel.
AcitretinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Acitretin.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Levonorgestrel.
AprepitantThe serum concentration of Levonorgestrel can be decreased when it is combined with Aprepitant.
ArtemetherThe serum concentration of Levonorgestrel can be decreased when it is combined with Artemether.
AtazanavirThe serum concentration of Levonorgestrel can be increased when it is combined with Atazanavir.
BexaroteneThe serum concentration of Levonorgestrel can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Levonorgestrel can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Levonorgestrel can be decreased when it is combined with Bosentan.
ButabarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Levonorgestrel may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Levonorgestrel.
CarbamazepineThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Carbamazepine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Levonorgestrel.
Citric AcidThe therapeutic efficacy of Citric Acid can be decreased when used in combination with Levonorgestrel.
ClobazamThe serum concentration of Levonorgestrel can be decreased when it is combined with Clobazam.
CobicistatThe serum concentration of Levonorgestrel can be increased when it is combined with Cobicistat.
ColesevelamThe serum concentration of Levonorgestrel can be decreased when it is combined with Colesevelam.
DabrafenibThe serum concentration of Levonorgestrel can be decreased when it is combined with Dabrafenib.
DalteparinThe therapeutic efficacy of Dalteparin can be decreased when used in combination with Levonorgestrel.
DarunavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Darunavir.
DeferasiroxThe serum concentration of Levonorgestrel can be decreased when it is combined with Deferasirox.
DicoumarolLevonorgestrel may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidThe therapeutic efficacy of Edetic Acid can be decreased when used in combination with Levonorgestrel.
EfavirenzThe serum concentration of Levonorgestrel can be decreased when it is combined with Efavirenz.
EnoxaparinThe therapeutic efficacy of Enoxaparin can be decreased when used in combination with Levonorgestrel.
Eslicarbazepine acetateThe serum concentration of Levonorgestrel can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Levonorgestrel.
ExenatideThe serum concentration of Levonorgestrel can be decreased when it is combined with Exenatide.
FelbamateThe serum concentration of Levonorgestrel can be decreased when it is combined with Felbamate.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Levonorgestrel.
Fondaparinux sodiumThe therapeutic efficacy of Fondaparinux sodium can be decreased when used in combination with Levonorgestrel.
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.
FosaprepitantThe serum concentration of Levonorgestrel can be decreased when it is combined with Fosaprepitant.
FosphenytoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Fosphenytoin.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Levonorgestrel.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Levonorgestrel.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Levonorgestrel.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Levonorgestrel.
GriseofulvinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Griseofulvin.
HeparinThe therapeutic efficacy of Heparin can be decreased when used in combination with Levonorgestrel.
HeptabarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Hexobarbital.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Levonorgestrel.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Levonorgestrel.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Levonorgestrel.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Levonorgestrel.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Levonorgestrel.
Insulin RegularThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Levonorgestrel.
Insulin, isophaneThe therapeutic efficacy of Insulin, isophane can be decreased when used in combination with Levonorgestrel.
LamotrigineThe serum concentration of Levonorgestrel can be decreased when it is combined with Lamotrigine.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Levonorgestrel.
LopinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Lopinavir.
LumacaftorThe serum concentration of Levonorgestrel can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Levonorgestrel.
MethohexitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Methohexital.
MetreleptinThe serum concentration of Levonorgestrel can be decreased when it is combined with Metreleptin.
MifepristoneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Mifepristone.
MitotaneThe serum concentration of Levonorgestrel can be decreased when it is combined with Mitotane.
Mycophenolic acidThe serum concentration of Levonorgestrel can be decreased when it is combined with Mycophenolic acid.
NelfinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Nelfinavir.
NevirapineThe serum concentration of Levonorgestrel can be decreased when it is combined with Nevirapine.
OxcarbazepineThe serum concentration of Levonorgestrel can be decreased when it is combined with Oxcarbazepine.
PentobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Pentobarbital.
PerampanelThe serum concentration of Levonorgestrel can be decreased when it is combined with Perampanel.
PhenindioneThe therapeutic efficacy of Phenindione can be decreased when used in combination with Levonorgestrel.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be decreased when used in combination with Levonorgestrel.
PhenytoinThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Phenytoin.
PrimidoneThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Primidone.
PrucaloprideThe serum concentration of Levonorgestrel can be decreased when it is combined with Prucalopride.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Levonorgestrel.
RifabutinThe serum concentration of Levonorgestrel can be decreased when it is combined with Rifabutin.
SaquinavirThe serum concentration of Levonorgestrel can be decreased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Levonorgestrel.
SecobarbitalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Secobarbital.
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Levonorgestrel.
SiltuximabThe serum concentration of Levonorgestrel can be decreased when it is combined with Siltuximab.
St. John's WortThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with St. John's Wort.
SugammadexThe serum concentration of Levonorgestrel can be decreased when it is combined with Sugammadex.
SulodexideThe therapeutic efficacy of Sulodexide can be decreased when used in combination with Levonorgestrel.
TelaprevirThe serum concentration of Levonorgestrel can be decreased when it is combined with Telaprevir.
ThalidomideLevonorgestrel may increase the thrombogenic activities of Thalidomide.
TipranavirThe serum concentration of Levonorgestrel can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Levonorgestrel can be decreased when it is combined with Tocilizumab.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Levonorgestrel.
TopiramateThe serum concentration of Levonorgestrel can be decreased when it is combined with Topiramate.
Tranexamic AcidLevonorgestrel may increase the thrombogenic activities of Tranexamic Acid.
TreprostinilThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Levonorgestrel.
UlipristalThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Ulipristal.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Levonorgestrel.
VoriconazoleThe serum concentration of Levonorgestrel can be increased when it is combined with Voriconazole.
WarfarinThe therapeutic efficacy of Warfarin can be decreased when used in combination with Levonorgestrel.
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.

Targets

1. Progesterone receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: binder

Components

Name UniProt ID Details
Progesterone receptor P06401 Details

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
  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
  3. Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. Pubmed
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
3-oxo-5-alpha-steroid 4-dehydrogenase 1 P18405 Details

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
  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

3. Estrogen receptor

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: other

Components

Name UniProt ID Details
Estrogen receptor P03372 Details

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
  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
  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
  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
  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

4. Androgen receptor

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

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
  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. Epub 2009 Oct 27. Pubmed
  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. Epub 2009 Oct 13. Pubmed
  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

Enzymes

1. Cytochrome P450 3A4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 19A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Aromatase P11511 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10