naloxone

Also known as (-)-naloxone, l-naloxone, Narcan®, 1-N-Allyl-14-hydroxynordihydromorphinone, 17-allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one, 17-allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one, (−)-naloxone

Naloxone, sold under the brand name Narcan among others, is an opioid antagonist, a medication used to reverse or reduce the effects of opioids. For example, it is used to restore breathing after an opioid overdose. Effects begin within two minutes when given intravenously, five minutes when injected into a muscle, and ten minutes as a nasal spray. Naloxone blocks the effects of opioids for 30 to 90 minutes.

OverviewAI-generated

Naloxone is a chemical compound with the formula C₁₉H₂₁NO₄. Its IUPAC name is (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one. The substance has a mass of 327.147 and a weight of 327.4. It possesses a charge of 0, an xlogp value of 2.1, and a topological polar surface area of 70. The molecule contains two hydrogen bond donors and five hydrogen bond acceptors.

The compound is associated with a PubMed query count of 38,824. It is referenced by 1,500 other encyclopedia articles.

Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

In the Vinony graph

Vinony's link graph records 1,500 inbound references to naloxone, and connects out to intravenous infusion and defusion, nasal administration and Papaver somniferum.

It is catalogued under topics including 4,5-Epoxymorphinans, Allylamines and Antidotes.

Vinony links it to 42 Wikipedia language editions.

Key facts

Drug.ATC_suffix: AH04
Drug.legal_AU: S4
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 440816974
Drug.image: Naloxone.svg
Drug.image_class: skin-invert-image
Drug.width: 225
Drug.image2: Naloxone-based-on-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.USAN: naloxone hydrochloride
Drug.tradename: Narcan, others
Drug.MedlinePlus: a612022
Drug.DailyMedID: Naloxone
Drug.pregnancy_AU: B1
Drug.pregnancy_category: US: C
Drug.routes_of_administration: Intranasal, intravenous, intramuscular

via Wikipedia infobox

Chemical data

Formula: C19H21NO4
Molecular weight: 327.4 g/mol
IUPAC name: (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
SMILES: C=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
InChIKey: UZHSEJADLWPNLE-GRGSLBFTSA-N
XLogP: 2.1
Polar surface area: 70 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1971
Admin. routes: oral, parenteral, topical
Indications: epilepsy, irritable bowel syndrome, obesity, hepatitis C virus infection

via ChEMBL · EBI

Research

38,824 papers

Naloxone.Annals of emergency medicine · 1983
Pharmacists' naloxone services beyond community pharmacy settings: A systematic review.Research in social & administrative pharmacy : RSAP · 2023
Naloxone's role in the national opioid crisis-past struggles, current efforts, and future opportunities.Translational research : the journal of laboratory and clinical medicine · 2021
Naloxone hydrochloride: a review.AANA journal · 1990
Buprenorphine-Naloxone Maintenance and Lactation.Journal of human lactation : official journal of International Lactation Consultant Association · 2024

via PubMed

Wikidata facts

Mass: 327.147
Has use: medication

Show 10 more facts

route of administration: intravenous infusion and defusion
Commons category: Naloxone
chemical formula: C₁₉H₂₁NO₄
medical condition treated: opioid overdose
canonical SMILES: C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
isomeric SMILES: C=CCN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
World Health Organisation international non-proprietary name: naloxonum
subject has role: antidote
found in taxon: Papaver somniferum
different from: naltrexone

Sources (6)

via Wikidata · CC0

~27 min read

Encyclopedic overview

28 sections

Contents

Medical uses
Opioid overdose
Clonidine overdose
Preventing recreational opioid use
Other uses
Special populations
Pregnancy and breastfeeding
Children
Geriatric use
Available forms
Intravenous
Intramuscular or subcutaneous
Intranasal
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
History
Society and culture
Misinformation
Names
Legal status and availability to law enforcement and emergency personnel
Community access
Veterinary use
References
Further reading
External links

Administration to opioid-dependent individuals may cause symptoms of opioid withdrawal, including restlessness, agitation, nausea, vomiting, a fast heart rate, and sweating. To prevent this, small doses every few minutes can be given until the desired effect is reached. In those with previous heart disease or taking medications that negatively affect the heart, further heart problems have occurred. There is limited data on naloxone's safety during pregnancy. Naloxone is a non-selective and competitive opioid receptor antagonist. It reverses the depression of the central nervous system and respiratory system caused by opioids.

Excerpted from Wikipedia’s “naloxone” article, available under the CC BY-SA 4.0 licence.