Structure via PubChem · Public domain (PubChem)
buprenorphine
Sign in to saveAlso 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
OverviewAI-generated
Buprenorphine is a chemical compound with the formula C₂₉H₄₁NO₄. Its molecular mass is listed as 467.304, while its weight is recorded as 467.6. The substance has a defined daily dose of 8.
Chemical properties include an xlogp value of 5 and a topological polar surface area of 62.2. The molecule contains two hydrogen bond donors and five hydrogen bond acceptors, with a charge of 0. It is referenced by 1,472 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.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 Ų
- 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
Wikidata facts
- Mass
- 467.304
- Has use
- medication
Show 12 more facts
- chemical formula
- C₂₉H₄₁NO₄
- route of administration
- sublingual administration
- medical condition treated
- opioid use disorder
- Commons category
- Buprenorphine
- World Health Organisation international non-proprietary name
- buprenorphine
- isomeric 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
- canonical SMILES
- CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
- defined daily dose
- 8
- subject has role
- narcotic
- found in taxon
- Papaver somniferum
- legal status (medicine)
- boxed warning
- significant drug interaction
- primidone
Sources (7)
via Wikidata · CC0
~25 min read
Encyclopedic overview
31 sectionsContents
- 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.