Ethambutol (CED0002018)

Record Information
Version1.0
Creation Date2016-05-25 03:28:10 UTC
Update Date2026-08-18 03:25:42 UTC
Accession NumberCHEM021374
Identification
Common NameEthambutol
ClassSmall Molecule
Description
Ethambutol is an organic compound with the chemical formula C10H24N2O2 and an average molecular weight of 204.31 g/mol. Ethambutol belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. It is identified as an antibiotic and a drug used for the treatment of tuberculosis. The compound acts as an inhibitor of three recorded protein targets: Probable arabinosyltransferase A (embA), Probable arabinosyltransferase B (embB), and Probable arabinosyltransferase C (embC). This substance is found in or released from 20 recorded sources across various categories. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as an antibiotic and for the treatment of tuberculosis. It is also associated with food, food processing, and cookware, specifically in the processing of meats. Other recorded sources include household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and two additional items. Furthermore, it is found in electrical and electronic equipment, including electric switches, antennas, amplifiers, electric hearing aids, electrically stimulated smoking devices, and five other sources. Recorded exposure routes for ethambutol include oral and inhalation.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(+)-2,2'-(Ethylenediimino)di-1-butanolChEBI
(+)-EthambutolChEBI
(+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamineChEBI
(+)-S,S-EthambutolChEBI
(2S,7S)-2,7-Diethyl-3,6-diazaoctane-1,8-diolChEBI
(S,S)-EthambutolChEBI
EMBChEBI
EtambutolChEBI
EthambutolumChEBI
S,S-EthambutolChEBI
ServambutolKegg
AethambutolumHMDB
D-EthambutolHMDB
EtambutoloHMDB
Ethambutol, racemic mixtureHMDB
Fatol brand OF ethambutol hydrochlorideHMDB
Sanavita brand OF ethambutol hydrochlorideHMDB
Wyeth brand OF ethambutol hydrochlorideHMDB
AHP brand OF ethambutol hydrochlorideHMDB
Hydrochloride, ethambutolHMDB
ICN brand OF ethambutol hydrochlorideHMDB
Lederle brand OF ethambutol hydrochlorideHMDB
MiambutolHMDB
EMB hefaHMDB
EMB-fatolHMDB
EMB-hefaHMDB
Etambutol llorenteHMDB
EtibiHMDB
Genopharm brand OF ethambutol hydrochlorideHMDB
Llorente brand OF ethambutol hydrochlorideHMDB
MyambutolHMDB
Riemser brand OF ethambutol hydrochlorideHMDB
DexambutolHMDB
EMB fatolHMDB
Elan brand OF ethambutol hydrochlorideHMDB
Ethambutol hydrochlorideHMDB
Llorente, etambutolHMDB
SERB brand OF ethambutol hydrochlorideHMDB
Wernigerode brand OF ethambutol hydrochlorideHMDB
Chemical FormulaC10H24N2O2
Average Molecular Mass204.310 g/mol
Monoisotopic Mass204.184 g/mol
CAS Registry Number74-55-5
IUPAC Name(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol
Traditional Nameethambutol
SMILESCC[C@@H](CO)NCCN[C@@H](CC)CO
InChI IdentifierInChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1
InChI KeyAEUTYOVWOVBAKS-UWVGGRQHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.58 g/LALOGPS
logP-0.12ALOGPS
logP-0.059ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.82ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area64.52 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity57.89 m³·mol⁻¹ChemAxon
Polarizability24.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ul0-5900000000-89e4dd363b62972788ddNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9835000000-a128bc7a900264abaa54Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-1c5922845499f5b38b9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-d6867efe25d3bd98a3d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c5e5bdae927a908239cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c5e5bdae927a908239cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-3fd99ca7b30bbde49d3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-f3bae435be629eb01dfbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0890000000-ccfd6d7643c035e85154Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-1c5922845499f5b38b9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c5e5bdae927a908239cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-f11341611c9cfa579095Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-4900000000-3b54453f7861fac2d856Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1920000000-9e3493ee255f54f383d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-0b03d6426c85fa730fc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-d4311c76cc80b7e3d396Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2900000000-377cd86c5dd9f4a8e1a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-4900000000-81bbfa4fd47c6e268bb3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-47e43dcfde5f0401e6e0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9300000000-d220d9d540fda89a590fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-5900000000-4f50a6985e4bd0f003c9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-2e0cf59ab910fb319866Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-a40eb492fd949be6c6d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0920000000-b3a907229a4d388acaa0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-262cc570805ec680a031Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-4bf76df5a3c7224c8d76Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-46a1606fbade9d3e2585Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-3fd99ca7b30bbde49d3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-8bbcb0a052460bd73ed0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-837829484aa9eb830925Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0890000000-ccfd6d7643c035e85154Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c5e5bdae927a908239cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-d4c30d7a1813604bc46aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-1950000000-54ab5015ec7767cea1cfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-f11341611c9cfa579095Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-1c5922845499f5b38b9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0940000000-432b9aca890b9ddce7c4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-1e4caec283d8560a8130Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-f3bae435be629eb01dfbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-3ada166ae83d354f6ea9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-5f736bfcad952eb38a13Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-d6867efe25d3bd98a3d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-0eb26696d97050e416d4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0920000000-0729ffe9de956725b762Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0920000000-addc5da8bfa04c819692Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-12f3ed1bf7231d0eb745Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-66f480f71eddfba4b6b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0920000000-1260c0cb63ec88e99274Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-352ce1ef3b8da03f41eaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2900000000-06869becd8c8da5a8f3cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-2cb2ef5b6835598c69afNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-7900000000-86d4b6290834034219b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-26f3f3ce9756b059a4acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-1970000000-ce1c06e6eb8996487768Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014j-6910000000-def39cb7a4a0a270d07cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0603-9300000000-19c8f4c824cb5cc892dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1390000000-8dcf9353517b3cd58746Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uki-3940000000-3f54617420cf5327e70aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05ar-9800000000-dd533e6e939cf8386b06Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-1590000000-841928d8fb76c0e5b6b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-6900000000-d63b11de093e4b5fda0bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-d229532776ca03c4e456Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0190000000-50cef38da1557c955ee2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-8890000000-844dfa2f9cd990cd04b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-d6bf13ef035cd9d19b89Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2113.0Log mg/kg[1200:3800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
349Drugs for treatment of tuberculosisHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureInterleukin-5 receptor subunit alphaP21183Mus musculusPredicted (SEA)5.60514
Click to view 3D structureCyclin-dependent kinase 5Q02399Bos taurusPredicted (SEA)44.1405
Ceramide transfer protein structureClick to view 3D structureCeramide transfer proteinQ9Y5P4HumansPredicted (SEA)141.841
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)5590.82
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)5739.75
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)6240.86
Click to view 3D structureGroup VII phospholipase A2Q6UB75Sus scrofaPredicted (SEA)49.8235
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)6599.28
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)7033.75
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)4963.82
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)7260.06
Casein kinase I isoform alpha structureClick to view 3D structureCasein kinase I isoform alphaP48729HumansPredicted (SEA)6990.39
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)2401.73
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)17.5939
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)7159.33
Dual specificity tyrosine-phosphorylation-regulated kinase 3 structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 3O43781HumansPredicted (SEA)6602.86
Cyclin-dependent kinase 7 structureClick to view 3D structureCyclin-dependent kinase 7P50613HumansPredicted (SEA)6801.45
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)208.714
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)7178.71
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)7165.09
Click to view 3D structureCAI-1 autoinducer sensor kinase/phosphatase CqsSQ9KM66Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)Predicted (SEA)56.285
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)5420.41
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)7477.34
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)6103.3
Cyclin-dependent kinase 9 structureClick to view 3D structureCyclin-dependent kinase 9P50750HumansPredicted (SEA)7018.96
Concentrations
StatusValueUnitSample LocationReference
External Links
DrugBank IDDB00330
HMDB IDHMDB0014474
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00037452
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthambutol
Chemspider ID13433
ChEBI ID4877
PubChem Compound ID14052
Kegg Compound IDC06984
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10649975
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10891117
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10966749
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12182855
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14695841
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14698152
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15225698
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16005211
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16759086
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16870429
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17210775
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17239593
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17276683
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17315960
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17331717
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=17562368
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=17851083
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=17888665
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=19524332
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=19648006
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=3934384