| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-09-11 05:16:08 UTC |
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| Update Date | 2016-11-09 01:09:12 UTC |
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| Accession Number | CHEM003734 |
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| Identification |
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| Common Name | Isoniazid |
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| Class | Small Molecule |
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| Description | Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. |
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| Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
- IARC Carcinogens Group 3
- STOFF IDENT Compounds
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Amide
- Amine
- Antitubercular Agent
- Drug
- Ester
- Fatty Acid Synthesis Inhibitor
- Food Toxin
- Hydrazine
- Metabolite
- Organic Compound
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 4-Pyridinecarbohydrazide | ChEBI | | Isonicotinic acid hydrazide | ChEBI | | Isonicotinic hydrazide | ChEBI | | Isonicotinohydrazide | ChEBI | | Isonicotinoylhydrazide | ChEBI | | Isonicotinsaeurehydrazid | ChEBI | | Pyridine-4-carboxylic acid hydrazide | ChEBI | | Laniazid | Kegg | | Isonicotinate hydrazide | Generator | | Pyridine-4-carboxylate hydrazide | Generator | | HIA | HMDB | | Hydrazid | HMDB | | Hydrazide | HMDB | | INH | HMDB | | Isohydrazide | HMDB | | Isonicotinhydrazid | HMDB | | Isonicotinoyl hydrazide | HMDB | | Isonicotinyl hydrazide | HMDB | | Isonicotinyl hydrazine | HMDB | | Isonicotinylhydrazine | HMDB | | Hydrazide, isonicotinic acid | HMDB | | Isonex | HMDB | | Tubazide | HMDB | | Vanillylidenehydrazide, isonicotinic acid | HMDB | | Acid vanillylidenehydrazide, isonicotinic | HMDB | | Isonicotinic acid vanillylidenehydrazide | HMDB | | Ftivazide | HMDB | | Phthivazide | HMDB | | Phthivazid | HMDB | | Isoniazid | ChEBI |
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| Chemical Formula | C6H7N3O |
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| Average Molecular Mass | 137.139 g/mol |
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| Monoisotopic Mass | 137.059 g/mol |
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| CAS Registry Number | 54-85-3 |
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| IUPAC Name | pyridine-4-carbohydrazide |
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| Traditional Name | isoniazid |
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| SMILES | NNC(=O)C1=CC=NC=C1 |
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| InChI Identifier | InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10) |
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| InChI Key | QRXWMOHMRWLFEY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pyridines and derivatives |
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| Sub Class | Pyridinecarboxylic acids and derivatives |
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| Direct Parent | Pyridinecarboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Pyridine carboxylic acid or derivatives
- Heteroaromatic compound
- Carboxylic acid hydrazide
- Azacycle
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 171.4°C | | Boiling Point | Not Available | | Solubility | 1.4E+005 mg/L (at 25°C) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-2900000000-d379ce585203e68cb06a | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-0900000000-3cf8f43d0df46334dcd9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052r-7900000000-3d43394feacded48669d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-263a0bcadf2e21536983 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-002f-9000000000-17100430370d37f834ce | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-9466b9291244c1a61f01 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-0900000000-afcf227eec118bec08a4 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-1900000000-d63af1f463124dbf7b65 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00fr-9600000000-1d50dedb0eea7ff8dccb | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9100000000-371fd6d67c48f373e2e5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9000000000-dee0012ebd004444b3d8 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-2900848c5042f3badc64 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-aeda0fc92729a2561248 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zgi-9200000000-8cdf3d4be1d99712a839 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-0de7d57696bde8b4ad72 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-4900000000-8760bef4d7b9a5b3360c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-056r-9100000000-7dfda590da30abf9e329 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0900000000-37604552ea11c4e9ae14 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-2900000000-0fe0a0315394b81d8b4e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9100000000-3169da9068df634af7d4 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002r-7900000000-1e1d0995890b4dca1772 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-c2850ce6846335b0374d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-fdff89cf4c9b7fb7a653 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0kdr-9600000000-f04526999a9b68d31861 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Readily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food. |
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| Mechanism of Toxicity | Isoniazid is a prodrug and must be activated by bacterial catalase. Specficially, activation is associated with reduction of the mycobacterial ferric KatG catalase-peroxidase by hydrazine and reaction with oxygen to form an oxyferrous enzyme complex. Once activated, isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. At therapeutic levels isoniazid is bacteriocidal against actively growing intracellular and extracellular Mycobacterium tuberculosis organisms. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA. |
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| Metabolism | Primarily hepatic. Isoniazid is acetylated by N -acetyl transferase to N -acetylisoniazid; it is then biotransformed to isonicotinic acid and monoacetylhydrazine. Monoacetylhydrazine is associated with hepatotoxicity via formation of a reactive intermediate metabolite when N-hydroxylated by the cytochrome P450 mixed oxidase system. The rate of acetylation is genetically determined. Slow acetylators are characterized by a relative lack of hepatic N -acetyltransferase.
Route of Elimination: From 50 to 70 percent of a dose of isoniazid is excreted in the urine within 24 hours.
Half Life: Fast acetylators: 0.5 to 1.6 hours. Slow acetylators: 2 to 5 hours. |
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| Toxicity Values | LD50 100 mg/kg (Human, oral). |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (1) |
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| Uses/Sources | For the treatment of all forms of tuberculosis in which organisms are susceptible. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Adverse reactions include rash, abnormal liver function tests, hepatitis, peripheral neuropathy, mild central nervous system (CNS) effects. In vivo, Isoniazid reacts with pyridoxal to form a hydrazone, and thus inhibits generation of pyridoxal phosphate. Isoniazid also combines with pyridoxal phosphate; high doses interfere with the coenzyme function of the latter. |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB00951 |
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| HMDB ID | HMDB0015086 |
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| FooDB ID | FDB029229 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | ISONIAZIDE |
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| METLIN ID | Not Available |
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| PDB ID | NIZ |
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| Wikipedia Link | Isoniazid |
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| Chemspider ID | 3635 |
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| ChEBI ID | 6030 |
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| PubChem Compound ID | 3767 |
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| Kegg Compound ID | C07054 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Costin Rentzea, Albrecht Harreus, Eberhard Ammermann, Gisela Lorenz, “Oxalyl hydrazide-hydroxamic acid derivatives, their preparation and their use as fungicides.” U.S. Patent US5399589, issued November, 1969. |
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| MSDS | Link |
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| General References | |
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