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    Chemistry

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    Also known as: 721-50-6, Propitocaine, Citanest, Prilocainum, Prilocaine base, N-(2-methylphenyl)-2-(propylamino)propanamide
    Molecular Formula
    C13H20N2O
    Molecular Weight
    220.31  g/mol
    InChI Key
    MVFGUOIZUNYYSO-UHFFFAOYSA-N
    FDA UNII
    046O35D44R
    Prilocaine
    A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.
    Prilocaine is an Amide Local Anesthetic. The physiologic effect of prilocaine is by means of Local Anesthesia.
    1 2D Structure

    Prilocaine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-(2-methylphenyl)-2-(propylamino)propanamide
    2.1.2 InChI
    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)
    2.1.3 InChI Key
    MVFGUOIZUNYYSO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCNC(C)C(=O)NC1=CC=CC=C1C
    2.2 Other Identifiers
    2.2.1 UNII
    046O35D44R
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Citanest

    2. Citanest Octapressin

    3. Prilocaine Hydrochloride

    4. Propitocaine

    5. Xylonest

    2.3.2 Depositor-Supplied Synonyms

    1. 721-50-6

    2. Propitocaine

    3. Citanest

    4. Prilocainum

    5. Prilocaine Base

    6. N-(2-methylphenyl)-2-(propylamino)propanamide

    7. Astra 1515

    8. O-methyl-2-propylaminopropionanilide

    9. Propanamide, N-(2-methylphenyl)-2-(propylamino)-

    10. Prilocaina

    11. 2-(propylamino)-o-propionotoluidide

    12. O-propionotoluidide, 2-(propylamino)-

    13. Astra 1512

    14. O-methyl-alpha-propylaminopropionanilide

    15. 2-methyl-alpha-propylaminopropionanilide

    16. Alpha-n-propylamino-2-methylpropionanilide

    17. Nsc 40027

    18. Propitocaine (jan)

    19. Chebi:8404

    20. 2-(propylamino)-n-(o-tolyl)propanamide

    21. 2-methyl-.alpha.-propylaminopropionanilide

    22. Nsc-40027

    23. Astra-1512

    24. Astra-1515

    25. O-propionotuluidide, 2-propylamino-

    26. 046o35d44r

    27. Prilocaine [usan]

    28. Propitocaine [jan]

    29. Prilocainum [inn-latin]

    30. Prilocaina [inn-spanish]

    31. L-67

    32. (+/-)-prilocaine

    33. Hsdb 3386

    34. Prilocaine (usp/inn)

    35. O-propionotoluidide, 2-propylamino-

    36. Einecs 211-957-0

    37. Brn 2108498

    38. Prilotekal

    39. Unii-046o35d44r

    40. Prilocaine [usan:usp:inn:ban]

    41. N-(2-methylphenyl)-n2-propylalaninamide

    42. Spectrum_001649

    43. L 67

    44. Prilocaine [mi]

    45. Prilocaine [inn]

    46. N-(2-methylphenyl)-n(2)-propylalaninamide

    47. N-(2-methylphenyl)-n~2~-propylalaninamide

    48. Prestwick0_000199

    49. Prestwick1_000199

    50. Prestwick2_000199

    51. Prestwick3_000199

    52. Spectrum2_001549

    53. Spectrum3_001052

    54. Spectrum4_001192

    55. Spectrum5_001175

    56. (.+/-.)-prilocaine

    57. Prilocaine [hsdb]

    58. Prilocaine [vandf]

    59. Prilocaine [mart.]

    60. Chembl1194

    61. Prilocaine [usp-rs]

    62. Prilocaine [who-dd]

    63. Lopac0_001005

    64. Schembl25467

    65. Bspbio_000157

    66. Bspbio_002604

    67. Kbiogr_001883

    68. Kbioss_002129

    69. Divk1c_000846

    70. Spbio_001398

    71. Spbio_002078

    72. Bpbio1_000173

    73. Gtpl7276

    74. Dl-(+/-)-prilocaine

    75. Emla Component Prilocaine

    76. Dtxsid7031955

    77. Prilocaine [orange Book]

    78. Kbio1_000846

    79. Kbio2_002129

    80. Kbio2_004697

    81. Kbio2_007265

    82. Kbio3_001824

    83. Prilocaine [ep Monograph]

    84. Ninds_000846

    85. Oraqix Component Prilocaine

    86. Hms3604h09

    87. Hms3651m13

    88. Hms3884a04

    89. Prilocaine [usp Monograph]

    90. Act04759

    91. Fortacin Component Prilocaine

    92. Hy-b0137

    93. Nsc40027

    94. Prilocaine Component Of Emla

    95. Bdbm50225477

    96. Mfcd00048681

    97. S1619

    98. Stl257086

    99. 2-(propylamino)-n-o-tolylpropanamide

    100. Prilocaine Component Of Oraqix

    101. Akos015889404

    102. Ac-2100

    103. Ccg-205085

    104. Cs-1929

    105. Db00750

    106. Prilocaine Component Of Fortacin

    107. Sdccgsbi-0050978.p004

    108. Idi1_000846

    109. Ncgc00015860-02

    110. Ncgc00015860-03

    111. Ncgc00015860-15

    112. Ncgc00162312-01

    113. As-14851

    114. O-methyl-.alpha.-propylaminopropionanilide

    115. Sbi-0050978.p003

    116. Db-055611

    117. Ab00053665

    118. Ft-0603506

    119. Ft-0660568

    120. Sw196783-3

    121. .alpha.-n-propyl-amino-2-methylpropionanilide

    122. 86p818

    123. C07531

    124. D00553

    125. Ab00053665-12

    126. Ab00053665_13

    127. Ab00053665_14

    128. A837435

    129. N-(2-methylphenyl)-2-(propylamino)propanamide #

    130. Q413598

    131. N-(2-methylphenyl)-2-(propylamino)propanimidic Acid

    132. Q-100809

    133. Brd-a53952395-003-05-3

    134. Brd-a53952395-003-15-2

    135. (+/-)-n-(2-propylaminopropionyl)-2-toluidine

    136. N-(2,6-dimethylphenyl)-2-(propylamino)propanamide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 220.31 g/mol
    Molecular Formula C13H20N2O
    XLogP32.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count5
    Exact Mass220.157563266 g/mol
    Monoisotopic Mass220.157563266 g/mol
    Topological Polar Surface Area41.1 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity218
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Anesthetics, Local

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    AN AGENT CHEMICALLY SIMILAR TO LIDOCAINE & MEPIVACAINE USED FOR LOCAL & REGIONAL-BLOCK ANESTHESIA. IN ONSET OF ACTION & EFFECTIVENESS 1-3% SOLN... EQUIVALENT TO LIDOCAINE & MEPIVACAINE IN 1%-2% CONCN. ITS DURATION OF ACTION IS INTERMEDIATE TO SHORTER-ACTING LIDOCAINE & LONGER-ACTING MEPIVACAINE. /PRILOCAINE HCL/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 994

    PRILOCAINE HYDROCHLORIDE ... HAS BEEN EMPLOYED ... FOR SPINAL ANESTHESIA. /PRILOCAINE HCL/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 390

    ... ACT ON ANY PART OF THE NERVOUS SYSTEM & ON EVERY TYPE OF NERVE FIBER. /LOCAL ANESTHETICS/

    Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 331

    For more Therapeutic Uses (Complete) data for PRILOCAINE (10 total), please visit the HSDB record page.

    4.2 Drug Warning

    AS WITH OTHER LOCAL ANESTHETICS, PRILOCAINE HCL IS CONTRAINDICATED IN PRESENCE OF SHOCK, SEVERE CARDIOVASCULAR DISEASE, OR HEART BLOCK. /PRILOCAINE HCL/

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 994

    ... SHOULD NOT BE ADMIN TO PT WITH IDIOPATHIC OR CONGENITAL METHEMOGLOBINEMIA, ANEMIA, OR CARDIAC OR VENTILATORY FAILURE WITH HYPOXIA; IT SHOULD BE USED WITH CAUTION FOR CONTINUOUS EPIDURAL ANESTHESIA SINCE THE METHEMOGLOBINEMIC EFFECT OF INDIVIDUAL DOSES IS ADDITIVE. /PRILOCAINE HCL/

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 170

    IN PRESENCE OF HEMORRHAGE, SYMPATHETIC BLOCK PRODUCED BY EPIDURAL ANESTHESIA BECOMES EXTREMELY SIGNIFICANT & MAY RESULT IN RAPID & DELETERIOUS CIRCULATORY CHANGES. /LOCAL ANESTHETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 399

    TWO OUTSTANDING DANGERS /OF CAUDAL ANESTHESIA/ ARE (1) INTRODUCING NEEDLE INTO VENOUS PLEXUS LINING SACRAL CANAL, WITH RESULTANT INTRAVASCULAR INJECTION OF DRUG, & (2) PENETRATING DURA, WITH DEVELOPMENT OF HIGH LEVEL OF SPINAL ANESTHESIA. /LOCAL ANESTHETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 399

    For more Drug Warnings (Complete) data for PRILOCAINE (16 total), please visit the HSDB record page.

    4.3 Drug Indication

    Used as a local anaesthetic and is often used in dentistry.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Prilocaine binds to the intracellular surface of sodium channels which blocks the subsequent influx of sodium into the cell. Action potential propagation and never function is, therefore, prevented. This block is reversible and when the drug diffuses away from the cell, sodium channel function is restored and nerve propagation returns.

    5.2 MeSH Pharmacological Classification

    Anesthetics, Local

    Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PRILOCAINE
    5.3.2 FDA UNII
    046O35D44R
    5.3.3 Pharmacological Classes
    Physiologic Effects [PE] - Local Anesthesia
    5.4 ATC Code

    N01BB04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N01 - Anesthetics

    N01B - Anesthetics, local

    N01BB - Amides

    N01BB04 - Prilocaine

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Prilocaine is metabolized in both the liver and the kidney and excreted via the kidney.

    /CONCERNING/ HYDROLYSIS OF AMIDE BOND OF PRILOCAINE... PLASMA CONCN OF R-(-)-ENANTIOMER WERE FOUND TO BE LOWER THAN THOSE OF THE S-(+)-ENANTIOMER AFTER IV ADMIN TO CAT. IN VITRO STUDIES USING LIVER PREPN FROM VARIOUS MAMMALS CONFIRMED THE R-(-)-ISOMER TO BE HYDROLYZED @ MUCH HIGHER RATES THAN THE S-(+) FORM...

    Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 241

    THERE IS...MORE RAPID PRODN OF METHEMOGLOBINEMIA BY D-(-) FORM, CAUSED PRESUMABLY BY HIGHER BLOOD LEVELS OF HYDROLYSIS PRODUCT, O-TOLUIDINE.

    The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 375

    PRILOCAINE FETAL/MATERNAL CONCN RATIO: 1.0 /FROM TABLE/

    LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 100

    PRILOCAINE DOSE 0.2 G IV GAVE BLOOD CONCN 0.26 MG% @ 0.3 HR & 0.14 MG% @ 0.17 HR; DOSE 0.4 G IV GAVE BLOOD CONCN 0.15 MG% @ 0.12 HR & 0.08 MG% @ 0.33 HR; DOSE 0.4 G EPIDURAL BLOCK GAVE BLOOD CONCN 0.26 MG% @ 0.25 HR (PEAK); DOSE 0.4 G INTERCOSTAL BLOCK GAVE BLOOD CONCN 0.40 MG% @ 0.25 HR. /FROM TABLE/

    Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 370

    5.6 Metabolism/Metabolites

    The amide-linked local anesthetics are, in general, degraded by the hepatic endoplasmic reticulum, the initial reactions involving N-dealkylation and subsequent hydrolysis. However, with prilocaine, the initial step is hydrolytic, forming o-toluidine metabolites that can cause methemoglobinemia.

    Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 338

    BIOTRANSFORMATION OF PRILOCAINE...IN RATS GAVE O-TOLUIDINE & N-PROPYLALANINE.

    The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 244

    5.7 Biological Half-Life

    MEPIVACAINE-HCL (I-HCL) & PRILOCAINE-HCL (II-HCL) WERE INFUSED IV 250 MG INTO HEALTHY VOLUNTEERS. T/2 FOR I WAS GENERALLY LONGER THAN II; TOTAL BODY CLEARANCE II CONSISTENTLY GREATER THAN I. II CLEARANCE EXCEEDED NORMAL HEPATIC BLOOD FLOW: EXTRA-HEPATIC METAB SITE IS POSTULATED.

    ARTHUR ET AL; BR J ANAESTH 51(6) 481 (1979)

    5.8 Mechanism of Action

    Prilocaine acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.

    ... BLOCK CONDUCTION IN NERVE PERHAPS BY COMPETING WITH CA @ SOME SITE THAT CONTROLS PERMEABILITY OF MEMBRANE ... CA IS ALSO INVOLVED IN ACTION OF LOCAL ANESTHETICS ON SMOOTH MUSCLE ... & ON ADRENAL MEDULLA ... /LOCAL ANESTHETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 380

    ... PREVENT THE GENERATION & THE CONDUCTION OF THE NERVE IMPULSE. THEIR PRIMARY SITE OF ACTION IS THE CELL MEMBRANE. ... BLOCK CONDUCTION BY DECREASING OR PREVENTING THE LARGE TRANSIENT INCREASE IN THE PERMEABILITY OF EXCITABLE MEMBRANES TO NA+ THAT NORMALLY IS PRODUCED BY A SLIGHT DEPOLARIZATION OF THE MEMBRANE. /LOCAL ANESTHETICS/

    Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 332

    AS ANESTHETIC ACTION PROGRESSIVELY DEVELOPS IN A NERVE, THRESHOLD FOR ELECTRICAL EXCITABILITY INCR & SAFETY FACTOR FOR CONDUCTION DECR; WHEN THIS ACTION IS SUFFICIENTLY WELL-DEVELOPED, BLOCK OF CONDUCTION IS PRODUCED. /LOCAL ANESTHETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 380

    .../2 POSSIBILITIES:/ ACHIEVE BLOCK BY INCR SURFACE PRESSURE OF LIPID LAYER THAT CONSTITUTES NERVE MEMBRANE...CLOSING PORES THROUGH WHICH IONS MOVE. ... /OR:/ AFFECT PERMEABILITY BY INCR DEGREE OF DISORDER OF MEMBRANE. /LOCAL ANESTHETICS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 382

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    07-Jan-2021
    21-Aug-2024
    KGS
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