Structure via PubChem · Public domain (PubChem)
prilocaine
Sign in to saveAlso known as ASTRA 1512, L-67, Prilotekal®, o-Methyl-alpha-propylaminopropionanilide, o-Methyl-2-propylaminopropionanilide, alpha-n-Propylamino-2-methylpropionanilide, Propitocaine, N-(2-Methylphenyl)-2-(propylamino)propanamide
Prilocaine () is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form (trade name Citanest), it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).
In the Vinony graph
Within Vinony's link graph, prilocaine is referenced by 392 other articles, and connects out to route of administration, local anesthetic and lidocaine/prilocaine.
It sits within the topics Amino acid derivatives, Anilides and Chemicals using indexlabels.
Its subject is documented across 23 Wikipedia language editions.
Chemical data
- Formula
- C13H20N2O
- Molecular weight
- 220.31 g/mol
- IUPAC name
- N-(2-methylphenyl)-2-(propylamino)propanamide
- SMILES
- CCCNC(C)C(=O)NC1=CC=CC=C1C
- InChIKey
- MVFGUOIZUNYYSO-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 41.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1965
- Admin. routes
- parenteral, topical
- Indications
- squamous cell carcinoma, actinic keratosis, pregnancy, pain
via ChEMBL · EBI
Research
2,924 papers- Lidocaine/prilocaine spray for premature ejaculation.Drug and therapeutics bulletin · 2017
- Prilocaine-induced Methemoglobinemia.Journal of the College of Physicians and Surgeons--Pakistan : JCPSP · 2017
- Spinal prilocaine for caesarean section: walking a fine line.Anaesthesia · 2021
- Prilocaine spinal anesthesia for ambulatory surgery: A review of the available studies.Anaesthesia, critical care & pain medicine · 2016
- Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.The Annals of pharmacotherapy · 2002
via PubMed
Wikidata facts
- Subclass of
- amides
- Mass
- 220.158
- Has use
- medication
Show 6 more facts
- World Health Organisation international non-proprietary name
- بريلوكائين
- chemical formula
- C₁₃H₂₀N₂O
- medical condition treated
- pain
- canonical SMILES
- CCCNC(C)C(=O)NC1=CC=CC=C1C
- Commons category
- Prilocaine
- subject has role
- local anesthetic
via Wikidata · CC0
~2 min read
Encyclopedic overview
7 sectionsContents
- Contraindications
- Combinations
- Compendial status
- Synthesis
- See also
- References
- External links
Prilocaine () is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form (trade name Citanest), it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).
== Contraindications == In some patients, ortho-toluidine, a metabolite of prilocaine, may cause methemoglobinemia, which may be treated with methylene blue. Prilocaine may also be contraindicated in people with sickle cell anemia, anemia, or symptomatic hypoxia.
Excerpted from Wikipedia’s “prilocaine” article, available under the CC BY-SA 4.0 licence.