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

Stem definitionDrug idCAS RN
Class I antiarrhythmics, procainamide and lidocaine derivatives 2270 51-06-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • procainamide
  • novocainamid
  • novocainamide
  • novocaine amide
  • novocamid
  • procaine amide
  • procanbid
  • procainamide hydrochloride
  • procainamide HCl
A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.
  • Molecular weight: 235.33
  • Formula: C13H21N3O
  • CLOGP: 1.42
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 58.36
  • ALOGS: -1.89
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
3 g O
3 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 4 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 67 % Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 81 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 212.47 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 83 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.84 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 2, 1950 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC C01BA02 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ia
FDA EPC N0000175426 Antiarrhythmic
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D026941 Sodium Channel Blockers
MeSH PA D061567 Voltage-Gated Sodium Channel Blockers
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:38633 sodium channel blockers
CHEBI has role CHEBI:50427 platelet aggregation inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Prolonged QT interval contraindication 111975006
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Thrombocytopenic disorder contraindication 302215000 DOID:1588
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 13.0 acidic
pKa2 8.94 Basic
pKa3 2.36 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 alpha subunit Ion channel BLOCKER CHEMBL CHEMBL
Acetylcholinesterase Enzyme Ki 6 WOMBAT-PK
DNA (cytosine-5)-methyltransferase 3B Enzyme WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 7.81 PDSP
DNA (cytosine-5)-methyltransferase 1 Enzyme WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 3.86 WOMBAT-PK
DNA (cytosine-5)-methyltransferase 3A Enzyme WOMBAT-PK
Acetylcholinesterase Enzyme Ki 6 CHEMBL

External reference:

IDSource
4019904 VUID
N0000147989 NUI
D00477 KEGG_DRUG
614-39-1 SECONDARY_CAS_RN
4017622 VANDF
4019904 VANDF
C0917852 UMLSCUI
CHEBI:8428 CHEBI
CHEMBL605 ChEMBL_ID
CHEMBL640 ChEMBL_ID
D011342 MESH_DESCRIPTOR_UI
DB01035 DRUGBANK_ID
4811 IUPHAR_LIGAND_ID
4179 INN_ID
L39WTC366D UNII
4913 PUBCHEM_CID
155056 RXNORM
5358 MMSL
6415 MMSL
792 MMSL
d00075 MMSL
000622 NDDF
004481 NDDF
11959009 SNOMEDCT_US
25254000 SNOMEDCT_US
372589008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-1902 INJECTION, SOLUTION 100 mg INTRAMUSCULAR ANDA 21 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-1903 INJECTION, SOLUTION 500 mg INTRAMUSCULAR ANDA 21 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 14789-900 INJECTION 500 mg INTRAVENOUS ANDA 21 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 14789-901 INJECTION 100 mg INTRAVENOUS ANDA 21 sections
PROCAINULLMIDE HCI HUMAN PRESCRIPTION DRUG LABEL 1 51662-1334 INJECTION, SOLUTION 100 mg INTRAMUSCULAR ANDA 13 sections
PROCAINULLMIDE HCI HUMAN PRESCRIPTION DRUG LABEL 1 51662-1392 INJECTION, SOLUTION 500 mg INTRAMUSCULAR ANDA 13 sections
PROCAINULLMIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52584-106 INJECTION, SOLUTION 500 mg INTRAMUSCULAR ANDA 12 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63739-459 INJECTION, SOLUTION 100 mg INTRAMUSCULAR ANDA 12 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 71872-7115 INJECTION 1000 mg INTRAVENOUS ANDA 21 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 71872-7170 INJECTION 1000 mg INTRAVENOUS ANDA 22 sections
Procainamide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 76329-3399 INJECTION 100 mg INTRAMUSCULAR ANDA 21 sections