Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H20N2O |
Molecular Weight | 220.3107 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCNC(C)C(=O)NC1=C(C)C=CC=C1
InChI
InChIKey=MVFGUOIZUNYYSO-UHFFFAOYSA-N
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)
Molecular Formula | C13H20N2O |
Molecular Weight | 220.3107 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00750
Sources: http://www.drugbank.ca/drugs/DB00750
Prilocaine is a local anesthetic that is similar pharmacologically to lidocaine. 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. 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. Currently, Prilocaine is used most often for infiltration anesthesia in dentistry.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833 |
|||
Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00750 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | ORAQIX Approved UseOraqix is an amide local anesthetic indicated for adults who require localized anesthesia in periodontal pockets during scaling and/or root planing. Launch Date1.07170562E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
106 ng/mL |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.07 μg/mL |
1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26000 ng × min/mL |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 h |
42.5 mg 5 times / 3 hours multiple, buccal dose: 42.5 mg route of administration: Buccal experiment type: MULTIPLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
70 min |
single, intravenous |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
1.5 g single, topical dose: 1.5 g route of administration: Topical experiment type: SINGLE co-administered: LIDOCAINE |
PRILOCAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
6 mg/kg single, transdermal Dose: 6 mg/kg Route: transdermal Route: single Dose: 6 mg/kg Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 Sources: |
Other AEs: Methemoglobinemia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Methemoglobinemia | 6 mg/kg single, transdermal Dose: 6 mg/kg Route: transdermal Route: single Dose: 6 mg/kg Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Age Group: 6 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
From cocaine to ropivacaine: the history of local anesthetic drugs. | 2001 Aug |
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Local anaesthetic block copolymer system undergoing phase transition on dilution with water. | 2001 Aug |
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[Neurotoxicity of intrathecal lidocaine]. | 2001 Aug-Sep |
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The tumescent facial block: tumescent local anesthesia and nerve block anesthesia for full-face laser resurfacing. | 2001 Dec |
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Intrapocket anesthesia for scaling and root planing: results of a double-blind multicenter trial using lidocaine prilocaine dental gel. | 2001 Jul |
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[Percutaneous topical anaesthesia applications in ocular surgery]. | 2001 Jul |
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A comparison of 1% prilocaine with 0.5% ropivacaine for outpatient-based surgery under axillary brachial plexus block. | 2001 Jul |
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Hot chili, a cook and EMLA. | 2001 Jul |
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Effects of prilocaine and articaine on human leucocytes and reactive oxygen species in vitro. | 2001 Jul |
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[Some aspects of epidural anesthesia in patients with chronic renal insufficiency]. | 2001 Jul-Aug |
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1% lidocaine injection, EMLA cream, or "numby stuff" for topical analgesia associated with peripheral intravenous cannulation. | 2001 Jun |
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Eutectic mixture of local anesthetics reduces pain during intravenous catheter insertion in the pediatric patient. | 2001 Jun |
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Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. | 2001 Jun 15 |
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[Anesthesia with EMLA cream: a promising application for plastic surgery]. | 2001 Jun-Jul |
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Dermal pharmacokinetics of microemulsion formulations determined by in vivo microdialysis. | 2001 Mar |
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[Peripheral nerve block. An overview of new developments in an old technique]. | 2001 May |
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Safety and pharmacokinetics of EMLA in the treatment of postburn pruritus in pediatric patients: a pilot study. | 2001 May-Jun |
|
[Can treatment of flat angiomas be proposed in the first months of life?]. | 2001 Nov |
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Efficacy of subcutaneous and topical local anaesthesia for pain relief after resection of malignant breast tumours. | 2001 Nov |
|
A randomized double-blind, placebo-controlled trial of the EMLA patch for the reduction of pain associated with intramuscular injection in four to six-year-old children. | 2001 Nov |
|
Blood flow changes in human dental pulps when capsaicin is applied to the adjacent gingival mucosa. | 2001 Nov |
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Plasma concentrations of lignocaine and prilocaine after a 24-h application of analgesic cream (EMLA) to leg ulcers. | 2001 Oct |
|
Pain on injection of prilocaine plain vs. lidocaine with epinephrine. A prospective double-blind study. | 2001 Oct |
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Re: reduction in pain associated with open carpal tunnel decompression. | 2001 Oct |
|
Antimicrobial activity of ropivacaine and other local anaesthetics. | 2001 Oct |
|
Effect of an intervention to reduce procedural pain and distress for children with HIV infection. | 2001 Oct-Nov |
|
[Ovarian puncture in fertilization in vitro: what analgesia?]. | 2001 Sep |
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Methemoglobinemia. | 2001 Sep |
|
EMLA versus nitrous oxide for venous cannulation in children. | 2001 Sep |
|
Treatment of gustatory sweating with botulinum toxin: special aspects. | 2001 Sep-Oct |
|
Noninvasive drug delivery. | 2001 Winter |
|
The use of EMLA for an intraoral soft-tissue biopsy in a needle phobic: a case report. | 2001 Winter |
|
Intravenous regional guanethidine blockade in the treatment of post-traumatic complex regional pain syndrome type 1 (algodystrophy) of the hand. | 2002 Apr |
|
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction. | 2002 Apr |
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Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children. | 2002 Apr |
|
EMLA cream prior to digital nerve block for ingrown nail surgery does not reduce pain at injection of anesthetic solution. | 2002 Feb |
|
A comparison of prilocaine and lidocaine for intravenous regional anaesthesia for forearm fracture reduction in children. | 2002 Feb |
|
[Tumescent technique for local anesthesia]. | 2002 Feb |
|
Effects of dental local anaesthetics in cardiac transplant recipients. | 2002 Feb 9 |
|
Local anesthesia with EMLA cream for maxillary sinus puncture. | 2002 Jan |
|
Use of negatively charged cyclodextrins for the simultaneous enantioseparation of selected anesthetic drugs by capillary electrophoresis-mass spectrometry. | 2002 Jan 15 |
|
In vitro effects of some anesthetic drugs on enzymatic activity of human red blood cell glucose 6-phosphate dehydrogenase. | 2002 Jan-Feb |
|
Reader questions pain and peritumoral injection. | 2002 Jan-Feb |
|
Use of EMLA cream with vasectomy. | 2002 Jul |
|
Lidocaine iontophoresis versus eutectic mixture of local anesthetics (EMLA) for IV placement in children. | 2002 Jun |
|
EMLA cream-induced irritant contact dermatitis. | 2002 Mar |
|
Reducing venipuncture and intravenous insertion pain with eutectic mixture of local anesthetic: a meta-analysis. | 2002 Mar-Apr |
|
Intravenous regional blocks with guanethidine and prilocaine combined with physiotherapy: two children with complex regional pain syndrome, type 1. | 2002 May |
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The effects of age on neural blockade and hemodynamic changes after epidural anesthesia with ropivacaine. | 2002 May |
|
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children. | 2002 May-Jun |
Sample Use Guides
Use the included blunt tipped applicator to apply gel to gingival margins and periodontal pockets
Route of Administration:
Dental
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11421833
Prilocaine inhibited FMLP-induced CL in human leucocytes (94+/-1%, at 1 mM). In cell-free experiments, prilocaine (22+/-6%, at 1 mM) caused concentration-dependent inhibition in xanthine-xanthine oxidase-induced CL.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 02:00:40 UTC 2022
by
admin
on
Sat Dec 17 02:00:40 UTC 2022
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Record UNII |
046O35D44R
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN01BB04
Created by
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EMA ASSESSMENT REPORTS |
FORTACIN (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
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WHO-ATC |
N01BB54
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NDF-RT |
N0000175682
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WHO-VATC |
QN01BB54
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WHO-ATC |
N01BB04
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NDF-RT |
N0000175976
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NDF-RT |
N0000007681
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EMA ASSESSMENT REPORTS |
PRILOCAINE (AUTHORIZED: SEXUAL DYSFUNCTION, PHYSIOLOGICAL)
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NCI_THESAURUS |
C245
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Code System | Code | Type | Description | ||
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PRILOCAINE
Created by
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PRIMARY | |||
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DB00750
Created by
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PRIMARY | |||
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M9132
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PRIMARY | Merck Index | ||
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1641
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PRIMARY | |||
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Prilocaine
Created by
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PRIMARY | |||
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DTXSID7031955
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PRIMARY | |||
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046O35D44R
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4906
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1560990
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40027
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7276
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211-957-0
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17676-07-2
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8404
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3386
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C47685
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D011318
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SUB10041MIG
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CHEMBL1194
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046O35D44R
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2265
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JJ-23
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8686
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721-50-6
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |