Dimethyl sulfoxide

Identification

Name
Dimethyl sulfoxide
Accession Number
DB01093
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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 78.133
Monoisotopic: 78.013935504
Chemical Formula
C2H6OS
Synonyms
  • Dimethyl sulfoxide
  • Dimethyl sulfur oxide
  • Dimethyl sulphoxide
  • Dimethyli sulfoxidum
  • Dimethylsulfoxid
  • Diméthylsulfoxyde
  • Dimetil sulfóxido
  • DMSO
  • Methylsulfinylmethane
  • S(O)Me2
  • Sulfinylbis(methane)
External IDs
  • NSC-763
  • SQ 9453
  • SQ-9453

Pharmacology

Indication

For the symptomatic relief of patients with interstitial cystitis.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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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.

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Route of elimination

Dimethyl sulfoxide and dimethyl sulfone are excreted in the urine and feces.

Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Dimethyl sulfoxide which could result in a higher serum level.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Dimethyl sulfoxide.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Dimethyl sulfoxide.
AcarboseAcarbose may decrease the excretion rate of Dimethyl sulfoxide which could result in a higher serum level.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Dimethyl sulfoxide.
AceclofenacAceclofenac may decrease the excretion rate of Dimethyl sulfoxide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dimethyl sulfoxide which could result in a higher serum level.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Dimethyl sulfoxide.
AcetaminophenThe metabolism of Dimethyl sulfoxide can be decreased when combined with Acetaminophen.
AcetazolamideAcetazolamide may increase the excretion rate of Dimethyl sulfoxide which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dimethyl Sulfoxide Irrigation USPSolutionIntravesicalSandoz Canada Incorporated2001-04-242019-08-01Canada flag
Kemsol Liquid 70%SolutionTopicalAxxess Pharma Inc.1977-12-312011-07-22Canada flag
Rimso-50Solution500 mgIntravesicalMylan Pharmaceuticals1980-12-31Not applicableCanada flag
Rimso-50Irrigant0.54 g/1mLIntravesicalMylan Institutional LLC1978-04-04Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
M02AX03 — Dimethyl sulfoxideG04BX13 — Dimethyl sulfoxide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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).
Kingdom
Organic compounds
Super Class
Organosulfur compounds
Class
Sulfoxides
Sub Class
Not Available
Direct Parent
Sulfoxides
Alternative Parents
Sulfinyl compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Sulfinyl compound / Sulfoxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
sulfoxide (CHEBI:28262) / a small molecule (DMSO)

Chemical Identifiers

UNII
YOW8V9698H
CAS number
67-68-5
InChI Key
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
InChI
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
IUPAC Name
methanesulfinylmethane
SMILES
CS(C)=O

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 References
Not Available
Human Metabolome Database
HMDB0002151
KEGG Drug
D01043
KEGG Compound
C11143
PubChem Compound
679
PubChem Substance
46505009
ChemSpider
659
BindingDB
50026472
RxNav
3455
ChEBI
28262
ChEMBL
CHEMBL504
ZINC
ZINC000005224188
PharmGKB
PA449342
PDBe Ligand
DMS
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Dimethyl_sulfoxide
AHFS Codes
  • 92:00.00 — Miscellaneous Therapeutic Agents
PDB Entries
1bju / 1bjv / 1c1p / 1c1r / 1c2f / 1c2g / 1c2i / 1d7h / 1dp0 / 1fj3
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MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentPrimary Thrombocytopenia,Unspecified / Thrombocytopenia / Thrombocytopenia Chemotherapy Induced1
3TerminatedTreatmentDetrusor Hyperreflexia / Urinary Bladder, Overactive / Urinary Incontinence (UI) / Urinary Incontinence, Urge / Urinary Urge Incontinence1
2RecruitingPreventionBreast Cancer / Radiation Dermatitis / Radiation Dermatitis Acute1
2TerminatedTreatmentBladder Diseases / Interstitial Cystitis1
2, 3Unknown StatusTreatmentBreast Capsular Contracture / Dimethyl Sulfoxide1
1CompletedOtherMalignancies1
1CompletedTreatmentMalignant Melanoma of Skin / Melanoma (Skin)1
1CompletedTreatmentThrombocytopenia1
1, 2CompletedTreatmentDetrusor Hyperreflexia / Detrusor Instability / Urinary Bladder, Overactive1
1, 2CompletedTreatmentOsteoarthritis Pain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Bryan Corp.
  • Edwards Lifesciences LLC
  • Medisca Inc.
Dosage Forms
FormRouteStrength
SolutionIntravesical
Cream10 g/100g
Cream25 g/100g
SolutionTopical10 mL/100mL
EmulsionTopical10 mL/100mL
SolutionTopical10 g/100mL
SolutionTopical
IrrigantIntravesical0.54 g/1mL
SolutionIntravesical500 mg
Gel8 g/100g
SolutionTopical8 g/100g
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.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)18.5 °CPhysProp
boiling point (°C)63Smedslund, 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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03fr-9000000000-f0f118841efd8b3297a3
GC-MS Spectrum - EI-BGC-MSsplash10-03fs-9000000000-945240052686ea267e2b
GC-MS Spectrum - EI-BGC-MSsplash10-03fs-9000000000-378b716bc39417224511
Mass Spectrum (Electron Ionization)MSsplash10-03fr-9000000000-1db858034b22d1646592
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-c8f7a9f09c8bb456283c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-d8d98568ae59afba65e6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-e0a36c290f004f302f0b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-89687ba96456a97fb486
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9000000000-04ddc1322b21e4817d57
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-d90c2fed7aad139b406c
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Enzymes

Kind
Protein
Organism
Humans
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Busby WF Jr, Ackermann JM, Crespi CL: Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. Drug Metab Dispos. 1999 Feb;27(2):246-9. [PubMed:9929510]
  2. Easterbrook J, Lu C, Sakai Y, Li AP: Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes. Drug Metab Dispos. 2001 Feb;29(2):141-4. [PubMed:11159803]
Kind
Protein
Organism
Humans
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Busby WF Jr, Ackermann JM, Crespi CL: Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. Drug Metab Dispos. 1999 Feb;27(2):246-9. [PubMed:9929510]
Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Busby WF Jr, Ackermann JM, Crespi CL: Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. Drug Metab Dispos. 1999 Feb;27(2):246-9. [PubMed:9929510]

Carriers

Kind
Protein
Organism
Humans
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
Uniprot Name
Transthyretin
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]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2020 01:55

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