Levonorgestrel

Identification

Summary

Levonorgestrel is a progestin found in oral and IUD contraceptives and at higher doses in emergency contraceptives.

Brand Names

Afirmelle 28 Day, Aftera, Alesse, Altavera 28 Day, Amethia 91 Day, Amethyst, Ashlyna 91 Day, Aubra 28 Day, Aviane 28, Ayuna 28 Day Pack, Balcoltra 28 Day, Bionafem, Camrese 91 Day, Camreselo 91 Day, Chateal 28 Day, Climara Pro, Curae, Daysee 91 Day, Delyla 28 Day, Dolishale 28 Day, Econtra, Enpresse 28 Day, Fallback Solo, Falmina 28 Day, Fayosim 91 Day, Her Style, Iclevia 91 Day, Indayo, Introvale 91 Day, Jaimiess 91 Day, Jolessa 91 Day, Joyeaux 28 Day, Kurvelo, Kyleena, Levonest 28 Day, Levora 0.15/30 28 Day, Liletta, Lo Simpesse, LoJaimiess, Loseasonique, Lutera 28 Day, Marlissa 28 Day, Min-ovral, Mirena, Morning After, My Choice, My Way, Myzilra 28 Day, New Day, Next Choice, Next Choice One Dose, Opcicon One-step, Option 2, Orsythia 28 Day, Plan B, Plan B One-step, Portia 28 Day, Preventeza, Quartette 91 Day Pack, React, Rivelsa 91 Day, Seasonale, Seasonique, Setlakin 91 Day, Simpesse, Skyla, Sronyx 28 Day, Take Action, Triquilar, Trivora 28 Day, Twirla 3 Count Weekly Patch, Tyblume 28 Day, Vienva 28 Day

Generic Name

Levonorgestrel

DrugBank Accession Number

DB00367

Background

Levonorgestrel (LNG) is a synthetic progestogen similar to Progesterone used in contraception and hormone therapy.^7,18 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.²⁹ In addition to the above uses, levonorgestrel is used as a component of long-term combination contraceptives.^8,19,21

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.^3,9,19

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 312.4458
Monoisotopic: 312.20893014
Chemical Formula: C₂₁H₂₈O₂

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
Levonorgestrel
Lèvonorgestrel
Levonorgestrelum

External IDs

Wy 5104
WY-5104

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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.¹⁹ 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.^3,19 It has shown a lower efficacy when it is used off label within 96 hours.¹⁸

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.²⁰ It is used in various hormone-releasing intrauterine devices for long-term contraception ranging for a duration of 3-5 years.^21,22,23 Product labeling for Mirena specifically mentions that it is recommended in women who have had at least 1 child and can be indicated for the prevention of pregnancy for up to 8 years.^21,30 A subdermal implant is also available for the prevention of pregnancy for up to 5 years.²⁹

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.²⁷Off-label, levonorgestrel may be used to treat menorrhagia, endometrial hyperplasia, and endometriosis.¹⁸

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Treatment of	Endometrial hyperplasia		••• •••••
Treatment of	Endometriosis		••• •••••
Treatment of	Heavy menstrual bleeding		••••••••••••	•••••••••••• ••••••
Management of	Menorrhagia		••• •••••	•••••••••••• ••••••
Used in combination to prevent	Osteoporosis, postmenopausal	Regimen in combination with: Estradiol (DB00783)	••••••••••••

Associated Therapies

Emergency Contraception

Contraindications & Blackbox Warnings

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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.^14,21,22 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.¹⁸

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.^21,22 Levonorgestrel is reported to alter the consistency of mucus in the cervix, which interferes with sperm migration into the uterus for fertilization. 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.^3,19

Effects on implantation*

The effects of levonorgestrel on endometrial receptivity are unclear, and the relevance of this mechanism to the therapeutic efficacy of levonorgestrel is contentious.^15,16 Prescribing information for levonorgestrel IUDs state that they exert local morphological changes to the endometrium (e.g. stromal pseudodecidualization, glandular atrophy) that may play a role in their contraceptive activity.^21,22

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.²⁸

Target	Actions	Organism
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

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.²⁹ After insertion of the subdermal implant, the Cmax of levonorgestrel is attained within 2-3 days.²⁹The 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%.²⁵

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.¹⁹

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.^11,19,22,29 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.²⁹

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.²⁹ Small quantities of 3α, 5α tetrahydrolevonorgestrel and 16βhydroxylevonorgestrel are also formed.¹⁹ No active metabolites have been identified.²⁵ The rate of metabolism may be considerably different according to the patient and may explain a wide variation in levonorgestrel clearance.¹⁹ Liver CYP3A4 and CYP3A5 hepatic enzymes are reported to be involved in the metabolism of levonorgestrel.^17,19

Hover over products below to view reaction partners

Levonorgestrel
- Glucuronide conjugates, levonorgestrel + Sulfate conjugates, levonorgestrel
- 16βhydroxylevonorgestrel + 3α, 5β-tetrahydrolevonorgestrel

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.¹⁹

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.²⁹

Adverse Effects

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Toxicity

The oral LD50 in rats is greater than 5000 mg/kg.²⁴

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.^19,25,26

Pathways

Not Available

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Interactions

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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.

Drug	Interaction
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Abametapir	The serum concentration of Levonorgestrel can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Levonorgestrel can be increased when combined with Abatacept.
Abciximab	The risk or severity of adverse effects can be increased when Levonorgestrel is combined with Abciximab.
Acalabrutinib	The metabolism of Levonorgestrel can be decreased when combined with Acalabrutinib.
Acarbose	The therapeutic efficacy of Acarbose can be decreased when used in combination with Levonorgestrel.

Food Interactions

Take at the same time every day.
Take with or without food. The effect of food on absorption has not been evaluated.

Products

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Product Images

International/Other Brands

Jadelle (Bayer) / Levonelle (Bayer) / Medonor (Medopharm) / Microlut (Bayer) / Microluton / Microval (Wyeth) / Neogest (Schering) / Norgeston (Bayer) / Norplant (Bayer) / Postinor (Gedeon Richter)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Jaydess	Insert, extended release	13.5 mg	Intrauterine	Bayer	2013-10-30	2018-12-20
Kyleena	Intrauterine device	19.5 mg/1	Intrauterine	Bayer HealthCare Pharmaceuticals Inc.	2016-09-19	Not applicable
Kyleena	Insert, extended release	19.5 mg	Intrauterine	Bayer	2017-01-10	Not applicable
Liletta	Intrauterine device	52 mg/1	Intrauterine	Actavis Pharma, Inc.	2015-02-26	2020-01-31
Liletta	Intrauterine device	52 mg/1	Intrauterine	Allergan, Inc.	2016-05-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Levonorgestrel	Tablet	1.5 mg/1	Oral	Novel Laboratories, Inc.	2013-02-22	Not applicable
Levonorgestrel	Tablet	1.5 mg/1	Oral	HRA Pharma America, Inc.	2020-11-01	Not applicable
Levonorgestrel	Tablet	1.5 mg/1	Oral	Novel Laboratories, Inc.	2013-02-15	Not applicable
Levonorgestrel	Tablet	1.5 mg/1	Oral	Actavis Pharma Company	2012-07-16	2015-08-31
Levonorgestrel	Tablet	0.75 mg/1	Oral	Lotus Pharmaceutical Co., Ltd. Nantou Plant	2020-09-01	2020-10-31

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
After Banger	Tablet	1.5 mg/1	Oral	Aurohealth LLC	2023-03-23	Not applicable
Aftera	Tablet	1.5 mg/1	Oral	Teva Women's Health, Inc.	2014-10-20	2020-05-31
Aftera	Tablet	1.5 mg/1	Oral	Foundation Consumer Healthcare LLC	2018-05-10	Not applicable
AfterPill	Tablet	1.5 mg/1	Oral	Syzygy Healthcare Solutions, LLC	2013-02-15	2017-09-01
AfterPill	Tablet	1.5 mg/1	Oral	Syzygy Healthcare Solutions, Llc Po Box 588, Westport, Ct 06880	2017-09-14	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ACTIVA 21	Levonorgestrel (150 mcg) + Ethinylestradiol (30 mcg)	Tablet, coated	Oral	FAES FARMA COLOMBIA S.A.S.	2008-04-10	Not applicable
ACTIVA 21 SUAVE®	Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)	Tablet, coated	Oral	FAES FARMA COLOMBIA S.A.S.	2014-05-23	Not applicable
Afirmelle	Levonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)	Kit; Tablet	Oral	Aurobindo Pharma Limited	2016-11-14	Not applicable
Alesse 21	Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)	Tablet	Oral	Pfizer Canada Ulc	1998-01-07	Not applicable
Alesse 28	Levonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)	Kit	Oral	Wyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.	1997-04-01	2008-02-29

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Falessa	Levonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1) + Folic acid (1 mg/1)	Kit	Oral	Avion Pharmaceuticals, Llc	2014-02-17	Not applicable
Minivlar 30	Levonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)	Tablet	Oral	OASIS TRADING	2018-11-21	Not applicable

Chemical Identifiers

UNII: 5W7SIA7YZW
CAS number: 797-63-7
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: (1R,3aS,3bR,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-1-hydroxy-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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]

References

Synthesis Reference

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

US20090069584

General References

Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [Article]
Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [Article]
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. [Article]
Kook K, Gabelnick H, Duncan G: Pharmacokinetics of levonorgestrel 0.75 mg tablets. Contraception. 2002 Jul;66(1):73-6. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [Article]
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. [Article]
Townsend S: Norplant: safe and highly effective. Netw Res Triangle Park N C. 1990 Dec;11(4):6-8. [Article]
Mozzanega B, Nardelli GB: UPA and LNG in emergency contraception: the information by EMA and the scientific evidences indicate a prevalent anti-implantation effect. Eur J Contracept Reprod Health Care. 2019 Jan 18:1-7. doi: 10.1080/13625187.2018.1555662. [Article]
Gemzell-Danielsson K, Berger C, Lalitkumar PG: Mechanisms of action of oral emergency contraception. Gynecol Endocrinol. 2014 Oct;30(10):685-7. doi: 10.3109/09513590.2014.950648. Epub 2014 Aug 12. [Article]
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. [Article]
Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.
Levonorgestrel FDA label [Link]
Alesse 28 FDA label [Link]
FDA Approved Drug Products: Mirena (levonorgestrel) intrauterine system [Link]
Kyleena IUD FDA label [Link]
Jaydess monograph [Link]
Levonorgestrel MSDS [Link]
Medicines UK, levonorgestrel [Link]
Birth control pill overdose, Medline [Link]
Climara pro FDA label [Link]
Cleveland clinic: hormone therapy [Link]
Norplant FDA label [Link]
FDA Approved Drug Products: Mirena (levonorgestrel) intrauterine system 2022 [Link]
FDA Approved Drug Products: LOSEASONIQUE® (levonorgestrel and ethinyl estradiol tablets; and ethinyl estradiol tablets) for oral use [Link]
FDA Approved Drug Products: LILETTA (levonorgestrel-releasing intrauterine system [Link]

External Links

Human Metabolome Database: HMDB0014511
KEGG Drug: D00950
KEGG Compound: C08153
PubChem Compound: 13109
PubChem Substance: 46508082
ChemSpider: 12560
BindingDB: 50410522
RxNav: 6373
ChEBI: 6443
ChEMBL: CHEMBL1389
ZINC: ZINC000003814395
Therapeutic Targets Database: DAP001207
PharmGKB: PA450218
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: NOG
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Levonorgestrel

PDB Entries

1lhv / 3d90

MSDS

Download (19.7 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Basic Science	ART / Contraception / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Not Available	Contraception / Epilepsy	1
4	Completed	Not Available	Endometriosis	1
4	Completed	Basic Science	Contraception	3
4	Completed	Basic Science	Contraceptive; Complications, Intrauterine / Mucosal Inflammation	1

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

Form	Route	Strength
Tablet, sugar coated	Oral
Kit	Oral
Insert	Vaginal	20 mcg/24hr
Intrauterine device	Intrauterine	52 mg
Patch	Transdermal
Kit; patch	Transdermal
Tablet	Oral	1.500 mg
Tablet	Oral	1.5 g
Patch, extended release	Transdermal
Tablet, sugar coated	Oral	0.03 mg
Implant	Parenteral	75.00 mg
Implant	Subcutaneous	75 mg
Insert, extended release	Intrauterine	13.5 mg
Intrauterine device	Intrauterine	13.5 MG
Intrauterine device	Intrauterine	1350000 mg
Tablet	Oral	0.150 mg
Insert, extended release	Intrauterine	19.5 mg
Intrauterine device	Intrauterine	19.5 mg/1
Intrauterine device	Intrauterine	19.5 MG
Tablet	Oral
Tablet, film coated	Oral	0.02 MG
Tablet	Oral
Tablet, coated	Oral	0.03 mg
Implant	Subcutaneous	75.00 mg
Kit; tablet	Oral
Tablet, coated	Oral	0.75 mg
Tablet, coated	Oral	0.02 MG
Tablet, film coated	Oral
Drug delivery system	Intrauterine	52.00 mg
Tablet, sugar coated	Oral	0.03 mg
Tablet, coated	Oral
Tablet, sugar coated	Oral
Tablet, coated	Oral
Drug delivery system	Intrauterine	19.500 mg
Implant	Intrauterine
Insert, extended release	Intrauterine	52 mg
Intrauterine device	Intrauterine	20 mcg/24hrs
Intrauterine device	Intrauterine	52 mg/1
Intrauterine device	Intrauterine	5200000 mg
Intrauterine device	Intrauterine
Intrauterine device	Intrauterine	20 Mikrogramm/24stunde
Drug delivery system	Intrauterine	52 mg
Tablet, delayed release	Oral
Tablet	Oral	1.5 mg/1.5mg
Tablet, coated	Oral	0.1 MG/0.02MG
Tablet	Oral	0.75 mg/1
Tablet	Oral	0750 MG
Tablet	Oral	750 mcg
Capsule
Intrauterine device	Intrauterine	36 mg
Implant	Subcutaneous	36 mg / imp
Tablet, film coated; tablet, sugar coated	Oral
Tablet	Oral	1.5 mg/1
Tablet	Oral	0.03 mg
Tablet	Oral	0.750 mg
Tablet	Oral	150000 mg
Kit; tablet, film coated	Oral
Kit; tablet, coated	Oral
Intrauterine device	Intrauterine	13.5 mg/1
Implant	Subcutaneous
Tablet, film coated	Oral	1.5 mg
Capsule, liquid filled	Oral
Implant		75 mg/implant
Tablet	Oral	0.75 mg
Tablet	Oral	1.5 mg
Tablet, film coated
Tablet, coated	Oral	1.5 mg
Tablet, film coated	Oral	0.75 mg
Intrauterine device	Intrauterine	52 mg/1piece

Prices

Unit description	Cost	Unit
Mirena system	843.66USD	each
Mirena System 52 mg Insert	363.54USD	insert
Nordette (28) 28 0.15-30 mg-mcg tablet Disp Pack	79.32USD	disp
Plan b one-step 1.5 mg tablet	40.62USD	tablet
Next choice 0.75 mg tablet	36.56USD	tablet
Levora 0.15/30 (28) 28 0.15-30 mg-mcg tablet Disp Pack	32.99USD	disp
Trivora (28) 28 tablet Box	29.99USD	box
Plan b 0.75 mg tablet	15.65USD	tablet
Nordette-28 tablet	2.75USD	tablet
Nordette-8 tablet	2.39USD	tablet
Levlen 28 tablet	1.3USD	tablet
Tri-levlen 28 tablet	1.25USD	tablet
Levora-28 tablet	1.1USD	tablet
Trivora-28 tablet	0.98USD	tablet
Acidophilus 10 bu/gm granules	0.6USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US6156742	No	2000-12-05	2020-12-05
US5785053	No	1998-07-28	2015-12-05
US5898032	No	1999-04-27	2017-06-23
USRE39861	No	2007-09-25	2017-06-23
US7320969	No	2008-01-22	2024-01-30
US7615545	No	2009-11-10	2023-06-15
US7855190	No	2010-12-21	2028-12-05
US7858605	No	2010-12-28	2023-06-23
US6500814	No	2002-12-31	2018-09-03
US7252839	No	2007-08-07	2023-11-13
US8450299	No	2013-05-28	2025-10-07
US8415332	No	2013-04-09	2029-03-11
US9668912	No	2017-06-06	2031-04-01
US9615965	No	2017-04-11	2029-09-16
US10028858	No	2018-07-24	2034-03-22
US6716814	No	2004-04-06	2021-08-16
US9050348	No	2015-06-09	2028-07-10
US8221784	No	2012-07-17	2021-03-14
US8747888	No	2014-06-10	2028-07-10
US8221785	No	2012-07-17	2021-03-14
US7384650	No	2008-06-10	2021-03-14
US8246978	No	2012-08-21	2028-08-26
US8883196	No	2014-11-11	2020-11-22
US7045145	No	2006-05-16	2021-03-14
US10561524	No	2020-02-18	2029-09-16
US10987244	No	2021-04-27	2031-04-01
US11090186	No	2021-08-17	2033-10-24
US7838042	No	2010-11-23	2027-06-01
US11571328	No	2020-09-07	2040-09-07
US11628088	No	2007-02-07	2027-02-07

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	232-239	https://www.fishersci.com/store/msds?partNumber=AC461100010&productDescription=LEVONORGESTREL%2C+98%25+1GR&vendorId=VN00032119&countryCode=US&language=en
boiling point (°C)	459.1	https://www.lookchem.com/Levonorgestrel/
water solubility	2.05 mg/L	http://www.t3db.ca/toxins/T3D4749
logP	3.8	http://www.hmdb.ca/metabolites/HMDB0014511
logS	-4.7	http://www.hmdb.ca/metabolites/HMDB0014511
pKa	17.91,-1.5	http://www.hmdb.ca/metabolites/HMDB0014511

Predicted Properties

Property	Value	Source
Water Solubility	0.00583 mg/mL	ALOGPS
logP	3.25	ALOGPS
logP	3.66	Chemaxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	17.91	Chemaxon
pKa (Strongest Basic)	-1.5	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	37.3 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	92.03 m³·mol^-1	Chemaxon
Polarizability	36.75 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9453
Caco-2 permeable	+	0.8094
P-glycoprotein substrate	Substrate	0.6648
P-glycoprotein inhibitor I	Inhibitor	0.5
P-glycoprotein inhibitor II	Non-inhibitor	0.8382
Renal organic cation transporter	Non-inhibitor	0.7697
CYP450 2C9 substrate	Non-substrate	0.7904
CYP450 2D6 substrate	Non-substrate	0.9165
CYP450 3A4 substrate	Substrate	0.7239
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9232
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Non-inhibitor	0.7772
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.516
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.9328
Biodegradation	Not ready biodegradable	0.9814
Rat acute toxicity	1.8264 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8205
hERG inhibition (predictor II)	Non-inhibitor	0.7408

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001i-0490000000-497c4ebd506c0b9c8ec3
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-066r-0931000000-4a863e895a5edd6cebeb
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-0439000000-bcbc7c657a115dced40a
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a5a-3920000000-edbd3785e7d20d9e81be
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-2920000000-a08b14b6d762cf4c42b1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0029000000-8f99dd0dd3dd66c78670
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-5e62a92c7270fa13358a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03xv-0961000000-80c5f72d918cca639af5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0009000000-31678a3a3ab82bb75e5e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01q9-0192000000-a7f63433e2d08a212992
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-046r-0900000000-3cbc1f5e11c4af0212be
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	187.5383773	predicted	DarkChem Lite v0.1.0
[M-H]-	187.1247773	predicted	DarkChem Lite v0.1.0
[M-H]-	187.9014773	predicted	DarkChem Lite v0.1.0
[M-H]-	175.88286	predicted	DeepCCS 1.0 (2019)
[M+H]+	187.7780773	predicted	DarkChem Lite v0.1.0
[M+H]+	187.8670773	predicted	DarkChem Lite v0.1.0
[M+H]+	188.6258773	predicted	DarkChem Lite v0.1.0
[M+H]+	177.85329	predicted	DeepCCS 1.0 (2019)
[M+Na]+	187.4737773	predicted	DarkChem Lite v0.1.0
[M+Na]+	187.1964773	predicted	DarkChem Lite v0.1.0
[M+Na]+	187.9607773	predicted	DarkChem Lite v0.1.0
[M+Na]+	183.90514	predicted	DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

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Details1. Progesterone receptor

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

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. [Article]
Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [Article]
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. [Article]
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. [Article]
Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.

Details2. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

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

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. [Article]
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. [Article]

Details3. Estrogen receptor alpha

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

Details4. Androgen receptor

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

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. [Article]
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. [Article]
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. [Article]
Christina Vrettakos; Tushar Bajaj (2019). Levonorgestrel. Stat Pearls NIH.

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	1.2	N/A	N/A	A27953

Details5. Sex hormone-binding globulin

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]

Details6. Glucocorticoid receptor

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

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. [Article]
PharmGKB, Levonorgestrel [Link]

Enzymes

Details1. Cytochrome P450 3A5

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

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. [Article]
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. [Article]
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. [Article]

Details2. Cytochrome P450 3A4

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

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. [Article]
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. [Article]
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. [Article]
Levonorgestrel FDA label [Link]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Levonorgestrel

Identification

Structure for Levonorgestrel (DB00367)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

References

Enzymes

References

References