Tìm theo
Naltrexone
Các tên gọi khác (8 ) :
  • 17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one
  • 17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one
  • N-Cyclopropylmethyl-14-hydroxydihydromorphinone
  • N-Cyclopropylmethylnoroxymorphone
  • Naltrexon
  • Naltrexona
  • Naltrexone
  • Naltrexonum
Thuốc cấp cứu & giải độc
Thuốc Gốc
Small Molecule
CAS: 16590-41-3
ATC: N07BB04
ĐG : Alkermes Inc. , http://www.alkermes.com
CTHH: C20H23NO4
PTK: 341.4009
Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of naloxone. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
341.4009
Monoisotopic mass
341.162708229
InChI
InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
InChI Key
InChIKey=DQCKKXVULJGBQN-XFWGSAIBSA-N
IUPAC Name
(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
Traditional IUPAC Name
naltrexone
SMILES
[H][[email protected]@]12OC3=C(O)C=CC4=C3[[email protected]@]11CCN(CC3CC3)[[email protected]]([H])(C4)[[email protected]]1(O)CCC2=O
Độ tan chảy
168-170 °C
Độ hòa tan
100 mg/mL (as hydrochloride salt)
logP
1.92
logS
-2
pKa (strongest acidic)
7.39
pKa (Strongest Basic)
11.54
PSA
70 Å2
Refractivity
91.5 m3·mol-1
Polarizability
35.97 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
6
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Naltrexone, a pure opioid antagonist, is a synthetic congener of oxymorphone with no opioid agonist properties. Naltrexone is indicated in the treatment of alcohol dependence and for the blockade of the effects of exogenously administered opioids. It markedly attenuates or completely blocks, reversibly, the subjective effects of intravenously administered opioids. When co-administered with morphine, on a chronic basis, naltrexone blocks the physical dependence to morphine, heroin and other opioids. In subjects physically dependent on opioids, naltrexone will precipitate withdrawal symptomatology.
Cơ Chế Tác Dụng : Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of naloxone. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence. [PubChem] Naltrexone is a pure opiate antagonist and has little or no agonist activity. The mechanism of action of naltrexone in alcoholism is not understood; however, involvement of the endogenous opioid system is suggested by preclinical data. Naltrexone is thought to act as a competitive antagonist at mc, κ, and δ receptors in the CNS, with the highest affintiy for the μ receptor. Naltrexone competitively binds to such receptors and may block the effects of endogenous opioids. This leads to the antagonization of most of the subjective and objective effects of opiates, including respiratory depression, miosis, euphoria, and drug craving. The major metabolite of naltrexone, 6-β-naltrexol, is also an opiate antagonist and may contribute to the antagonistic activity of the drug.
Dược Động Học :
▧ Absorption :
Although well absorbed orally, naltrexone is subject to significant first pass metabolism with oral bioavailability estimates ranging from 5 to 40%.
▧ Volume of Distribution :
* 1350 L [intravenous administration]
▧ Protein binding :
21% bound to plasma proteins over the therapeutic dose range.
▧ Metabolism :
Hepatic. When administered orally, naltrexone undergoes extensive biotransformation and is metabolized to 6 beta-naltrexol (which may contribute to the therapeutic effect) and other minor metabolites.
▧ Route of Elimination :
Both parent drug and metabolites are excreted primarily by the kidney (53% to 79% of the dose), however, urinary excretion of unchanged naltrexone accounts for less than 2% of an oral dose and fecal excretion is a minor elimination pathway. The renal clearance for naltrexone ranges from 30 to 127 mL/min and suggests that renal elimination is primarily by glomerular filtration.
▧ Half Life :
4 hours for naltrexone and 13 hours for the active metabolite 6 beta-naltrexol.
▧ Clearance :
* ~ 3.5 L/min [after IV administration]
Độc Tính : In the mouse, rat and guinea pig, the oral LD50s were 1,100-1,550 mg/kg; 1,450 mg/kg; and 1,490 mg/kg; respectively. High doses of naltrexone (generally ≥1,000 mg/kg) produce salivation, depression/reduced activity, tremors, and convulsions.
Chỉ Định : Used as an adjunct to a medically supervised behaviour modification program in the maintenance of opiate cessation in individuals who were formerly physically dependent on opiates and who have successfully undergone detoxification. Also used for the management of alcohol dependence in conjunction with a behavioural modification program.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
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