Structure via PubChem · Public domain (PubChem)
naloxone
Sign in to saveAlso 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.
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 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
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
~27 min read
Encyclopedic overview
28 sectionsContents
- 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
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.
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.