Tìm theo
Methadone
Các tên gọi khác (6 ) :
  • (+-)-Methadone
  • (+/-)-Methadone
  • (±)-methadone
  • 6-Dimethylamino-4,4-diphenyl-3-heptanone
  • dl-Methadone
  • Methadonum
Thuốc giảm đau có opioid
Thuốc Gốc
Small Molecule
CAS: 76-99-3
ATC: N02AC52, N07BC02, R05DA06
ĐG : AAIPharma Inc. , http://www.aaipharma.com
CTHH: C21H27NO
PTK: 309.4452
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. It also has a depressant action on the cough center and may be given to control intractable cough associated with terminal lung cancer. Methadone is also used as part of the treatment of dependence on opioid drugs, although prolonged use of methadone itself may result in dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). In Australia methadone is a Schedule 8 (controlled) drug.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H27NO
Phân tử khối
309.4452
Monoisotopic mass
309.209264491
InChI
InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
InChI Key
InChIKey=USSIQXCVUWKGNF-UHFFFAOYSA-N
IUPAC Name
6-(dimethylamino)-4,4-diphenylheptan-3-one
Traditional IUPAC Name
methadone
SMILES
CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
Độ tan chảy
235.0 °C
Độ hòa tan
5.90e-03 g/l
logP
3.93
logS
-4.7
pKa (strongest acidic)
18.78
pKa (Strongest Basic)
9.12
PSA
20.31 Å2
Refractivity
97.27 m3·mol-1
Polarizability
36.29 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
2
H Bond Donor Count
0
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Ghose Filter
true
pKa
8.94 (at 25 °C)
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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. It also has a depressant action on the cough center and may be given to control intractable cough associated with terminal lung cancer. Methadone is also used as part of the treatment of dependence on opioid drugs, although prolonged use of methadone itself may result in dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). In Australia methadone is a Schedule 8 (controlled) drug. 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.
Dược Động Học :
▧ Absorption :
Well absorbed following oral administration. The bioavailability of methadone ranges between 36 to 100%.
▧ Volume of Distribution :
* 1.0 to 8.0 L/kg
▧ Protein binding :
In plasma, methadone is predominantly bound to α1-acid glycoprotein (85% to 90%).
▧ Metabolism :
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
Độc Tính : In severe overdosage, particularly by the intravenous route, apnea, circulatory collapse, cardiac arrest, and death may occur.
Chỉ Định : For the treatment of dry cough, drug withdrawal syndrome, opioid type drug dependence, and pain.
Tương Tác Thuốc :
  • Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
  • Amobarbital The barbiturate, amobarbital, decreases the effect of methadone.
  • Amprenavir The protease inhibitor, amprenavir, may decrease the effect of methadone.
  • Aprobarbital The barbiturate, aprobarbital, decreases the effect of methadone.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Butabarbital The barbiturate, butabarbital, decreases the effect of methadone.
  • Butalbital The barbiturate, butalbital, decreases the effect of methadone.
  • Butethal The barbiturate, butethal, decreases the effect of methadone.
  • 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.
  • 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.
  • Dihydroquinidine barbiturate The barbiturate, dihydroquinidine barbiturate, 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.
  • Eltrombopag Increases levels of Methadone via metabolism decrease. UDP-glucuronosyltransferase inhibition with unclear significance.
  • Ethotoin The hydantoin decreases the effect of methadone
  • Etravirine Methadone, when used concomitantly with etravirine, may experience a decrease in serum concentration. It is recommended to monitor methadone therapy for decrease effectiveness and symptoms of withdrawal.
  • Fluvoxamine Fluvoxamine increases the effect and toxicity of methadone
  • Fosamprenavir The protease inhibitor, fosamprenavir, may decrease the effect of methadone.
  • Fosphenytoin The hydantoin decreases the effect of methadone
  • Heptabarbital The barbiturate, heptabarbital, decreases the effect of methadone.
  • Hexobarbital The barbiturate, hexobarbital, decreases the effect of methadone.
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mephenytoin The hydantoin decreases the effect of methadone
  • Methohexital The barbiturate, methohexital, decreases the effect of methadone.
  • Methylphenobarbital The barbiturate, methylphenobarbital, decreases the effect of methadone.
  • Nelfinavir Nelfinavir decreases the effect of methadone
  • Nevirapine The antiretroviral agent decreases the effect of methadone
  • Pentobarbital The barbiturate, pentobarbital, decreases the effect of methadone.
  • Phenobarbital The barbiturate, phenobarbital, decreases the effect of methadone.
  • Phenytoin The hydantoin decreases the effect of methadone
  • Primidone The barbiturate, primidone, decreases the effect of methadone.
  • Quinidine barbiturate The barbiturate, quinidine barbiturate, decreases the effect of methadone.
  • Rifabutin The rifamycin decreases the effect of methadone
  • Rifampicin The rifamycin decreases the effect of methadone
  • Rifapentine The rifamycin decreases the effect of methadone
  • Rilpivirine Dose adjustment and clinical monitoring of rilpivirine may be necessary if coadministered with methadone.
  • Ritonavir The protease inhibitor, ritonavir, may decrease the effect of methadone.
  • Secobarbital The barbiturate, secobarbital, decreases the effect of methadone.
  • St. John's Wort St. John's Wort decreases levels/effect of methadone
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Talbutal The barbiturate, talbutal, decreases the effect of methadone.
  • Tamoxifen Methadone may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • 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.
  • Telaprevir Telaprevir decreases exposure of methane by 30% however opioid withdrawal was not observed in patients.
  • 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.
  • Thiopental Thiopental may decrease the effect of Methadone by increasing Methadone metabolism. Methadone withdrawal may occur.
  • 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.
  • Tipranavir Tipranavir, co-administered with Ritonavir, decreases the Methadone concentration. Monitor for symptoms of opiate withdrawal.
  • 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.
  • Tramadol Methadone may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Triprolidine The CNS depressants, Triprolidine and Methadone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • 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.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Zidovudine Methadone increases the effect and toxicity of zidovudine
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • 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).
Liều Lượng & Cách Dùng : Liquid - Oral
Solution - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
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    Sản phẩm biệt dược : Heptadon
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    Sản phẩm biệt dược : Heptanon
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    Sản phẩm biệt dược : Mephenon
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    Sản phẩm biệt dược : METHADOSE
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00333
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4095
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505722
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07163
ChemSpider
http://www.chemspider.com/Chemical-Structure.3953.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/64019-553-67
PharmGKB
http://www.pharmgkb.org/drug/PA450401
Wikipedia
http://en.wikipedia.org/wiki/Methadone
RxList
http://www.rxlist.com/cgi/generic/methdone.htm
Drugs.com
http://www.drugs.com/methadone.html
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