PRILOCAINE

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
 PrilocaineCAS 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); GB839943; N. Löfgren, C. Tegner, US3160662 (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 

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 (/ˈpraɪləˌkeɪn/^[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 anemia, anemia, 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.

Compendial status

• United States Pharmacopeia 31 ^[4]

Table 1 The common types of local anesthetics

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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

SYN

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

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”. Drug Information Portal. U.S. National Library of Medicine.
• “Prilocaine hydrochloride”. Drug Information Portal. U.S. National Library of Medicine.

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

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