Prilocaine

Source: Wikipedia, the free encyclopedia.
Prilocaine
Clinical data
Trade namesCitanest
AHFS/Drugs.comMonograph
MedlinePlusa603026
License data
Pregnancy
category
  • AU: A
Subcutaneous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding55%
MetabolismLiver and kidney
Elimination half-life10-150 minutes, longer with impaired liver or kidney function
Identifiers
  • (RS)-N-(2-methylphenyl)-N2-propylalaninamide
JSmol)
ChiralityRacemic mixture
Melting point37 to 38 °C (99 to 100 °F)
  • O=C(Nc1ccccc1C)C(NCCC)C
  • InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16) checkY
  • Key:MVFGUOIZUNYYSO-UHFFFAOYSA-N checkY
  (verify)

Prilocaine (

intravenous regional anaesthesia
(IVRA).

Contraindications

In some patients, ortho-toluidine, a metabolite of prilocaine, may cause

hypoxia.[2]

Combinations

It is given as a

eutectic mixture with lidocaine, 50% w/w, as lidocaine/prilocaine. The mixture is an oil with a melting point of 18 °C (64 °F). A 5% emulsion preparation, containing 2.5% each of lidocaine/prilocaine, is marketed by APP Pharmaceuticals under the trade name EMLA (an abbreviation for eutectic mixture of local anesthetics).[3]

Compendial status

Synthesis

Synthesis:[5] Patents:[6][7] Revised:[8] Sino:[9]

The amidation between

o-toluidine [95-53-4] (1) and 2-bromopropionyl bromide [563-76-8] (2) leads to 2-bromo-N-(2-methylphenyl)propanamide [19397-79-6] (3). Displacement of the remaining halide with propylamine
[107-10-8] (4) completed the synthesis of prilocaine (5).

See also

References

  1. ^ "Prilocaine". Merriam-Webster.com Dictionary. Retrieved 2016-01-21.
  2. ISBN 9780199585618
    .
  3. ^ "Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics". Medscape.com. Retrieved 2014-01-07.
  4. ^ The United States Pharmacopeial Convention, Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test, archived from the original on 5 July 2010, retrieved 10 July 2009
  5. ^ Löfgren, Nils; Tegnér, Claës; Arwidsson, Barbro; Varde, E.; Westin, Gertrud (1960). "Studies on Local Anesthetics. XX. Synthesis of Some alpha-Monoalkylamino-2-methylpropionanilides. A New Useful Local Anesthetic.". Acta Chemica Scandinavica 14: 486–490. doi:10.3891/acta.chem.scand.14-0486.
  6. ^ Anon., GB 839943  (to Astra Apotekarnes Kem Fab).
  7. ^ Lofgren Nils Magnus, Tegner Claes Philip, U.S. patent 3,160,662 (1964 to Astra Apotekarnes Kem Fab).
  8. ^ Demare, Patricia; Regla, Ignacio (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of Chemical Education. 89 (1): 147–149. doi:10.1021/ed100838a.
  9. ^ 沈文晖, 杨忠鑫, 葛小强, 张宇生, 邹玉龙, 张强, 杨继斌, 蔡中文, CN 105439887  (2016 to 重庆康乐制药有限公司).

External links

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