DrugBank: Dimethyl sulfoxide (DB01093)

enzymes (3) carriers (1)

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

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

Brand names

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

Brand name mixtures

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 (8.1 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

Patents

Not Available

Properties

State

liquid

Melting point

18.5 oC

Experimental Properties

Property	Value	Source
water solubility	1E+006 mg/L	PhysProp
logP	-0.7	PhysProp

Predicted Properties

Property	Value	Source
water solubility	6.57e+01 g/l	ALOGPS
logP	-1.09	ALOGPS
logP	-1.41	ChemAxon Molconvert
logS	-0.08	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	1	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	17.07	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	20.73	ChemAxon Molconvert
polarizability	7.91	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D01043
KEGG Compound	C11143
PubChem Compound	679
PubChem Substance	46505009
ChemSpider	659
ChEBI	28262
ChEMBL	28262
PharmGKB	PA449342
HET	DMS
Drug Product Database	2243231
RxList	http://www.rxlist.com/cgi/generic/dmso.htm
Drugs.com	http://www.drugs.com/cdi/dimethyl-sulfoxide.html
PDRhealth	http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/dim_0098.shtml
Wikipedia	http://en.wikipedia.org/wiki/Dimethyl_sulfoxide

ATC Codes

G04BX13
M02AX03

AHFS Codes

92:00.00
40:36.00

PDB Entries

1JM0

FDA label

Not Available

MSDS

show (77.2 KB)

Interactions

Drug Interactions

Drug	Interaction

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 Gene: CYP2C19 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: CYP2D6 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

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:

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:

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:

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 Gene: TTR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Carriers

1. Transthyretin

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

UniProt ID: P02766 Link_out

Gene: TTR

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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 November 10, 2010 13:45

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.