Identification

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Name
Levonorgestrel
Accession Number
DB00367  (APRD00754, DB00506, APRD00106)
Type
Small Molecule
Groups
Approved, Investigational
Description

Levonorgestrel (LNG) is a synthetic progestogen similar to Progesterone used in contraception and hormone therapy.7,15 Also known as Plan B, it is used as a single agent in emergency contraception, and as a hormonal contraceptive released from an intrauterine device, commonly referred to as an IUD. Some of these devices are known as Jaydess, Kyleena, and Mirena. A subdermal implant of levonorgestrel that slowly releases the hormone over a long-term period is also available.26 In addition to the above uses, levonorgestrel is used as a component of long-term combination contraceptives.8,16,18

Globally, levonorgestrel is the most commonly used emergency contraceptive. It was initially granted FDA approval in 1982 and was the first emergency contraceptive containing only progesterone, showing high levels of efficacy and a lack of estrogenic adverse effects when compared to older emergency contraceptive regimens.3,9,16

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
  • Lèvonorgestrel
  • Levonorgestrel
  • Levonorgestrelum
External IDs
Wy 5104 / WY-5104
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
JaydessInsert, extended releaseIntrauterineBayer2013-10-302018-12-20Canada
KyleenaInsert, extended release19.5 mgIntrauterineBayer2017-01-10Not applicableCanada
KyleenaIntrauterine device19.5 mg/1IntrauterineBayer HealthCare Pharmaceuticals Inc.2016-09-19Not applicableUs
LilettaIntrauterine device52 mg/1IntrauterineActavis Pharma, Inc.2015-02-262020-01-31Us
LilettaIntrauterine device52 mg/1IntrauterineAllergan, Inc.2016-05-31Not applicableUs
MirenaInsert, extended release52 mgIntrauterineBayer2001-02-22Not applicableCanada
MirenaIntrauterine device52 mg/1IntrauterineBayer2009-10-012017-11-10Us
MirenaIntrauterine device52 mg/1IntrauterineBayer HealthCare Pharmaceuticals Inc.2009-10-01Not applicableUs
Norplant System Kit 36mg/implantImplantSubcutaneousWyeth Ayerst Canada Inc.1994-03-212002-09-24Canada
Plan BTablet0.75 mg/1OralPhysicians Total Care, Inc.2003-08-14Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-15Not applicableUs
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-22Not applicableUs
LevonorgestrelTablet1.5 mg/1OralPharmacist Pharmaceutical, LLC2013-06-11Not applicableUs
LevonorgestrelTablet1.5 mg/1OralActavis Pharma Company2012-07-162015-08-31Us
Levonorgestrel Emergency ContraceptiveTablet0.75 mg/1OralPerrigo New York Inc.2011-03-102016-04-01Us
My WayTablet1.5 mg/1OralGavis Pharmaceuticals, LLC.2013-02-22Not applicableUs
Next ChoiceTablet0.75 mg/1OralRebel Distributors2009-07-21Not applicableUs
Next ChoiceTablet0.75 mg/1OralActavis Pharma Company2009-09-042014-02-28Us
Next ChoiceTablet0.75 mg/1OralWatson Pharma, Inc.2009-07-21Not applicableUs
Next ChoiceTablet0.75 mg/1OralPreferreed Pharmaceuticals Inc.2012-02-142017-12-08Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AfteraTablet1.5 mg/1OralTeva Women's Health, Inc.2014-10-202020-05-31Us
AfteraTablet1.5 mg/1OralFoundation Consumer Healthcare LLC2018-05-10Not applicableUs
AfterPillTablet1.5 mg/1OralSyzygy Healthcare Solutions, LLC2013-02-152017-09-01Us
AfterPillTablet1.5 mg/1OralSyzygy Healthcare Solutions, Llc Po Box 588, Westport, Ct 068802017-09-14Not applicableUs
AfterPlanTablet1.5 mg/1OralSun Pharmaceutical Industries, Inc.2017-05-12Not applicableUs
Athentia NextTablet1.5 mg/1OralAurohealth LLC2015-12-08Not applicableUs
Backup PlanTabletOralApotex CorporationNot applicableNot applicableCanada
Backup Plan OnestepTabletOralApotex Corporation2016-06-07Not applicableCanada
BionaFemTablet1.5 mg/1OralBionpharma Inc.2019-04-14Not applicableUs
ContingencyTabletOralJai Pharma LimitedNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AfirmelleLevonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)OralAurobindo Pharma Limited2019-05-31Not applicableUs
Alesse 21Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralPfizer Canada Ulc1998-01-07Not applicableCanada
Alesse 28Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralPfizer Canada Ulc1998-01-07Not applicableCanada
Alesse 28Levonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)KitOralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1997-04-012008-02-29Us
AltaveraLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)OralXiromed, Llc.2018-01-01Not applicableUs
AltaveraLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralSandoz2010-08-03Not applicableUs
Alysena 21Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralApotex Corporation2012-11-19Not applicableCanada
Alysena 28Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralApotex Corporation2012-11-19Not applicableCanada
AmethiaLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.01 mg/1) + Ethinylestradiol (0.03 mg/1)KitOralWatson Pharma, Inc.2011-05-312018-05-04Us52544 0268 84 nlmimage10 d23a6973
AmethiaLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1) + Ethinylestradiol (0.01 mg/1)KitOralMayne Pharma Inc2016-10-12Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FalessaLevonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1) + Folic acid (1 mg/1)KitOralAvion Pharmaceuticals, Llc2014-02-17Not applicableUs
Minivlar 30Levonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)TabletOralOASIS TRADING2018-11-21Not applicableUs
International/Other Brands
Jadelle (Bayer) / Levonelle (Bayer) / Medonor (Medopharm) / Microlut (Bayer) / Microluton / Microval (Wyeth) / Neogest (Schering) / Norgeston (Bayer) / Norplant (Bayer) / Postinor (Gedeon Richter)
Categories
UNII
5W7SIA7YZW
CAS number
797-63-7
Weight
Average: 312.4458
Monoisotopic: 312.20893014
Chemical Formula
C21H28O2
InChI Key
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]

Pharmacology

Indication

Emergency contraception

Levonorgestrel, in the single-agent emergency contraceptive form, is indicated for the prevention of pregnancy after the confirmed or suspected failure of contraception methods or following unprotected intercourse. It is distributed by prescription for patients under 17, and over the counter for those above this age.16 This levonorgestrel-only form of contraception is not indicated for regular contraception and must be taken as soon as possible within 72 hours after intercourse.3,16 It has shown a lower efficacy when it is used off label within 96 hours.15

Long-term contraception or nonemergency contraception

In addition to the above indication in emergency contraception, levonorgestrel is combined with other contraceptives in contraceptive formulations designed for regular use, for example with ethinyl estradiol.17 It is used in various hormone-releasing intrauterine devices for long-term contraception ranging for a duration of 3-5 years.18,19,20 Product labeling for Mirena specifically mentions that it is recommended in women who have had at least 1 child.18 A subdermal implant is also available for the prevention of pregnancy for up to 5 years.26

Hormone therapy and off-label uses

Levonorgestrel is prescribed in combination with estradiol as hormone therapy during menopause to manage vasomotor symptoms and to prevent osteoporosis.24Off-label, levonorgestrel may be used to treat menorrhagia, endometrial hyperplasia, and endometriosis.15

Associated Conditions
Associated Therapies
Pharmacodynamics

Levonorgestrel prevents pregnancy by interfering with ovulation, fertilization, and implantation. The levonorgestrel-only containing emergency contraceptive tablet is 89% effective if it is used according to prescribing information within 72 hours after intercourse.3,7 The intrauterine and implantable devices releasing levonorgestrel are more than 99% in preventing pregnancy.14,18,19 Levonorgestrel utilized as a component of hormonal therapy helps to prevent endometrial carcinoma associated with unopposed estrogen administration.13

Mechanism of action

Mechanism of action on ovulation

Oral contraceptives containing levonorgestrel suppress gonadotropins, inhibiting ovulation. Specifically, levonorgestrel binds to progesterone and androgen receptors and slows the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus. This process results in the suppression of the normal physiological luteinizing hormone (LH) surge that precedes ovulation. It inhibits the rupture of follicles and viable egg release from the ovaries. Levonorgestrel has been proven to be more effective when administered before ovulation.15

Mechanism of action in cervical mucus changes

Similar to other levonorgestrel-containing contraceptives, the intrauterine (IUD) forms of levonorgestrel likely prevent pregnancy by increasing the thickness of cervical mucus, interfering with the movement and survival of sperm, and inducing changes in the endometrium, where a fertilized ovum is usually implanted.18,19 Levonorgestrel is reported to alter the consistency of mucus in the cervix, which interferes with sperm migration into the uterus for implantation. Levonorgestrel is not effective after implantation has occurred.3 Interestingly, recent evidence has refuted the commonly believed notion that levonorgestrel changes the consistency of cervical mucus when it is taken over a short-term period, as in emergency contraception. Over a long-term period, however, levonorgestrel has been proven to thicken cervical mucus.3 The exact mechanism of action of levonorgestrel is not completely understood and remains a topic of controversy and ongoing investigation.3,16

Mechanism of action in hormone therapy

When combined with estrogens for the treatment of menopausal symptoms and prevention of osteoporosis, levonorgestrel serves to lower the carcinogenic risk of unopposed estrogen therapy via the inhibition of endometrial proliferation. Unregulated endometrial proliferation sometimes leads to endometrial cancer after estrogen use.25

TargetActionsOrganism
AProgesterone receptor
modulator
Humans
A3-oxo-5-alpha-steroid 4-dehydrogenase 1
inhibitor
Humans
AEstrogen receptor alpha
other/unknown
Humans
UAndrogen receptor
binder
Humans
USex hormone-binding globulin
inhibitor
binder
Humans
UGlucocorticoid receptor
binder
Humans
Additional Data Available
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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Orally administered levonorgestrel is absorbed in the gastrointestinal tract while levonorgestrel administered through an IUD device is absorbed in the endometrium. Levonorgestrel is absorbed immediately in the interstitial fluids when it is inserted as a subdermal implant.26 After insertion of the subdermal implant, the Cmax of levonorgestrel is attained within 2-3 days.26The Cmax following one dose of 0.75 mg of oral levonorgestrel is reached within the hour after administration, according to one reference.3 In a pharmacokinetic study of 1.5 mg of levonorgestrel in women with a normal BMI and those considered to be obese (BMI>30), mean Cmax was found to be 16.2 ng/mL and 10.5 ng/mL respectively. Tmax was found to be 2 hours for those with normal BMI and 2.5 hours for patients with increased BMI.6 The bioavailability of levonorgestrel approaches 100%.22

Mean AUC has been shown to be higher in patients with a normal BMI, measuring at 360.1 h × ng/mL versus a range of 197.28 to 208.1 h × ng/mL in an obese group of patients. Obesity may contribute to decreased efficacy of levonorgestrel in contraception.6

Volume of distribution

One pharmacokinetic study determined a mean steady-state volume of distribution of 1.5 mg of levonorgestrel to be 162.2 L in those with normal BMI and in the range of 404.7 L to 466.4 L in obese patients with a body mass index of at least 30.6 Mean volume of distribution in 16 patients receiving 0.75 mg of levonorgestrel in another pharmacokinetic study was 260 L.4 The Plan B one-step FDA label reports an apparent volume of distribution of 1.8 L/kg.16

Protein binding

The protein binding of levonorgestrel ranges from 97.5-99%, and it is mainly bound to sex hormone-binding globulin (SHBG). Levonorgestrel is also bound to albumin.11,16,19,26 The prescribing information for the implanted levonorgestrel indicates that the concentration of sex hormone-binding globulin (SHBG) is reduced in the span of a few days after levonorgestrel administration, decreasing the levels of the drug.26

Metabolism

After absorption of the oral emergency contraceptive preparation, levonorgestrel is conjugated and forms a large number of sulfate conjugates. In addition, glucuronide conjugates have been identified in the plasma.12 High levels of conjugated and unconjugated 3α, 5β-tetrahydrolevonorgestrel are found in the plasma. The entire metabolic pathway for levonorgestrel has not been studied, however, 16β-hydroxylation is one pathway that has been identified.26 Small quantities of 3α, 5α­ tetrahydrolevonorgestrel and 16βhydroxylevonorgestrel are also formed.16 No active metabolites have been identified.22 The rate of metabolism may be considerably different according to the patient and may explain a wide variation in levonorgestrel clearance.16 Liver CYP3A4 and CYP3A5 hepatic enzymes are reported to be involved in the metabolism of levonorgestrel.16

Route of elimination

Approximately 45% of an oral levonorgestrel dose and its conjugated or sulfate metabolites are found to be excreted in the urine. Approximately 32% of an orally ingested dose is found excreted in feces, primarily in the form of glucuronide conjugates of levonorgestrel.16

Half life

The elimination half-life of a 0.75 mg dose of 1.5 mg of levonorgestrel ranges between 20-60 hours post-administration.3 A pharmacokinetic study of women with a normal BMI and BMI over revealed an elimination half-life of 29.7 h and 41.0-46.4 hours, respectively.6 Another pharmacokinetic study revealed a mean elimination half-life of 24.4 hours after a 0.75 mg dose of levonorgestrel was administered to 16 patients.4

Clearance

Clearance was found to 4.8 L/h in healthy female volunteers with a normal BMI, and 7.70-8.51 L/h in obese patients after a single 1.5 mg dose.6 After a 0.75 mg dose of levonorgestrel in 16 patients in another pharmacokinetic study, mean clearance was calculated at 7.06 L/h.4 Following levonorgestrel implant removal, the serum concentration falls below 100 pg/mL within the first 96 hours and further falls below the sensitivity of detection within the range of 5 days to 2 weeks.26

Toxicity

The oral LD50 in rats is greater than 5000 mg/kg.21

An overdose of this drug, like other contraceptives, may cause nausea and withdrawal bleeding. Provide symptomatic treatment in the case of a levonorgestrel overdose and contact the local poison control center. There is no specific antidote for a levonorgestrel overdose.16,22,23

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinLevonorgestrel may decrease the anticoagulant activities of (R)-warfarin.
(S)-WarfarinLevonorgestrel may decrease the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Levonorgestrel.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be decreased when used in combination with Levonorgestrel.
4-OxoretinolThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with 4-Oxoretinol.
7-NitroindazoleThe metabolism of Levonorgestrel can be increased when combined with 7-Nitroindazole.
AbataceptThe metabolism of Levonorgestrel can be increased when combined with Abatacept.
AbciximabLevonorgestrel may decrease the anticoagulant activities of Abciximab.
AcalabrutinibThe metabolism of Levonorgestrel can be decreased when combined with Acalabrutinib.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Levonorgestrel.
Additional Data Available
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    Extended Description

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  • Severity
    Severity

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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]
  3. Kahlenborn C, Peck R, Severs WB: Mechanism of action of levonorgestrel emergency contraception. Linacre Q. 2015 Feb;82(1):18-33. doi: 10.1179/2050854914Y.0000000026. [PubMed:25698840]
  4. Kook K, Gabelnick H, Duncan G: Pharmacokinetics of levonorgestrel 0.75 mg tablets. Contraception. 2002 Jul;66(1):73-6. [PubMed:12169384]
  5. Sambol NC, Harper CC, Kim L, Liu CY, Darney P, Raine TR: Pharmacokinetics of single-dose levonorgestrel in adolescents. Contraception. 2006 Aug;74(2):104-9. doi: 10.1016/j.contraception.2006.01.011. Epub 2006 Jun 16. [PubMed:16860047]
  6. Natavio M, Stanczyk FZ, Molins EAG, Nelson A, Jusko WJ: Pharmacokinetics of the 1.5 mg levonorgestrel emergency contraceptive in women with normal, obese and extremely obese body mass index. Contraception. 2019 May;99(5):306-311. doi: 10.1016/j.contraception.2019.01.003. Epub 2019 Jan 28. [PubMed:30703352]
  7. Shohel M, Rahman MM, Zaman A, Uddin MM, Al-Amin MM, Reza HM: A systematic review of effectiveness and safety of different regimens of levonorgestrel oral tablets for emergency contraception. BMC Womens Health. 2014 Apr 4;14:54. doi: 10.1186/1472-6874-14-54. [PubMed:24708837]
  8. Polis CB, Phillips SJ, Hillier SL, Achilles SL: Levonorgestrel in contraceptives and multipurpose prevention technologies: does this progestin increase HIV risk or interact with antiretrovirals? AIDS. 2016 Nov 13;30(17):2571-2576. doi: 10.1097/QAD.0000000000001229. [PubMed:27525548]
  9. Raymond EG, Coeytaux F, Gemzell-Danielsson K, Moore K, Trussell J, Winikoff B: Embracing post-fertilisation methods of family planning: a call to action. J Fam Plann Reprod Health Care. 2013 Oct;39(4):244-6. doi: 10.1136/jfprhc-2013-100702. [PubMed:24062495]
  10. Beatty MN, Blumenthal PD: The levonorgestrel-releasing intrauterine system: Safety, efficacy, and patient acceptability. Ther Clin Risk Manag. 2009 Jun;5(3):561-74. doi: 10.2147/tcrm.s5624. Epub 2009 Aug 3. [PubMed:19707273]
  11. Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. doi: 10.1016/0002-9378(90)90559-p. [PubMed:2175153]
  12. Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [PubMed:2143719]
  13. Brinton LA, Felix AS: Menopausal hormone therapy and risk of endometrial cancer. J Steroid Biochem Mol Biol. 2014 Jul;142:83-9. doi: 10.1016/j.jsbmb.2013.05.001. Epub 2013 May 13. [PubMed:23680641]
  14. Townsend S: Norplant: safe and highly effective. Netw Res Triangle Park N C. 1990 Dec;11(4):6-8. [PubMed:12283720]
  15. Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.
  16. Levonorgestrel FDA label [Link]
  17. Alesse 28 FDA label [Link]
  18. FDA label, Mirena IUD [Link]
  19. Kyleena IUD FDA label [Link]
  20. Jaydess monograph [Link]
  21. Levonorgestrel MSDS [Link]
  22. Medicines UK, levonorgestrel [Link]
  23. Birth control pill overdose, Medline [Link]
  24. Climara pro FDA label [Link]
  25. Cleveland clinic: hormone therapy [Link]
  26. Norplant FDA label [Link]
External Links
Human Metabolome Database
HMDB0014511
KEGG Drug
D00950
KEGG Compound
C08153
PubChem Compound
13109
PubChem Substance
46508082
ChemSpider
12560
BindingDB
50410522
ChEBI
6443
ChEMBL
CHEMBL1389
Therapeutic Targets Database
DAP001207
PharmGKB
PA450218
Guide to Pharmacology
GtP Drug Page
HET
NOG
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Levonorgestrel
ATC Codes
G03AB03 — Levonorgestrel and ethinylestradiolG03AD01 — LevonorgestrelG03AC03 — LevonorgestrelG03FB09 — Levonorgestrel and estrogenG03AA07 — Levonorgestrel and ethinylestradiolG03FA11 — Levonorgestrel and estrogen
AHFS Codes
  • 68:12.00 — Contraceptives
PDB Entries
1lhv / 3d90
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingOtherContraception1
1CompletedNot AvailableContraception / Postcoital Contraception2
1CompletedNot AvailableContraceptives, Postcoital1
1CompletedNot AvailableInfections, Human Immunodeficiency Virus and Hepatitis1
1CompletedBasic ScienceFollicle Count / Follicle Size / Induction of follicle development / Oral Contraception / Ovarian Follicle1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Mirabegron1
1CompletedDiagnosticEndometriosis1
1CompletedOtherBiological Availability1
1CompletedOtherHealthy Females1
1CompletedOtherHealthy Volunteers2
1CompletedOtherLeukemia, Lymphocytic, Chronic, B-Cell1
1CompletedPreventionAnti-Infective Agents / Anti-Retroviral Agents / Contraceptive Usage1
1CompletedPreventionFemale Contraception1
1CompletedPreventionHIV Prevention1
1CompletedPreventionHealthy Volunteers1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
1CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV) Infections / Pharmacokinetics1
1CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentType 2 Diabetes Mellitus1
1Not Yet RecruitingTreatmentHIV-1-infection1
1Not Yet RecruitingTreatmentHepatitis B Chronic Infection1
1RecruitingBasic ScienceMalignancies, Hematologic1
1TerminatedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
1WithdrawnBasic ScienceHealthy Volunteers1
1WithdrawnTreatmentContraception1
1, 2CompletedPreventionContraception1
1, 2CompletedPreventionContraception / Hemostasis Parameter / Liver Metabolism1
1, 2CompletedTreatmentHealthy Volunteers1
2Active Not RecruitingTreatmentContraception1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedBasic ScienceHemostasis / Oral Contraception1
2CompletedPreventionBreakthrough Bleeding1
2CompletedPreventionContraception3
2CompletedPreventionEndometrial Cancer1
2CompletedPreventionMigraine1
2CompletedPreventionOvarian Cancer / Ovarian Carcinoma1
2CompletedTreatmentAnorexia Nervosa (AN) / Osteoporosis1
2CompletedTreatmentBone Mineral Density1
2CompletedTreatmentContraception1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentEndometriosis1
2CompletedTreatmentMenstrual Cramps1
2CompletedTreatmentOvulation1
2CompletedTreatmentOvulation Suppression1
2CompletedTreatmentWomen in Need of Long Acting Reversibel Cntraception With the Intrauterine Levonorgestrel Releasing System, Mirena1
2Enrolling by InvitationPreventionAnti-Retroviral Agent / Contraception / Human Immunodeficiency Virus (HIV) / Prevention1
2Enrolling by InvitationTreatmentEndometrial Cancer1
2RecruitingOtherHealthy Volunteers / Male Contraception / Men1
2RecruitingTreatmentComplex Endometrial Hyperplasia With Atypia / Grade 1 Endometrial Endometrioid Adenocarcinoma1
2RecruitingTreatmentContraception / HIV-1-infection1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2TerminatedTreatmentContraception1
2TerminatedTreatmentPelvic Pain Associated With Refractory Endometriosis1
2, 3CompletedTreatmentAnorexia Nervosa (AN)1
2, 3CompletedTreatmentEmergency Contraception1
2, 3RecruitingTreatmentEmergency Contraception1
2, 3SuspendedTreatmentEndometriosis1
3Active Not RecruitingTreatmentContraception3
3CompletedNot AvailableContraception1
3CompletedEducational/Counseling/TrainingOral Contraception1
3CompletedPreventionContraception9
3CompletedPreventionHealthy Volunteers1
3CompletedPreventionMenstruation Disturbances / Premenstrual Syndrome2
3CompletedPreventionPregnancy Prevention1
3CompletedPreventionPremenstrual Syndrome1
3CompletedTreatmentAnorexia Nervosa (AN)1
3CompletedTreatmentContraception3
3CompletedTreatmentEmergency Contraception1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeavy Menstrual Bleeding1
3CompletedTreatmentHypermenorrhea2
3CompletedTreatmentMenstrual Cramps2
3CompletedTreatmentMenstrual Irregularities1
3CompletedTreatmentPrimary Dysmenorrhoea1
3RecruitingPreventionMigraine / Migraine;Menstrual1
3RecruitingTreatmentBladder Cancers / Transitional Cell Carcinoma / Ureteral Cancer1
3RecruitingTreatmentHypermenorrhea1
3TerminatedPreventionContraception1
3Unknown StatusTreatmentOral Contraception1
3WithdrawnTreatmentOsteopenia1
4Active Not RecruitingBasic ScienceContraception1
4CompletedNot AvailableContraception1
4CompletedNot AvailableContraception / Epilepsies1
4CompletedNot AvailableEndometriosis1
4CompletedBasic ScienceContraception2
4CompletedDiagnosticBody Weights / Contraception1
4CompletedDiagnosticBody Weights / Contraceptive Usage1
4CompletedHealth Services ResearchPost Partum1
4CompletedOtherContraception / Human Immunodeficiency Virus (HIV)1
4CompletedPreventionBacteria Levels in the Mouth / Oral Bacteria Levels in the Mouth1
4CompletedPreventionContraception2
4CompletedPreventionPostpartum Contraception1
4CompletedPreventionPregnancy Prevention1
4CompletedPreventionUnplanned Pregnancy1
4CompletedTreatmentBreastfeeding / Post Partum1
4CompletedTreatmentContraception3
4CompletedTreatmentContraception / Hypermenorrhea1
4CompletedTreatmentContraception / Medicated Intrauterine Devices1
4CompletedTreatmentContraceptive Usage1
4CompletedTreatmentEmergency Contraception1
4CompletedTreatmentEndometriosis1
4CompletedTreatmentHot Flushes1
4CompletedTreatmentHypermenorrhea1
4CompletedTreatmentInfertility1
4CompletedTreatmentUterine Hemorrhage1
4RecruitingPreventionContraception2
4RecruitingPreventionContraception / Malposition of Intrauterine Contraceptive Device1
4RecruitingTreatmentBMI >30 kg/m21
4RecruitingTreatmentContraception1
4RecruitingTreatmentHeavy Menstrual Bleeding / Hypermenorrhea / Uterine Leiomyomas1
4TerminatedPreventionContraception1
4TerminatedTreatmentAbnormal Uterine Bleeding / Uterine Bleeding Heavy1
4TerminatedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
4WithdrawnTreatmentBariatric Surgery Candidate / Contraception1
Not AvailableActive Not RecruitingNot AvailableContraception3
Not AvailableActive Not RecruitingNot AvailableContraception / Human Immunodeficiency Virus (HIV) / Immune Cells (Mucosal and Systemic)1
Not AvailableActive Not RecruitingNot AvailableMenorrhagia, Dysmenorrhea1
Not AvailableActive Not RecruitingPreventionContraception1
Not AvailableCompletedNot AvailableBMI >30 kg/m21
Not AvailableCompletedNot AvailableContraception6
Not AvailableCompletedNot AvailableContraception / Endometrial Hyperplasia / Estrogen Replacement Therapy / Hypermenorrhea1
Not AvailableCompletedNot AvailableEmergency Contraception1
Not AvailableCompletedNot AvailableFemale Contraception1
Not AvailableCompletedNot AvailableHypermenorrhea2
Not AvailableCompletedNot AvailableHypothalamic-pituitary-ovarian Axis, Gonadotropins, Ethinyl Estradiol, Contraceptive Efficacy1
Not AvailableCompletedNot AvailableIdiopathic Menorrhagia2
Not AvailableCompletedNot AvailableIntrauterine Devices, Medicated1
Not AvailableCompletedNot AvailableNulliparous1
Not AvailableCompletedNot AvailablePregnancy2
Not AvailableCompletedNot AvailablePulmonary Embolism / Sinus Thrombosis, Intracranial / Thrombosis, Venous1
Not AvailableCompletedNot AvailableQuality of Life1
Not AvailableCompletedBasic ScienceCoronary Heart Disease (CHD)1
Not AvailableCompletedBasic ScienceGenital Tract Microflora / Genital Tract Mucosal Immunity1
Not AvailableCompletedOtherContraception / Human Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionPregnancy2
Not AvailableCompletedTreatmentEndometrial Hyperplasia1
Not AvailableCompletedTreatmentHeavy Menstrual Bleeding1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentInfertility1
Not AvailableCompletedTreatmentMenopausal and Other Perimenopausal Disorders1
Not AvailableCompletedTreatmentOral Contraception1
Not AvailableCompletedTreatmentTemporomandibular Joint Disorders1
Not AvailableNot Yet RecruitingNot AvailableAbnormal Uterine Bleeding / Endometriosis of Uterus1
Not AvailableNot Yet RecruitingNot AvailablePregnancy Related1
Not AvailableNot Yet RecruitingTreatmentChronic Pelvic Pain / Endometriosis of Uterus1
Not AvailableRecruitingNot AvailableContraception / Contraceptive implant therapy / Emergency Contraception / IUD1
Not AvailableRecruitingNot AvailableHormonal Contraception1
Not AvailableRecruitingNot AvailableHypermenorrhea1
Not AvailableRecruitingBasic SciencePolycystic Ovaries Syndrome1
Not AvailableRecruitingPreventionContraception1
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
  • 3M Health Care
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Bayer Healthcare
  • Berlex Labs
  • Cardinal Health
  • Chemical Works Of Gedeon Richter Ltd.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Gynetics Inc.
  • Patheon Inc.
  • PCAS Finland Oy
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Professional Co.
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Schering Corp.
  • SCS Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
  • Womens Capital Corp.
  • Wyeth Pharmaceuticals
Dosage forms
FormRouteStrength
PatchTransdermal
Insert, extended releaseIntrauterine
Insert, extended releaseIntrauterine19.5 mg
Intrauterine deviceIntrauterine19.5 mg/1
TabletOral
Tablet, film coatedOral
Insert, extended releaseIntrauterine52 mg
Intrauterine deviceIntrauterine52 mg/1
TabletOral1.5 mg/1.5mg
TabletOral0.75 mg/1
TabletOral
ImplantSubcutaneous
TabletOral0.75 mg
TabletOral1.5 mg
TabletOral1.5 mg/1
Intrauterine deviceIntrauterine13.5 mg/1
KitOral
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)
US6156742No2000-12-052020-12-05Us
US5785053No1998-07-282015-12-05Us
US5898032No1999-04-272017-06-23Us
USRE39861No2007-09-252017-06-23Us
US7320969No2008-01-222024-01-30Us
US7615545No2009-11-102023-06-15Us
US7855190No2010-12-212028-12-05Us
US7858605No2010-12-282023-06-23Us
US6500814No2002-12-312018-09-03Us
US7252839No2007-08-072023-11-13Us
US8450299No2013-05-282025-10-07Us
US8415332No2013-04-092029-03-11Us
US9668912No2017-06-062031-04-01Us
US9615965No2017-04-112029-09-16Us
US10028858No2018-07-242034-03-22Us
US6716814No2004-04-062021-08-16Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240 °Chttps://www.scbt.com/scbt/product/levonorgestrel-797-63-7
boiling point (°C)459.1https://www.lookchem.com/Levonorgestrel/
water solubility0.0058 g/Lhttp://www.t3db.ca/toxins/T3D4749
logP3.8http://www.hmdb.ca/metabolites/HMDB0014511
logS-4.7http://www.hmdb.ca/metabolites/HMDB0014511
pKa17.91,-1.5http://www.hmdb.ca/metabolites/HMDB0014511
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 RuleNoChemAxon
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0439000000-bcbc7c657a115dced40a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a5a-3920000000-edbd3785e7d20d9e81be
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2920000000-a08b14b6d762cf4c42b1
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-4-steroid / Cyclohexenone / Ynone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:6443) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. 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. Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506]
  3. 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]
  4. 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]
  5. Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
This target action is based on data from in vitro studies.
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 andro...
Gene Name
SRD5A1
Uniprot ID
P18405
Uniprot Name
3-oxo-5-alpha-steroid 4-dehydrogenase 1
Molecular Weight
29458.18 Da
References
  1. 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]
  2. Cassidenti DL, Paulson RJ, Serafini P, Stanczyk FZ, Lobo RA: Effects of sex steroids on skin 5 alpha-reductase activity in vitro. Obstet Gynecol. 1991 Jul;78(1):103-7. [PubMed:1828548]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Other/unknown
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 tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
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. 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]
  3. Lv XH, Shi DZ: Effects of levonorgestrel on reproductive hormone levels and their receptor expression in Mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(4):363-71. doi: 10.1538/expanim.60.363. [PubMed:21791876]
  4. Garcia-Becerra R, Borja-Cacho E, Cooney AJ, Jackson KJ, Lemus AE, Perez-Palacios G, Larrea F: The intrinsic transcriptional estrogenic activity of a non-phenolic derivative of levonorgestrel is mediated via the estrogen receptor-alpha. J Steroid Biochem Mol Biol. 2002 Nov;82(4-5):333-41. [PubMed:12589940]
  5. Lemus AE, Vilchis F, Damsky R, Chavez BA, Garcia GA, Grillasca I, Perez-Palacios G: Mechanism of action of levonorgestrel: in vitro metabolism and specific interactions with steroid receptors in target organs. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):881-90. [PubMed:1562565]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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, 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]
  3. 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]
  4. Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Binder
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hammond GL, Abrams LS, Creasy GW, Natarajan J, Allen JG, Siiteri PK: Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. Contraception. 2003 Feb;67(2):93-9. [PubMed:12586319]
  2. 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]
  3. Alvarez F, Brache V, Tejada AS, Cochon L, Faundes A: Sex hormone binding globulin and free levonorgestrel index in the first week after insertion of Norplant implants. Contraception. 1998 Oct;58(4):211-4. [PubMed:9866001]
  4. Song S, Chen JK, He ML, Fotherby K: Effect of some oral contraceptives on serum concentrations of sex hormone binding globulin and ceruloplasmin. Contraception. 1989 Apr;39(4):385-99. [PubMed:2498034]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. doi: 10.1016/0002-9378(90)90559-p. [PubMed:2175153]
  2. PharmGKB, Levonorgestrel [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Moreno I, Quinones L, Catalan J, Miranda C, Roco A, Sasso J, Tamayo E, Caceres D, Tchernitchin AN, Gaete L, Saavedra I: [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012. [PubMed:23715232]
  2. Edelman A, Munar M, Elman MR, Koop D, Cherala G: Effect of the ethinylestradiol/levonorgestrel combined oral contraceptive on the activity of cytochrome P4503A in obese women. Br J Clin Pharmacol. 2012 Sep;74(3):510-4. doi: 10.1111/j.1365-2125.2012.04209.x. [PubMed:22299599]
  3. Hatorp V, Hansen KT, Thomsen MS: Influence of drugs interacting with CYP3A4 on the pharmacokinetics, pharmacodynamics, and safety of the prandial glucose regulator repaglinide. J Clin Pharmacol. 2003 Jun;43(6):649-60. [PubMed:12817528]
  4. Levonorgestrel FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Moreno I, Quinones L, Catalan J, Miranda C, Roco A, Sasso J, Tamayo E, Caceres D, Tchernitchin AN, Gaete L, Saavedra I: [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012. [PubMed:23715232]
  2. Edelman A, Munar M, Elman MR, Koop D, Cherala G: Effect of the ethinylestradiol/levonorgestrel combined oral contraceptive on the activity of cytochrome P4503A in obese women. Br J Clin Pharmacol. 2012 Sep;74(3):510-4. doi: 10.1111/j.1365-2125.2012.04209.x. [PubMed:22299599]
  3. Neary M, Lamorde M, Olagunju A, Darin KM, Merry C, Byakika-Kibwika P, Back DJ, Siccardi M, Owen A, Scarsi KK: The Effect of Gene Variants on Levonorgestrel Pharmacokinetics When Combined With Antiretroviral Therapy Containing Efavirenz or Nevirapine. Clin Pharmacol Ther. 2017 Sep;102(3):529-536. doi: 10.1002/cpt.667. Epub 2017 May 30. [PubMed:28187506]

Drug created on June 13, 2005 07:24 / Updated on December 07, 2019 14:19