Naltrexone Hydrochloride

HCID 5485201CAS 16676-29-2

Grundinformationen

Standard-SMILES
Cl.O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
InChIKey
RHBRMCOKKKZVRY-ITLPAZOVSA-N
Summenformel
C20H24ClNO4
Durchschnittliche Molmasse
377,9 g/mol
Monoisotopische Masse
377,13938593

Überblick

Naltrexone hydrochloride is a hydrochloride obtained by reaction of oxycodone with one molar equivalent of hydrochloric acid. it is a -opioid receptor antagonist that is used to treat alcohol dependence. It has a role as a central nervous system depressant, a mu-opioid receptor antagonist and an antidote to opioid poisoning. It contains a naltrexone(1+).

Namen und Bezeichner

Bevorzugter Name
Naltrexone Hydrochloride
IUPAC
(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;hydrochloride

Namen und Synonyme

Naltrexone hydrochloride16676-29-2Naltrexone HclDepadenaltrexone.HClEn 1639AEN-1639AN-Cyclopropylmethyl-noroxymorphone hydrochlorideZ6375YW9SFEN-1639A (AS HYDROCHLORIDE)(5alpha)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride17-(Cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-one hydrochloride
Weitere Namen anzeigen
Naltrexone hydrochloride (USP)Naltrexone hydrochloride [USP]CHEBI:134687DTXSID50937236TROXYCA COMPONENT NALTREXONE HYDROCHLORIDECONTRAVE COMPONENT NALTREXONE HYDROCHLORIDETrexonilRefChem:56740

Datenbank-Bezeichner

CAS
16676-29-2
PubChem CID
5485201
DTXSID
DTXSID50937236
ChEMBL
CHEMBL1201149
ChEBI
CHEBI:134687
UNII
Z6375YW9SF
EC Number
240-723-0

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
70 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

Solubility>56.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Alcohol Deterrents; Narcotic Antagonists

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsActive Ingredients (Naltrexone Hydrochloride) -> FDA Greenbook
Collision Cross Section176 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 83 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (97.6%)

Toxikologische Informationen

TreatmentPatients should be treated symptomatically in a closely supervised environment. (L1712)
Health Effects · 1 Eintrag

Tolerance can develop, in which the person needs larger doses to achieve the desired effect; this can lead to overdose and death. Accidents or injury can also occur due to the side effects of loss of coordination, slowed reaction time, sleepiness and impaired judgment. Drugs in this category have a high potential for physical and psychological dependence.

Exposure RoutesAlthough well absorbed orally, naltrexone is subject to significant first pass metabolism with oral bioavailability estimates ranging from 5 to 40%.
Toxicity Summary · 1 Eintrag

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, kappa, and delta receptors in the CNS, with the highest affintiy for the mu 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-beta-naltrexol, is also an opiate antagonist and may contribute to the antagonistic activity of the drug.

Signs and SymptomsHigh doses of naltrexone (generally ≥1,000 mg/kg) produce salivation, depression/reduced activity, tremors, and convulsions.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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.

FDA Pharmacological Classification · 2 Einträge

NALTREXONE HYDROCHLORIDE

Opioid Antagonists [MoA]; Opioid Antagonist [EPC]

MeSH Pharmacological Classification · 2 Einträge

Substances interfering with the metabolism of ethyl alcohol, causing unpleasant side effects thought to discourage the drinking of alcoholic beverages. Alcohol deterrents are used in the treatment of alcoholism.

Agents inhibiting the effect of narcotics on the central nervous system.

Verwendung und Herstellung

Uses · 1 Eintrag

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.

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

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