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Identification
NameSodium lauryl sulfate
Accession NumberDB00815  (APRD01606)
TypeSmall Molecule
GroupsApproved
DescriptionSodium Lauryl Sulfate (SLS) is an anionic surfactant naturally derived from coconut and/or palm kernel oil. It usually consists 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
Laurylsiran sodny
NaDS
Natrium laurylsulfuricum
SDS
SLS
Sodium dodecyl sulfate
Sodium dodecyl sulphate
Sodium dodecylsulfate
Sodium laurilsulfate
Sodium lauryl sulfate
Sodium lauryl sulphate
External Identifiers
  • Caswell No. 779
  • Rhodapon SB 8208S
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bamboo SaltPaste, dentifrice.7675 g/100gOralHanul Trading Co., Ltd.2015-03-19Not applicableUs
Bamboo Salt 160gPaste, dentifrice1.21 g/160gOralHanul Trading Co., Ltd.2015-03-19Not applicableUs
SensiblePaste2 g/100gDentalGuardian Angel of Preventive Dentistry2014-07-11Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dr.g Hydra Intensive Moist Cleansing GelLiquid25 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-10Not applicableUs
International Brands
NameCompany
AnticerumenNot Available
Emal 10Not Available
EmpicolNot Available
Genapol LSSNot Available
IriumNot Available
Brand mixtures
NameLabellerIngredients
For SopeRougier Pharma Division Of Ratiopharm Inc
Medi Hydro Dp CleanserMbg Inc (Korea Institute of Science Development)
Plax Anti-plaque Dental RinseJohnson & Johnson Inc
Trimo SanCooper Surgical, Inc.
SaltsNot Available
Categories
UNII368GB5141J
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
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.
Structured Indications Not Available
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
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 References
  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:1681644 ]
  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:16679819 ]
  3. Loffler H, Effendy I: Skin susceptibility of atopic individuals. Contact Dermatitis. 1999 May;40(5):239-42. [PubMed:10344477 ]
  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:9656847 ]
  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:8811135 ]
  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:11899262 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.2 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9391
Blood Brain Barrier+0.9611
Caco-2 permeable-0.6041
P-glycoprotein substrateNon-substrate0.7529
P-glycoprotein inhibitor INon-inhibitor0.73
P-glycoprotein inhibitor IINon-inhibitor0.9563
Renal organic cation transporterNon-inhibitor0.9123
CYP450 2C9 substrateNon-substrate0.8755
CYP450 2D6 substrateNon-substrate0.8532
CYP450 3A4 substrateNon-substrate0.5576
CYP450 1A2 substrateNon-inhibitor0.7976
CYP450 2C9 inhibitorNon-inhibitor0.8219
CYP450 2D6 inhibitorNon-inhibitor0.8946
CYP450 2C19 inhibitorNon-inhibitor0.7743
CYP450 3A4 inhibitorNon-inhibitor0.9845
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8892
Ames testNon AMES toxic0.6075
CarcinogenicityCarcinogens 0.7009
BiodegradationReady biodegradable0.9703
Rat acute toxicity2.3453 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5379
hERG inhibition (predictor II)Non-inhibitor0.7424
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Paste, dentifriceOral.7675 g/100g
Paste, dentifriceOral1.21 g/160g
LiquidTopical25 g/100mL
LiquidTopical
CreamTopical
LiquidDental
PasteDental2 g/100g
JellyVaginal
Prices
Unit descriptionCostUnit
Monogen powder0.09USD g
Sodium lauryl sulfate cryst0.03USD g
Carrington whirlpool solution0.01USD ml
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 Solubility0.0121 mg/mLALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-12b55f58de196159b535View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-55a0d8975342d4745eeeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-55a0d8975342d4745eeeView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassSulfuric acid esters
Direct ParentSulfuric acid monoesters
Alternative Parents
Substituents
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfate-ester
  • Hydrocarbon derivative
  • Organic alkali metal salt
  • Organic sodium salt
  • Organic salt
  • Organooxygen compound
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
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:16085141 ]
  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:16256532 ]
  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:16256620 ]
  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:16379295 ]
  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:16457837 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23