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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
SynonymLanguageCode
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-oneNot AvailableNot Available
(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-oneNot AvailableIUPAC
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-oneNot AvailableNot Available
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-oneNot AvailableNot Available
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-oneNot AvailableNot Available
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-oneNot AvailableNot Available
17-alpha-Ethynyl-13-ethyl-19-nortestosteroneNot AvailableNot Available
17-Ethynyl-18-methyl-19-nortestosteroneNot AvailableNot Available
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-olNot AvailableNot Available
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-oneNot AvailableNot Available
17alpha-Ethynyl-18-homo-19-nortestosteroneNot AvailableNot Available
18-Methyl-17-alpha-ethynyl-19-nortestosteroneNot AvailableNot Available
18-MethylnorethisteroneNot AvailableNot Available
d(-)-NorgestrelNot AvailableNot Available
JadelleNot AvailableNot Available
LevonelleNot AvailableNot Available
LevonorgestrelNot AvailableBAN, DCIT, USAN, BP 2011, Ph. Eur. 7, Ph. Int. 4, USP 34
LévonorgestrelNot AvailableDCF
LevonorgestrelumLatinINN
LevonovaNot AvailableNot Available
MicrolutNot AvailableNot Available
MicrolutonNot AvailableNot Available
MicrovalNot AvailableNot Available
MirenaNot AvailableNot Available
NorLevoNot AvailableNot Available
Plan bNot AvailableNot Available
PostinorNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Plan B One-steptablet1.5 mgoralRebel Distributors Corp2009-07-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenaintrauterine device52 mgintrauterineBayer Health Care Pharmaceuticals Inc.2009-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Skylaintrauterine device13.5 mgintrauterineBayer Health Care Pharmaceuticals Inc.2013-01-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenaintrauterine device52 mgintrauterineBayer Health Care Pharmaceuticals Inc.2009-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2009-07-282016-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2009-09-142016-04-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan Btablet.75 mgoralPhysicians Total Care, Inc.2003-08-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mirenainsert (extended-release)52 mgintrauterineBayer IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Jaydessinsert (extended-release)13.5 mgintrauterineBayer IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Next Choicetablet.75 mgoralRebel Distributors Corp.2009-07-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mgoralNovel Laboratories, Inc.2013-02-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mgoralNovel Laboratories, Inc.2013-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
My Waytablet1.5 mgoralGavis Pharmaceuticals, LLC.2013-02-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestrel Emergency Contraceptivetablet.75 mgoralPerrigo New York Inc2011-03-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mgoralWatson Pharma, Inc.2009-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mgoralWatson Pharma, Inc.2012-07-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mgoralWatson Pharma, Inc.2009-07-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mgoralH.J. Harkins Company, Inc.2009-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mgoralPharmacist Pharmaceutical, LLC2013-06-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mgoralDispensing Solutions, Inc.2009-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choicetablet.75 mgoralPreferred Pharmaceuticals, Inc2012-02-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
My Waytablet1.5 mgoralGAVIS Pharmaceuticals, LLC2013-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Econtra Eztablet1.5 mgoralAfaxys Inc.2015-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Take Actiontablet1.5 mgoralTeva Women's Health, Inc.2014-02-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Afteratablet1.5 mgoralTeva Women's Health, Inc.2014-10-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2013-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2013-12-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2013-08-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Plan B One-steptablet1.5 mgoralTeva Women's Health, Inc.2013-07-082016-09-30Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Next Choice One Dosetablet1.5 mgoralWatson Pharma, Inc.2014-05-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Opcicon One-steptablet1.5 mgoralSun Pharmaceutical Industries Limited2014-09-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Levonorgestreltablet1.5 mgoralPharmacist Pharmaceutical, LLC2014-03-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Afterpilltablet1.5 mgoralSyzygy Healthcare Solutions, LLC2013-02-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fallback Solotablet1.5 mgoralLupin Pharmaceuticals, Inc.2014-07-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Norlevotablet0.75 mgoralLaboratoire HRA PharmaNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International Brands
NameCompany
JadelleBayer
LevonelleBayer
MedonorMedopharm
MicrolutBayer
MicrovalWyeth
NeogestSchering
NorgestonBayer
NorplantBayer
PostinorGedeon Richter
Brand mixtures
Brand NameIngredients
AlesseEthinyl Estradiol + Levonorgestrel
AmethystLevonorgestrel + Ethinyl Estradiol
AvianeEthinyl Estradiol + Levonorgestrel
EnpresseEthinyl Estradiol + Levonorgestrel
JolessaEthinyl Estradiol + Levonorgestrel
LessinaEthinyl Estradiol + Levonorgestrel
LevlenEthinyl Estradiol + Levonorgestrel
LevoraEthinyl Estradiol + Levonorgestrel
Lo/OvralEthinyl Estradiol + Levonorgestrel
LogynonEthinyl Estradiol + Levonorgestrel
Logynon EDEthinyl Estradiol + Levonorgestrel
LuteraEthinyl Estradiol + Levonorgestrel
LybrelEthinyl Estradiol + Levonorgestrel
MicrogynEthinyl Estradiol + Levonorgestrel
Microgynon 30Ethinyl Estradiol + Levonorgestrel
Microgynon 30 EDEthinyl Estradiol + Levonorgestrel
Min-OvralEthinyl Estradiol + Levonorgestrel
NordetteEthinyl Estradiol + Levonorgestrel
NordiolEthinyl Estradiol + Levonorgestrel
OvranetteEthinyl Estradiol + Levonorgestrel
PortiaEthinyl Estradiol + Levonorgestrel
PrevenEthinyl Estradiol + Levonorgestrel
QuartetteLevonorgestrel/Ethinyl Estradiol + Ethinyl Estradiol
QuasenseEthinyl Estradiol + Levonorgestrel
RigevidonEthinyl Estradiol + Levonorgestrel
SeasonaleEthinyl Estradiol + Levonorgestrel
SeasoniqueEthinyl Estradiol + Levonorgestrel
SronyxEthinyl Estradiol + Levonorgestrel
StedirilEthinyl Estradiol + Levonorgestrel
Tri-Levlen 21Ethinyl Estradiol + Levonorgestrel
Trifeme 28Ethinyl Estradiol + Levonorgestrel
TrinordiolEthinyl Estradiol + Levonorgestrel
TriphasilEthinyl Estradiol + Levonorgestrel
TriquilarEthinyl Estradiol + Levonorgestrel
TrivoraEthinyl Estradiol + Levonorgestrel
SaltsNot Available
Categories
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]
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 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9232
CYP450 2C19 substrateInhibitor0.8994
CYP450 3A4 substrateNon-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
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
Insert (extended-release)intrauterine13.5 mg
Insert (extended-release)intrauterine52 mg
Intrauterine deviceintrauterine13.5 mg
Intrauterine deviceintrauterine52 mg
Tabletoral.75 mg
Tabletoral0.75 mg
Tabletoral1.5 mg
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
Spectra1D NMR
References
Synthesis Reference

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

US20090069584
General Reference
  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
AbciximabProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
AcenocoumarolProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
AcetohexamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AcitretinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
AlogliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AminoglutethimideMay increase the metabolism of Progestins.
AprepitantMay decrease the serum concentration of Contraceptives (Progestins).
ArtemetherMay decrease the serum concentration of Contraceptives (Progestins).
AtazanavirMay increase the serum concentration of Contraceptives (Progestins).
BoceprevirMay increase the serum concentration of Contraceptives (Progestins). This has been seen specifically with drospirenone. Boceprevir may increase the serum concentration of Contraceptives (Progestins). This has been seen specifically with norethindrone.
BosentanMay decrease the serum concentration of Contraceptives (Progestins).
ButabarbitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
ButethalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
CanagliflozinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
CarbamazepineMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
ChlorpropamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Citric AcidProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
ClobazamMay decrease the serum concentration of Contraceptives (Progestins).
ColesevelamMay decrease the serum concentration of Contraceptives (Progestins).
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DalteparinProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
DarunavirMay decrease the serum concentration of Contraceptives (Progestins).
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DicoumarolProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Edetic AcidProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
EfavirenzMay decrease the serum concentration of Contraceptives (Progestins).
EnoxaparinProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Ethyl biscoumacetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
ExenatideMay decrease the serum concentration of Oral Contraceptive (Progestins).
FelbamateMay decrease the serum concentration of Contraceptives (Progestins).
Fondaparinux sodiumProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
FosamprenavirContraceptives (Progestins) may decrease serum concentrations of the active metabolite(s) of Fosamprenavir. Fosamprenavir may decrease the serum concentration of Contraceptives (Progestins).
FosaprepitantMay decrease the serum concentration of Contraceptives (Progestins). The active metabolite aprepitant is likely responsible for this effect.
FosphenytoinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
GliclazideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlimepirideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GliquidoneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlyburideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GriseofulvinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
HeparinProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
HeptabarbitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
HexobarbitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
Insulin AspartHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin DetemirHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlargineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlulisineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin LisproHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin RegularHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin, isophaneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
LamotrigineMay decrease the serum concentration of Contraceptives (Progestins).
LinagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
LopinavirMay decrease the serum concentration of Contraceptives (Progestins). Lopinavir may increase the serum concentration of Contraceptives (Progestins).
MetforminHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
MethohexitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
MetreleptinMay decrease the serum concentration of Contraceptives (Progestins). Metreleptin may increase the serum concentration of Contraceptives (Progestins).
MifepristoneMay diminish the therapeutic effect of Contraceptives (Progestins). Mifepristone may increase the serum concentration of Contraceptives (Progestins).
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
NelfinavirMay decrease the serum concentration of Contraceptives (Progestins).
NevirapineMay decrease the serum concentration of Contraceptives (Progestins).
OxcarbazepineMay decrease the serum concentration of Contraceptives (Progestins).
PentobarbitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
PerampanelMay decrease the serum concentration of Contraceptives (Progestins).
PhenindioneProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
PhenprocoumonProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
PhenytoinMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
PrimidoneMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
prucaloprideMay decrease the serum concentration of Contraceptives (Progestins).
RepaglinideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
SaquinavirMay decrease the serum concentration of Contraceptives (Progestins).
SaxagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
SecobarbitalMay diminish the therapeutic effect of Contraceptives (Progestins). Contraceptive failure is possible.
SelegilineContraceptives (Progestins) may increase the serum concentration of Selegiline.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SugammadexMay decrease the serum concentration of Contraceptives (Progestins).
SulodexideProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
TelaprevirMay decrease the serum concentration of Contraceptives (Progestins).
ThalidomideContraceptives (Progestins) may enhance the thrombogenic effect of Thalidomide.
TipranavirMay increase the serum concentration of Contraceptives (Progestins).
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TolbutamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
TopiramateMay decrease the serum concentration of Contraceptives (Progestins).
Tranexamic AcidContraceptives (Progestins) may enhance the thrombogenic effect of Tranexamic Acid.
TreprostinilProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
UlipristalMay diminish the therapeutic effect of Progestins. Progestins may diminish the therapeutic effect of Ulipristal.
VildagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
VoriconazoleMay increase the serum concentration of Contraceptives (Progestins). Contraceptives (Progestins) may increase the serum concentration of Voriconazole.
WarfarinProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
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
Cytochrome P450 19A1 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