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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-50Not Available
Brand mixtures
Brand NameIngredients
Synotic Otic SolutionDimethyl sulfoxide + Fluocinolone acetonide
Categories
CAS number67-68-5
WeightAverage: 78.133
Monoisotopic: 78.013935504
Chemical FormulaC2H6OS
InChI KeyInChIKey=IAZDPXIOMUYVGZ-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
    Dimethyl sulfideDetails
    Dimethyl sulfoxide
      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 point189 °CPhysProp
      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

      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

      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

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