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Identification
NameDimethyl sulfoxide
Accession NumberDB01093  (APRD00925, EXPT01231)
Typesmall molecule
Groupsapproved
Description

A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
Dimethyl sulfur oxideNot AvailableNot Available
Dimethyl sulphoxideNot AvailableNot Available
DMSONot AvailableNot Available
MethylsulfinylmethaneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Rimso-50Alveda
Brand mixtures
Brand NameIngredients
Synotic Otic SolutionDimethyl sulfoxide + Fluocinolone acetonide
Categories
CAS number67-68-5
WeightAverage: 78.133
Monoisotopic: 78.013935504
Chemical FormulaC2H6OS
InChI KeyIAZDPXIOMUYVGZ-UHFFFAOYSA-N
InChI
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
IUPAC Name
methanesulfinylmethane
SMILES
CS(C)=O
Mass Specshow(8.05 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganosulfur Compounds
ClassSulfoxides
SubclassNot Available
Direct parentSulfoxides
Alternative parentsPolyamines
Substituentspolyamine
Classification descriptionThis compound belongs to the sulfoxides. These are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
Pharmacology
IndicationFor the symptomatic relief of patients with interstitial cystitis.
PharmacodynamicsDimethyl Sulfoxide may have anti-inflammatory, antioxidant and analgesic activities. Dimethyl Sulfoxide also readily penetrates cellular membranes. The membrane-penetrating ability of dimethyl sulfoxide may enhance diffusion of other substances through the skin. For this reason, mixtures of idoxuridine and dimethyl sulfoxide have been used for topical treatment of herpes zoster in the United Kingdom.
Mechanism of actionThe mechanism of dimethyl sulfoxide's actions is not well understood. Dimethyl sulfoxide has demonstrated antioxidant activity in certain biological settings. For example, the cardiovascular protective effect of dimethyl sulfoxide in copper-deficient rats is thought to occur by an antioxidant mechanism. It is also thought that dimethyl sulfoxide's possible anti-inflammatory activity is due to antioxidant action.
AbsorptionReadily and rapidly absorbed following administration by all routes and distributed throughout the body.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Dimethyl sulfoxide is metabolized in man by oxidation to dimethyl sulfone or by reduction in dimethyl sulfide. Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.

SubstrateEnzymesProduct
Dimethyl sulfoxide
Not Available
Dimethyl sulfideDetails
Dimethyl sulfoxide
Not Available
Dimethyl sulfoneDetails
Route of eliminationDimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
Half lifeNot Available
ClearanceNot Available
ToxicityThe oral LD50 of dimethyl sulfoxide in the dog is greater than 10 gm/kg. It is improbable that this dosage level could be obtained with intravesical instillation of dimethyl sulfoxide in the patient.
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 + 0.9968
Blood Brain Barrier + 0.978
Caco-2 permeable + 0.5211
P-glycoprotein substrate Non-substrate 0.8417
P-glycoprotein inhibitor I Non-inhibitor 0.9231
P-glycoprotein inhibitor II Non-inhibitor 1.0
Renal organic cation transporter Non-inhibitor 0.9156
CYP450 2C9 substrate Non-substrate 0.8276
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.6799
CYP450 1A2 substrate Non-inhibitor 0.7652
CYP450 2C9 substrate Non-inhibitor 0.8233
CYP450 2D6 substrate Non-inhibitor 0.9184
CYP450 2C19 substrate Non-inhibitor 0.7648
CYP450 3A4 substrate Non-inhibitor 0.9523
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9021
Ames test Non AMES toxic 0.9133
Carcinogenicity Carcinogens 0.7154
Biodegradation Not ready biodegradable 0.8004
Rat acute toxicity 0.7619 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8931
hERG inhibition (predictor II) Non-inhibitor 0.9432
Pharmacoeconomics
Manufacturers
  • Bioniche pharma usa llc
  • Bryan corp
Packagers
Dosage forms
FormRouteStrength
SolutionIntravesical
SolutionTopical
Prices
Unit descriptionCostUnit
Rimso-50 50% Solution 50ml Vial111.2USDvial
Sclerosol intrapleural aero3.98USDg
Rimso-50 50 % Solution1.25USDml
Rimso-50 solution1.15USDml
Dimethyl Sulfoxide Irrigation 50 % Solution1.05USDml
Dimethyl sulfoxide liquid0.77USDml
Kemsol 70 % Solution0.31USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point18.5 °CPhysProp
boiling point63Smedslund, T.H.; U.S. Patent 2,581,050; January 1,1952; assigned to A.B. Centrallaboratorium Helsinki. Coma, J.G. and Gerttula, V.G.; U.S. Patent 3,045,051; July 17, 1962; assigned to Crown Zellerbach Corp.
water solubility1E+006 mg/LDORIGAN,J ET AL. (1976A) @2ND
logP-1.35HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility6.57e+01 g/lALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.08ALOGPS
pKa (strongest basic)-6.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area17.07ChemAxon
rotatable bond count0ChemAxon
refractivity20.73ChemAxon
polarizability7.91ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Zhi Guo, Indra Prakash, “Synthesis and purification of 3,3-dimethylbutyraldehyde via oxidation of 1-chloro-3,3-dimethylbutane with dimethyl sulfoxide.” U.S. Patent US5905175, issued October, 1990.

US5905175
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01043
KEGG CompoundC11143
PubChem Compound679
PubChem Substance46505009
ChemSpider659
ChEBI28262
ChEMBLCHEMBL504
PharmGKBPA449342
HETDMS
Drug Product Database2243231
RxListhttp://www.rxlist.com/cgi/generic/dmso.htm
Drugs.comhttp://www.drugs.com/cdi/dimethyl-sulfoxide.html
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/dim_0098.shtml
WikipediaDimethyl_sulfoxide
ATC CodesG04BX13M02AX03
AHFS Codes
  • 92:00.00
  • 40:36.00
PDB Entries
FDA labelNot Available
MSDSshow(77.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Transthyretin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Transthyretin P02766 Details

References:

  1. Lehigh Shirey EA, Jelaso Langerveld A, Mihalko D, Ide CF: Polychlorinated biphenyl exposure delays metamorphosis and alters thyroid hormone system gene expression in developing Xenopus laevis. Environ Res. 2006 Oct;102(2):205-14. Epub 2006 May 23. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 12, 2014 21:08