Naloxone

Not to be confused with Naltrexone or Naloxegol.

Naloxone
Clinical data
Trade namesNarcan, others
Other namesEN-1530; N-Allylnoroxymorphone; 17-Allyl-4,5α-epoxy-3,14-dihydroxymorphinan-6-one, naloxone hydrochloride (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa612022
License data
Pregnancy
category
Routes of
administration		Intranasal, intravenous, intramuscular
Drug classOpioid antagonist
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S3 (Pharmacist Only Medicine)[2]
  • BR: Class C1 (Other controlled substances)[3]
  • CA: OTC[4]
  • DE: § 48 AMG/§ 1 MPAV (Prescription only)
  • UK: POM (Prescription only)[5]
  • US: OTC / Rx-only[6][7][8][9][10][11]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability2% (by mouth, 90% absorption but high first-pass metabolism)
43–54% (intranasal)
98% (intramuscular, subcutaneous)[12][13]
MetabolismLiver
Onset of actionIVTooltip intravenous injection: 2 min,
IMTooltip intramuscular injection: 5 min[13]
Elimination half-life1–1.5 h
Duration of actionINTooltip Intranasal: 30–90 min
IVTooltip Intravenous: 45 min
IMTooltip Intramuscular: 30–120 min
ExcretionUrine, bile
Identifiers
IUPAC name
  • (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-(prop-2-en-1-yl)-2,3,4,4a,5,6-hexahydro-1H-4,12-methano[1]benzofurano[3,2-e]isoquinolin-7(7aH)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.697
Chemical and physical data
FormulaC19H21NO4
Molar mass327.380 g·mol−1
3D model (JSmol)
SMILES
  • O=C1[C@@H]2OC3=C(O)C=CC4=C3[C@@]2([C@]5(CC1)O)CCN(CC=C)[C@@H]5C4
InChI
  • InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1 Y
  • Key:UZHSEJADLWPNLE-GRGSLBFTSA-N Y
 NY (what is this?)  (verify)

Naloxone, sold under the brand name Narcan among others, is an opioid antagonist, a medication used to reverse or reduce the effects of opioids.[13] For example, it is used to restore breathing after an opioid overdose.[13] Effects begin within two minutes when given intravenously, five minutes when injected into a muscle,[13] and ten minutes as a nasal spray.[14] Naloxone blocks the effects of opioids for 30 to 90 minutes.[15]

Administration to opioid-dependent individuals may cause symptoms of opioid withdrawal, including restlessness, agitation, nausea, vomiting, a fast heart rate, and sweating.[13] To prevent this, small doses every few minutes can be given until the desired effect is reached.[13] In those with previous heart disease or taking medications that negatively affect the heart, further heart problems have occurred.[13] It appears to be safe in pregnancy, after having been given to a limited number of women.[16] Naloxone is a non-selective and competitive opioid receptor antagonist.[6][17] It reverses the depression of the central nervous system and respiratory system caused by opioids.[13]

Naloxone was patented in 1961 and approved for opioid overdose in the United States in 1971.[18][19] It is on the World Health Organization's List of Essential Medicines.[20]

  1. ^ "Naloxone Use During Pregnancy". Drugs.com. 2 September 2019. Archived from the original on 25 April 2020. Retrieved 13 May 2020.
  2. ^ Cite error: The named reference doi 10.5694/mja15.01181 was invoked but never defined (see the help page).
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ "Frequently Asked Questions: Access to naloxone in Canada (including Narcan Nasal Spray)". Health Canada. 6 July 2016. Archived from the original on 16 August 2021. Retrieved 16 August 2021.
  5. ^ "Naloxone 400 micrograms/ml solution for Injection/Infusion – Summary of Product Characteristics (SmPC)". (emc). 6 February 2019. Archived from the original on 4 August 2020. Retrieved 13 May 2020.
  6. ^ a b Cite error: The named reference Narcan FDA label was invoked but never defined (see the help page).
  7. ^ "Evzio- naloxone hydrochloride injection, solution". DailyMed. 1 February 2018. Archived from the original on 8 October 2020. Retrieved 5 October 2020.
  8. ^ "Zimhi- naloxone hydrochloride injection, solution". DailyMed. 29 September 2022. Archived from the original on 7 January 2023. Retrieved 7 January 2023.
  9. ^ Cite error: The named reference Kloxxado FDA label was invoked but never defined (see the help page).
  10. ^ "Narcan- naloxone hydrochloride nasal spray". DailyMed. 8 August 2023. Retrieved 5 September 2024.
  11. ^ "Rivive- naloxone hydrochloride spray". DailyMed. 10 January 2024. Retrieved 5 September 2024.
  12. ^ Ryan SA, Dunne RB (May 2018). "Pharmacokinetic properties of intranasal and injectable formulations of naloxone for community use: a systematic review". Pain Management. 8 (3): 231–245. doi:10.2217/pmt-2017-0060. PMID 29683378.
  13. ^ a b c d e f g h i "Naloxone Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 2 January 2015. Retrieved 2 January 2015.
  14. ^ McDonald R, Lorch U, Woodward J, Bosse B, Dooner H, Mundin G, et al. (March 2018). "Pharmacokinetics of concentrated naloxone nasal spray for opioid overdose reversal: Phase I healthy volunteer study". Addiction. 113 (3): 484–493. doi:10.1111/add.14033. PMC 5836974. PMID 29143400.
  15. ^ "Naloxone DrugFacts". National Institute on Drug Abuse. 1 June 2021. Archived from the original on 6 January 2022. Retrieved 5 January 2022.
  16. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  17. ^ Cite error: The named reference NHM-Naloxone pharmacology was invoked but never defined (see the help page).
  18. ^ Yardley W (14 December 2013). "Jack Fishman Dies at 83; Saved Many From Overdose". The New York Times. Archived from the original on 15 December 2013. Retrieved 6 July 2015.
  19. ^ US patent 3493657, Jack Fishman & Mozes Juda Lewenstein, "Therapeutic compositions of n-allyl-14-hydroxy - dihydronormorphinane and morphine", published 3 February 1970, issued 3 February 1970, assigned to Mozes Juda Lewenstein  Archived 7 December 2022 at the Wayback Machine
  20. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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