Dimethyl sulfoxide

Identification

Summary

Dimethyl sulfoxide is a reversible mitogen-activated extracellular signal-regulated kinase-1 (MEK1) and MEK2 inhibitor used to treat certain types of melanoma, metastatic non-small cell lung cancer, and locally advanced or metastatic anaplastic thyroid cancer.

Brand Names
Rimso-50
Generic Name
Dimethyl sulfoxide
DrugBank Accession Number
DB01093
Background

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
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.

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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.

TargetActionsOrganism
UInterleukin-5 receptor subunit alpha
downregulator
Humans
UMucin-16
downregulator
Humans
UMyc proto-oncogene protein
downregulator
Humans
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
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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.

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.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Dimethyl sulfoxide.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Dimethyl sulfoxide.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Dimethyl sulfoxide.
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 Acetaminophen can be decreased when combined with Dimethyl sulfoxide.
AcetazolamideAcetazolamide may increase the excretion rate of Dimethyl sulfoxide which could result in a lower serum level and potentially a reduction in efficacy.
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Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dimethyl Sulfoxide Irrigation USPSolution500 mg / gIntravesicalSandoz Canada Incorporated2001-04-242019-08-01Canada flag
Kemsol Liquid 70%Solution70 %TopicalAxxess Pharma Inc.1977-12-312011-07-22Canada flag
Rimso-50Irrigant0.54 g/1mLIntravesicalMylan Institutional LLC1978-04-04Not applicableUS flag
Rimso-50Solution500 mg / gIntravesicalMylan Pharmaceuticals1980-12-31Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dolobene ratiopharm - GelDimethyl sulfoxide (15 g) + Dexpanthenol (2.5 g) + Heparin sodium (50000 IU)GelTopicalTeva B.V.1997-04-22Not applicableAustria flag
VERRUMAL SOLUTIONDimethyl sulfoxide (8 g/100g) + Fluorouracil (0.5 g/100g) + Salicylic acid (10 g/100g)SolutionTopicalZUELLIG PHARMA PTE. LTD.1990-04-30Not applicableSingapore flag
เวอร์รูมาลDimethyl sulfoxide (8 %) + Fluorouracil (0.5 %) + Salicylic acid (10 %)SolutionTopicalบริษัท ซิลลิค ฟาร์มา จำกัด2017-03-14Not applicableThailand flag

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)
Affected organisms
  • Humans and other mammals

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
PDB Entries
1bju / 1bjv / 1c1p / 1c1r / 1c2f / 1c2g / 1c2i / 1d7h / 1dp0 / 1fj3
show 4162 more
MSDS
Download (77.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentInterstitial Cystitis / Painful Bladder Syndrome (PBS)1
4TerminatedTreatmentChemotherapy-Induced Thrombocytopenia / Primary Thrombocytopenia,Unspecified / Thrombocytopenia1
3TerminatedTreatmentDetrusor Hyperreflexia / Overactive Bladder Syndrome (OABS) / Urinary Incontinence (UI) / Urinary Urge Incontinence1
2CompletedPreventionBreast Cancer / Radiation Dermatitis / Radiation Dermatitis Acute1
2TerminatedTreatmentBladder Diseases / Interstitial Cystitis1
2, 3Unknown StatusTreatmentBreast Capsular Contracture / Dimethyl Sulfoxide1
1CompletedOtherCancer1
1CompletedTreatmentMelanoma1
1CompletedTreatmentThrombocytopenia1
1, 2CompletedTreatmentDetrusor Hyperreflexia / Detrusor Instability / Overactive Bladder Syndrome (OABS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Bryan Corp.
  • Edwards Lifesciences LLC
  • Medisca Inc.
Dosage Forms
FormRouteStrength
GelTopical
SolutionTopical70 %
IrrigantIntravesical0.54 g/1mL
SolutionIntravesical500 mg / g
SolutionTopical
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)-8Chemaxon
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

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Interleukin-5 receptor activity
Specific Function
This is the receptor for interleukin-5. The alpha chain binds to IL5.
Gene Name
IL5RA
Uniprot ID
Q01344
Uniprot Name
Interleukin-5 receptor subunit alpha
Molecular Weight
47684.225 Da
References
  1. Ingley E, Young IG: Characterization of a receptor for interleukin-5 on human eosinophils and the myeloid leukemia line HL-60. Blood. 1991 Jul 15;78(2):339-44. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Not Available
Specific Function
Thought to provide a protective, lubricating barrier against particles and infectious agents at mucosal surfaces.
Gene Name
MUC16
Uniprot ID
Q8WXI7
Uniprot Name
Mucin-16
Molecular Weight
1519158.08 Da
References
  1. Langdon SP, Hawkes MM, Hay FG, Lawrie SS, Schol DJ, Hilgers J, Leonard RC, Smyth JF: Effect of sodium butyrate and other differentiation inducers on poorly differentiated human ovarian adenocarcinoma cell lines. Cancer Res. 1988 Nov 1;48(21):6161-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Transcription factor that binds DNA in a non-specific manner, yet also specifically recognizes the core sequence 5'-CAC[GA]TG-3'. Activates the transcription of growth-related genes.
Gene Name
MYC
Uniprot ID
P01106
Uniprot Name
Myc proto-oncogene protein
Molecular Weight
48803.55 Da
References
  1. Tinel M, Elkahwaji J, Robin MA, Fardel N, Descatoire V, Haouzi D, Berson A, Pessayre D: Interleukin-2 overexpresses c-myc and down-regulates cytochrome P-450 in rat hepatocytes. J Pharmacol Exp Ther. 1999 May;289(2):649-55. [Article]

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. [Article]
  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. [Article]
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. [Article]
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. [Article]

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. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 03, 2023 06:21