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Identification
NameSodium lauryl sulfate
Accession NumberDB00815  (APRD01606)
TypeSmall Molecule
GroupsApproved
Description

Sodium Lauryl Sulfate (SLS) is an anionic surfactant naturally derived from coconut and/or palm kernel oil. It usually consisting of a mixture of sodium alkyl sulfates, mainly the lauryl. SLS lowers surface tension of aqueous solutions and is used as fat emulsifier, wetting agent, and detergent in cosmetics, pharmaceuticals and toothpastes. It is also used in creams and pastes to properly disperse the ingredients and as research tool in protein biochemistry. SLS also has some microbicidal activity.

Structure
Thumb
Synonyms
SynonymLanguageCode
Laurylsiran sodnyCzechNot Available
NaDSNot AvailableNot Available
Natrium laurylsulfuricumLatinNot Available
SDSNot AvailableNot Available
SLSNot AvailableNot Available
Sodium dodecyl sulfateNot AvailableNot Available
Sodium dodecyl sulphateNot AvailableNot Available
Sodium dodecylsulfateNot AvailableNot Available
Sodium laurilsulfateNot AvailableNot Available
Sodium lauryl sulfateNot AvailableNot Available
Sodium lauryl sulphateNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AnticerumenNot Available
Emal 10Not Available
EmpicolNot Available
Genapol LSSNot Available
IriumNot Available
Brand mixtures
Brand NameIngredients
Plax anti-plaque den rinse peppermint liqsodium benzoate + sodium lauryl sulfate + sodium salicylate
Plax anti-plaque dent rinse soft mint liqsodium benzoate + sodium lauryl sulfate + sodium salicylate
Plax anti-plaque dental rinsesodium benzoate + sodium lauryl sulfate + sodium salicylate
Categories
CAS number151-21-3
WeightAverage: 288.379
Monoisotopic: 288.137124653
Chemical FormulaC12H25NaO4S
InChI KeyDBMJMQXJHONAFJ-UHFFFAOYSA-M
InChI
InChI=1S/C12H26O4S.Na/c1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15;/h2-12H2,1H3,(H,13,14,15);/q;+1/p-1
IUPAC Name
sodium dodecyl sulfate
SMILES
[Na+].CCCCCCCCCCCCOS([O-])(=O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassOrganic Sulfuric Acids and Derivatives
SubclassSulfuric Acid Monoesters
Direct parentSulfuric Acid Monoesters
Alternative parentsPolyamines
Substituentspolyamine
Classification descriptionThis compound belongs to the sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group.
Pharmacology
IndicationSLS is used as a surfactant in shampoos and toothpastes. SLS also has microbicidal activities against both enveloped (Herpes simplex viruses, HIV-1, Semliki Forest virus) and nonenveloped (papillomaviruses, reovirus, rotavirus and poliovirus) viruses, although it has not been approved for this use.
PharmacodynamicsSLS is an anionic surfactant. Its amphiphilic properties make it an ideal detergent.
Mechanism of actionLike other surfactants, SLS is amphiphilic. It thus migrates to the surface of liquids, where its alignment and aggregation with other SLS molecules lowers the surface tension. This allows for easier spreading and mixing of the liquid. SLS has potent protein denaturing activity and inhibits the infectivity of viruses by by solubilizing the viral envelope and/or by denaturing envelope and/or capsid proteins.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral (LD50): Acute: 1288 mg/kg [Rat]
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9391
Blood Brain Barrier + 0.9611
Caco-2 permeable - 0.6041
P-glycoprotein substrate Non-substrate 0.7529
P-glycoprotein inhibitor I Non-inhibitor 0.73
P-glycoprotein inhibitor II Non-inhibitor 0.9563
Renal organic cation transporter Non-inhibitor 0.9123
CYP450 2C9 substrate Non-substrate 0.8755
CYP450 2D6 substrate Non-substrate 0.8532
CYP450 3A4 substrate Non-substrate 0.5576
CYP450 1A2 substrate Non-inhibitor 0.7976
CYP450 2C9 substrate Non-inhibitor 0.8219
CYP450 2D6 substrate Non-inhibitor 0.8946
CYP450 2C19 substrate Non-inhibitor 0.7743
CYP450 3A4 substrate Non-inhibitor 0.9845
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8892
Ames test Non AMES toxic 0.6075
Carcinogenicity Carcinogens 0.7009
Biodegradation Ready biodegradable 0.9703
Rat acute toxicity 2.3453 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5379
hERG inhibition (predictor II) Non-inhibitor 0.7424
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Monogen powder0.09USDg
Sodium lauryl sulfate cryst0.03USDg
Carrington whirlpool solution0.01USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point205.5 °CPhysProp
water solubility1E+005 mg/LSINGER,MM & TJEERDEMA,RS (1993)
logP1.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0121ALOGPS
logP3.86ALOGPS
logP4.42ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity67.81 m3·mol-1ChemAxon
Polarizability31.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraMS/MS1D NMR
References
Synthesis Reference

Willi Breitzke, Hermann Hensen, “Aqueous preparations of sodium lauryl sulfate and myristyl sulfate having a low cloud point useful in making toothpastes.” U.S. Patent US4876035, issued June, 1960.

US4876035
General Reference
  1. Agner T: Susceptibility of atopic dermatitis patients to irritant dermatitis caused by sodium lauryl sulphate. Acta Derm Venereol. 1991;71(4):296-300. Pubmed
  2. Marrakchi S, Maibach HI: Sodium lauryl sulfate-induced irritation in the human face: regional and age-related differences. Skin Pharmacol Physiol. 2006;19(3):177-80. Epub 2006 May 4. Pubmed
  3. Loffler H, Effendy I: Skin susceptibility of atopic individuals. Contact Dermatitis. 1999 May;40(5):239-42. Pubmed
  4. Chahine L, Sempson N, Wagoner C: The effect of sodium lauryl sulfate on recurrent aphthous ulcers: a clinical study. Compend Contin Educ Dent. 1997 Dec;18(12):1238-40. Pubmed
  5. Herlofson BB, Barkvoll P: The effect of two toothpaste detergents on the frequency of recurrent aphthous ulcers. Acta Odontol Scand. 1996 Jun;54(3):150-3. Pubmed
  6. Piret J, Desormeaux A, Bergeron MG: Sodium lauryl sulfate, a microbicide effective against enveloped and nonenveloped viruses. Curr Drug Targets. 2002 Feb;3(1):17-30. Pubmed
External Links
ResourceLink
KEGG DrugD01045
KEGG CompoundC11166
ChEBI8984
ChEMBLCHEMBL23393
Therapeutic Targets DatabaseDAP001227
PharmGKBPA451398
WikipediaSodium_lauryl_sulfate
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(75.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Chang-Ying Y, An-Xin H, Yi L, Hui T, Song-Sheng Q: Some properties of the interaction between 2,2’-diselenadibenzoic acid and serum albumins. J Pharm Biomed Anal. 2005 Sep 1;39(1-2):263-7. Pubmed
  2. Choi EJ, Foster MD: Surfactant displacement of human serum albumin adsorbed on loosely packed self-assembled monolayers: cetyltrimethylammonium bromide versus sodium dodecyl sulfate. J Colloid Interface Sci. 2003 May 15;261(2):273-82. Pubmed
  3. Santos SF, Zanette D, Fischer H, Itri R: A systematic study of bovine serum albumin (BSA) and sodium dodecyl sulfate (SDS) interactions by surface tension and small angle X-ray scattering. J Colloid Interface Sci. 2003 Jun 15;262(2):400-8. Pubmed
  4. Cao WG, Jiao QC, Liu Q: [Spatial orientation interaction mechanism of three component complex of protein—BSA/SDS/Azur a system] Guang Pu Xue Yu Guang Pu Fen Xi. 2005 Sep;25(9):1478-81. Pubmed
  5. Schweitzer B, Felippe AC, Dal Bo A, Minatti E, Zanette D, Lopes A: Sodium dodecyl sulfate promoting a cooperative association process of sodium cholate with bovine serum albumin. J Colloid Interface Sci. 2006 Jun 1;298(1):457-66. Epub 2006 Feb 2. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12