PRILOCAINE

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Prilocaine.svg

PRILOCAINE

  • Molecular FormulaC13H20N2O
  • Average mass220.311 Da
Propanamide, N-(2-methylphenyl)-2-(propylamino)-
прилокаин [Russian] [INN]
بريلوكائين [Arabic] [INN]
丙胺卡因 [Chinese] [INN]
1641
211-957-0 [EINECS]
721-50-6 [RN]
N-(2-Methylphenyl)-2-(propylamino)propanamid
N-(2-méthylphényl)-2-(propylamino)propanamide
 Prilocaine
CAS Registry Number: 721-50-6
CAS Name: N-(2-Methylphenyl)-2-(propylamino)propanamide
Additional Names: 2-(propylamino)-o-propionotoluidide; N-(a-propylaminopropionyl)-o-toluidine; a-propylamino-2-methylpropionanilide; propitocaine
Molecular Formula: C13H20N2O
Molecular Weight: 220.31
Percent Composition: C 70.87%, H 9.15%, N 12.72%, O 7.26%
Literature References: Prepn: N. Löfgren, C. Tegner, Acta Chem. Scand. 14, 486 (1960); GB 839943; N. Löfgren, C. Tegner, US 3160662 (1960, 1964 both to Astra).
Properties: Needles, mp 37-38°. bp0.1 159-162°. nD20 1.5298.
Melting point: mp 37-38°
Boiling point: bp0.1 159-162°
Index of refraction: nD20 1.5298
Derivative Type: Hydrochloride
CAS Registry Number: 1786-81-8
Manufacturers’ Codes: L-67
Trademarks: Citanest (AstraZeneca); Xylonest (AstraZeneca)
Molecular Formula: C13H20N2O.HCl
Molecular Weight: 256.77
Percent Composition: C 60.81%, H 8.24%, N 10.91%, O 6.23%, Cl 13.81%
Properties: Crystals from ethanol + isopropyl ether, mp 167-168°. Readily sol in water.
Melting point: mp 167-168°
Therap-Cat: Anesthetic (local).
Keywords: Anesthetic (Local).
  • ASTRA 1512
  • ASTRA 1515
  • ASTRA-1512
  • ASTRA-1515
  • L 67

Product Ingredients

INGREDIENT UNII CAS INCHI KEY
Prilocaine hydrochloride MJW015BAPH 1786-81-8 BJPJNTKRKALCPP-UHFFFAOYSA-N

 

Agoneaze, Anodyne Lpt, Citanest, Citanest Forte, Dermacinrx Prikaan, Dermacinrx Prizopak, Emla, Fortacin, Lido Bdk, Lido-prilo Caine Pack, Lidopril, Oraqix, Prilolid, Prizotral, Relador

Prilocaine is a local anesthetic used in dental procedures.

A local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)

Prilocaine (/ˈprləˌkn/[1]) 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 anemiaanemia, or symptomatic hypoxia.[2]

Combinations

It is given as a combination with the vasoconstrictor epinephrine under the trade name Citanest Forte. It is used as an 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]

NMR

1 H-nuclear magnetic resonance ( 1 H-NMR) spectra of prilocaine solution after sterilization with the assignment of the prilocaine hydrogens. [Prilocaine] = 5 mM, 20°C, 500 MHz.  1 H-nuclear magnetic resonance ( 1 H-NMR) spectra of prilocaine solution after sterilization with the assignment of the prilocaine hydrogens. [Prilocaine] = 5 mM, 20°C, 500 MHz.

Wed May 313 52017 GMT 07000 Figure 2: IR Spectrum of prilocaine hydrochloride 2.5-3.5 ppm 13H 6.2 ppm 1H 5.5 ppm 2H 8.7 ppm AH Figure 3: H NMR of prilocaine hydrochloride

Compendial status

Table 1 The common types of local anesthetics

COMPOUND STRUCTURE TIME TO MARKET APPLICATION METHODS
Procaine 1904 Infiltration anesthesia, conduction anesthesia, subarachnoid anesthesia and epidural anesthesia
Chloroprocaine 1952 Infiltration anesthesia, epidural anesthesia and conduction anesthesia
Hydroxyprocaine 1960 Infiltration anesthesia
Tetracaine 1988 Conduction anesthesia, subarachnoid anesthesia and epidural anesthesia
Oxybuprocaine 1975 Topical anesthesia
Tutocaine 1976 Topical anesthesia and infiltration anesthesia
Butacaine 1976 Topical anesthesia and infiltration anesthesia
Dimethocaine 1938 Topical anesthesia and infiltration anesthesia
Thiocaine Halt sales Topical anesthesia and infiltration anesthesia
Lidocaine 1948 Conduction anesthesia and epidural anesthesia
Mepivacaine 1986 Infiltration anesthesia, conduction anesthesia, epidural anesthesia and topical anesthesia
Bupivacaine 2000 Infiltration anesthesia, conduction anesthesia and epidural anesthesia
Ropivacaine 1996 Infiltration anesthesia, conduction anesthesia and epidural anesthesia
Trimecaine 1965 Infiltration anesthesia, surface anesthesia and epidural anesthesia
Prilocaine 1993 Infiltration anesthesia, topical anesthesia and epidural anesthesia
Etidocaine 1976 Epidural anesthesia
Pyrrocaine 1964 Conduction anesthesia and epidural anesthesia
Butanilicaine 1982 Infiltration anesthesia and conduction anesthesia
Cinchocaine 1985 Topical anesthesia, subarachnoid anesthesia and epidural anesthesia
Articaine 2002 Infiltration anesthesia and subarachnoid anesthesia
Dyclonine 1956 Topical anesthesia
Falicaine 1957 Topical anesthesia
Quinisocaine 1957 Topical anesthesia
Pramocaine 1977 Topical anesthesia
Diperodon 1980 Topical anesthesia
Heptacaine 1984 Infiltration anesthesia
wdt-16

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Synthesis Reference

US3160662

SYN

English: N. Lofgren and C. Tegner, Acta Chem. Scand., 14, 486 (1960). DOI number: 10.3891/acta.chem.scand.14-0486

File:Prilocaine synthesis.png

SYN

CH3 CH3 NH2 1) H2SO4 NH2 H+ NH2 CH 2) CH3CI/AICI: HO3S NH 1 2 3 NH CH3 CH3 CH3 Br NH HO H3C NH 1) HCN CH3 H30+ 8 HO CH3 CH3 2

SUN

Prilocaine, 2-(propylamino)-o-propiontoluidine (2.2.14), is structurally related to the exact same group as ethidocaine, yet it differs structurally in that during synthesis, o-toluidine is used instead of 2,6-dimethylaniline, and instead of a butyric acid, a fragment of propionic acid, and a terminal propylethylamine group is replaced with a propylamine group. In order to synthesize prilocaine, o-toluidine is reacted with bromopropionyl bromide, and the resulting bromopropionyltoluidide (2.2.13) is then reacted with propylamine, which gives prilocaine [22,23].

SYN

SYN

images

 

Prilocaine
Prilocaine.svg
Clinical data
Trade names Citanest
AHFS/Drugs.com Monograph
MedlinePlus a603026
License data
Pregnancy
category
  • AU: A
Routes of
administration
Subcutaneous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 55%
Metabolism Liver and kidney
Elimination half-life 10-150 minutes, longer with impaired liver or kidney function
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.010.871 Edit this at Wikidata
Chemical and physical data
Formula C13H20N2O
Molar mass 220.316 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
Melting point 37 to 38 °C (99 to 100 °F)
  (verify)

References

  1. ^ “Prilocaine”Merriam-Webster Dictionary. Retrieved 2016-01-21.
  2. ^ Patel V, Morrissey J (2011-09-15). Practical and Professional Clinical Skills. Oxford University Press. p. 267. 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

External links

 

//////////PRILOCAINE, Anesthetic, ASTRA 1512, ASTRA 1515, ASTRA-1512, ASTRA-1515, L 67,

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