buprenorphine

Also known as Buprenex®, Temgesic®, (-)-buprenorphine, 21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine, 2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol, 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol, 21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine, 2-(N-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 457118559
Drug.image: Buprenorphine.svg
Drug.image_class: skin-invert-image
Drug.width: 220
Drug.alt: Skeletal formula of buprenorphine
Drug.image2: Buprenorphine molecule from xtal ball.png
Drug.image_class2: bg-transparent
Drug.width2: 220
Drug.alt2: Ball-and-stick model of the buprenorphine molecule
Drug.pronounce: bew-pre-nor-feen
Drug.tradename: Subutex, Sublocade, Belbuca, Brixadi, others
Drug.MedlinePlus: a605002
Drug.DailyMedID: Buprenorphine
Drug.pregnancy_AU: C
Drug.dependency_liability: Psychological: High Physical: Moderate
Drug.routes_of_administration: Sublingual, buccal, intramuscular, intravenous, transdermal, intranasal, rectal, subcutaneous

via Wikipedia infobox

Chemical data

Formula: C29H41NO4
Molecular weight: 467.6 g/mol
IUPAC name: (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O
InChIKey: RMRJXGBAOAMLHD-IHFGGWKQSA-N
XLogP: 5
Polar surface area: 62.2 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

12,852 papers

Understanding Buprenorphine for Use in Chronic Pain: Expert Opinion.Pain medicine (Malden, Mass.) · 2020
Microinduction of Buprenorphine/Naloxone: A Review of the Literature.The American journal on addictions · 2021
Buprenorphine for Pain: A Narrative Review and Practical Applications.The American journal of medicine · 2024
Buprenorphine: clinical pharmacokinetics in the treatment of opioid dependence.Clinical pharmacokinetics · 2005
Buprenorphine.Drug and alcohol dependence · 1985

via PubMed

~25 min read

Encyclopedic overview

31 sections

Contents

Medical uses
Opioid use disorder
Buprenorphine versus methadone
Chronic pain
Potency
Adverse effects
Respiratory effects
Buprenorphine dependence
Pain management
Pharmacology
Pharmacodynamics
Opioid receptor modulator
Other actions
Pharmacokinetics
Chemistry
Detection in body fluids
History
Society and culture
Regulation
United States
Europe
Barriers to access
Brand names
Research
Microdosing
Depression
Cocaine dependence
Neonatal abstinence
Veterinary use
References
External links

Buprenorphine, is an opioid used to treat opioid use disorder, acute pain, and chronic pain. 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.

In the United States, the combination formulation of buprenorphine/naloxone (Suboxone) is usually prescribed to discourage misuse by injection. Maximum pain relief is generally within an hour with effects up to 24 hours. Buprenorphine affects different types of opioid receptors in different ways. Depending on the type of opioid receptor, it may be an agonist, partial agonist, or antagonist. 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 (primarily when first starting treatment if one is not already opioid tolerant/dependent), 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.

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