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PRILOCAINE

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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 

INGREDIENTUNIICASINCHI KEY
Prilocaine hydrochlorideMJW015BAPH1786-81-8BJPJNTKRKALCPP-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 (/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 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

COMPOUNDSTRUCTURETIME TO MARKETAPPLICATION METHODS
Procaine1904Infiltration anesthesia, conduction anesthesia, subarachnoid anesthesia and epidural anesthesia
Chloroprocaine1952Infiltration anesthesia, epidural anesthesia and conduction anesthesia
Hydroxyprocaine1960Infiltration anesthesia
Tetracaine1988Conduction anesthesia, subarachnoid anesthesia and epidural anesthesia
Oxybuprocaine1975Topical anesthesia
Tutocaine1976Topical anesthesia and infiltration anesthesia
Butacaine1976Topical anesthesia and infiltration anesthesia
Dimethocaine1938Topical anesthesia and infiltration anesthesia
ThiocaineHalt salesTopical anesthesia and infiltration anesthesia
Lidocaine1948Conduction anesthesia and epidural anesthesia
Mepivacaine1986Infiltration anesthesia, conduction anesthesia, epidural anesthesia and topical anesthesia
Bupivacaine2000Infiltration anesthesia, conduction anesthesia and epidural anesthesia
Ropivacaine1996Infiltration anesthesia, conduction anesthesia and epidural anesthesia
Trimecaine1965Infiltration anesthesia, surface anesthesia and epidural anesthesia
Prilocaine1993Infiltration anesthesia, topical anesthesia and epidural anesthesia
Etidocaine1976Epidural anesthesia
Pyrrocaine1964Conduction anesthesia and epidural anesthesia
Butanilicaine1982Infiltration anesthesia and conduction anesthesia
Cinchocaine1985Topical anesthesia, subarachnoid anesthesia and epidural anesthesia
Articaine2002Infiltration anesthesia and subarachnoid anesthesia
Dyclonine1956Topical anesthesia
Falicaine1957Topical anesthesia
Quinisocaine1957Topical anesthesia
Pramocaine1977Topical anesthesia
Diperodon1980Topical anesthesia
Heptacaine1984Infiltration 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
Clinical data
Trade namesCitanest
AHFS/Drugs.comMonograph
MedlinePlusa603026
License dataEU EMAby INNUS DailyMedPrilocaine
Pregnancy
category
AU: A
Routes of
administration
Subcutaneous
ATC codeN01BB04 (WHO)
Legal status
Legal statusAU: S4 (Prescription only)US: ℞-only
Pharmacokinetic data
Protein binding55%
MetabolismLiver and kidney
Elimination half-life10-150 minutes, longer with impaired liver or kidney function
Identifiers
showIUPAC name
CAS Number721-50-6 
PubChem CID4906
IUPHAR/BPS7276
DrugBankDB00750 
ChemSpider4737 
UNII046O35D44R
KEGGD00553 as HCl: D01243 
ChEBICHEBI:8404 
ChEMBLChEMBL1194 
CompTox Dashboard (EPA)DTXSID7031955 
ECHA InfoCard100.010.871 
Chemical and physical data
FormulaC13H20N2O
Molar mass220.316 g·mol−1
3D model (JSmol)Interactive image
ChiralityRacemic mixture
Melting point37 to 38 °C (99 to 100 °F)
showSMILES
showInChI
  (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, 

CCCNC(C)C(=O)NC1=CC=CC=C1C

wdt-23

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK LIFE SCIENCES LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 PLUS year tenure till date June 2021, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 33 lakh plus views on New Drug Approvals Blog in 233 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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