Sodium lauryl sulfate

Identification

Name
Sodium lauryl sulfate
Accession Number
DB00815  (APRD01606)
Type
Small Molecule
Groups
Approved
Description

Sodium 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 IDs
Caswell No. 779 / Rhodapon SB 8208S
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bamboo SaltPaste, dentifrice.7675 g/100gOralHanul Trading Co., Ltd.2015-03-192017-06-27Us
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/Other Brands
Anticerumen / Emal 10 / Empicol / Genapol LSS / Irium
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
For SopeSodium lauryl sulfate (97 %) + Stearic acid (1.5 %)LiquidTopicalRougier Pharma Division Of Ratiopharm Inc1960-12-311999-09-27Canada
Medi Hydro DP CleanserSodium lauryl sulfate (.15 g/100g) + Allantoin (.005 g/100g) + Titanium dioxide (.05 g/100g)CreamTopicalMbg Inc (Korea Institute of Science Development)2016-08-152017-08-15Us
Plax Anti-plaque Dental RinseSodium lauryl sulfate (0.25 %) + Sodium benzoate (2 %) + Sodium salicylate (0.2 %)LiquidDentalJohnson & Johnson1988-12-312010-08-04Canada
Trimo SanSodium lauryl sulfate (.1 mg/g) + Oxyquinoline sulfate (.25 mg/g)JellyVaginalCooper Surgical, Inc.1977-04-01Not applicableUs
Categories
UNII
368GB5141J
CAS number
151-21-3
Weight
Average: 288.379
Monoisotopic: 288.137124653
Chemical Formula
C12H25NaO4S
InChI Key
DBMJMQXJHONAFJ-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

Indication

SLS 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
Pharmacodynamics

SLS is an anionic surfactant. Its amphiphilic properties make it an ideal detergent.

Mechanism of action

Like 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.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral (LD50): Acute: 1288 mg/kg [Rat]

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

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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
KEGG Drug
D01045
KEGG Compound
C11166
PubChem Compound
3423265
PubChem Substance
46508769
ChemSpider
8677
ChEBI
8984
ChEMBL
CHEMBL23393
Therapeutic Targets Database
DAP001227
PharmGKB
PA451398
Wikipedia
Sodium_lauryl_sulfate
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (75.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableSurgical Site Infections1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic SciencePain2
1CompletedOtherPain1
1CompletedPreventionIrritation/Irritant1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentLice of the head1
1Unknown StatusTreatmentDiltiazem Skin Sensitivity1
1Unknown StatusTreatmentSkin Irritation1
Not AvailableCompletedTreatmentWound Healing1

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205.5 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0090000000-12b55f58de196159b535
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00di-9000000000-55a0d8975342d4745eee
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00di-9000000000-55a0d8975342d4745eee
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This 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).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic sulfuric acids and derivatives
Sub Class
Sulfuric acid esters
Direct Parent
Sulfuric acid monoesters
Alternative Parents
Alkyl sulfates / Organooxygen compounds / Organic sodium salts / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl sulfate / Sulfate-ester / Sulfuric acid monoester / Organic alkali metal salt / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organic sodium salt / Organic salt / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
alkyl sulfate (CHEBI:8984)

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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:46