procaine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
local anaesthetics 2271 59-46-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • procaine
  • diethylaminoethyl p-aminobenzoate
  • procain
  • spinocaine
  • isocaine
  • isocain
  • herocaine
  • irocaine
  • procaine hydrochloride
  • procaine HCl
A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).
  • Molecular weight: 236.32
  • Formula: C13H20N2O2
  • CLOGP: 2.54
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 55.56
  • ALOGS: -1.54
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 60.45 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 1, 1954 FDA LEDERLE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 69.31 0 14 7 46629 2311435

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC C05AD05 CARDIOVASCULAR SYSTEM
VASOPROTECTIVES
AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
Local anesthetics
ATC N01BA02 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Esters of aminobenzoic acid
ATC N01BA52 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, LOCAL
Esters of aminobenzoic acid
ATC S01HA05 SENSORY ORGANS
OPHTHALMOLOGICALS
LOCAL ANESTHETICS
Local anesthetics
MeSH PA D000777 Anesthetics
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:36333 local anaesthetic
CHEBI has role CHEBI:35488 central nervous system depressant
CHEBI has role CHEBI:49110 peripheral nervous system drug
MeSH PA D000779 Anesthetics, Local
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Local anesthesia indication 386761002
Life-Threatening Ventricular Tachycardia indication
Bundle branch block contraindication 6374002
Poisoning by digitalis glycoside contraindication 12876009
Hyperkalemia contraindication 14140009
Agranulocytosis contraindication 17182001 DOID:12987
Complete atrioventricular block contraindication 27885002
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Bleeding hemorrhoids contraindication 51551000
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Disorder of mucous membrane contraindication 95351003
Prolonged QT interval contraindication 111975006
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Infectious mononucleosis contraindication 271558008 DOID:8568
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Deficiency of cholinesterase contraindication 360607009
Pseudomembranous enterocolitis contraindication 397683000
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000
Procainamide Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.8 Basic
pKa2 2.5 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 10 subunit alpha Ion channel BLOCKER DRUGBANK CHEMBL
Acetylcholine receptor Ion channel IC50 4.34 WOMBAT-PK
5-hydroxytryptamine receptor 3A Ion channel IC50 5.57 WOMBAT-PK
Ryanodine receptor 1 Ion channel IC50 2.22 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 3A Ion channel IC50 3.53 WOMBAT-PK

External reference:

IDSource
4019905 VUID
N0000147990 NUI
C0033218 UMLSCUI
D00740 KEGG_DRUG
4Z8Y51M438 UNII
975 INN_ID
42514000 SNOMEDCT_US
4019905 VANDF
7218 MMSL
8701 RXNORM
387238009 SNOMEDCT_US
5359 MMSL
d01394 MMSL
004565 NDDF
51-05-8 SECONDARY_CAS_RN
4914 PUBCHEM_CID
CHEBI:8430 CHEBI
CHEMBL569 ChEMBL_ID
DB00721 DRUGBANK_ID
CHEMBL1200841 ChEMBL_ID
D011343 MESH_DESCRIPTOR_UI
4291 IUPHAR_LIGAND_ID

Pharmaceutical products:

None