Identification

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

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

Structure
Thumb
Synonyms
  • (-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one
  • 13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
  • 13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one
  • 13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one
  • 17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one
  • 17-alpha-Ethynyl-13-ethyl-19-nortestosterone
  • 17-Ethynyl-18-methyl-19-nortestosterone
  • 17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
  • 17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
  • 17alpha-Ethynyl-18-homo-19-nortestosterone
  • 18-Methyl-17-alpha-ethynyl-19-nortestosterone
  • 18-Methylnorethisterone
  • d(-)-Norgestrel
  • Jadelle
  • Levonelle
  • Levonorgestrel
  • Lévonorgestrel
  • Levonorgestrelum
  • Levonova
  • Microlut
  • Microluton
  • Microval
  • NorLevo
  • Postinor
External IDs
Wy 5104 / WY-5104
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
JaydessInsert, extended release13.5 mgIntrauterineBayer2013-10-30Not applicableCanada
KyleenaIntrauterine device19.5 mg/1IntrauterineBayer2016-09-19Not applicableUs
KyleenaInsert, extended release19.5 mgIntrauterineBayer2017-01-10Not applicableCanada
LilettaIntrauterine device52 mg/1IntrauterineAllergan, Inc.2016-05-31Not applicableUs
LilettaIntrauterine device52 mg/1IntrauterineActavis Pharma Company2015-02-262020-01-31Us
MirenaIntrauterine device52 mg/1IntrauterineBayer HealthCare Pharmaceuticals Inc.2009-10-01Not applicableUs
MirenaInsert, extended release52 mgIntrauterineBayer2001-02-22Not applicableCanada
MirenaIntrauterine device52 mg/1IntrauterineBayer2009-10-012017-11-10Us
Norplant System Kit 36mg/implantImplant36 mgSubcutaneousWyeth Ayerst Canada Inc.1994-03-212002-09-24Canada
Plan BTablet0.75 mg/1OralDuramed Pharmaceuticals, Inc.1999-07-282013-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-15Not applicableUs
LevonorgestrelTablet1.5 mg/1OralActavis Pharma Company2012-07-162015-08-31Us
LevonorgestrelTablet1.5 mg/1OralPharmacist Pharmaceutical, LLC2013-06-11Not applicableUs
LevonorgestrelTablet1.5 mg/1OralNovel Laboratories, Inc.2013-02-22Not applicableUs
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/1OralH.J. Harkins Company2009-09-04Not applicableUs
Next ChoiceTablet0.75 mg/1OralWatson Pharma, Inc.2009-07-21Not applicableUs
Next ChoiceTablet0.75 mg/1OralDispensing Solutions, Inc.2009-09-04Not applicableUs
Next ChoiceTablet0.75 mg/1OralActavis Pharma Company2009-09-042014-02-28Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AfteraTablet1.5 mg/1OralTeva Women's Health, Inc.2014-10-20Not applicableUs
AfteraTablet1.5 mg/1OralFoundation Consumer Healthcare LLC2018-05-10Not applicableUs
AfterPillTablet1.5 mg/1OralSyzygy Healthcare Solutions, Llc Po Box 588, Westport, Ct 068802017-09-14Not applicableUs
AfterPillTablet1.5 mg/1OralSyzygy Healthcare Solutions, LLC2013-02-152017-09-01Us
AfterPlanTablet1.5 mg/1OralSun Pharmaceutical Industries, Inc.2017-05-12Not applicableUs
Athentia NextTablet1.5 mg/1OralAurohealth LLC2015-12-08Not applicableUs
Backup PlanTablet0.75 mgOralApotex CorporationNot applicableNot applicableCanada
Backup Plan OnestepTablet1.5 mgOralApotex Corporation2016-06-07Not applicableCanada
ContingencyTablet0.75 mgOralJai Pharma LimitedNot applicableNot applicableCanada
Contingency OneTablet1.5 mgOralMylan Pharmaceuticals2015-08-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AfirmelleLevonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)KitAurobindo Pharma2016-11-14Not applicableUs
Alesse 21Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralPfizer1998-01-07Not applicableCanada
Alesse 28Levonorgestrel (100 mcg) + Ethinylestradiol (20 mcg)TabletOralPfizer1998-01-07Not applicableCanada
Alesse 28Levonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1)KitWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1997-04-012008-02-29Us
AltaveraLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)KitSandoz2010-08-03Not applicableUs
AltaveraLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.03 mg/1)KitXiromed, Llc.2018-01-01Not 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 (0.03 mg/1) + Ethinylestradiol (0.01 mg/1)KitMayne Pharma2016-10-12Not applicableUs
AmethiaLevonorgestrel (0.15 mg/1) + Ethinylestradiol (0.01 mg/1) + Ethinylestradiol (0.03 mg/1)KitWatson Pharma, Inc.2011-05-312018-05-04Us52544 0268 84 nlmimage10 d23a6973
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FalessaLevonorgestrel (0.1 mg/1) + Ethinylestradiol (0.02 mg/1) + Folic Acid (1 mg/1)KitAvion Pharmaceuticals, Llc2014-02-17Not applicableUs
International/Other Brands
Jadelle (Bayer) / Levonelle (Bayer) / Medonor (Medopharm) / Microlut (Bayer) / Microval (Wyeth) / Mirena / Neogest (Schering) / Norgeston (Bayer) / Norplant (Bayer) / Plan b / 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

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

Associated Conditions
Associated Therapies
Pharmacodynamics

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

Mechanism of action

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

TargetActionsOrganism
AProgesterone receptor
binder
Human
A3-oxo-5-alpha-steroid 4-dehydrogenase 1
inhibitor
Human
AEstrogen receptor alpha
other
Human
UAndrogen receptor
agonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption

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

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

55%

Metabolism

Hepatic

Route of elimination

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

Half life
Not Available
Clearance
  • 7.7 +/- 2.7 L/h [Healthy Female Volunteers under Fasting Conditions]
Toxicity

LD50 >5000 mg/kg (orally in rats)

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

Interactions

Drug Interactions
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.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Levonorgestrel.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Levonorgestrel.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Levonorgestrel.
6-Deoxyerythronolide BThe metabolism of Levonorgestrel can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Levonorgestrel.
AbciximabLevonorgestrel may decrease the anticoagulant activities of Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Levonorgestrel.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take at the same time everyday.
  • Take with food.

References

Synthesis Reference

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

US20090069584
General References
  1. Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [PubMed:10715364]
  2. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771]
External Links
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
IUPHAR
2881
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
G03FA11 — Levonorgestrel and estrogenG03AC03 — LevonorgestrelG03FB09 — Levonorgestrel and estrogenG03AB03 — Levonorgestrel and ethinylestradiolG03AD01 — LevonorgestrelG03AA07 — Levonorgestrel and ethinylestradiol
AHFS Codes
  • 68:12.00 — Contraceptives
PDB Entries
1lhv / 3d90
FDA label
Download (8.04 KB)
MSDS
Download (19.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingOtherBiological Availability1
1Active Not RecruitingOtherLeukemia, Lymphocytic, Chronic, B-Cell1
1CompletedNot AvailableContraception / Postcoital Contraception2
1CompletedNot AvailableInfections, Human Immunodeficiency Virus and Hepatitis1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Mirabegron1
1CompletedDiagnosticEndometriosis1
1CompletedPreventionFemale Contraception1
1CompletedPreventionHIV Prevention1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
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 RecruitingBasic ScienceMalignancies, Hematologic1
1Not Yet RecruitingTreatmentHIV-1-infection1
1RecruitingOtherHealthy Females1
1RecruitingPreventionContraception1
1TerminatedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
1WithdrawnBasic ScienceHealthy Volunteers1
1, 2CompletedPreventionContraception / Hemostasis Parameter / Liver Metabolism1
1, 2CompletedTreatmentHealthy Volunteers1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedBasic ScienceHemostasis / Oral Contraceptives (OC)1
2CompletedPreventionBreakthrough Bleeding1
2CompletedPreventionContraception2
2CompletedPreventionEndometrial Cancers1
2CompletedPreventionMigraines1
2CompletedTreatmentAnorexia Nervosa (AN) / Osteoporosis1
2CompletedTreatmentBone Mineral Density1
2CompletedTreatmentContraception1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentDysmenorrhea1
2CompletedTreatmentEndometriosis1
2CompletedTreatmentOvulation1
2CompletedTreatmentOvulation Suppression1
2Not Yet RecruitingTreatmentRett's Syndrome1
2RecruitingOtherHealthy Volunteers / Male Contraception / Men1
2RecruitingTreatmentComplex Endometrial Hyperplasia With Atypia / Grade 1 Endometrial Endometrioid Adenocarcinoma1
2RecruitingTreatmentContraception1
2RecruitingTreatmentContraception / HIV-1-infection1
2Unknown StatusPreventionCancer of the Ovary1
2, 3CompletedTreatmentEmergency Contraception1
2, 3RecruitingTreatmentEmergency Contraception1
2, 3SuspendedTreatmentEndometriosis1
3Active Not RecruitingTreatmentContraception3
3CompletedEducational/Counseling/TrainingOral Contraceptives (OC)1
3CompletedPreventionContraception6
3CompletedPreventionHealthy Volunteers1
3CompletedPreventionPregnancy Prevention1
3CompletedTreatmentContraception1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentEmergency Contraception1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeavy Menstrual Bleeding1
3CompletedTreatmentHypermenorrhea2
3RecruitingTreatmentBladder Cancers / Transitional Cell Carcinoma / Ureteral Cancer1
3Unknown StatusTreatmentOral Contraceptives (OC)1
3WithdrawnTreatmentOsteopenia1
4Active Not RecruitingBasic ScienceContraception1
4Active Not RecruitingTreatmentBreastfeeding / Post Partum1
4CompletedNot AvailableContraception1
4CompletedNot AvailableContraception / Epilepsies1
4CompletedNot AvailableEndometriosis1
4CompletedBasic ScienceContraception1
4CompletedDiagnosticBody Weights / Contraceptive Usage1
4CompletedHealth Services ResearchPost Partum1
4CompletedOtherBody Weights / Contraception1
4CompletedOtherContraception / Human Immunodeficiency Virus (HIV)1
4CompletedPreventionContraception1
4CompletedPreventionPostpartum Contraception1
4CompletedTreatmentContraception3
4CompletedTreatmentContraception / Hypermenorrhea1
4CompletedTreatmentContraception / Medicated Intrauterine Devices1
4CompletedTreatmentContraceptive Usage1
4CompletedTreatmentEmergency Contraception1
4CompletedTreatmentEndometriosis1
4CompletedTreatmentInfertilities1
4CompletedTreatmentMenopausal Hot Flushes1
4CompletedTreatmentUterine Hemorrhage1
4RecruitingBasic ScienceHormonal Contraception1
4RecruitingPreventionContraception1
4RecruitingPreventionContraception / Malposition of Intrauterine Contraceptive Device1
4RecruitingTreatmentBMI >30 kg/m21
4RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
4TerminatedTreatmentAbnormal Uterine Bleeding, Unspecified / Uterine Bleeding Heavy1
Not AvailableActive Not RecruitingNot AvailableBMI >30 kg/m21
Not AvailableActive Not RecruitingNot AvailableContraception1
Not AvailableActive Not RecruitingNot AvailableContraception / Human Immunodeficiency Virus (HIV) / Immune Cells (Mucosal and Systemic)1
Not AvailableActive Not RecruitingPreventionContraception1
Not AvailableCompletedNot AvailableContraception5
Not AvailableCompletedNot AvailableContraception / Endometrial Hyperplasia / Estrogen Replacement Therapy / Hypermenorrhea1
Not AvailableCompletedNot AvailableFemale Contraception1
Not AvailableCompletedNot AvailableHypermenorrhea2
Not AvailableCompletedNot AvailableIdiopathic Menorrhagia2
Not AvailableCompletedNot AvailableIntrauterine Devices, Medicated1
Not AvailableCompletedNot AvailableNulliparous1
Not AvailableCompletedNot AvailablePregnancy2
Not AvailableCompletedNot AvailableQuality of Life1
Not AvailableCompletedBasic ScienceCoronary Heart Disease (CHD)1
Not AvailableCompletedPreventionPregnancy2
Not AvailableCompletedTreatmentInfertilities1
Not AvailableCompletedTreatmentMenopausal and Other Perimenopausal Disorders1
Not AvailableCompletedTreatmentTemporomandibular Joint Disorders1
Not AvailableNot Yet RecruitingNot AvailableDysfunctional Uterine Bleeding / Endometriosis of Uterus1
Not AvailableRecruitingNot AvailableContraception1
Not AvailableRecruitingNot AvailableMenorrhagia, Dysmenorrhea1
Not AvailableTerminatedNot AvailableInitiation of Depo-Provera (DMPA) / Initiation of Mirena (LNG-IUD) / Initiation of Oral Contraception (OC)1
Not AvailableUnknown StatusPreventionContraception1
Not AvailableUnknown StatusTreatmentFemale Contraception1

Pharmacoeconomics

Manufacturers
  • Wyeth pharmaceuticals inc
  • Population council
  • Population council center for biomedical research
  • Bayer healthcare pharmaceuticals inc
  • Watson laboratories inc
  • Duramed pharmaceuticals inc
Packagers
  • 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
Kit
PatchTransdermal
Insert, extended releaseIntrauterine13.5 mg
Insert, extended releaseIntrauterine19.5 mg
Intrauterine deviceIntrauterine19.5 mg/1
Tablet, film coatedOral
TabletOral
Insert, extended releaseIntrauterine52 mg
Intrauterine deviceIntrauterine52 mg/1
TabletOral1.5 mg/1.5mg
TabletOral0.75 mg/1
TabletOral1.5 mg
ImplantSubcutaneous36 mg
TabletOral0.75 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
US10028858No2014-03-222034-03-22Us
US6716814No2004-04-062021-08-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240 °CPhysProp
water solubility2.05 mg/LNot Available
logP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00583 mg/mLALOGPS
logP3.25ALOGPS
logP3.66ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.03 m3·mol-1ChemAxon
Polarizability36.73 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like 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
Human
Pharmacological action
Yes
Actions
Binder
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
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. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894]
  3. Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506]
  4. Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229]
  5. Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...
Gene Name
SRD5A1
Uniprot ID
P18405
Uniprot Name
3-oxo-5-alpha-steroid 4-dehydrogenase 1
Molecular Weight
29458.18 Da
References
  1. Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [PubMed:11521119]
  2. Rabe T, Kowald A, Ortmann J, Rehberger-Schneider S: Inhibition of skin 5 alpha-reductase by oral contraceptive progestins in vitro. Gynecol Endocrinol. 2000 Aug;14(4):223-30. [PubMed:11075290]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Other
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target 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. Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894]
  3. Abdel-Aleem H, Shaaban OM, Amin AF, Abdel-Aleem AM: Tamoxifen treatment of bleeding irregularities associated with Norplant use. Contraception. 2005 Dec;72(6):432-7. Epub 2005 Aug 9. [PubMed:16307966]
  4. Sun D, Yan C, Jacobson A, Jiang H, Carroll MA, Huang A: Contribution of epoxyeicosatrienoic acids to flow-induced dilation in arteries of male ERalpha knockout mice: role of aromatase. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1239-46. Epub 2007 Jul 18. [PubMed:17634204]
  5. Vijayanathan V, Venkiteswaran S, Nair SK, Verma A, Thomas TJ, Zhu BT, Thomas T: Physiologic levels of 2-methoxyestradiol interfere with nongenomic signaling of 17beta-estradiol in human breast cancer cells. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2038-48. [PubMed:16609013]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
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, Witters H, Weimer M, Lofink W, Berckmans P, Ahr HJ: Screening for (anti)androgenic properties using a standard operation protocol based on the human stably transfected androgen sensitive PALM cell line. First steps towards validation. Reprod Toxicol. 2010 Aug;30(1):9-17. doi: 10.1016/j.reprotox.2009.10.002. Epub 2009 Oct 27. [PubMed:19836445]
  3. Freyberger A, Weimer M, Tran HS, Ahr HJ: Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. [PubMed:19833195]
  4. Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 10:00