Prilocaine
Identification
- Summary
Prilocaine is a local anesthetic used in dental procedures.
- Brand Names
- Agoneaze, Anodyne Lpt, Citanest, Citanest Forte, Dermacinrx Prikaan, Emla, Fortacin, Lido Bdk, Lido-prilo Caine Pack, Lidopril, Oraqix, Prilolid, Prizotral, Relador
- Generic Name
- Prilocaine
- DrugBank Accession Number
- DB00750
- Background
A local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 220.3107
Monoisotopic: 220.157563272 - Chemical Formula
- C13H20N2O
- Synonyms
- 2-(Propylamino)-o-propionotoluidide
- 2-Methyl-alpha-propylaminopropionanilide
- alpha-n-Propylamino-2-methylpropionanilide
- N-(2-Methylphenyl)-2-(propylamino)propanamide
- o-Methyl-2-propylaminopropionanilide
- o-Methyl-alpha-propylaminopropionanilide
- Prilocain
- Prilocaina
- Prilocaïne
- Prilocaine
- Prilocaine base
- Prilocainum
- Propitocaine
- External IDs
- ASTRA 1512
- ASTRA 1515
- ASTRA-1512
- ASTRA-1515
- L 67
Pharmacology
- Indication
Used as a local anaesthetic and is often used in dentistry.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
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.
- 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.
Target Actions Organism ASodium channel protein type 5 subunit alpha inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Prilocaine is 55% protein bound in plasma at a concentraion of 0.5-1.0 mg/mL.1
- Metabolism
- Not Available
- Route of elimination
Prilocaine is metabolized in both the liver and the kidney and excreted via the kidney.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Prilocaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Glucose-6-phosphate 1-dehydrogenase Villeurbanne Not Available 1000_1002delACC ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Torun Not Available 1006A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sunderland Not Available 105_107delCAT ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Iwatsuki Not Available 1081G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Serres Not Available 1082C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tondela Not Available 1084_1101delCTGAACGAGCGCAAGGCC ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Loma Linda Not Available 1089C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aachen Not Available 1089C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tenri Not Available 1096A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Montpellier Not Available 1132G>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Calvo Mackenna Not Available 1138A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Riley Not Available 1139T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Olomouc Not Available 1141T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tomah Not Available 1153T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lynwood Not Available 1154G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Madrid Not Available 1155C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Iowa, Walter Reed, Springfield Not Available 1156A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Beverly Hills, Genova, Iwate, Niigata, Yamaguchi Not Available 1160G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hartford Not Available 1162A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Praha Not Available 1166A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Krakow Not Available 1175T>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wisconsin Not Available 1177C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nashville, Anaheim, Portici Not Available 1178G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Alhambra Not Available 1180G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bari Not Available 1187C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Puerto Limon Not Available 1192G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Covao do Lobo Not Available 1205C>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Clinic Not Available 1215G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Utrecht Not Available 1225C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Suwalki Not Available 1226C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Riverside Not Available 1228G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Japan, Shinagawa Not Available 1229G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kawasaki Not Available 1229G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Munich Not Available 1231A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Georgia Not Available 1284C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sumare Not Available 1292T->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Telti/Kobe Not Available 1318C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago de Cuba, Morioka Not Available 1339G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Harima Not Available 1358T->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Figuera da Foz Not Available 1366G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amiens Not Available 1367A>T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Noi Not Available 1376G->T, 1502T->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Fukaya Not Available 1462G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Campinas Not Available 1463G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Buenos Aires Not Available 1465C>T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Arakawa Not Available 1466C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Brighton Not Available 1488_1490delGAA ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kozukata Not Available 159G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amsterdam Not Available 180_182delTCT ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase No name Not Available 202G->A, 376A->G, 1264C>G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Swansea Not Available 224T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Urayasu Not Available 281_283delAGA ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Vancouver Not Available 317C->G544C->T592C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mt Sinai Not Available 376A->G, 1159C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Plymouth Not Available 488G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Volendam Not Available 514C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Shinshu Not Available 527A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chikugo Not Available 535A->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tsukui Not Available 561_563delCTC ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Pedoplis-Ckaro Not Available 573C>G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santiago Not Available 593G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Minnesota, Marion, Gastonia, LeJeune Not Available 637G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cincinnati Not Available 637G->T, 1037A->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Harilaou Not Available 648T->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase North Dallas Not Available 683_685delACA ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Asahikawa Not Available 695G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Durham Not Available 713A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Stonybrook Not Available 724_729delGGCACT ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wayne Not Available 769C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aveiro Not Available 806G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cleveland Corum Not Available 820G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lille Not Available 821A>T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bangkok Not Available 825G>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sugao Not Available 826C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase La Jolla Not Available 832T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Wexham Not Available 833C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Piotrkow Not Available 851T>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase West Virginia Not Available 910G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Omiya Not Available 921G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nara Not Available 953_976delCCACCAAAGGGTACCTGGAC GACC ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Manhattan Not Available 962G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Rehevot Not Available 964T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Honiara Not Available 99A->G / 1360C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Tokyo, Fukushima Not Available 1246G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chatham Not Available 1003G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Fushan Not Available 1004C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Partenope Not Available 1052G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ierapetra Not Available 1057C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Anadia Not Available 1193A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Abeno Not Available 1220A->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Surabaya Not Available 1291G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Pawnee Not Available 1316G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase S. Antioco Not Available 1342A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cassano Not Available 1347G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hermoupolis Not Available 1347G->C / 1360C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Union,Maewo, Chinese-2, Kalo Not Available 1360C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Andalus Not Available 1361G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Cosenza Not Available 1376G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Canton, Taiwan- Hakka, Gifu-like, Agrigento-like Not Available 1376G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Flores Not Available 1387C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kaiping, Anant, Dhon, Sapporo-like, Wosera Not Available 1388G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kamogawa Not Available 169C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Costanzo Not Available 179T>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Amazonia Not Available 185C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Songklanagarind Not Available 196T->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hechi Not Available 202G->A / 871G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Namouru Not Available 208T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bao Loc Not Available 352T>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Crispim Not Available 375G->T, 379G->T383T->C384C>T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Acrokorinthos Not Available 376A->G / 463C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Santa Maria Not Available 376A->G / 542A->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ananindeua Not Available 376A->G / 871G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Vanua Lava Not Available 383T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Valladolid Not Available 406C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Belem Not Available 409C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Liuzhou Not Available 442G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Shenzen Not Available 473G>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Taipei ‚ÄúChinese- 3‚Äù Not Available 493A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Toledo Not Available 496C>T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Naone Not Available 497G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nankang Not Available 517T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Miaoli Not Available 519C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham Not Available 563C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Coimbra Shunde Not Available 592C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nilgiri Not Available 593G>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Radlowo Not Available 679C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Roubaix Not Available 811G>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Haikou Not Available 835A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-1 Not Available 835A->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mizushima Not Available 848A>G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Osaka Not Available 853C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Viangchan, Jammu Not Available 871G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Seoul Not Available 916G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ludhiana Not Available 929G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Farroupilha Not Available 977C->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Chinese-5 Not Available 1024C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Rignano Not Available 130G>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Orissa Not Available 131C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase G6PDNice Not Available 1380G>C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kamiube, Keelung Not Available 1387C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Neapolis Not Available 1400C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Aures Not Available 143T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Split Not Available 1442C->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kambos Not Available 148C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Palestrina Not Available 170G>A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Metaponto Not Available 172G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Musashino Not Available 185C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Asahi Not Available 202G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (202), Ferrara I Not Available 202G->A / 376A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Murcia Oristano Not Available 209A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ube Konan Not Available 241C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lagosanto Not Available 242G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Guangzhou Not Available 274C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Hammersmith Not Available 323T->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sinnai Not Available 34G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (680) Not Available 376A->G / 680G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase A- (968), Betica,Selma, Guantanamo Not Available 376A->G / 968T->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Salerno Pyrgos Not Available 383T>G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Quing Yan Not Available 392G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Lages Not Available 40G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Ilesha Not Available 466G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mahidol Not Available 487G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Malaga Not Available 542A->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Sibari Not Available 634A->G ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Mexico City Not Available 680G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Nanning Not Available 703C->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Seattle, Lodi, Modena, Ferrara II, Athens-like Not Available 844G->C ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Bajo Maumere Not Available 844G->T ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Montalbano Not Available 854G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Kalyan-Kerala, Jamnaga, Rohini Not Available 949G->A ADR Inferred Increased risk of Methemoglobinemia. Details Glucose-6-phosphate 1-dehydrogenase Gaohe Not Available 95A->G ADR Inferred Increased risk of Methemoglobinemia. Details NADH-cytochrome b5 reductase 3 --- Not Available Exon 2 c.129C>A / Exon 2 c.149G>A … show all ADR Inferred Increased risk of Methemoglobinemia. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Prilocaine is combined with 1,2-Benzodiazepine. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Prilocaine. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Prilocaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Prilocaine. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Prilocaine. - Food Interactions
- Take separate from meals. This is only required when prilocaine is used in the mouth, as it may cause numbness, which can cause bite injury when eating.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Prilocaine hydrochloride MJW015BAPH 1786-81-8 BJPJNTKRKALCPP-UHFFFAOYSA-N - International/Other Brands
- Citanest (AstraZeneca) / Prilotekal (Goldshield) / Takipril (Meduna) / Xylonest (AstraZeneca)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 4% Citanest Plain Dental Solution 40 mg / mL Infiltration Dentsply Pharmaceutical 2015-12-23 Not applicable Canada Citanest Plain Injection, solution 40 mg/1mL Dental Dentsply Pharmaceutical 2007-03-02 2007-03-02 US Dentsply 4% Prilocaine Hydrochloride Dental Injection Solution 40 mg / mL Infiltration Dentsply Pharmaceutical 1964-12-31 2016-06-03 Canada Truemed Group LLC Injection 54 mg/54mg Intramuscular Truemed Group LLC 2022-09-17 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Citanest Plain Injection, solution 40 mg/1mL Submucosal Dentsply Pharmaceutical Inc. 1965-11-18 Not applicable US Prilocaine Hydrochloride Injection, solution 40 mg/1mL Subcutaneous Septodont 2011-01-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 4% Citanest Forte Dental With Epinephrine 1:200,000 Prilocaine hydrochloride (40 mg / mL) + Epinephrine (0.005 mg / mL) Solution Infiltration Dentsply Pharmaceutical 2011-01-18 Not applicable Canada ANESDERM Prilocaine (25 MG/G) + Lidocaine (25 MG/G) Cream Cutaneous Pierre Fabre Italia S.P.A. 2015-12-23 Not applicable Italy ANESDERM Prilocaine (25 MG/G) + Lidocaine (25 MG/G) Cream Cutaneous Pierre Fabre Italia S.P.A. 2015-12-23 Not applicable Italy ANESDERM Prilocaine (25 MG/G) + Lidocaine (25 MG/G) Cream Cutaneous Pierre Fabre Italia S.P.A. 2015-12-23 Not applicable Italy Anodyne LPT Prilocaine (25 mg/1g) + Lidocaine (25 mg/1g) Kit Topical Fortus Pharma, Llc 2017-03-22 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACAT SUK Kit (Accelerated COVID-19 Antibody Test Single Use Kit) Prilocaine (25 mg/1g) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (25 mg/1g) Kit Topical Asclemed Usa, Inc. 2020-04-25 Not applicable US ACT Kit (Accelerated COVID-19 Test Kit) Prilocaine (25 mg/1g) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (25 mg/1g) Kit Topical Asclemed Usa, Inc. 2020-04-13 Not applicable US AgonEaze Prilocaine (25 mg/1g) + Prilocaine (25 mg/1g) + Lidocaine (25 mg/1g) + Lidocaine (25 mg/1g) Kit Topical Alvix Laboratories 2016-01-12 Not applicable US AgonEaze Prilocaine (25 mg/1g) + Prilocaine (25 mg/1g) + Lidocaine (25 mg/1g) + Lidocaine (25 mg/1g) Kit Topical Alvix Laboratories 2016-01-12 Not applicable US Aprizio Pak Prilocaine (25 mg/1g) + Lidocaine (25 mg/1g) Kit Topical PureTek Corporation 2018-06-06 Not applicable US
Categories
- ATC Codes
- N01BB54 — Prilocaine, combinationsN01BB04 — Prilocaine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid amides
- Alternative Parents
- Alanine and derivatives / Anilides / N-arylamides / Toluenes / Secondary carboxylic acid amides / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alanine or derivatives / Alpha-amino acid amide / Amine / Anilide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monocarboxylic acid amide, amino acid amide (CHEBI:8404)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 046O35D44R
- CAS number
- 721-50-6
- InChI Key
- MVFGUOIZUNYYSO-UHFFFAOYSA-N
- 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)
- IUPAC Name
- N-(2-methylphenyl)-2-(propylamino)propanamide
- SMILES
- CCCNC(C)C(=O)NC1=CC=CC=C1C
References
- Synthesis Reference
- US3160662
- General References
- DailyMed: Prilocaine Hydrochloride Subcutaneous Injection [Link]
- External Links
- Human Metabolome Database
- HMDB0014888
- KEGG Drug
- D00553
- KEGG Compound
- C07531
- PubChem Compound
- 4906
- PubChem Substance
- 46505066
- ChemSpider
- 4737
- BindingDB
- 50225477
- 8686
- ChEBI
- 8404
- ChEMBL
- CHEMBL1194
- Therapeutic Targets Database
- DAP000511
- PharmGKB
- PA451101
- Wikipedia
- Prilocaine
- MSDS
- Download (73.4 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Anesthesia therapy / Anesthetics Adverse Reaction 1 4 Completed Not Available Haemorrhoids / Peri-anal Fistulas 1 4 Completed Other Forehead Rhytides / Forehead Wrinkles 1 4 Completed Other Periodontal Disease 1 4 Completed Prevention Improving Quality of Life 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- APP Pharmaceuticals
- Astra Pharma Inc.
- AstraZeneca Inc.
- DENTSPLY International
- Diversified Healthcare Services Inc.
- E. Fougera and Co.
- Hi Tech Pharmacal Co. Inc.
- Medisca Inc.
- Nycomed Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Recipharm AB
- Sandoz
- Tolmar Inc.
- Dosage Forms
Form Route Strength Solution Infiltration Solution Infiltration 40 mg / mL Injection 2 % Injection, solution Submucosal Injection, solution Parenteral Injection Buccal Injection, solution Dental 40 mg/1mL Injection, solution Submucosal 40 mg/1mL Cream; kit; tablet, film coated Oral; Topical Cream; injection, suspension; kit Intra-articular; Intramuscular; Topical Cream; kit Topical Ointment Topical Cream; gel; kit Topical Cream Cutaneous Cream Occlusive dressing technique Patch Cutaneous Plaster Topical Patch Transdermal Spray Cutaneous Kit Oral; Topical Kit Intravenous; Topical Cream Topical Solution Topical Gel Topical Gel Dental Gel Periodontal Solution Subcutaneous Solution Infiltration 40 mg Solution Infiltration 4000000 mg Solution Parenteral Solution Parenteral 72 mg Cream; kit; patch Cutaneous; Topical Patch Topical Powder Not applicable 1 g/1g Injection, solution Subcutaneous 40 mg/1mL Injection, solution Subcutaneous Capsule; cream; kit Oral; Topical Injection, solution 2 % Injection, solution Spray Topical Cream Topical 2.5 %w/w Injection Injection, solution Parenteral 2 % Injection, solution Intrathecal 20.00 mg/ml Cream Injection Intramuscular 54 mg/54mg Kit Topical - Prices
Unit description Cost Unit Prilocaine hcl powder 3.98USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6031007 No 2000-02-29 2017-04-01 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 37-38 °C PhysProp boiling point (°C) 159-162 °C at 1.00E-01 mm Hg PhysProp water solubility 541 mg/L Not Available logP 2.11 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.326 mg/mL ALOGPS logP 1.87 ALOGPS logP 2.68 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 13.51 Chemaxon pKa (Strongest Basic) 8.82 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.13 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 67.86 m3·mol-1 Chemaxon Polarizability 25.98 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9557 Blood Brain Barrier + 0.9285 Caco-2 permeable + 0.7888 P-glycoprotein substrate Substrate 0.6968 P-glycoprotein inhibitor I Non-inhibitor 0.8019 P-glycoprotein inhibitor II Non-inhibitor 0.9165 Renal organic cation transporter Non-inhibitor 0.895 CYP450 2C9 substrate Non-substrate 0.7803 CYP450 2D6 substrate Non-substrate 0.5124 CYP450 3A4 substrate Non-substrate 0.5253 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6298 Ames test Non AMES toxic 0.7941 Carcinogenicity Non-carcinogens 0.6653 Biodegradation Not ready biodegradable 0.9577 Rat acute toxicity 2.1374 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9676 hERG inhibition (predictor II) Non-inhibitor 0.8577
Spectra
- Mass Spec (NIST)
- Download (8.45 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 163.385515 predictedDarkChem Lite v0.1.0 [M-H]- 151.50673 predictedDeepCCS 1.0 (2019) [M+H]+ 164.051615 predictedDarkChem Lite v0.1.0 [M+H]+ 153.86473 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.439915 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.91217 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55