Buprenorphine

Not to be confused with Bupropion.

Buprenorphine
Skeletal formula of buprenorphine
Ball-and-stick model of the buprenorphine molecule
Clinical data
Pronunciationbew-pre-nor-feen
Trade namesSubutex, Sublocade, Belbuca, Brixadi, others
Other namesSK-2110; SK2110
AHFS/Drugs.comMonograph
MedlinePlusa605002
License data
Pregnancy
category
Dependence
liability		Psychological: High Physical: Moderate[3]
Routes of
administration		Sublingual, buccal, intramuscular, intravenous, transdermal, intranasal, rectal, subcutaneous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilitySublingual: 30%[14]
Intranasal: 48%[15]
Buccal: 65%[16][17]
Protein binding96%
MetabolismLiver (CYP3A4, CYP2C8)
Onset of actionWithin 30 min[18]
Elimination half-life37 hours (range 20–70 hours)
Duration of actionUp to 24 hrs[18]
ExcretionBile duct and kidney
Identifiers
  • (2S)-2-[(5R,6R,7R,14S)-17-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.052.664 Edit this at Wikidata
Chemical and physical data
FormulaC29H41NO4
Molar mass467.650 g·mol−1
3D model (JSmol)
  • Oc7ccc5c1c7O[C@H]3[C@]6(OC)[C@H](C[C@@]2([C@H](N(CC[C@@]123)CC4CC4)C5)CC6)[C@@](O)(C)C(C)(C)C
  • InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1 checkY
  • Key:RMRJXGBAOAMLHD-IHFGGWKQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Buprenorphine, sold under the brand name Subutex among others, is an opioid used to treat opioid use disorder, acute pain, and chronic pain.[18] It can be used under the tongue (sublingual), in the cheek (buccal), by injection (intravenous and subcutaneous), as a skin patch (transdermal), or as an implant.[18][19] For opioid use disorder, the patient must have moderate opioid withdrawal symptoms before buprenorphine can be administered under direct observation of a health-care provider.[18]

In the United States, the combination formulation of buprenorphine/naloxone (Suboxone) is usually prescribed to discourage misuse by injection.[18] However, more recently the efficacy of naloxone in preventing misuse has been brought into question, and preparations of buprenorphine combined with naloxone could potentially be less safe than buprenorphine alone.[20] Maximum pain relief is generally within an hour with effects up to 24 hours.[18] Buprenorphine affects different types of opioid receptors in different ways.[18] Depending on the type of opioid receptor, it may be an agonist, partial agonist, or antagonist.[18] Buprenorphine's activity as an agonist/antagonist is important in the treatment of opioid use disorder: it relieves withdrawal symptoms from other opioids and induces some euphoria, but also blocks the ability for many other opioids, including heroin, to cause an effect. Unlike full agonists like heroin or methadone, buprenorphine has a ceiling effect, such that taking more medicine past a certain point will not increase the effects of the drug.[21]

Side effects may include respiratory depression (decreased breathing), sleepiness, adrenal insufficiency, QT prolongation, low blood pressure, allergic reactions, constipation, and opioid addiction.[18][22] Among those with a history of seizures, a risk exists of further seizures.[18] Opioid withdrawal following stopping buprenorphine is generally less severe than with other opioids.[18] Whether use during pregnancy is safe is unclear, but use while breastfeeding is probably safe, since the dose the infant receives is 1-2% that of the maternal dose, on a weight basis.[23][18]

Buprenorphine was patented in 1965, and approved for medical use in the United States in 1981.[18][24] It is on the World Health Organization's List of Essential Medicines.[25] In addition to prescription as an analgesic it is a common medication used to treat opioid use disorders, such as addiction to heroin.[26] In 2020, it was the 186th most commonly prescribed medication in the United States, with more than 2.8 million prescriptions.[27][28] Buprenorphine may also be used recreationally for the high it can produce.[26] In the United States, buprenorphine is a schedule III controlled substance.[26]

  1. ^ "Buprenorphine Use During Pregnancy". Drugs.com. 14 October 2019. Archived from the original on 10 November 2020. Retrieved 17 May 2020.
  2. ^ a b Australian Public Assessment Report for Buprenorphine (PDF) (Report). Therapeutic Goods Administration. November 2019. Archived (PDF) from the original on 20 March 2024.
  3. ^ Bonewit-West K, Hunt AS, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506. Archived from the original on 10 January 2023. Retrieved 16 February 2020.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ 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.
  6. ^ "ARCHIVED - Report Stakeholder Workshop on a National Buprenorphine Program". Health Canada. 6 December 2004. Archived from the original on 26 March 2020. Retrieved 10 January 2020.
  7. ^ "Neurological therapies". Health Canada. 9 May 2018. Retrieved 13 April 2024.
  8. ^ "Subutex (buprenorphine sublingual tablets), CIII Initial U.S. Approval: 1981". DailyMed. Archived from the original on 27 May 2023. Retrieved 26 May 2023.
  9. ^ "Sublocade- buprenorphine solution". DailyMed. 15 March 2023. Archived from the original on 27 May 2023. Retrieved 26 May 2023.
  10. ^ "Butrans- buprenorphine patch, extended release". DailyMed. 26 June 2022. Archived from the original on 27 May 2023. Retrieved 26 May 2023.
  11. ^ "Brixadi- buprenorphine injection". DailyMed. 21 June 2023. Archived from the original on 26 June 2023. Retrieved 25 June 2023.
  12. ^ "FDA Approves New Buprenorphine Treatment Option for Opioid Use Disorder". U.S. Food and Drug Administration (Press release). 23 May 2023. Retrieved 26 May 2023.
  13. ^ "Buvidal EPAR". European Medicines Agency (EMA). 20 November 2018. Retrieved 10 August 2024.
  14. ^ Mendelson J, Upton RA, Everhart ET, Jacob P, Jones RT (January 1997). "Bioavailability of sublingual buprenorphine". Journal of Clinical Pharmacology. 37 (1): 31–37. doi:10.1177/009127009703700106. PMID 9048270. S2CID 31735116.
  15. ^ Eriksen J, Jensen NH, Kamp-Jensen M, Bjarnø H, Friis P, Brewster D (November 1989). "The systemic availability of buprenorphine administered by nasal spray". The Journal of Pharmacy and Pharmacology. 41 (11): 803–805. doi:10.1111/j.2042-7158.1989.tb06374.x. PMID 2576057. S2CID 1286222.
  16. ^ "Buprenorphine / Naloxone Buccal Film (BUNAVAIL) C-III" (PDF). Pharmacy Benefits Management (PBM) Services. September 2014. Archived (PDF) from the original on 20 October 2020. Retrieved 10 February 2020.
  17. ^ "Bunavail (buprenorphine and naloxone buccal film), CIII Initial U.S. Approval: 2002". DailyMed. Archived from the original on 27 May 2023. Retrieved 26 May 2023.
  18. ^ a b c d e f g h i j k l m n "Buprenorphine Hydrochloride". drugs.com. American Society of Health-System Pharmacists. 26 January 2017. Archived from the original on 18 July 2017. Retrieved 17 March 2017.
  19. ^ "FDA approves first buprenorphine implant for treatment of opioid dependence". U.S. Food and Drug Administration (Press release). 26 May 2016. Archived from the original on 30 November 2017. Retrieved 12 December 2017.
  20. ^ Blazes CK, Morrow JD (11 September 2020). "Reconsidering the Usefulness of Adding Naloxone to Buprenorphine". Frontiers in Psychiatry. 11: 549272. doi:10.3389/fpsyt.2020.549272. PMC 7517938. PMID 33061915.
  21. ^ Whelan PJ, Remski K (January 2012). "Buprenorphine vs methadone treatment: A review of evidence in both developed and developing worlds". Journal of Neurosciences in Rural Practice. 3 (1): 45–50. doi:10.4103/0976-3147.91934. PMC 3271614. PMID 22346191.
  22. ^ "Buprenorphine". The Substance Abuse and Mental Health Services Administration. 15 June 2015. Archived from the original on 26 August 2020. Retrieved 14 October 2020.
  23. ^ "Buprenorphine use while Breastfeeding". Drugs.com. Archived from the original on 10 November 2020. Retrieved 7 February 2021.
  24. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 528. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 29 May 2020.
  25. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  26. ^ a b c "Buprenorphine". SAMHSA Center for Substance Abuse Treatment (CSAT). July 2019. Archived from the original on 20 August 2020. Retrieved 9 January 2020.
  27. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 7 October 2022.
  28. ^ "Buprenorphine - Drug Usage Statistics". ClinCalc. Archived from the original on 11 October 2022. Retrieved 7 October 2022.