Drug General Information (ID: D0110)
  Drug Name
Articaine
  Drug Type Small molecule
  Drug Synonymous
Articaine; Carticaine; 23964-58-1; Articaine [INN:BAN]; Articainum [INN-Latin]; Articaina [INN-Spanish]; Hoe-045; Ultracain; HOE 045; methyl 4-methyl-3-[(N-propylalanyl)amino]thiophene-2-carboxylate; methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate; Methyl (4-methyl-3-(2-(propylamino)propionamido)-2-thiophencarboxylat); Q-200652; Articainum; Articaina; 4-Methyl-3-(2-(propylamino)propionamido)-2-thiophenecarboxylic acid, methyl ester; 2-Thiophenecarboxylicacid, 4-methyl-3-[[1-oxo-2-(propylamino)propy
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  Disease Class 9A76-9A78: Corneal disease
  Therapeutic Class Local Anesthetics
  Structure Could Not Find 2D Structure
3D Structure 2D Structure
  Formula C13H20N2O3S
  InChI 1S/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16)
  InChIKey QTGIAADRBBLJGA-UHFFFAOYSA-N
  Canonical SMILES CCCNC(C)C(=O)NC1=C(SC=C1C)C(=O)OC
  External Link
Pubchem ID 32170
CAS Number 23964-58-1
CHEBI ID 91834
TTD ID D0I5HV

Drug-Drug Interaction Network
  Sunburst Graph
AM003  Affected organization distribution
AM004  Affected intra/extra-hepatic metabolism
AM006  Pharmacodynamic additive effects
AM007  Pharmacodynamic antagonistic effects
BM013  Competitive binding of plasma proteins
BM017  CYP450 enzyme inhibition
BM038  Additive CNS depression effects
BM042  Additive hypotensive effects
BM049  Increased risk of atrioventricular block
BM051  Increased risk of bradycardia
BM071  Increased risk of methemoglobinemia
BM107  Attenuated pharmacological effects (Unspecific)
  Relation Graph
 Full list of drugs interacting with Articaine
      Affected organization distribution
   Competitive binding of plasma proteins Drug Num:  1
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1001
 
Meperidine
 
C15H21NO2
 
4058 
Minor    Inter Info   
[17]
      Affected intra/extra-hepatic metabolism
   CYP450 enzyme inhibition Drug Num:  1
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0035
 
Alfentanil
 
C21H32N6O3
 
51263 
Minor    Inter Info   
[14], [15], [16]
      Pharmacodynamic additive effects
   Additive CNS depression effects Drug Num:  15
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0045
 
Alprazolam
 
C17H13ClN4
 
2118 
Moderate    Inter Info   
[6], [7], [8]
D1391
 
Remimazolam
 
C21H19BrN4O2
 
9867812 
Moderate    Inter Info   
[6], [7], [8]
D0317
 
Chlordiazepoxide
 
C16H14ClN3O
 
2712 
Moderate    Inter Info   
[6], [7], [8]
D0356
 
Clobazam
 
C16H13ClN2O2
 
2789 
Moderate    Inter Info   
[6], [7], [8]
D0362
 
Clonazepam
 
C15H10ClN3O3
 
2802 
Moderate    Inter Info   
[6], [7], [8]
D0365
 
Clorazepic acid
 
C16H11ClN2O3
 
2809 
Moderate    Inter Info   
[6], [7], [8]
D0473
 
Diazepam
 
C16H13ClN2O
 
3016 
Moderate    Inter Info   
[6], [7], [8]
D0604
 
Estazolam
 
C16H11ClN4
 
3261 
Moderate    Inter Info   
[6], [7], [8]
D0748
 
Halazepam
 
C17H12ClF3N2O
 
31640 
Moderate    Inter Info   
[6], [7], [8]
D0951
 
Lorazepam
 
C15H10Cl2N2O2
 
3958 
Moderate    Inter Info   
[6], [7], [8]
D1060
 
Midazolam
 
C18H13ClFN3
 
4192 
Moderate    Inter Info   
[6], [7], [8]
D1197
 
Oxazepam
 
C15H11ClN2O2
 
4616 
Moderate    Inter Info   
[6], [7], [8]
D1367
 
Quazepam
 
C17H11ClF4N2S
 
4999 
Moderate    Inter Info   
[6], [7], [8]
D1547
 
Temazepam
 
C16H13ClN2O2
 
5391 
Moderate    Inter Info   
[6], [7], [8]
D1632
 
Triazolam
 
C17H12Cl2N4
 
5556 
Moderate    Inter Info   
[6], [7], [8]
   Additive hypotensive effects Drug Num:  1
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1752
 
Bupivacaine (liposome)
 
C18H28N2O
 
2474 
Major    Inter Info   
[4], [5]
   Increased risk of bradycardia Drug Num:  5
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D0066
 
Amiodarone
 
C25H29I2NO3
 
2157 
Moderate    Inter Info   
[9], [10]
D0200
 
Bretylium
 
C11H17BrN+
 
2431 
Moderate    Inter Info   
[9], [10]
D0513
 
Dofetilide
 
C19H27N3O5S2
 
71329 
Moderate    Inter Info   
[9], [10]
D0787
 
Ibutilide
 
C20H36N2O3S
 
60753 
Moderate    Inter Info   
[9], [10]
D1428
 
Ropivacaine
 
C17H26N2O
 
175805 
Moderate    Inter Info   
[10]
   Increased risk of methemoglobinemia Drug Num:  9
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1148
 
Nitrous acid
 
HNO2
 
24529 
Major    Inter Info   
[1], [2], [3]
D1904
 
Tetracaine (ophthalmic)
 
C15H24N2O2
 
5411 
Moderate    Inter Info   
[7], [11], [12]
D1562
 
Tetracaine (topical)
 
C15H24N2O2
 
5411 
Moderate    Inter Info   
[7], [11], [12]
D0163
 
Benzocaine (topical)
 
C9H11NO2
 
2337 
Moderate    Inter Info   
[7], [11], [12]
D0339
 
Cinchocaine (topical)
 
C20H29N3O2
 
3025 
Moderate    Inter Info   
[7], [11], [12]
D1835
 
Lidocaine (ophthalmic)
 
C14H22N2O
 
3676 
Moderate    Inter Info   
[7], [11], [12]
D0928
 
Lidocaine (topical)
 
C14H22N2O
 
3676 
Moderate    Inter Info   
[7], [11], [12]
D1852
 
Oxybuprocaine (ophthalmic)
 
C17H28N2O3
 
4633 
Moderate    Inter Info   
[7], [11], [12]
D1870
 
Proparacaine (ophthalmic)
 
C16H26N2O3
 
4935 
Moderate    Inter Info   
[7], [11], [12]
      Pharmacodynamic antagonistic effects
   Attenuated pharmacological effects (Unspecific) Drug Num:  1
Drug ID
 
Drug Name
Formula Pubchem ID Severity Level Interaction Detail REF
D1909
 
Tilmanocept
 
NA
 
NA
Moderate    Inter Info   
[13]
References
1 Coleman MD, Coleman NA "Drug-induced methaemoglobinaemia: treatment issues." Drug Saf 14 (1996): 394-405. [PMID: 8828017]
2 Product Information. Sodium Nitrite (sodium nitrite). Hope Pharmaceuticals, Scottsdale, AZ.
3 Rehman HU "Methemoglobinemia." West J Med 175 (2001): 193-6. [PMID: 11527852]
4 Product Information. Exparel (bupivacaine liposome). Pacira Pharmaceuticals Inc, San Diego, CA.
5 Kharitonov V "A review of the compatibility of liposome bupivacaine with other drug products and commonly used implant materials." Postgrad Med 126 (2014): 129-38. [PMID: 24393760]
6 Cerner Multum, Inc. "Australian Product Information.".
7 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
8 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA."
9 Keidar S, Grenadier E, Palant A "Sinoatrial arrest due to lidocaine injection in sick sinus syndrome during amiodarone administration." Am Heart J 104 (1982): 1384-5. [PMID: 7148661]
10 Product Information. Naropin (ropivacaine). Astra USA, Westborough, MA.
11 Guay J "Methemoglobinemia related to local anesthetics: a summary of 242 episodes." Anesth Analg 108 (2009): 837-45. [PMID: 19224791]
12 Product Information. Hurricaine (benzocaine topical). Beutlich, Waukegan, IL.
13 Product Information. Lymphoseek (tilmanocept). Navidea Biopharmaceuticals, Dublin, OH.
14 Kharasch ED, Thummel KE "Human alfentanil metabolism by cytochrome P450 3A3/4. An explanation for the interindividual variability in alfentanil clearance?" Anesth Analg 76 (1993): 1033-9. [PMID: 8484504]
15 Koehntop DE, Noormohamed SE, Fletcher CV "Effects of long-term drugs on alfentanil clearance in patients undergoing renal transplantation." Pharmacotherapy 14 (1994): 592-9. [PMID: 7997393]
16 Yun CH, Wood M, Wood AJ, Guengerich FP "Identification of the pharmacogenetic determinants of alfentanil metabolism: cytochrome P-450 3A4: an explanation of the variable elimination clearance." Anesthesiology 77 (1992): 467-74. [PMID: 1519785]
17 Ghoneim MM, Pandya H "Plasma protein binding of bupivacaine and its interaction with other drugs in man." Br J Anaesth 46 (1974): 435-8. [PMID: 4458761]