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enzymes (3) carriers (1)
for drugs
Identification
Name Dimethyl sulfoxide
Accession Number DB01093 (APRD00925, EXPT01231)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Diemthyl sulfoxide
Dimethyl sulfoxide BP
Dimethyl sulfur oxide
Dimethyl sulphoxide
Dimethyl sulpoxide
Dimexidum
Methyl sulfoxide
Methylsulfinylmethane
Sulfinylbis-methane
Sulfinylbismethane
Sulfinyldimethane
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Salts Not Available
Brand names
Name Company
Decap
Deltan
Demasorb
Demavet
Demeso
Demsodrox
Dermasorb
Dimexide
Dipirartril-tropico
Dolicur
Doligur
Domoso
Dromisol
Durasorb
Gamasol 90
Hyadur
Infiltrina
Kemsol
Rimso 50
Sclerosol
Somipront
Syntexan
Topsym
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Brand mixtures
Brand Name Ingredients
Synotic Otic Solution Dimethyl sulfoxide + Fluocinolone acetonide
Categories
  • Free Radical Scavengers
  • Analgesics, Non-Narcotic
  • Solvents
  • Cryoprotective Agents
CAS number 67-68-5
Weight Average: 78.133
Monoisotopic: 78.013935504
Chemical Formula C2H6OS
InChI Key InChIKey=IAZDPXIOMUYVGZ-UHFFFAOYSA-N
InChI
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
Plain Text
IUPAC Name
methanesulfinylmethane
SMILES
CS(C)=O
Plain Text
Mass Spec show (8.05 KB)
Taxonomy
Kingdom Organic
Classes
  • Sulfoxides
Substructures
  • Sulfoxides
Pharmacology
Indication For the symptomatic relief of patients with interstitial cystitis.
Pharmacodynamics Dimethyl 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 action The 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.
Absorption Readily and rapidly absorbed following administration by all routes and distributed throughout the body.
Volume of distribution Not Available
Protein binding Not 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.
Route of elimination Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.
Half life Not Available
Clearance Not Available
Toxicity The 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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bioniche pharma usa llc
  • Bryan corp
Packagers
Dosage forms
Form Route Strength
Solution Intravesical
Solution Topical
Prices
Unit description Cost Unit
Rimso-50 50% Solution 50ml Vial 111.2 USD vial
Sclerosol intrapleural aero 3.98 USD g
Rimso-50 50 % Solution 1.25 USD ml
Rimso-50 solution 1.15 USD ml
Dimethyl Sulfoxide Irrigation 50 % Solution 1.05 USD ml
Dimethyl sulfoxide liquid 0.77 USD ml
Kemsol 70 % Solution 0.31 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 18.5 °C PhysProp
boiling point 189 °C PhysProp
water solubility 1E+006 mg/L DORIGAN,J ET AL. (1976A) @2ND
logP -1.35 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 6.57e+01 g/l ALOGPS
logP -1.1 ALOGPS
logP -1.4 ChemAxon
logS -0.08 ALOGPS
pKa (strongest basic) -6.2 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 17.07 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 20.73 ChemAxon
polarizability 7.91 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01043 Link_out
KEGG Compound C11143 Link_out
PubChem Compound 679 Link_out
PubChem Substance 46505009 Link_out
ChemSpider 659 Link_out
ChEBI 28262 Link_out
ChEMBL 28262 Link_out
PharmGKB PA449342 Link_out
HET DMS Link_out
Drug Product Database 2243231 Link_out
RxList http://www.rxlist.com/cgi/generic/dmso.htm Link_out
Drugs.com http://www.drugs.com/cdi/dimethyl-sulfoxide.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/dim_0098.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Dimethyl_sulfoxide Link_out
ATC Codes
  • G04BX13
  • M02AX03
AHFS Codes
  • 92:00.00
  • 40:36.00
PDB Entries
FDA label Not Available
MSDS show (77.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Enzymes

1. Cytochrome P450 2C19

Actions: inhibitor

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

UniProt ID: P33261 Link_out
Gene: CYP2C19 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

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

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

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 xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain

UniProt ID: P02766 Link_out
Gene: TTR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19