Drug Information

General Information
Drug ID
DR00292
Drug Name
Procainamide
Synonyms
2-Diethylaminoethylamid kyseliny p-aminobenzoove; 2-Diethylaminoethylamid kyseliny p-aminobenzoove [Czech]; 4-Amino-N-(2-(Diethylamino)Ethyl)Benzamide Sulfate; 4-Amino-N-(2-(diethylamino)ethyl)benzamide; 4-Amino-N-[2-(diethylamino)ethyl]benzamide; 4-amino-N-(2-diethylaminoethyl)-benzamide; 4-amino-N-(2-diethylaminoethyl)benzamide; Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-(9CI); Biocoryl; Novocainamid; Novocainamide; Novocaine amide; Novocamid; P-Amino-N-(2-diethylaminoethyl)benzamide; P-Aminobenzoic diethylaminoethylamide; Procainamida; Procainamida [INN-Spanish]; Procainamide (INN); Procainamide [INN:BAN]; Procainamidum; Procainamidum [INN-Latin]; Procaine amide; Procamide; Procan; Procan (TN); Procanbid; Procanbid (TN); Procapan; Procapan (free base); Pronestyl; Pronestyl (TN); Pronestyl-Sr
Drug Type
Small molecular drug
Indication Ventricular arrhythmias [ICD11:BC71] Approved [1]
Therapeutic Class
Antiarrhythmic Agents
Structure
3D MOL 2D MOL
Formula
C13H21N3O
Canonical SMILES
CCN(CC)CCNC(=O)C1=CC=C(C=C1)N
InChI
InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)
InChIKey
REQCZEXYDRLIBE-UHFFFAOYSA-N
CAS Number
CAS 51-06-9
Pharmaceutical Properties Molecular Weight 235.33 Topological Polar Surface Area 58.4
Heavy Atom Count 17 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
XLogP
0.9
PubChem CID
4913
PubChem SID
10524666 ,11111690 ,11111691 ,11120271 ,11120759 ,11121247 ,11121528 ,11122008 ,11132695 ,11336106 ,11361345 ,11362597 ,11363730 ,11365159 ,11366292 ,11367721 ,11368854 ,11370465 ,11370466 ,11371829 ,11373322 ,11374112 ,11375883 ,11377016 ,11382660 ,11462317 ,11466365 ,11467485 ,11485065 ,11486030 ,11489111 ,11490371 ,11492302 ,11494650 ,15220788 ,26751611 ,26751612 ,29223991 ,3138733 ,3296200 ,46507313 ,47216907 ,47440400 ,47662439 ,47810893 ,5227620 ,7980387 ,8153024 ,87927 ,9605
ChEBI ID
ChEBI:8428
TTD Drug ID
D0U5SI
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
MATE1 Transporter Info Multidrug and toxin extrusion protein 1 Substrate [3]
MATE2 Transporter Info Multidrug and toxin extrusion protein 2 Substrate [3]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MATE1 Transporter Info Km =1230 microM Human embryonic kidney cells (HEK293)-MATE1 [3]
MATE2 Transporter Info Km =1580 microM Human embryonic kidney cells (HEK293)-MATE2K [3]
MATE2 Transporter Info Km =4100 microM Human embryonic kidney cells (HEK293)-MATE2K [4]
References
1 Procainamide was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
3 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
4 Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2. J Am Soc Nephrol. 2006 Aug;17(8):2127-35.

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