Identification

Name
Dimethyl sulfoxide
Accession Number
DB01093  (APRD00925, EXPT01231)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • (CH3)2SO
  • Dimethyl sulfoxide
  • Dimethyl sulfur oxide
  • Dimethyl sulphoxide
  • Dimethyli sulfoxidum
  • Dimethylsulfoxid
  • Dimethylsulfoxyde
  • Dimetil sulfoxido
  • DMSO
  • Methylsulfinylmethane
  • S(O)Me2
  • Sulfinylbis(methane)
External IDs
NSC-763 / SQ 9453 / SQ-9453
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 Institutional1978-04-04Not applicableUs
Rimso-50Solution500 mgIntravesicalMylan Pharmaceuticals1980-12-31Not applicableCanada
Categories
UNII
YOW8V9698H
CAS number
67-68-5
Weight
Average: 78.133
Monoisotopic: 78.013935504
Chemical Formula
C2H6OS
InChI Key
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
InChI
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3
IUPAC Name
methanesulfinylmethane
SMILES
CS(C)=O

Pharmacology

Indication

For the symptomatic relief of patients with interstitial cystitis.

Structured Indications
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AtorvastatinThe risk or severity of adverse effects can be increased when Dimethyl sulfoxide is combined with Atorvastatin.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Dimethyl sulfoxide.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Dimethyl sulfoxide.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Dimethyl sulfoxide.Withdrawn
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
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Dimethyl sulfoxide.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Dimethyl sulfoxide.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Dimethyl sulfoxide.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Dimethyl sulfoxide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Dimethyl sulfoxide.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Dimethyl sulfoxide.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Dimethyl sulfoxide.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Dimethyl sulfoxide.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Dimethyl sulfoxide.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Dimethyl sulfoxide.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Dimethyl sulfoxide.Illicit, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Dimethyl sulfoxide.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Dimethyl sulfoxide.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Dimethyl sulfoxide.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Dimethyl sulfoxide.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Dimethyl sulfoxide.Experimental
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Dimethyl sulfoxide.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Dimethyl sulfoxide.Approved, Vet Approved, Withdrawn
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Dimethyl sulfoxide.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Dimethyl sulfoxide.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Dimethyl sulfoxide.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Dimethyl sulfoxide.Approved
SulindacThe metabolism of Sulindac can be decreased when combined with Dimethyl sulfoxide.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Dimethyl sulfoxide.Experimental
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Dimethyl sulfoxide.Withdrawn
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Dimethyl sulfoxide.Experimental
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB02151
KEGG Drug
D01043
KEGG Compound
C11143
PubChem Compound
679
PubChem Substance
46505009
ChemSpider
659
BindingDB
50026472
ChEBI
28262
ChEMBL
CHEMBL504
PharmGKB
PA449342
HET
DMS
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Dimethyl_sulfoxide
ATC Codes
G04BX13 — Dimethyl sulfoxideM02AX03 — Dimethyl sulfoxide
AHFS Codes
  • 92:00.00 — Miscellaneous Therapeutic Agents
PDB Entries
1bju / 1bjv / 1c1p / 1c1r / 1c2f / 1c2g / 1c2i / 1d7h / 1dp0 / 1fj3
show 1449 more
MSDS
Download (77.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentBladder Pain Syndrome1
1CompletedTreatmentDentist-Patient Relations1
1CompletedTreatmentMelanoma (Skin)1
1, 2CompletedTreatmentDetrusor Hyperreflexia / Detrusor Instability / Overactive Bladder1
2TerminatedTreatmentBladder Diseases / Interstitial Cystitis1
2, 3Not Yet RecruitingTreatmentBreast Capsular Contracture / Dimethyl Sulfoxide1
3TerminatedTreatmentDetrusor Hyperreflexia / Overactive Bladder / Urge Incontinence / Urinary Incontinence (UI) / Urinary Urge Incontinence1
Not AvailableCompletedNot AvailableComplex Regional Pain Syndrome (CRPS) / Complex Regional Pain Syndrome Type I / Neurocostal neuralgia / Postherpetic Neuralgia1
Not AvailableCompletedTreatmentTemporomandibular Degenerative Joint Disease1
Not AvailableUnknown StatusTreatmentInterstitial Cystitis2

Pharmacoeconomics

Manufacturers
Not 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.
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)
Download (8.05 KB)
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

Taxonomy

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
Sulfoxide / Sulfinyl compound / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
sulfoxide (CHEBI:28262) / a small molecule (DMSO)

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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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
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, 2017 09:35