naltrexone

Also known as (-)naltrexone, naltrexone HCl, ReVia®, N-Cyclopropylmethylnoroxymorphone, N-Cyclopropylmethyl-14-hydroxydihydromorphinone, 17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one, 17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one

Key facts

Drug.Verifiedfields: verified
Drug.Watchedfields: verified
Drug.verifiedrevid: 464372546
Drug.image: Naltrexone_skeletal.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Naltrexone-from-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Revia, Vivitrol, Depade, others
Drug.MedlinePlus: a685041
Drug.DailyMedID: Naltrexone
Drug.pregnancy_AU: B3
Drug.routes_of_administration: By mouth, intramuscular, subcutaneous implant
Drug.ATC_prefix: N07
Drug.ATC_suffix: BB04
Drug.legal_AU: S4
Drug.legal_BR: C1

via Wikipedia infobox

Chemical data

Formula: C20H23NO4
Molecular weight: 341.4 g/mol
IUPAC name: (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
SMILES: C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O
InChIKey: DQCKKXVULJGBQN-XFWGSAIBSA-N
XLogP: 1.9
Polar surface area: 70 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

12,325 papers

The use of low-dose naltrexone (LDN) as a novel anti-inflammatory treatment for chronic pain.Clinical rheumatology · 2014
The Safety and Efficacy of Low-Dose Naltrexone in the Management of Chronic Pain and Inflammation in Multiple Sclerosis, Fibromyalgia, Crohn's Disease, and Other Chronic Pain Disorders.Pharmacotherapy · 2018
Naltrexone at low doses (LDN) and its relevance to cancer therapy.Expert review of anticancer therapy · 2022
Morphine/naltrexone.CNS drugs · 2010
Naltrexone: A Pan-Addiction Treatment?CNS drugs · 2016

via PubMed

Wikidata facts

Mass: 341.162708

Show 7 more facts

Commons category: Naltrexone
chemical formula: C₂₀H₂₃NO₄
canonical SMILES: C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O
isomeric SMILES: C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O
World Health Organisation international non-proprietary name: naltrexone
defined daily dose: 50
native label: Naltrexone

Sources (5)

via Wikidata · CC0

~35 min read

Article

38 sections

Contents

Medical uses
Alcohol use disorder
Opioid use disorder
Others
Available forms
Contraindications
Side effects
Opioid withdrawal
Adverse effects
Liver damage
Overdose
Pharmacology
Pharmacodynamics
Opioid receptor blockade
Other activities
Pharmacokinetics
Absorption
Distribution
Metabolism
Elimination
Pharmacogenetics
Chemistry
Analogues
History
Society and culture
Generic names
Brand names
Controversies
Research
Depersonalization
Low-dose naltrexone
Self-injury
Behavioral disorders
Interferon alpha
Critical addiction studies
Sexual addiction
Veterinary use
References

Naltrexone, sold under the brand name Revia among others, is a medication primarily used to manage alcohol use or opioid use disorder by reducing cravings and feelings of euphoria associated with substance use disorder. It has also been found effective in the treatment of other addictions and may be used for them off-label. It is taken orally or by injection into a muscle. Effects begin within 30 minutes, though a decreased desire for opioids may take a few weeks to occur.

Side effects may include trouble sleeping, anxiety, nausea, and headaches. In those still on opioids, opioid withdrawal may occur. Use is not recommended in people with liver failure. It is unclear if use is safe during pregnancy. Naltrexone is an opioid antagonist and works by blocking the effects of opioids, including both opioid drugs as well as opioids naturally produced in the brain.