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Identification
NameDimethyl sulfoxide
Accession NumberDB01093  (APRD00925, EXPT01231)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA 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
(CH3)2SO
Dimethyl sulfoxide
Dimethyl sulfur oxide
Dimethyl sulphoxide
Dimethyli sulfoxidum
Dimethylsulfoxid
Dimethylsulfoxyde
Dimetil sulfoxido
DMSO
Methylsulfinylmethane
S(O)Me2
Sulfinylbis(methane)
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dimethyl Sulfoxide Irrigation USPSolution500 mgIntravesicalSandoz Canada Incorporated2001-04-24Not applicableCanada
Kemsol Liquid 70%Solution70 %TopicalAxxess Pharma Inc.1977-12-312011-07-22Canada
Rimso-50Irrigant.54 g/mLIntravesicalMylan Institutional LLC1978-04-04Not applicableUs
Rimso-50Solution500 mgIntravesicalMylan Pharmaceuticals Ulc1980-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIYOW8V9698H
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
Pharmacology
IndicationFor the symptomatic relief of patients with interstitial cystitis.
Structured Indications
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.
Related Articles
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
Interactions
Drug Interactions
DrugInteractionDrug group
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Dimethyl sulfoxide.Approved
DexrazoxaneThe therapeutic efficacy of Dexrazoxane can be decreased when used in combination with Dimethyl sulfoxide.Approved, Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Dimethyl sulfoxide.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Dimethyl sulfoxide.Approved, Investigational
SulindacThe metabolism of Sulindac can be decreased when combined with Dimethyl sulfoxide.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Dimethyl sulfoxide.Approved
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesG04BX13M02AX03
AHFS Codes
  • 40:36.00
  • 92:00.00
PDB Entries
FDA labelNot Available
MSDSDownload (77.2 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9968
Blood Brain Barrier+0.978
Caco-2 permeable+0.5211
P-glycoprotein substrateNon-substrate0.8417
P-glycoprotein inhibitor INon-inhibitor0.9231
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9156
CYP450 2C9 substrateNon-substrate0.8276
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6799
CYP450 1A2 substrateNon-inhibitor0.7652
CYP450 2C9 inhibitorNon-inhibitor0.8233
CYP450 2D6 inhibitorNon-inhibitor0.9184
CYP450 2C19 inhibitorNon-inhibitor0.7648
CYP450 3A4 inhibitorNon-inhibitor0.9523
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9021
Ames testNon AMES toxic0.9133
CarcinogenicityCarcinogens 0.7154
BiodegradationNot ready biodegradable0.8004
Rat acute toxicity0.7619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8931
hERG inhibition (predictor II)Non-inhibitor0.9432
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
SolutionTopical70 %
IrrigantIntravesical.54 g/mL
SolutionIntravesical500 mg
Prices
Unit descriptionCostUnit
Rimso-50 50% Solution 50ml Vial111.2USD vial
Sclerosol intrapleural aero3.98USD g
Rimso-50 50 % Solution1.25USD ml
Rimso-50 solution1.15USD ml
Dimethyl Sulfoxide Irrigation 50 % Solution1.05USD ml
Dimethyl sulfoxide liquid0.77USD ml
Kemsol 70 % Solution0.31USD ml
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 Solubility65.7 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.08ALOGPS
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.73 m3·mol-1ChemAxon
Polarizability7.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.05 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-c8f7a9f09c8bb456283cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-d8d98568ae59afba65e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-e0a36c290f004f302f0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-89687ba96456a97fb486View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-9000000000-04ddc1322b21e4817d57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-d90c2fed7aad139b406cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03fr-9000000000-1db858034b22d1646592View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfoxides. These are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Sulfoxide
  • Sulfinyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Identical protein binding
Specific Function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name:
TTR
Uniprot ID:
P02766
Molecular Weight:
15886.88 Da
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:16720020 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23