Structure via PubChem · Public domain (PubChem)
dibucaine
Sign in to saveAlso known as Cincain ®, cincaine chloride, Nupercaine ®, CINCHOCAINE, 2-butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide, alpha-butyloxycinchoninic acid diethylethylenediamide, 2-butoxy-N-(beta-diethylaminoethyl)cinchoninamide
Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.
Chemical data
- Formula
- C20H29N3O2
- Molecular weight
- 343.5 g/mol
- IUPAC name
- 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
- SMILES
- CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
- InChIKey
- PUFQVTATUTYEAL-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 54.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- parenteral
- Indications
- Pruritus, hemorrhoid, sunburn
via ChEMBL · EBI
Research
1,511 papers- Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi.Parasitology research · 2006
- [Dibucaine number].Minerva anestesiologica · 1976
- Phentolamine Reverses Epinephrine-Enhanced Skin Antinociception of Dibucaine in Rats.Anesthesia and analgesia · 2019
- Pre-clinical evaluation of new dibucaine formulations for preventive analgesia.Journal of liposome research · 2021
- Calpain activator dibucaine induces platelet apoptosis.International journal of molecular sciences · 2011
via PubMed
Wikidata facts
- Subclass of
- allergen
- Mass
- 343.225977
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₀H₂₉N₃O₂
- Commons category
- Cinchocaine
- isomeric SMILES
- CCCCOC1=CC(=C2C=CC=CC2=N1)/C(=N/CCN(CC)CC)/O
- canonical SMILES
- CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
- World Health Organisation international non-proprietary name
- cinchocaine
- medical condition treated
- pain
- subject has role
- local anesthetic
via Wikidata · CC0
~1 min read
Encyclopedic overview
5 sectionsContents
- Medical use
- Physical properties
- See also
- References
- Further reading
Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.
==Medical use== Cinchocaine is the active ingredient in some topical hemorrhoid creams such as Proctosedyl. It is also a component of the veterinary drug Somulose, used for euthanasia of horses and cattle.
Excerpted from Wikipedia’s “dibucaine” article, available under the CC BY-SA 4.0 licence.