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MedKoo Cat#: 317630 | Name: Disulfiram
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Disulfiram is used to support the treatment of chronic alcoholism by producing an acute sensitivity to ethanol. Disulfiram works by inhibiting the enzyme acetaldehyde dehydrogenase.

Chemical Structure

Disulfiram
Disulfiram
CAS#97-77-8

Theoretical Analysis

MedKoo Cat#: 317630

Name: Disulfiram

CAS#: 97-77-8

Chemical Formula: C10H20N2S4

Exact Mass: 296.0509

Molecular Weight: 296.54

Elemental Analysis: C, 40.50; H, 6.80; N, 9.45; S, 43.25

Price and Availability

Size Price Availability Quantity
10g USD 150.00 Ready to ship
20g USD 250.00 Ready to ship
50g USD 450.00 Ready to ship
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Related CAS #
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Synonym
NSC 190940; NSC-190940; NSC190940; Disulfiram; Dicupral; Disetil; Disulfan
IUPAC/Chemical Name
Bis(diethylthiocarbamyl) disulfide
InChi Key
AUZONCFQVSMFAP-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
SMILES Code
S=C(SSC(N(CC)CC)=S)N(CC)CC
Appearance
White to off-white solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T20C04I23
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Disulfiram (Tetraethylthiuram disulfide) is a specific inhibitor of aldehyde-dehydrogenase (ALDH1).
In vitro activity:
These data suggested that DSF (Disulfiram) increased lipid peroxidation. CellRox Green Reagent, which detects oxidative stress, exhibited bright green fluorescence in DSF treated GBM cells. These results indicated that DSF led to increased total ROS in U251 and LN229 cells (Figure 2B and C). The study also tested the levels of ferrous iron with a colorimetric assay kit and results showed that DSF increased levels of ferrous iron (Figure 2D). Levels of proteins that block ferroptosis, xCT and GPX-4, decreased in the presence of DSF in a dose-dependent manner (Figure 2E). Transmission electron microscopy also revealed the shrunken morphology of mitochondria in DSF treated GBM cells (red arrows, Figure 2F) and the enhanced density of mitochondrial membranes (Figure 2F). Iron chelator deferoxamine mesylate (DFO) and ferroptosis inhibitor ferrostatin-1 (Fer-1) were used to verify whether these results were iron- and ferroptosis-dependent. This study found that DFO and Fer-1 inhibited DSF-induced up-regulation of lipid peroxidation (Figure 2G) and cytotoxic effect (Figure 2H). All together, these data demonstrated that DSF triggered ferroptosis in GBM. Reference: Onco Targets Ther. 2020; 13: 10631–10640. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7585819/
In vivo activity:
Finally, to investigate the effect of Dsf (disulfiram) on OSCC (oral squamous cell carcinoma) growth, this study established a subcutaneous tumor model in BALB/c nude mice with CAL27 cells. As shown in Figure 5, A and B, compared with the control group, tumor volume in the Dsf-treated group was suppressed markedly. To evaluate the proliferation status of tumors, the study performed immunohistochemical staining of Ki67 (Figure 5C). Ki67 expression was inhibited significantly in the Dsf-treatment group, which indicated Dsf anticancer activity in OSCC. The EMT status of these tumors was also investigated. This study found obvious expression of vimentin and Snail at the infiltrative border in the control group, while expression of these EMT markers was blocked when mice were administered Dsf (Figure 5C), suggesting that Dsf can inhibit tumor growth and EMT in vivo. Reference: Cancer Manag Res. 2019; 11: 3887–3898. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6504671/
Solvent mg/mL mM
Solubility
DMSO 40.0 134.82
DMF 30.0 101.17
DMF:PBS (pH 7.2) (1:4) 0.2 0.67
Ethanol 34.6 116.51
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 296.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Qiu C, Zhang X, Huang B, Wang S, Zhou W, Li C, Li X, Wang J, Yang N. Disulfiram, a Ferroptosis Inducer, Triggers Lysosomal Membrane Permeabilization by Up-Regulating ROS in Glioblastoma. Onco Targets Ther. 2020 Oct 20;13:10631-10640. doi: 10.2147/OTT.S272312. PMID: 33116640; PMCID: PMC7585819. 2. Sun T, Yang W, Toprani SM, Guo W, He L, DeLeo AB, Ferrone S, Zhang G, Wang E, Lin Z, Hu P, Wang X. Induction of immunogenic cell death in radiation-resistant breast cancer stem cells by repurposing anti-alcoholism drug disulfiram. Cell Commun Signal. 2020 Mar 5;18(1):36. doi: 10.1186/s12964-019-0507-3. Erratum in: Cell Commun Signal. 2020 Apr 2;18(1):53. PMID: 32138738; PMCID: PMC7057578. 3. Wang R, Shen J, Yan H, Gao X, Dong T, Wang P, Zhou J. The Evolving Role of Disulfiram in Radiobiology and the Treatment of Breast Cancer. Onco Targets Ther. 2020 Oct 14;13:10441-10446. doi: 10.2147/OTT.S271532. PMID: 33116623; PMCID: PMC7569069. 4. Bu W, Wang Z, Meng L, Li X, Liu X, Chen Y, Xin Y, Li B, Sun H. Disulfiram inhibits epithelial-mesenchymal transition through TGFβ-ERK-Snail pathway independently of Smad4 to decrease oral squamous cell carcinoma metastasis. Cancer Manag Res. 2019 May 1;11:3887-3898. doi: 10.2147/CMAR.S199912. Erratum in: Cancer Manag Res. 2019 May 22;11:4617. PMID: 31118804; PMCID: PMC6504671.
In vitro protocol:
1. Qiu C, Zhang X, Huang B, Wang S, Zhou W, Li C, Li X, Wang J, Yang N. Disulfiram, a Ferroptosis Inducer, Triggers Lysosomal Membrane Permeabilization by Up-Regulating ROS in Glioblastoma. Onco Targets Ther. 2020 Oct 20;13:10631-10640. doi: 10.2147/OTT.S272312. PMID: 33116640; PMCID: PMC7585819. 2. Sun T, Yang W, Toprani SM, Guo W, He L, DeLeo AB, Ferrone S, Zhang G, Wang E, Lin Z, Hu P, Wang X. Induction of immunogenic cell death in radiation-resistant breast cancer stem cells by repurposing anti-alcoholism drug disulfiram. Cell Commun Signal. 2020 Mar 5;18(1):36. doi: 10.1186/s12964-019-0507-3. Erratum in: Cell Commun Signal. 2020 Apr 2;18(1):53. PMID: 32138738; PMCID: PMC7057578.
In vivo protocol:
1. Wang R, Shen J, Yan H, Gao X, Dong T, Wang P, Zhou J. The Evolving Role of Disulfiram in Radiobiology and the Treatment of Breast Cancer. Onco Targets Ther. 2020 Oct 14;13:10441-10446. doi: 10.2147/OTT.S271532. PMID: 33116623; PMCID: PMC7569069. 2. Bu W, Wang Z, Meng L, Li X, Liu X, Chen Y, Xin Y, Li B, Sun H. Disulfiram inhibits epithelial-mesenchymal transition through TGFβ-ERK-Snail pathway independently of Smad4 to decrease oral squamous cell carcinoma metastasis. Cancer Manag Res. 2019 May 1;11:3887-3898. doi: 10.2147/CMAR.S199912. Erratum in: Cancer Manag Res. 2019 May 22;11:4617. PMID: 31118804; PMCID: PMC6504671.
1: Triscott J, Rose Pambid M, Dunn SE. Concise review: bullseye: targeting cancer stem cells to improve the treatment of gliomas by repurposing disulfiram. Stem Cells. 2015 Apr;33(4):1042-6. doi: 10.1002/stem.1956. Review. PubMed PMID: 25588723. 2: Kulkarni RR, Pradeep AV, Bairy BK. Disulfiram-induced combined irreversible anterior ischemic optic neuropathy and reversible peripheral neuropathy: a prospective case report and review of the literature. J Neuropsychiatry Clin Neurosci. 2013 Fall;25(4):339-42. doi: 10.1176/appi.neuropsych.12120410. Review. PubMed PMID: 24247861. 3: Mutschler J, Kiefer F. [Mechanism of action of disulfiram and treatment optimization in prevention of recurrent alcoholism]. Praxis (Bern 1994). 2013 Jan 30;102(3):139-46. doi: 10.1024/1661-8157/a001178. Review. German. PubMed PMID: 23384983. 4: Kast RE, Halatsch ME. Matrix metalloproteinase-2 and -9 in glioblastoma: a trio of old drugs-captopril, disulfiram and nelfinavir-are inhibitors with potential as adjunctive treatments in glioblastoma. Arch Med Res. 2012 Apr;43(3):243-7. doi: 10.1016/j.arcmed.2012.04.005. Epub 2012 May 5. Review. PubMed PMID: 22564423. 5: De Mulder I, Dom G. [Disulfiram as a treatment for cocaine dependency]. Tijdschr Psychiatr. 2012;54(1):51-8. Review. Dutch. PubMed PMID: 22237610. 6: Petrov I, Krogh J, Nordentoft M. [Meta-analysis of pharmacological therapy with acamprosate, naltrexone, and disulfiram--a systematic review]. Ugeskr Laeger. 2011 Nov 28;173(48):3103-9. Review. Danish. PubMed PMID: 22118653. 7: Jørgensen CH, Pedersen B, Tønnesen H. The efficacy of disulfiram for the treatment of alcohol use disorder. Alcohol Clin Exp Res. 2011 Oct;35(10):1749-58. doi: 10.1111/j.1530-0277.2011.01523.x. Epub 2011 May 25. Review. PubMed PMID: 21615426. 8: Charpeaud T, Geneste J, Schmidt J, Llorca PM, Brousse G. [Disulfiram and addiction: reminders and new perspectives of use]. Therapie. 2011 May-Jun;66(3):273-80. Epub 2011 Aug 9. Review. French. PubMed PMID: 21924121. 9: Cvek B. Targeting malignancies with disulfiram (Antabuse): multidrug resistance, angiogenesis, and proteasome. Curr Cancer Drug Targets. 2011 Mar;11(3):332-7. Review. PubMed PMID: 21247389. 10: Kona FR, Buac D, M Burger A. Disulfiram, and disulfiram derivatives as novel potential anticancer drugs targeting the ubiquitin-proteasome system in both preclinical and clinical studies. Curr Cancer Drug Targets. 2011 Mar;11(3):338-46. Review. PubMed PMID: 21247383. 11: Barth KS, Malcolm RJ. Disulfiram: an old therapeutic with new applications. CNS Neurol Disord Drug Targets. 2010 Mar;9(1):5-12. Review. PubMed PMID: 20201810. 12: Krampe H, Ehrenreich H. Supervised disulfiram as adjunct to psychotherapy in alcoholism treatment. Curr Pharm Des. 2010;16(19):2076-90. Review. PubMed PMID: 20482514. 13: Pani PP, Trogu E, Vacca R, Amato L, Vecchi S, Davoli M. Disulfiram for the treatment of cocaine dependence. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD007024. doi: 10.1002/14651858.CD007024.pub2. Review. PubMed PMID: 20091613. 14: Gaval-Cruz M, Weinshenker D. mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. Review. PubMed PMID: 19720750; PubMed Central PMCID: PMC2861803. 15: Malcolm R, Olive MF, Lechner W. The safety of disulfiram for the treatment of alcohol and cocaine dependence in randomized clinical trials: guidance for clinical practice. Expert Opin Drug Saf. 2008 Jul;7(4):459-72. doi: 10.1517/14740338.7.4.459 . Review. PubMed PMID: 18613809. 16: Cvek B, Dvorak Z. The value of proteasome inhibition in cancer. Can the old drug, disulfiram, have a bright new future as a novel proteasome inhibitor? Drug Discov Today. 2008 Aug;13(15-16):716-22. doi: 10.1016/j.drudis.2008.05.003. Epub 2008 Jun 23. Review. PubMed PMID: 18579431. 17: Kast RE. Ritonavir and disulfiram may be synergistic in lowering active interleukin-18 levels in acute pancreatitis, and thereby hasten recovery. JOP. 2008 May 8;9(3):350-3. Review. PubMed PMID: 18469453. 18: Khan S, Singhal S, Mathur T, Upadhyay DJ, Rattan A. Antifungal potential of disulfiram. Nihon Ishinkin Gakkai Zasshi. 2007;48(3):109-13. Review. PubMed PMID: 17667894. 19: Blanc M, Daeppen JB. [Does disulfiram still have a role in alcoholism treatment?]. Rev Med Suisse. 2005 Jun 29;1(26):1728-30, 1732-3. Review. French. PubMed PMID: 16117046. 20: Nucifora G, Cassin M, Brun F, Nicolosi GL. [Anterior myocardial infarction in a chronic alcoholic man on disulfiram therapy: a case report]. Ital Heart J Suppl. 2004 Dec;5(12):900-4. Review. Italian. PubMed PMID: 15709459.

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