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Drug-Target Interaction

Drug

show drug details
PubChem ID:3676
Structure:
Synonyms:
"lidocaine (73-58-6 (monohydrochloride); 6108-05-0 (monohydrochloride monohydrate))"
.alpha.-(Diethylamino)-2,6-acetoxylidide
.alpha.-Diethylamino-2,6-dimethylacetanilide
.alpha.-Diethylaminoaceto-2,6-xylidide
.omega.-Diethylamino-2,6-dimethylacetanilide
137-58-6
2',6'-Acetoxylidide, 2-(diethylamino)-
2-(Diethylamino)-2',6'-acetoxylidide
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide
2-Diethylamino-N-(2,6-dimethyl-phenyl)-acetamide
2-Diethylamino-N-(2,6-dimethylphenyl)acetamide
4-12-00-02538 (Beilstein Handbook Reference)
6108-05-0
6108-05-0 (mono-hydrochloride, mono-hydrate)
6108-05-0 (MONOHYDROCHLORIDE
73-78-9
73-78-9 (mono-hydrochloride)
8059-42-5
8059-66-3
91484-71-8
AB00053581
AC-10282
AC1L1GGQ
AC1Q2Z7J
Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-
After Burn Double Strength Gel
After Burn Double Strength Spray
After Burn Gel
After Burn Spray
AKOS001026768
alfa-Dietilamino-2,6-dimetilacetanilide
alfa-Dietilamino-2,6-dimetilacetanilide [Italian]
alpha-Diethylamino-2,6-dimethylacetanilide
ALPHACAINE
Anestacon
Anestacon Jelly
ARONIS23855
BIDD:GT0342
Bio-0767
Bio1_000379
Bio1_000868
Bio1_001357
Bio2_000079
Bio2_000559
BPBio1_000197
BRD-K52662033-001-02-6
BRD-K52662033-003-05-5
BRN 2215784
BSPBio_000179
BSPBio_001359
BSPBio_003004
C07073
C14H22N2O
Cappicaine
CAS-73-78-9
CCG-100824
CDS1_000283
CHEBI:6456
CHEMBL79
Cito optadren
CPD000058189
Cuivasil
D00358
Dalcaine
DB00281
Dentipatch
Dentipatch (TN)
DermaFlex
Diethylaminoaceto-2,6-xylidide
Dilocaine
DivK1c_000174
DivK1c_001323
Duncaine
EINECS 205-302-8
ELA-Max
EMBOLEX
EMLA
Emla Cream
Esracaine
FT-0082378
Gravocain
HMS1791D21
HMS1989D21
HMS2051C21
HMS2089E15
HMS2235O14
HMS548M19
HSDB 3350
I01-2704
IDI1_000174
IDI1_033829
Isicaina
Isicaine
Jetocaine
KBio1_000174
KBio2_000079
KBio2_001598
KBio2_002647
KBio2_004166
KBio2_005215
KBio2_006734
KBio3_000157
KBio3_000158
KBio3_002224
KBioGR_000079
KBioGR_000599
KBioSS_000079
KBioSS_001598
L-Caine
L0156
L1026_SIGMA
L7757_SIGMA
LANABIOTIC
Leostesin
Lida-Mantle
Lidaform-HC
Lidamantle-HC
Lidocaina
Lidocaina [INN-Spanish]
Lidocaine
LIDOCAINE (73-58-6 (MONOHYDROCHLORIDE)
LIDOCAINE (73-58-6 (MONOHYDROCHLORIDE); 6108-05-0 (MONOHYDROCHLORIDE MONOHYDRATE))
Lidocaine (JP15/USP/INN)
Lidocaine (JP16/USP/INN)
Lidocaine (VAN)
Lidocaine Carbonate
Lidocaine Hydrocarbonate
Lidocaine hydrochloride
Lidocaine Monohydrochloride
Lidocaine [USAN:INN:JAN]
Lidocainum
Lidocainum [INN-Latin]
Lidocaton
Lidoderm
Lidoject-1
Lidoject-2
LIDOPEN
Lignocaine
Lignocainum
Lingocaine
Lopac-L-5647
Lopac0_000669
LS-805
Maricaine
Maybridge1_002571
Mixture Name
MLS000069724
MLS000758263
MLS001074177
N-(2,6-dimethylphenyl)-N(2),N(2)-diethylglycinamide
N-(2,6-dimethylphenyl)-N~2~,N~2~-diethylglycinamide
NCGC00015611-01
NCGC00015611-02
NCGC00015611-03
NCGC00015611-04
NCGC00015611-05
NCGC00015611-06
NCGC00015611-07
NCGC00015611-08
NCGC00015611-09
NCGC00015611-10
NCGC00015611-11
NCGC00015611-12
NCGC00015611-13
NCGC00015611-14
NCGC00015611-15
NCGC00015611-16
NCGC00022176-05
NCGC00022176-06
NCGC00022176-07
NCGC00022176-08
NCGC00022176-09
nchembio.65-comp16
Neosporin Plus
NINDS_000174
Norwood Sunburn Spray
NSC 40030
NSC40030
Octocaine
Octocaine-100
Octocaine-50
Oraqix
Prestwick0_000050
Prestwick1_000050
Prestwick2_000050
Prestwick3_000050
Remicaine
ROCEPHIN KIT
Rucaina
S1357_Selleck
SAM001247018
SMR000058189
Solarcaine aloe extra burn relief cream
Solcain
SPBio_001525
SPBio_002100
Spectrum2_001343
Spectrum3_001392
Spectrum4_000070
Spectrum5_001549
Spectrum_001118
ST023341
STK552033
UNII-98PI200987
WLN: 2N2 & 1VMR B1 F1
Xilina
Xilocaina
Xilocaina [Italian]
Xllina
Xycaine
Xylestesin
Xylesthesin
Xylocain
Xylocaine
Xylocaine (TN)
Xylocaine 5% Spinal
Xylocaine CO2
Xylocaine Dental Ointment
Xylocaine Endotracheal
Xylocaine Test Dose
Xylocaine Viscous
Xylocaine-Mpf
Xylocaine-Mpf with Glucose
Xylocard
Xylocitin
Xyloneural
Xyloneural (free base)
Xylotox
Zilactin-L
Zingo
ATC-Codes:
Side-Effects:
Side-EffectFrequency
asthenia0.0010
pain0.0010
paresthesia0.0010
cardiovascular collapse0.0010
tinnitus0.0010
tremors0.0010
unconsciousness0.0010
vomiting0.0010
lightheadedness0.0010
blurred vision0.0010
bradycardia0.0010
numbness0.0010
nervousness0.0010
confusion0.0010
convulsions0.0010
double vision0.0010
dizziness0.0010
somnolence0.0010
flushing0.0010
headache0.0010
hyperesthesia0.0010
hypotension0.0010
nausea0.0010
seizures0
burning sensation0
urinary retention0
gingivitis0
meningismus0
petechiae0
dermatitis0
tachycardia0
ventricular fibrillation0
skin irritation0
weakness0
dyspnea0
neuropathy0
anaphylaxis0
anxiety0
apprehension0
euphoria0
excitement0
hyperacusis0
allergic reaction0
hemorrhage0
infection0
increased sweating0
sneezing0
meningitis0
venous thrombosis0
syncope0
unconsciousness0
urticaria0
fever0
apnea0
acidosis0
hypopigmentation0
bronchospasm0
angioedema0
back pain0
agitation0
phlebitis0
atrial flutter0
erythema0
dysarthria0
chills0
respiratory arrest0
blistering0
paralysis0
cardiac arrest0
hypertension0
edema0
vascular disorders0
urinary incontinence0
heart block0
arachnoiditis0
hypersensitivity0
stomatitis0
sore throat0
methemoglobinemia0

Target

show target details
Uniprot ID:CP1A2_HUMAN
Synonyms:
CYPIA2
Cytochrome P450 1A2
P(3)450
P450 4
P450-P3
EC-Numbers:1.14.14.1
Organism:Homo sapiens
Human
PDB IDs:2HI4
Structure:
2HI4

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----
----
----
----
----
----
----

References:

10215663
Inhibition of human liver cytochrome P-450 1A2 by the class IB antiarrhythmics mexiletine, lidocaine, and tocainide.. X Wei; R Dai; S Zhai; K E Thummel; F K Friedman; R E Vestal (1999) The Journal of pharmacology and experimental therapeutics display abstract
Mexiletine, lidocaine, and tocainide are class IB antiarrhythmic drugs that are used for the treatment of ventricular arrhythmias and are known to inhibit drug metabolism. The objectives of this study were to characterize the inhibitory effects of mexiletine, lidocaine, and tocainide on cytochrome P-450 1A2 (CYP1A2) activity in human liver microsomes and to evaluate their relative inhibitory potencies by using a molecular model of this P-450 isozyme. The inhibitory effect of mexiletine, lidocaine, and tocainide on cytochrome CYP1A2 in human liver microsomes was examined with methoxyresorufin O-demethylase activity as an index of the catalytic activity of this P-450 isozyme. The kinetic inhibition types and Ki values were determined by Lineweaver-Burk plots and Dixon plots, respectively. Molecular modeling was used to assess the interaction of these agents with the CYP1A2 active site. Methoxyresorufin O-demethylase activity was inhibited 67 +/- 8%, 20 +/- 5%, and 7 +/- 4% by 2 mM mexiletine, lidocaine, and tocainide, respectively. Mexiletine and lidocaine exhibited competitive inhibition with Ki values of 0.28 +/- 0.12 mM and 1.54 +/- 0.74 mM, respectively, whereas the inhibition type of tocainide could not be determined because of its weak potency. A charge interaction between mexiletine and the Asp313 side chain in the CYP1A2 active site was found, and varying degrees of hydrogen bond formation between these three compounds and the CYP1A2 active site were observed. The in vitro inhibitory potencies in human liver microsomes (mexiletine > lidocaine > tocainide) are consistent with the structural interactions found in a molecular model of the active site of CYP1A2.
10510747
10901707
14749694
Cytochrome P450 1A2 is a major determinant of lidocaine metabolism in vivo: effects of liver function.. Rocco Orlando; Pierpaolo Piccoli; Sara De Martin; Roberto Padrini; Maura Floreani; Pietro Palatini (2004) Clinical pharmacology and therapeutics display abstract
OBJECTIVES: This study was designed (1) to evaluate the effect of a cytochrome P450 (CYP) 1A2 inhibitor, fluvoxamine, on the pharmacokinetics of intravenous lidocaine and its 2 pharmacologically active metabolites, monoethylglycinexylidide (MEGX) and glycinexylidide (GX), to confirm recent in vitro results indicating that CYP1A2 is the main isoform responsible for lidocaine biotransformation and (2) to assess whether liver function has any influence on the fluvoxamine-lidocaine interaction. METHODS: The study was carried out in 10 healthy volunteers and 20 patients with cirrhosis, 10 with mild (Child grade A) and 10 with severe (Child grade C) liver dysfunction, according to a randomized, double-blind, 2-phase, crossover design. In one phase all participants received placebo for 6 days; in the other phase they received 50 mg fluvoxamine for 2 days and 100 mg fluvoxamine for the next 4 days. On day 6, a 1-mg/kg lidocaine dose was administered intravenously 2 hours after the last dose of fluvoxamine or placebo. Plasma concentrations of lidocaine, MEGX, GX, and fluvoxamine were measured up to 12 hours after lidocaine injection. RESULTS: The effects of fluvoxamine coadministration were dependent on liver function. Lidocaine clearance was decreased on average by 60% (from 12.1 mL/min.kg to 4.85 mL/min.kg, P
15447735
Effect of itraconazole on the pharmacokinetics of inhaled lidocaine.. Mika H Isohanni; Pertti J Neuvonen; Klaus T Olkkola (2004) Basic & clinical pharmacology & toxicology display abstract
Lidocaine is metabolized by cytochrome P450 3A4 and 1A2 enzymes (CYP3A4 and CYP1A2) in vitro. However, their relative contribution to the elimination of lidocaine depends on lidocaine concentration. We have studied the effect of a potent CYP3A4 inhibitor, itraconazole, on the pharmacokinetics of inhaled lidocaine in ten healthy volunteers using a randomized, two-phase cross-over study design. The interval between the phases was four weeks. The subjects were given orally itraconazole (200 mg once a day) or placebo for four days. On day 4, each subject inhaled a single dose of 1.5 mg/kg of lidocaine by nebulizer. Plasma samples were collected until 10 hr and the concentrations of lidocaine and its major metabolite monoethylglycinexylidide were measured by gas chromatography. The areas under the lidocaine and monoethylglycinexylidide concentration time curves were similar during both phases. No statistically significant differences were observed in any of the pharmacokinetic parameters; peak concentrations, concentration peak times or elimination half-lives of lidocaine or monoethylglycinexylidide. The clinical implication of this study is that no lidocaine dosage adjustments are necessary if it is used to prepare the airway prior to endoscopic procedures or intubation in patients using itraconazole or other inhibitors of CYP3A4.
15845683
The effect of erythromycin and fluvoxamine on the pharmacokinetics of intravenous lidocaine.. Klaus T Olkkola; Mika H Isohanni; Katri Hamunen; Pertti J Neuvonen (2005) Anesthesia and analgesia display abstract
Inhibitors of CYP3A4 (cytochrome P450 3A4) have a minor effect on lidocaine pharmacokinetics. We studied the effect of coadministration of the antidepressant fluvoxamine (CYP1A2 inhibitor) and antimicrobial drug erythromycin (CYP3A4 inhibitor) on lidocaine pharmacokinetics in a double-blind, randomized, three-way crossover study. Nine volunteers ingested daily 100 mg fluvoxamine and placebo, 100 mg fluvoxamine and 1500 mg erythromycin, or their corresponding placebos for 5 days. On day 6, 1.5 mg/kg lidocaine was administered IV over 60 min. Concentrations of lidocaine and its major metabolite monoethylglycinexylidide were measured for 10 h. Fluvoxamine alone decreased the clearance of lidocaine by 41% (P < 0.001) and prolonged its elimination half-life from 2.6 to 3.5 h (P < 0.01). During the combination of fluvoxamine and erythromycin, lidocaine clearance was 53% smaller than during placebo (P < 0.001) and 21% smaller than during fluvoxamine alone (P < 0.05). During the combination phase the half-life of lidocaine (4.3 h) was longer than during the placebo (2.6 h; P < 0.001) or fluvoxamine (3.5 h; P < 0.01). We conclude that inhibition of CYP1A2 by fluvoxamine considerably reduces elimination of lidocaine and may increase the risk of lidocaine toxicity. Concomitant use of both fluvoxamine and a CYP3A4 inhibitor such as erythromycin can further increase plasma lidocaine concentrations by decreasing its clearance.
9806111