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1. Citanest
2. Citanest Octapressin
3. Prilocaine Hydrochloride
4. Propitocaine
5. Xylonest
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
| Molecular Weight | 220.31 g/mol |
|---|---|
| Molecular Formula | C13H20N2O |
| XLogP3 | 2.1 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 5 |
| Exact Mass | 220.157563266 g/mol |
| Monoisotopic Mass | 220.157563266 g/mol |
| Topological Polar Surface Area | 41.1 Ų |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Complexity | 218 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
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.
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.
Used as a local anaesthetic and is often used in dentistry.
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.
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.)
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
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
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
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)
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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