Isoniazid
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Basic Info
| Common Name | Isoniazid(F05507) |
| 2D Structure | |
| Description | Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. |
| FRCD ID | F05507 |
| CAS Number | 54-85-3 |
| PubChem CID | 3767 |
| Formula | C6H7N3O |
| IUPAC Name | pyridine-4-carbohydrazide |
| InChI Key | QRXWMOHMRWLFEY-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10) |
| Canonical SMILES | C1=CN=CC=C1C(=O)NN |
| Isomeric SMILES | C1=CN=CC=C1C(=O)NN |
| Wikipedia | Isoniazid |
| Synonyms |
pyridine-4-carbohydrazide
isoniazid
Isonicotinic acid hydrazide
54-85-3
Isonicotinohydrazide
Rimifon
Isoniazide
Nydrazid
Isonicotinic hydrazide
Laniazid
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridinecarboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridinecarboxylic acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 137.142 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 120 |
| Monoisotopic Mass | 137.059 |
| Exact Mass | 137.059 |
| XLogP | -0.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9895 |
| Human Intestinal Absorption | HIA+ | 0.9892 |
| Caco-2 Permeability | Caco2+ | 0.6959 |
| P-glycoprotein Substrate | Non-substrate | 0.8315 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9778 |
| Non-inhibitor | 0.9960 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9054 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7026 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9088 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.7557 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6482 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9273 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9443 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9513 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5111 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9342 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9872 |
| Non-inhibitor | 0.9586 | |
| AMES Toxicity | AMES toxic | 0.8557 |
| Carcinogens | Non-carcinogens | 0.7514 |
| Fish Toxicity | Low FHMT | 0.9451 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.7464 |
| Honey Bee Toxicity | Low HBT | 0.8399 |
| Biodegradation | Not ready biodegradable | 0.9810 |
| Acute Oral Toxicity | III | 0.8032 |
| Carcinogenicity (Three-class) | Warning | 0.4786 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.0521 | LogS |
| Caco-2 Permeability | 1.2413 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0713 | LD50, mol/kg |
| Fish Toxicity | 2.5840 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.7209 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The reliability of rifampicin resistance as a proxy for multidrug-resistanttuberculosis: a systematic review of studies from Iran. | Eur J Clin Microbiol Infect Dis | 2018 Jan | 28823010 |
| Oleanolic Acid-Mediated Inhibition of Pregnane X Receptor and ConstitutiveAndrostane Receptor Attenuates Rifampin-Isoniazid Cytotoxicity. | J Agric Food Chem | 2017 Oct 4 | 28945086 |
| Microparticles prepared with 50-190kDa chitosan as promising non-toxic carriers for pulmonary delivery of isoniazid. | Carbohydr Polym | 2017 Oct 15 | 28821088 |
| Evaluation of HepaRG cells for the assessment of indirect drug-induced hepatotoxicity using INH as a model substance. | Hum Cell | 2017 Oct | 28527127 |
| Comparative Modulation of Levels of Oxidative Stress in the Liver ofAnti-Tuberculosis Drug Treated Wistar Rats by Vitamin B12, Beta-Carotene, andSpirulina fusiformis: Role of NF-κB, iNOS, IL-6, and IL-10. | J Cell Biochem | 2017 Nov | 28387444 |
| A framework for multi-scale simulation of crystal growth in the presence ofpolymers. | Soft Matter | 2017 Mar 1 | 28181622 |
| Discovery of Indeno[1,2-c]quinoline Derivatives as Potent Dual Antituberculosisand Anti-Inflammatory Agents. | Molecules | 2017 Jun 16 | 28621733 |
| Preclinical safety evaluation of IQG-607 in rats: Acute and repeated dose toxicity studies. | Regul Toxicol Pharmacol | 2017 Jun | 28232042 |
| Enhanced Prophylaxis plus Antiretroviral Therapy for Advanced HIV Infection in Africa. | N Engl J Med | 2017 Jul 20 | 28723333 |
| First Report in China on the Identification and Drug Sensitivity of Mycobacteriumelephantis Isolated from the Milk of a Cow with Mastitis. | Biomed Environ Sci | 2017 Jul | 28756809 |
| The challenges of pharmacokinetic variability of first-line anti-TB drugs. | Expert Rev Clin Pharmacol | 2017 Jan | 27724114 |
| Evaluation of ameliorative ability of Silibinin against zidovudine and isoniazid-induced hepatotoxicity and hyperlipidaemia in rats: Role of Silibinin in Phase I and II drug metabolism. | Chem Biol Interact | 2017 Aug 1 | 28619387 |
| Metallothionein protects against isoniazid-induced liver injury through theinhibition of CYP2E1-dependent oxidative and nitrosative impairment in mice. | Food Chem Toxicol | 2017 Apr | 28126494 |
| Food significantly reduces plasma concentrations of first-line anti-tuberculosis drugs. | Indian J Med Res | 2017 Apr | 28862186 |
| Zidovudine and isoniazid induced liver toxicity and oxidative stress: Evaluation of mitigating properties of silibinin. | Environ Toxicol Pharmacol | 2016 Sep | 27497728 |
| Caffeic Acid Phenethyl Ester: A Review of Its Antioxidant Activity, ProtectiveEffects against Ischemia-reperfusion Injury and Drug Adverse Reactions. | Crit Rev Food Sci Nutr | 2016 Oct 2 | 25365228 |
| NAT2 slow acetylator associated with anti-tuberculosis drug-induced liver injury in Thai patients. | Int J Tuberc Lung Dis | 2016 Oct | 27725049 |
| Performance of the BacT Alert 3D System Versus Solid Media for Recovery and Drug Susceptibility Testing of Mycobacterium tuberculosis in a Tertiary Hospital inKorea. | Tuberc Respir Dis (Seoul) | 2016 Oct | 27790280 |
| A new strategy for strain improvement of Aurantiochytrium sp. based on heavy-ionsmutagenesis and synergistic effects of cold stress and inhibitors of enoyl-ACPreductase. | Enzyme Microb Technol | 2016 Nov | 27702480 |
| Isoniazid-resistant tuberculosis in Iran: A systematic review. | Tuberculosis (Edinb) | 2016 May | 27156625 |
Targets
- Uniprot ID:
- P05184
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]