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tetraethylthioperoxydicarbonic diamide ([[(C2H5)2N]C(S)]2S2)
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97-77-8 Usage

Chemical Properties

yellow-white crystals or grey powder

Brand name

Antabuse (Odyssey) .

Warning and precaution

The following tips should be pay attention during administration of disulfiram[9].
Disulfiram is not allowed if the patients have consumed alcohol within the past 12 hours. Do not drink alcohol while taking disulfiram and for up to 14 days after stop taking disulfiram.
It is not known whether disulfiram will harm an unborn baby. Tell your doctor if you are pregnant or plan to become pregnant while using this medicine. It is not known whether disulfiram passes into breast milk or if it could harm a nursing baby. You should not breast-feed while using this medicine. People less than 18 years old should also disabled.
Disulfiram should not be used in the following cases:
Allergic people; those who have recently taken metronidazole (Flagyl) or paraldehyde; or have consumed any foods or products that contain alcohol;
People of the following cases should consult the doctors:
Liver or kidney disease; heart disease, high blood pressure, history of heart attack or stroke;
Underactive thyroid; diabetes; seizures or epilepsy; head injury or brain damage; a history of mental illness or psychosis; an allergy to rubber; or taking phenytoin (Dilantin), tuberculosis medicine, or a blood thinner (warfarin, Coumadin, Jantoven).

General Introduction

Alcohol dependence is a chronic disorder that may have multiple relapses and remissions, increased mortality and low long-term abstinence rates that lead to increased psychosocial losses. Many drugs have been used in the treatment of this disorder such as the anti-craving agents, acamprosate, naltrexone and the aversive agent, disulfiram[1, 2]. Disulfiram (trade name: Antabuse) has been in use since the early 1940s for the treatment of alcohol dependence and is the first FDA-approved medication for the treatment of this disorder[3,4,5]. Disulfiram has thus completed almost 60 years of use in alcohol use disorders and has stood the test of time[6]. A large number of studies have been done on this molecule, ever since some proving its superiority over other drugs while others negating it.
The mechanism of action of disulfiram is through inhibiting the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake causing an accumulation of acetaldehyde in the blood producing highly unpleasant symptoms. Disulfiram blocks the oxidation of alcohol through irreversibly inactivating the aldehyde dehydrogenase, which acts in the second step of ethanol utilization[7].

Contact allergens

TETD is a rubber accelerator of the thiuram group, contained in “thiuram mix.” It can cross-react with other thiurams, especially TMTD. TETD is used to aid those trying to break their dependence on alcohol. The disulfiram-alcohol reaction is not allergic but due to the accumulation of toxic levels of acetaldehyde. The implanted drug can, however, lead to local or generalized dermatitis, for example ingested disulfiram, mainly in previously rubber-sensitized patients. As an adjunctive treatment of alcoholism, it caused occupational contact dermatitis in a nurse.

Hazard

Toxic symptoms when ingested with alcohol; animal teratogen. Vasodilation and nausea. Questionable carcinogen.

Indications

Disulfiram is used as a second line treatment of alcohol dependence, behind acamprosate and naltrexone[8]. It is an aid for the management of selected chronic alcohol patients who want to remain in a state of enforced sobriety so that supportive and psychotherapeutic treatment may be applied to best advantage. However, it should be noted that disulfiram is not a cure for alcoholism. When used alone, without proper motivation and supportive therapy, it is unlikely that it will have any substantive effect on the drinking pattern of the chronic alcoholic dependence[5]. Disulfiram should not be taken if alcohol has been consumed in the last 12 hours[9].
Recently, more and more studies have shown that disulfiram has the potential for the treatment of cancer[12, 13] and HIV infections[10, 11]. Disulfiram (DSF) can reactivate latent HIV-1 expression in a primary cell model of virus latency and has the potential to deplete the latent HIV-1 reservoir in patients on combination antiretroviral therapy. DSF can reactivate latent HIV-1 expression via the Akt signaling pathway through depletion of PTEN[10]. Recent studies have disclosed a surprising, but mechanistically consistent, anticancer activity of disulfiram. Disulfiram has been successfully used to suppress hepatic metastases originating from ocular melanoma[12]. The anticancer mechanism of disulfiram is through inhibiting the 26S proteasome (The orderly degradation of cellular proteins is critical for normal cell cycling and function, and inhibition of the proteasome pathway results in cell-cycle arrest and apoptosis)[12-14]. Moreover, disulfiram was also found to have specific activity against zinc fingers and RING-finger ubiquitin E3 ligases that play an important role in cancer development[12, 13].

Uses

For the treatment and management of chronic alcoholism

Definition

ChEBI: An organic disulfide that results from the formal oxidative dimerisation of N,N-diethyldithiocarbamic acid. A multi-enzyme inhibitor that is used in alcohol aversion therapy and also exhibits anticancer properties.

Mode of action

Ethanol undergoes metabolism in the liver initially by alcohol dehydrogenase (ADH) forming acetaldehyde; this is removed from the body primarily by oxidation into acetate by acetaldehyde dehydrogenase (ALDH)[15], which finally enters the citric acid cycle. Disulfiram acts by inhibiting the enzyme ALDH via its metabolite S-methyl N, N-diethyl-dithio-carbamate-sulphoxide[16], leading to accumulation of acetaldehyde in blood. This gives rise to various manifestations of disulfiram-alcohol reaction (DER)[17]. Since the inhibition of ALDH by disulfiram is irreversible, the DER will get terminated only after production of new ALDH oncedisulfiram is stopped. The new ALDH takes about a week’s time to be produced. Hence patients should be advised to take alcohol only after 2 weeks of stopping disulfiram[18]. In addition to this, disulfiram also acts on the dopaminergic system, both disulfiram and its metabolite carbon disulfide leading to inhibition of dopamine beta-hydroxylase (DBH) that leads to increase in the levels of dopamine. This may give rise to several neuropsychiatric manifestations such as delirium, paranoia, impairment of memory, ataxia, dysarthria and frontal lobe release signs[19]. Besides this action, disulfiram is also known to inhibit dopamine beta-hydroxylase leading to an increase in dopamine concentrations but decreased norepinephrine in the brain[20]. This may suggest an anti-craving role of disulfiram in alcohol dependence[21].

Uses

Alcohol deterrent;Dopamine beta-hydroxylase inhibitor

Uses

Disulfiram is a copper and zinc chelator and an irreversible inhibitor of aldehyde dehydrogenase (IC50 = 0.1 mM) that has been indicated for the treatment of alcohol dependence. It also inhibits the copper-dependent enzyme dopamine β-hydroxylase, which prevents the breakdown of dopamine and has been considered as a treatment for cocaine dependence. When in complex with copper, disulfiram has been shown to inhibit purified 20S proteasome (IC50 = 7.5 μM) and 26S proteasome (IC50 = 20 μM) from MDA-MB-0231 breast cancer cells. Because disulfiram targets the ubiquitin-proteasome pathway, it has been investigated as an anti-cancer agent. Furthermore, at 250 nM it has been shown to induce reactive oxygen species, to activate JNK and p38 pathways, and to inhibit NF-κB activity, which suppresses self-renewal in cancer stem cells.

Adverse reactions

In severe cases, hepatitis such as both cholestatic and fulminant hepatitis, as well as hepatic failure resulting in transplantation or death, could occur upon treatment of disulfiram[5]. In a small number of patients, side effects include a transient mild drowsiness, fatigability, impotence, headache, acneform eruptions, allergic dermatitis, or a metallic or garlic-like aftertaste during the first two weeks of therapy. These reactions often disappear spontaneously with the continuation of therapy, or with reduced dosage. High dosage, combined toxicity (with metronidazole or isoniazid), or to the unmasking of underlying psychoses can cause psychotic reactions[5].

Fire Hazard

Flash point data for Disulfiram are not available; however, Disulfiram is probably combustible.

Air & Water Reactions

Insoluble in water.

General Description

Odorless or almost odorless white or almost white to tan powder. Unpleasant taste with metallic or garlic aftertaste. pH of a solution obtained by shaking 1 g with 30 mL of water is 6 to 8.

Biological Activity

Inhibitor of aldehyde dehydrogenase that displays antialcoholism activity. Shown to reversibly stimulated Ca 2+ -ATPase activity and inhibit V-ATPase (EC 50 = 26 μ M). Also inhibits expression of MMP-2 and MMP-9 and displays anti-invasive activity.

Reactivity Profile

Disulfiram is sensitive to light. Disulfiram is incompatible with strong acids, strong oxidizers and nitrosating agents (e.g. N-Nitrosodiphenylamine). .

References

  1. Bouza, C., Angeles, M., Muñoz, A., & Amate, J. M. (2015). Efficacy and safety of naltrexone and acamprosate in the treatment of alcohol dependence: a systematic review. Addiction, 99(7), 811-828.
  2. Laaksonen, E., Koskijännes, A., Salaspuro, M., Ahtinen, H., & Alho, H. (2008). A randomized, multicentre, open-label, comparative trial of disulfiram, naltrexone and acamprosate in the treatment of alcohol dependence. Alcohol & Alcoholism, 43(1), 53.
  3. Petrakis, I.L., Nich, C. and Ralevski, E. (2006) Psychotic spectrum disorders and alcohol abuse: A review of pharmacotherapeutic strategies and a report on the effective-ness of naltrexone and disulfiram. Schizophrenia Bulletin, 32, 644-654.
  4. De Sousa, A. (2010) The pharmacotherapy of alcohol dependence: A state of the art review. Mens Sana Monographs, 8, 69-82.
  5. https://www.rxlist.com/antabuse-drug.htm
  6. Krampe, H., & Ehrenreich, H. (2010). Supervised disulfiram as adjunct to psychotherapy in alcoholism treatment. Current Pharmaceutical Design, 16(19), (60 years)
  7. Johansson, B. (1992) A review of the pharmacokinetics and pharmacodynamics of disulfiram and its metabolites. Acta Psychiatrica Scandanavica, 362, 15-26.
  8. https://www.ncbi.nlm.nih.gov/books/NBK459340/
  9. https://www.drugs.com/pro/disulfiram.html
  10. Doyon, G., Zerbato, J., Mellors, J. W., & Sluiscremer, N. (2013). Disulfiram reactivates latent hiv-1 expression through depletion of the phosphatase and tensin homolog. Aids, 27(2), F7-F11.
  11. Rasmussen, TA; Lewin, SR (July 2016). "Shocking HIV out of hiding: where are we with clinical trials of latency reversing agents?". Current Opinion in HIV and AIDS.
  12. Cvek, B., & Dvorak, Z. (2008). The value of proteasome inhibition in cancer: can the old drug, disulfiram, have a bright new future as a novel proteasome inhibitor?. Drug Discovery Today, 13(15), 716-722.
  13. Kona, F. R., Buac, D., & A, M. B. (2011). Disulfiram, and disulfiram derivatives as novel potential anticancer drugs targeting the ubiquitin-proteasome system in both preclinical and clinical studies. Current Cancer Drug Targets, 11(3).
  14. Rajkumar, S. V., Richardson, P. G., Hideshima, T., & Anderson, K. C. (2005). Proteasome inhibition as a novel therapeutic target in human cancer. Journal of Clinical Oncology, 23(3), 630-639.
  15. Deitrich, R.A., Petersen, D. and Vasiliou, V. (2007) Removal of acetaldehyde from the body. Novartis Foundation Symposia, 285, 23-40.
  16. Pike, M.G., Mays, D.C., Macomber, D.W. and Lipsky, J.J. (2001) Metabolism of a disulfiram metabolite S-methyl N,N-diethyldithiocarbamate by flavinmonooxygenase in human renal microsomes. Drug Metabolism & Disposition, 29, 127-132.
  17. Larsen, V. (1948) The effects on experimental animals of antabuse (tetraethylthiuram disulfide) in combination with alcohol. Acta Pharmacologica Toxicology, 4, 321-332. 
  18. Krampe, H. and Ehrenreich, H. (2010) Supervised disulfiram as adjunct to psychotherapy in alcoholism treatment. Current Pharmaceutical Design, 16, 2076-2090. 
  19. Fuller, R.K. and Gordis, E. (2004) Does disulfiram have a role in alcoholism treatment today? Addiction, 99, 21-24. 
  20. Vaccari, A., Saba, P.L., Ruiu, S., Collu, M. and Devoto, P. (1996) Disulfiram and diethyldithiocarbamate intoxica-tion affects the storage and release of striatal dopamine. Toxicology & Applied Pharmacology, 139, 102-108. 
  21. Muller, C.A. and Banas, R. (2011) Disulfiram: An anti-craving substance? American Journal of Psychiatry, 168, 98. 

Uses

It is used as rubber accelerator; vulcanizer; seed disinfectant; fungicide; alcohol deterrent.
InChI:InChI=1/C10H20N2O3S/c1-5-11(6-2)9(13)14-10(16)15-12(7-3)8-4/h5-8H2,1-4H3

97-77-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (86720)  Tetraethylthiuramdisulfide  ≥97.0% (S) 97-77-8 86720-1KG 2,602.08CNY Detail
Aldrich (86720)  Tetraethylthiuramdisulfide  ≥97.0% (S) 97-77-8 86720-250G 1,404.00CNY Detail
Aldrich (86720)  Tetraethylthiuramdisulfide  ≥97.0% (S) 97-77-8 86720-50G 538.20CNY Detail
Sigma-Aldrich (D2950000)  Disulfiram  European Pharmacopoeia (EP) Reference Standard 97-77-8 D2950000 1,880.19CNY Detail
Alfa Aesar (B20721)  Tetraethylthiuram disulfide, 97%    97-77-8 5000g 5189.0CNY Detail
Alfa Aesar (B20721)  Tetraethylthiuram disulfide, 97%    97-77-8 1000g 1224.0CNY Detail
Alfa Aesar (B20721)  Tetraethylthiuram disulfide, 97%    97-77-8 250g 383.0CNY Detail
Alfa Aesar (B20721)  Tetraethylthiuram disulfide, 97%    97-77-8 100g 256.0CNY Detail
TCI America (B0479)  Tetraethylthiuram Disulfide  >97.0%(T) 97-77-8 500g 590.00CNY Detail
TCI America (B0479)  Tetraethylthiuram Disulfide  >97.0%(T) 97-77-8 25g 160.00CNY Detail

97-77-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name disulfiram

1.2 Other means of identification

Product number -
Other names Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetraethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

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