Disulfiram
 |
|
 |
|
| Clinical data | |
|---|---|
| Trade names | Antabuse |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682602 |
| Pregnancy category |
|
| Routes of administration |
Oral, subdermal implant |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Metabolism | Hepatic to diethylthiocarbamate |
| Biological half-life | 60–120 hours |
| Identifiers | |
|
|
| Synonyms | 1-(diethylthiocarbamoyldisulfanyl)-N,N-diethyl-methanethioamide |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| NIAID ChemDB | |
| ECHA InfoCard | 100.002.371 |
| Chemical and physical data | |
| Formula | C10H20N2S4 |
| Molar mass | 296.539 g/mol |
| 3D model (Jmol) | |
|
|
|
|
  (what is this?)
|
|
Disulfiram (sold under the trade names Antabuse and Antabus) is a drug discovered in the 1920s used to support the treatment of chronic alcoholism by producing an acute sensitivity to ethanol (drinking alcohol). Disulfiram works by inhibiting the enzyme acetaldehyde dehydrogenase, which means that many of the effects of a "hangover" are felt immediately after alcohol is consumed. "Disulfiram plus alcohol, even small amounts, produce flushing, throbbing in head and neck, throbbing headache, respiratory difficulty, nausea, copious vomiting, sweating, thirst, chest pain, palpitation, dyspnea, hyperventilation, tachycardia, hypotension, syncope, marked uneasiness, weakness, vertigo, blurred vision, and confusion. In severe reactions there may be respiratory depression, cardiovascular collapse, arrhythmias, myocardial infarction, acute congestive heart failure, unconsciousness, convulsions, and death"
In the body, alcohol is converted to acetaldehyde, which is then broken down by aldehyde dehydrogenase. If the dehydrogenase enzyme is inhibited, acetaldehyde builds up and causes unpleasant effects. Disulfiram should be used in conjunction with counseling and support.
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, elevated blood pressure, restlessness, and other unpleasant symptoms. Several studies have reported that it has antiprotozoal activity, as well. Disulfiram is the subject of research for treatment of cancer and HIV (to activate the reservoir of HIV-infected resting CD4 cells).
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 a harmless acetic acid derivative (acetyl coenzyme A). Disulfiram blocks this reaction at the intermediate stage by blocking acetaldehyde dehydrogenase. After alcohol intake under the influence of disulfiram, the concentration of acetaldehyde in the blood may be five 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 five to 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 syncope, and circulatory collapse.
...
Wikipedia