disulfiram

[DISULFI(DE) + (thiu)ram, chemical name (THI(O)- + UR(EA) + AM(IDE)).]

Brand names: Antabuse®

Chemical formula:

Drug Forms:
• Disulfiram Oral tablet (below)
• Disulfiram tablets

Español:
• Disulfiram, Tableta oral
• Tabletas de disulfiram

Disulfiram Oral tablet

What is this medicine?

DISULFIRAM can help patients with an alcohol abuse problem not to drink alcohol. When taken with alcohol, this medicine produces unpleasant effects. This medicine is part of a recovery program that includes medical supervision and counseling. It is not a cure.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of the following conditions:
•brain damage
•diabetes
•heart disease
•kidney disease
•liver disease
•psychotic disease
•recently exposure to alcohol or any product that contains alcohol
•seizures
•taking metronidazole or paraldehyde
•under-active thyroid
•an unusual or allergic reaction to disulfiram, pesticides or rubber products, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a full glass of water. Follow the directions on the prescription label. You must never take this medicine within 12 hours of taking any alcohol. The tablets can be crushed and mixed with liquid before taking. Take your medicine at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What if I miss a dose?

What may interact with this medicine?

Do not take this medicine with any of the following medications:
•alcohol or any product that contains alcohol
•amprenavir
•cocaine
•lopinavir; ritonavir
•metronidazole
•oral solutions of ritonavir or sertraline
•paclitaxel
•paraldehyde
•tranylcypromine

This medicine may also interact with the following medications:
•isoniazid
•medicines that treat or prevent blood clots like warfarin
•phenytoin

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Visit your doctor or health care professional for regular checks on your progress.

Never take this medicine if you have been drinking alcohol. Make sure that family members or others in your household know about this medicine and what to do in an emergency. When this medicine is taken with even small amounts of alcohol, it will produce very unpleasant effects. You may get a throbbing headache, flushing, vomiting, weakness and chest pain. Breathing and heart problems, seizures and death can occur. This medicine can react with alcohol even 14 days after you take your last dose.

Never take products or use toiletries that contain alcohol. Always read labels carefully. Many cough syrups, liquid pain medications, tonics, mouthwashes, after shave lotions, colognes, liniments, vinegar's, and sauces contain alcohol.

Wear a medical identification bracelet or chain to say you are taking this medicine. Carry an identification card with your name, name and dose of medicine being used, and name and phone number of your doctor and/or person to contact in an emergency.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•changes in vision
•confusion, disorientation, irritability
•dark urine
•general ill feeling or flu-like symptoms
•loss of appetite, nausea
•loss of contact with reality
•numbness, pain or tingling
•right upper belly pain
•unusually weak or tired
•yellowing of the eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•change in sex drive or performance
•dizziness
•drowsy, tired
•headache
•metallic or garlic taste
•nausea, vomiting

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 20 and 25 degrees C (68 and 77 degrees F). Keep in a tight light resistant container. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

An antioxidant used in the treatment of chronic alcoholism that interferes with the normal metabolic degradation of alcohol in the body, producing an unpleasant reaction when a small quantity of alcohol is consumed.

The noun has one meaning:

Meaning #1: a drug (trade name Antabuse) used in the treatment of alcoholism; causes nausea and vomiting if alcohol is ingested
  Synonym: Antabuse

Disulfiram
Systematic (IUPAC) name
1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane
Identifiers
CAS number	97-77-8
ATC code	N07BB01 P03AA04
PubChem	3117
DrugBank	APRD00767
ChemSpider	3005
Chemical data
Formula	C10H20N2S4
Mol. mass	296.539 g/mol
SMILES	eMolecules & PubChem
Synonyms	1-(diethylthiocarbamoyldisulfanyl)-N,N-diethyl-methanethioamide
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic to diethylthiocarbamate
Half life	60-120 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	C (US)
Legal status
Routes	Oral, subdermal implant
Y(what is this?)  (verify)

Disulfiram is a drug used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol. Trade names for disulfiram in different countries are Antabuse and Antabus manufactured by Odyssey Pharmaceuticals. Disulfiram is also being studied as a treatment for cocaine dependence, as it prevents the breakdown of dopamine (a neurotransmitter whose release is stimulated by cocaine); the excess dopamine results in increased anxiety, higher blood pressure, restlessness and other unpleasant symptoms. Several studies have reported that it has anti-protozoal activity as well.^[1][2] Research for possible disulfiram use in cancer therapy has been announced.

Contents 1 Interaction with alcohol 2 Dosage 3 Preparation 4 History 5 Antiprotozoal and anti-scabies use 6 Similarly acting substances 7 Disulfiram and cancer treatment 8 Disulfiram Effect 9 See also 10 Literary References 11 References 12 External links

Interaction with alcohol

This section does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (August 2009)

Under normal metabolism, alcohol is broken down in the liver by the enzyme alcohol dehydrogenase to acetaldehyde, which is then converted by the enzyme acetaldehyde dehydrogenase to the harmless acetic acid. Disulfiram blocks this reaction at the intermediate stage by blocking the enzyme acetaldehyde dehydrogenase. After alcohol intake under the influence of disulfiram, the concentration of acetaldehyde in the blood may be 5 to 10 times higher than that found during metabolism of the same amount of alcohol alone. As acetaldehyde is one of the major causes of the symptoms of a "hangover" this produces immediate and severe negative reaction to alcohol intake. Some 5–10 minutes after alcohol intake, the patient may experience the effects of a severe hangover for a period of 30 minutes up to several hours. Symptoms include flushing of the skin, accelerated heart rate, shortness of breath, nausea, vomiting, throbbing headache, visual disturbance, mental confusion, postural fainting, and circulatory collapse.

Disulfiram should not be taken if alcohol has been consumed in the last 12 hours. There is no tolerance to disulfiram: the longer it is taken, the stronger its effects. As disulfiram is absorbed slowly through the digestive tract and eliminated slowly by the body the effects may last for up to 2 weeks after the initial intake; consequently, medical ethics dictate that patients must be fully informed about the disulfiram-alcohol reaction. Possible side effects while taking Disulfiram are numbness or tingling of the lower legs and shortness of breath.

A recent 9-year study found that incorporation of supervised disulfiram and a related compound calcium carbimide into a comprehensive treatment program resulted in an abstinence rate of over 50%.^[3]

Dosage

Disulfiram is supplied in 200 mg, 250 mg, and 500 mg tablets. The usual initial dose is 500 mg for 1 to 2 weeks, followed by a maintenance dose of 250 mg (range 125 mg–500 mg) per day. The total daily dosage should not exceed 500 mg.

Preparation

Disulfiram may be prepared from oxidation of sodium diethyldithiocarbamate with iodine:

2 NaS₂CNEt₂ + I₂ → Et₂NC(S)S-SC(S)NEt₂ + 2 NaI (Et = C₂H₅)

History

The drug's action was discovered by accident in 1948 by the researchers Erik Jacobsen, Jens Hald, and Keneth Ferguson at the Danish drug company Medicinalco.^[4] The substance was intended to provide a remedy for parasitic infestations; however, workers testing the substance on themselves reported severe symptoms after alcohol consumption.

Antiprotozoal and anti-scabies use

A study reported that it may be potentially useful in the treatment of Giardia infection.^[1] Another study found that it had activity against Trichomonas vaginalis which was resistant to the most common treatment, metronidazole.^[2]

Use in the treatment of scabies has also been described.^[5]

Similarly acting substances

Coprine (N5-1-hydroxycyclopropyl-L-glutamine) which metabolises to 1-aminocyclopropanol, a closely-related chemical having the same metabolic effects, occurs naturally in the otherwise edible mushroom, the common ink cap (Coprinopsis atramentaria). Similar reactions have been recorded with Clitocybe clavipes and Boletus luridus, although the agent in those species is unknown.

Temposil, or citrated calcium carbimide, has the same function as disulfiram, but is weaker and safer.

Griseofulvin, an oral anti-fungal drug.

Disulfiram and cancer treatment

A patient with metastatic ocular melanoma was successfully treated by disulfiram with zinc gluconate ^[6]. This can be explained as disulfiram creating complexes with metals (dithiocarbamate complexes) is proteasome inhibitor ^[7] and can represent a new approach to proteasome inhibition.^[8] Clinical trials are recommended.^[9] There is ongoing clinical trial of disulfiram with copper gluconate against liver cancer in Utah (ClinicalTrials.gov Identifier: NCT00742911) and clinical trial of disulfiram as adjuvant against lung cancer in Israel (ClinicalTrials.gov Identifier: NCT00312819).

Disulfiram Effect

In medicine, the term "disulfiram effect" refers to an adverse effect of a particular medication in causing an unpleasant hypersensitivity to alcohol, similar to the effect caused by disulfiram administration.

Examples:

• Antibiotics (Nitroimidazoles)

See also

• Naltrexone

Literary References

Disulfiram is mentioned in John Healy's autobiographical book The Grass Arena. It is called by the commercial name "Antabuse" in the novel, whereby several alcoholics are given the drug, allegedly without their consent in a clinical trial of some kind (pages 107-110).

References

1. ^ ^{a b} Nash T, Rice WG (1998). "Efficacies of zinc-finger-active drugs against Giardia lamblia". Antimicrob. Agents Chemother. 42 (6): 1488–92. PMID 9624499. 
2. ^ ^{a b} Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP (1998). "Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus". J. Antimicrob. Chemother. 42 (6): 817–20. doi:10.1093/jac/42.6.817. PMID 10052908. 
3. ^ Krampe H, Stawicki S, Wagner T, et al. (January 2006). "Follow-up of 180 alcoholic patients for up to 7 years after outpatient treatment: impact of alcohol deterrents on outcome". Alcoholism, clinical and experimental research 30 (1): 86–95. doi:10.1111/j.1530-0277.2006.00013.x. ISSN 0145-6008. PMID 16433735. 
4. ^ Hvad er antabus, a Danish site describing the discovery of the drug’s effects.
5. ^ Landegren J, Borglund E, Storgårds K (1979). "Treatment of scabies with disulfiram and benzyl benzoate emulsion: a controlled study". Acta Derm. Venereol. 59 (3): 274–6. PMID 87094. 
6. ^ Brar SS, Grigg C, Wilson KS, et al. (Sep 2004). "Disulfiram inhibits activating transcription factor/cyclic AMP-responsive element binding protein and human melanoma growth in a metal-dependent manner in vitro, in mice and in a patient with metastatic disease". Molecular Cancer Therapeutics 3 (9): 1049–60. PMID 15367699. http://mct.aacrjournals.org/cgi/pmidlookup?view=long&pmid=15367699. 
7. ^ Cvek B, Dvorak Z (2007). "Targeting of nuclear factor-kappaB and proteasome by dithiocarbamate complexes with metals". Current Pharmaceutical Design 13 (30): 3155–67. doi:10.2174/138161207782110390. PMID 17979756. http://www.bentham-direct.org/pages/content.php?CPD/2007/00000013/00000030/0010B.SGM. 
8. ^ Cvek B, Dvorak Z (Aug 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 (15-16): 716–22. doi:10.1016/j.drudis.2008.05.003. PMID 18579431. 
9. ^ Wickström M, Danielsson K, Rickardson L, et al. (Jan 2007). "Pharmacological profiling of disulfiram using human tumor cell lines and human tumor cells from patients". Biochem Pharmacology 73 (1): 25–33. doi:10.1016/j.bcp.2006.08.016. PMID 17026967. 

External links

• Disulfiram (patient information)
• Toxicity, Mushroom - Disulfiramlike Toxins at eMedicine

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