General Information of Drug (ID: DR0886)
Drug Name
Isoniazid
Prodrug Info Isoniazid is the prodrug of Isonicotinic acyl-NADH
Synonyms
Iscotin; Isobicina; Isocidene; Isohydrazide; Isolyn; Isonex; Isoniazide; Isonicotan; Isonicotinhydrazid; Isonicotinic acid hydrazide; Isonicotinic hydrazide; Isonicotinohydrazide; Isonicotinylhydrazine; Isonidrin; Isonikazid; Isonindon; Isonizide; Isotebezid; Laniazid; Mybasan; Neoteben; Neumandin; Nicizina; Niconyl; Nicotibina; Nicozide; Nydrazid; Andrazide; Antimicina; Chemiazid; Cotinazin; Dinacrin; Ditubin; Hidranizil; Hydrazid; Pycazide; Pyricidin; Pyrizidin; Rimifon; Stanozide; Tubazide; isoniazid; pyridine-4-carbohydrazide; 54-85-3; Hyzyd
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 137.14 Topological Polar Surface Area 68
Heavy Atom Count 10 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3767
PubChem SID
9266 ; 75070 ; 602898 ; 855769 ; 3133579 ; 7647563 ; 7847412 ; 7979658 ; 8145964 ; 8149391 ; 8152384 ; 10321551 ; 10526641 ; 11112128 ; 11335245 ; 11360484 ; 11363747 ; 11366309 ; 11368871 ; 11371524 ; 11373562 ; 11377033 ; 11461456 ; 11466189 ; 11467309 ; 11483830 ; 11485678 ; 11487923 ; 11490288 ; 11491837 ; 11494667 ; 12016103 ; 15321438 ; 17389848 ; 22389388 ; 22400349 ; 24429259 ; 24896031 ; 26611787 ; 26679247 ; 26746988 ; 26746989 ; 26751504 ; 29222886 ; 33726819 ; 38671754 ; 38671759 ; 38671761 ; 46506039 ; 47216622
ChEBI ID
ChEBI:6030
CAS Number
54-85-3
TTD Drug ID
D09XQF
Formula
C6H7N3O
Canonical SMILES
C1=CN=CC=C1C(=O)NN
InChI
1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
InChIKey
QRXWMOHMRWLFEY-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Acetylisoniazid DM001004
71602
Conjugation - Acetylation 1 [5] , [6] , [7] , [8]
Hydrazine DM001007
9321
Unclear 1 [5] , [7]
Isonicotinic acyl-NADH DM020053
129320363
Multi-steps Reaction - Reduction; Oxidation 1 [9]
Motesanib Mx DM001009
5922
Unclear 1 [5]
Acethydrazide DM001005
14039
Conjugation - Acetylation 2 [5]
Acethydrazide DM001005
14039
Unclear 2 [5]
Isoniazid reactive metabolite DM001008 N. A. Unclear 2 [5]
Motesanib Mx DM001009
5922
Unclear 2 [5]
Diacetylhydrazine DM001006
72884
Conjugation - Acetylation 3 [5]
Hydrazine DM001007
9321
Oxidation - Deacetylation 3 [5]
Isoniazid reactive metabolite DM001008 N. A. Unclear 3 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001239 Isoniazid Acetylisoniazid Conjugation - Acetylation Unclear [5], [6], [7], [8]
MR001240 Isoniazid Hydrazine Unclear Unclear [5], [7]
MR001241 Isoniazid Isonicotinic acid Unclear Unclear [5]
MR014190 Isoniazid Isonicotinic acyl-NADH Multi-steps Reaction - Reduction; Oxidation POD [9]
MR001232 Acetylisoniazid Acethydrazide Unclear NAT2 [5]
MR001233 Acetylisoniazid Isonicotinic acid Unclear CYP2E1 [5]
MR001237 Hydrazine Acethydrazide Conjugation - Acetylation NAT2 [5]
MR001238 Hydrazine Isoniazid reactive metabolite Unclear CYP2E1 [5]
MR001234 Acethydrazide Diacetylhydrazine Conjugation - Acetylation Unclear [5]
MR001235 Acethydrazide Hydrazine Oxidation - Deacetylation NAT2 [5]
MR001236 Acethydrazide Isoniazid reactive metabolite Unclear NAT2 [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arylamine N-acetyltransferase (NAT) DME1321 Tsukamurella paurometabola
A0A3P8LE58_TSUPA
2.3.1.5
[2]
Catalase-peroxidase (katG) DME1301 Synechococcus elongatus
KATG_SYNE7
1.11.1.21
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[5]
References
1 Isoniazid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The actinobacterium Tsukamurella paurometabola has a functionally divergent arylamine N-acetyltransferase (NAT) homolog. World J Microbiol Biotechnol. 2019 Oct 31;35(11):174.
3 Crystal structure of the catalase-peroxidase KatG W78F mutant from Synechococcus elongatus PCC7942 in complex with the antitubercular pro-drug isoniazid. FEBS Lett. 2015 Jan 2;589(1):131-7.
4 Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Biochem Pharmacol. 2005 Apr 1;69(7):1081-93.
5 Exploration of inhibition potential of isoniazid and its metabolites towards CYP2E1 in human liver microsomes through LC-MS/MS analysis J Pharm Biomed Anal. 2021 Sep 5;203:114223. doi: 10.1016/j.jpba.2021.114223.
6 Molecular mechanism for the activation of the potent hepatotoxin acetylhydrazine: Identification of the initial N-centered radical and the secondary C-centered radical intermediates. Free Radic Biol Med. 2023 Aug 1;204:20-27. doi: 10.1016/j.freeradbiomed.2023.04.010.
7 Quantitative Analysis of Isoniazid and Its Four Primary Metabolites in Plasma of Tuberculosis Patients Using LC-MS/MS. Molecules. 2022 Dec 6;27(23):8607. doi: 10.3390/molecules27238607.
8 Isoniazid level and flu-like symptoms during rifapentine-based tuberculosis preventive therapy: A population pharmacokinetic analysis. Br J Clin Pharmacol. 2023 Feb;89(2):714-726. doi: 10.1111/bcp.15527.
9 The tuberculosis prodrug isoniazid bound to activating peroxidases

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.