QuickView for Methadone (compound)

Summary
General Info

PubChem

PubChem Compound 14184

Name:	Methadone
PubChem Compound ID:	14184
Description:	A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3)
Molecular formula:	C₂₁H₂₈ClNO
Molecular weight:	345.906 g/mol
Synonyms:	6-Dimethylamino-4,4-diphenyl-3-heptanone.HCl; Racemic methadone hydrochloride; Meth; NSC 19600; 1095-90-5; Dolophine; Algolysin; 70172-45-1; Polamidon; 3-Heptanone, dl-6-dimethylamino-4,4-diphenyl-, hydrochloride. show more » 6-Dimethylamino-4,4-diphenyl-3-heptanone.HCl; Racemic methadone hydrochloride; Meth; NSC 19600; 1095-90-5; Dolophine; Algolysin; 70172-45-1; Polamidon; 3-Heptanone, dl-6-dimethylamino-4,4-diphenyl-, hydrochloride; Ketalgin; 125-56-4; Adanon; Dolofin hydrochloride; Methadone hydrochloride dl-; Physeptone; Amidon; Dolly; AN-148; Methadone hydrochloride (USP); Depridol; Tussol:; Mecodin; D02102; 1,1-Diphenyl-1-(2-dimethylaminopropyl)-2-butanone hydrochloride; 70181-39-4; Algidon; Adolan; dl-6-Dimethylamino-4,4-diphenyl-3-heptanone hydrochloride; Phenadone; Phenadone hydrochloride; 6-(Dimethylamino)-4,4-diphenyl-3-heptanone hydrochloride; Ketalgin hydrochloride; Dolophin; 3-Heptanone, 6-(dimethylamino)-4,4-diphenyl-, hydrochloride, (+-)-; Fenadon; Moheptan; 3-Heptanone, 6-(dimethylamino)-4,4-diphenyl-, hydrochloride (8CI,9CI); Dollies; Althose hydrochloride; Butalgin; CCRIS 3320; (+/-)-Tussal; (+-)-Tussal; 76-99-3; AN 148; Diaminon hydrochloride; Tussal; 6-Dimethylamino-4,4-diphenyl-3-heptanone hydrochloride; DRG-0023; Miadone; Dolophine (TN); 3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, HYDROCHLORIDE; Hoechst 10820; Methadone hydrochloride; EINECS 214-140-7; 4,4-Diphenyl-6-dimethylamino-3-heptanone hydrochloride; 4,4-Diphenyl-6-dimethylamino-3-heptanone hydrochloride (+/-)-; Biscuits; Methadose; Mephenon; Medicine; Dolophin hydrochloride; Dolohepton; Adanon hydrochloride; Heptanon; (+/-)-Methadone hydrochloride; Fenadone; Heptadon; DL-Methadone hydrochloride; (+-)-Methadone hydrochloride show less «

DrugBank

Identification

Name:	Methadone
Name (isomeric):	DB00333
Drug Type:	small molecule
Description:	A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3)
Synonyms:	Phenadone hydrochloride; Methadone hydrochloride; (+/-)-Methadone hydrochloride; dl-Methadone; Methadon; Methadone HCL; (+/-)-Methadone; DL-Methadone hydrochloride
Brand:	Polamidon, (+/-)-Tussal, Mephenon, Dolohepton, Moheptan, Amidone, Methadose, Dolofin hydrochloride, Fenadone, Adanon hydrochloride, Tussol, Algolysin, Algovetin, Adanon, Diaminon, Westadone, Methaquaione, Mecodin, Dolophine, Biscuits, Ketalgin, Heptanon, Adolan, Depridol, Heptadone, Phenadone, Dolophin, Diaminon hydrochloride, Polamidone, Althose hydrochloride, Dolly, Miadone, Algidon, Dollies, Heptadon, Butalgin, Methadone M, Methadone HCL Intensol, Amidon, Fenadon, Ketalgin hydrochloride, Dolophine HCL, Physeptone, Dolophin hydrochloride
Category:	Narcotics, Analgesics, Antitussive Agents, Antitussives, Opiate Agonists, Analgesics, Opioid
CAS number:	76-99-3

Pharmacology

Indication:	For the treatment of dry cough, drug withdrawal syndrome, opioid type drug dependence, and pain.
Pharmacology:	Methadone is a synthetic opioid analgesic with multiple actions quantitatively similar to those at morphine, the most prominent of which involve the central nervous system and organs composed of smooth muscle. However, Methadone is more active and more toxic than morphine. Methadone is indicated for relief of severe pain, for detoxification treatme... show more » Methadone is a synthetic opioid analgesic with multiple actions quantitatively similar to those at morphine, the most prominent of which involve the central nervous system and organs composed of smooth muscle. However, Methadone is more active and more toxic than morphine. Methadone is indicated for relief of severe pain, for detoxification treatment of narcotic addiction, and for temporary maintenance treatment of narcotic addiction. The principal actions of therapeutic value are analgesia and sedation and detoxification or temporary maintenance in narcotic addiction. The Methadone abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less severe. show less «
Mechanism of Action:	Methadone is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine, the most prominent of which involves the central nervous system and organs composed of smooth muscle. The principal therapeutic uses for methadone are for analgesia and for detoxification or maintenance in opioid addiction. The ... show more » Methadone is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine, the most prominent of which involves the central nervous system and organs composed of smooth muscle. The principal therapeutic uses for methadone are for analgesia and for detoxification or maintenance in opioid addiction. The methadone abstinence syndrome, although qualitatively similar to that of morphine, differs in that the onset is slower, the course is more prolonged, and the symptoms are less severe. Some data also indicate that methadone acts as an antagonist at the N-methyl-D-aspartate (NMDA) receptor. The contribution of NMDA receptor antagonism to methadone's efficacy is unknown. Other NMDA receptor antagonists have been shown to produce neurotoxic effects in animals. show less «
Absorption:	Well absorbed following oral administration. The bioavailability of methadone ranges between 36 to 100%.
Protein binding:	In plasma, methadone is predominantly bound to α1-acid glycoprotein (85% to 90%).
Biotransformation:	Hepatic. Cytochrome P450 enzymes, primarily CYP3A4, CYP2B6, and CYP2C19 and to a lesser extent CYP2C9 and CYP2D6, are responsible for conversion of methadone to EDDP and other inactive metabolites, which are excreted mainly in the urine.
Route of elimination:	The elimination of methadone is mediated by extensive biotransformation, followed by renal and fecal excretion. Unmetabolized methadone and its metabolites are excreted in urine to a variable degree.
Half Life:	24-36 hours
Clearance:	1.4 to 126 L/h
Toxicity:	In severe overdosage, particularly by the intravenous route, apnea, circulatory collapse, cardiac arrest, and death may occur.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals. Avoid alcohol. Usually diluted in fruit juice.

Drug interaction:

Fluvoxamine	Fluvoxamine increases the effect and toxicity of methadone
Tamsulosin	Methadone, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Methadone is initiated, discontinued, or dose changed.
Amobarbital	The barbiturate, amobarbital, decreases the effect of methadone.
Ethotoin	The hydantoin decreases the effect of methadone
Talbutal	The barbiturate, talbutal, decreases the effect of methadone.

Fluvoxamine	Fluvoxamine increases the effect and toxicity of methadone
Tamsulosin	Methadone, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Methadone is initiated, discontinued, or dose changed.
Amobarbital	The barbiturate, amobarbital, decreases the effect of methadone.
Ethotoin	The hydantoin decreases the effect of methadone
Talbutal	The barbiturate, talbutal, decreases the effect of methadone.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of methadone by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of methadone if voriconazole is initiated, discontinued or dose changed.
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Quinidine barbiturate	The barbiturate, quinidine barbiturate, decreases the effect of methadone.
Telithromycin	Telithromycin may reduce clearance of Methadone. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Methadone if Telithromycin is initiated, discontinued or dose changed.
Phenobarbital	The barbiturate, phenobarbital, decreases the effect of methadone.
Zidovudine	Methadone increases the effect and toxicity of zidovudine
Carbamazepine	Carbamazepine may decrease the serum level of methadone. Monitor for changes in the therapeutic and adverse effects of methadone if carbamazepine is initiated, discontinued or dose changed.
Rifapentine	The rifamycin decreases the effect of methadone
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Pentobarbital	The barbiturate, pentobarbital, decreases the effect of methadone.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Rifampin	The rifamycin decreases the effect of methadone
Efavirenz	Efavirenz may decrease the serum concentration of methadone by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of methadone if efavirenz is initiated, discontinued or dose changed.
Fosamprenavir	The protease inhibitor, fosamprenavir, may decrease the effect of methadone.
Butalbital	The barbiturate, butalbital, decreases the effect of methadone.
Dihydroquinidine barbiturate	The barbiturate, dihydroquinidine barbiturate, decreases the effect of methadone.
Rifabutin	The rifamycin decreases the effect of methadone
Mephenytoin	The hydantoin decreases the effect of methadone
Cimetidine	Cimetidine, a moderate CYP3A4 inhibitor, may increase the serum concentration of metahdone, a CYP3A4 substrate. Monitor for changes in the therapeutic and adverse effects of methadone if cimetidine is initiatied, discontinued or dose changed.
St. John's Wort	St. John's Wort decreases levels/effect of methadone
Butethal	The barbiturate, butethal, decreases the effect of methadone.
Hexobarbital	The barbiturate, hexobarbital, decreases the effect of methadone.
Heptabarbital	The barbiturate, heptabarbital, decreases the effect of methadone.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Phenytoin	The hydantoin decreases the effect of methadone
Methylphenobarbital	The barbiturate, methylphenobarbital, decreases the effect of methadone.
Tramadol	Methadone may decrease the effect of Tramadol by decreasing active metabolite production.
Tipranavir	Tipranavir, co-administered with Ritonavir, decreases the Methadone concentration. Monitor for symptoms of opiate withdrawal.
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Nelfinavir	Nelfinavir decreases the effect of methadone
Ritonavir	The protease inhibitor, ritonavir, may decrease the effect of methadone.
Thiopental	Thiopental may decrease the effect of Methadone by increasing Methadone metabolism. Methadone withdrawal may occur.
Butabarbital	The barbiturate, butabarbital, decreases the effect of methadone.
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Methohexital	The barbiturate, methohexital, decreases the effect of methadone.
Aprobarbital	The barbiturate, aprobarbital, decreases the effect of methadone.
Nevirapine	The antiretroviral agent decreases the effect of methadone
Amprenavir	The protease inhibitor, amprenavir, may decrease the effect of methadone.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Fosphenytoin	The hydantoin decreases the effect of methadone
Secobarbital	The barbiturate, secobarbital, decreases the effect of methadone.
Primidone	The barbiturate, primidone, decreases the effect of methadone.
Tamoxifen	Methadone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Triprolidine	The CNS depressants, Triprolidine and Methadone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.