Levonorgestrel (CHEM003706)

Record Information
Version1.0
Creation Date2014-09-11 05:14:42 UTC
Update Date2026-08-21 19:46:01 UTC
Accession NumberCHEM003706
Identification
Common NameLevonorgestrel
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Contraceptive Agent
  • Contraceptive Agent, Female
  • Contraceptive, Oral, Synthetic
  • Drug
  • Ester
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-oneChEBI
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-oneChEBI
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-oneChEBI
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-oneChEBI
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-oneChEBI
17-alpha-Ethynyl-13-ethyl-19-nortestosteroneChEBI
17-Ethynyl-18-methyl-19-nortestosteroneChEBI
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-olChEBI
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-oneChEBI
17alpha-Ethynyl-18-homo-19-nortestosteroneChEBI
18-Methyl-17-alpha-ethynyl-19-nortestosteroneChEBI
18-MethylnorethisteroneChEBI
D(-)-NorgestrelChEBI
JadelleChEBI
LevonelleChEBI
LevonorgestrelumChEBI
LevonovaChEBI
MicrolutChEBI
MicrolutonChEBI
MicrovalChEBI
MirenaChEBI
NorLevoChEBI
Plan bChEBI
PostinorChEBI
(+-)-NorgestrelKegg
OvretteKegg
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-oneGenerator
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-oneGenerator
13-b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-oneGenerator
13-Β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-oneGenerator
13-Ethyl-17-a-ethynyl-17-b-hydroxy-4-gonen-3-oneGenerator
13-Ethyl-17-α-ethynyl-17-β-hydroxy-4-gonen-3-oneGenerator
13-Ethyl-17-a-ethynylgon-4-en-17-b-ol-3-oneGenerator
13-Ethyl-17-α-ethynylgon-4-en-17-β-ol-3-oneGenerator
17-a-Ethinyl-13-b-ethyl-17-b-hydroxy-4-estren-3-oneGenerator
17-Α-ethinyl-13-β-ethyl-17-β-hydroxy-4-estren-3-oneGenerator
17-a-Ethynyl-13-ethyl-19-nortestosteroneGenerator
17-Α-ethynyl-13-ethyl-19-nortestosteroneGenerator
17a-Ethynyl-13b-ethyl-3-oxo-4-estren-17b-olGenerator
17Α-ethynyl-13β-ethyl-3-oxo-4-estren-17β-olGenerator
17a-Ethynyl-17-hydroxy-18-methylestr-4-en-3-oneGenerator
17Α-ethynyl-17-hydroxy-18-methylestr-4-en-3-oneGenerator
17a-Ethynyl-18-homo-19-nortestosteroneGenerator
17Α-ethynyl-18-homo-19-nortestosteroneGenerator
18-Methyl-17-a-ethynyl-19-nortestosteroneGenerator
18-Methyl-17-α-ethynyl-19-nortestosteroneGenerator
Levonorgestrel alcala brandHMDB
Levonorgestrel hexal brandHMDB
NorplantHMDB
Paladin brand OF levonorgestrelHMDB
VikelaHMDB
Wyeth brand OF levonorgestrelHMDB
DuofemHMDB
L-NorgestrelHMDB
Aventis pharma brand OF levonorgestrelHMDB
Berlex brand OF levonorgestrelHMDB
HRA brand 1 OF levonorgestrelHMDB
Hexal brand OF levonorgestrelHMDB
Levonorgestrel paladin brandHMDB
Levonorgestrel wyeth brandHMDB
Norplant 2HMDB
Alcala brand OF levonorgestrelHMDB
CapronorHMDB
CerazetHMDB
D-NorgestrelHMDB
HRA brand 2 OF levonorgestrelHMDB
Norplant-2HMDB
Schering brand 3 OF levonorgestrelHMDB
L NorgestrelHMDB
D NorgestrelHMDB
Levonorgestrel berlex brandHMDB
NorgestonHMDB
Norplant2HMDB
Schering brand 1 OF levonorgestrelHMDB
Schering brand 2 OF levonorgestrelHMDB
Women's capital brand OF levonorgestrelHMDB
LevonorgestrelMeSH
Chemical FormulaC21H28O2
Average Molecular Mass312.446 g/mol
Monoisotopic Mass312.209 g/mol
CAS Registry Number797-63-7
IUPAC Name(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]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]
InChI IdentifierInChI=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
InChI KeyWWYNJERNGUHSAO-XUDSTZEESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ynone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Acetylide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • terminal acetylenic compound (CHEBI:6443 )
  • 3-oxo Delta(4)-steroid (CHEBI:6443 )
  • 17beta-hydroxy steroid (CHEBI:6443 )
  • Pregnane and derivatives [Fig] (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119 )
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point240°C
Boiling PointNot Available
Solubility2.05 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.03 m³·mol⁻¹ChemAxon
Polarizability36.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureLevonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.
Mechanism of ToxicityBinds 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.
MetabolismHepatic. 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.
Toxicity ValuesLD50 >5000 mg/kg (orally in rats)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Norgestrel: Group 2B, possibly carcinogenic to humans. (3)
Uses/SourcesFor the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00367
HMDB IDHMDB0014511
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevonorgestrel
Chemspider ID12560
ChEBI ID6443
PubChem Compound ID13109
Kegg Compound IDC08153
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

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

MSDSLink
General References
1. Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313.
2. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. FDA label.
8. The lipid handbook with CD-ROM