Compound: isoniazid
SMILES: O=C(NN)c1ccncc1
InChIKey: QRXWMOHMRWLFEY-UHFFFAOYSA-N
Synonyms: isoniazid, 54-85-3, Isonicotinic acid hydrazide, Isonicotinohydrazide, pyridine-4-carbohydrazide, Isoniazide, Rimifon, Nydrazid, Cotinazin, Hydrazid, Mybasan, Hidrasonil, Isonicotan, Armazide, Dinacrin, Ditubin, Ertuban, Iscotin, Isidrina, Isobicina, Laniazid, Neumandin, Cedin, Atcotibine, Nicotibina, Armazid, Eralon, Isolyn, Isonex, Neoteben, Nicizina, Niconyl, Nicozide, Pycazide, Hyzyd, Isonicotinylhydrazine, Andrazide, Eutizon, Hycozid, Isocotin, Isonicid, Isonico, Isonidrin, Isonilex, Isonindon, Isonizide, Isotebezid, Isozide, Niadrin, Nicetal, Nidaton, Nidrazid, Nikozid, Nyscozid, Pelazid, Rimitsid, Stanozide, Tubazide, Isocid, Isozyd, Neoxin, Niplen, Nevin, Inah, Isonicotinic hydrazide, Isohydrazide, Isonicotinhydrazid, Antimicina, Chemiazid, Chemidon, Fimalene, Hidranizil, Hidrulta, Ismazide, Isocidene, Isonerit, Isonicotil, Isonikazid, Isonirit, Isoniton, Pyricidin, Pyrizidin, Raumanon, Retozide, Teebaconin, 4-Pyridinecarboxylic acid, hydrazide, Azuren, Cemidon, Defonin, Diforin, Ebidene, Evalon, Hidrun, Idrazil, Inizid, Isonide, Isonin, Nitadon, Rimicid, Tubazid, Antituberkulosum, Ido-tebin, Isonicazide, Nicotibine, Nicotisan, Rimiphone, Tisiodrazida, Tubilysin, Isotebe, Isotinyl, Nicazide, Phthisen, Pyreazid, Percin, Razide, Tyvid, Neo-Tizide, Isoniazid SA, Preparation 6424, Armacide, Cortinazine, Cotinizin, GINK, Isotamine, Robisellin, Sauterazid, Tibinide, Unicozyde, Vazadrine, Zonazide, Isonicotinyl hydrazide, Tebecid, Tekazin, Tubeco, Tubicon, Tubomel, Vederon, Zinadon, Isonicotinoyl hydrazide, Dow-Isoniazid, 4-Pyridinecarboxylic acid hydrazide, TB-Razide, Sanohidrazina, Robiselin, Tibizide, Tuberian, Niteban, Roxifen, Tebenic, Tebexin, Tebilon, Tibison, Tibivis, Tibusan, Tizide, Tebos, Tisin, TB-Vis, FSR 3, TB-Phlogin, Isoniazidum, Isozid, Isonicotinoylhydrazine, In-73, Cedin (Aerosol), bacillen, FSR-3, tebemid, tubercid, Isonizida, 4-Pyridinecarbonylhydrazine, 4-(Hydrazinocarbonyl)pyridine, BP 5015, 4-Pyridylcarbonylhydrazide, Dianicotyl, Ipcazide, Isonicotinsaeurehydrazid, NSC 9659, 4-Pyridinecarboxylic hydrazide, isonicotinoylhydrazide, Isonicotinyl hydrazine, pyridine-4-carboxylic acid hydrazide, 5015 R.P., 5015 RP, DTXSID8020755, L 1945, RP 5015, NSC-9659, V83O1VOZ8L, CHEBI:6030, NSC9659, DTXCID20755, Hydrazide, Isonicotinic Acid, Isoniazid 300 mg, Acid Vanillylidenehydrazide, Isonicotinic, RefChem:5917, Vanillylidenehydrazide, Isonicotinic Acid, 200-214-6, Niazid, Isoniacid, Dibutin, Hyozid, Laniozid, Pyridicin, Sauterzid, Tibazide, Tubizid, Unicocyde, Inh-Burgthal, INH, Isoniazida, Zidafimia, Isokin, Nitebannsc 9659, RU-EF-Tb, 4-pyridinecarbohydrazide, MFCD00006426, HIA, RP-5015, Isonicotinylhydrazide, CHEMBL64, MLS000069444, Hydra, s1937, CAS-54-85-3, NCGC00016244-09, Continazine, Tubecotubercid, Abdizide, Anidrasona, SMR000059082, Tibemid, Tibiazide, Fetefu, LANIZID, RY-EF-Tb, Isoniazid; pyridine-4-carbohydrazide, Isoniazidum [INN-Latin], Isoniazida [INN-Spanish], FRS-3, Isoniazid & EEP, Laniazid (TN), CCRIS 351, Usaf cb-2, Isoniazid & Propolis, HSDB 1647, Isonicotinsaeurehydrazid [German], INHd20, SR-01000003025, EINECS 200-214-6, UNII-V83O1VOZ8L, lsoniazid, Mayambutol, AI3-23936, I.A.I., Idrazide dell'acido isonicotinico [Italian], Isoniazid RS, isoniazid (inh), Isoniazid CRS, Idrazide dell'acido isonicotinico, Isoniazid [USP:INN:BAN:JAN], isonicotinhydrazide, NIZ, Prestwick_578, Isoniazid (Tubizid), Isoniazid(Tubizid)?, Isoniazid (Standard), Rifater (Salt/Mix), isonicotinate hydrazide, Isonicotinic acid hydrazide (Isoniazid), Isonicotinicacidhydrazide, Spectrum_000853, ISONIAZID [INN], ISONIAZID [JAN], Opera_ID_454, ISONIAZID [MI], isonicotinicacid hydrazide, ISONIAZID [HSDB], isonicotinic acid hydrazid, Prestwick0_000161, Prestwick1_000161, Prestwick2_000161, Prestwick3_000161, Spectrum2_000107, Spectrum3_000472, Spectrum4_000022, Spectrum5_000876, ISONIAZID [VANDF], I0138, WLN: T6NJ DVMZ, isonicotinic acid hydrazone, SCHEMBL228, Biomol-NT_000288, Epitope ID:141801, ISONIAZID [MART.], 4-Pyridylcarbonyl hydrazide, ISONIAZID [USP-RS], ISONIAZID [WHO-DD], ISONIAZID [WHO-IP], Oprea1_396155, BSPBio_000021, BSPBio_002204, KBioGR_000423, KBioSS_001333, MLS001055327, BIDD:GT0140, DivK1c_000070, SPECTRUM1500355, SPBio_000094, SPBio_001942, Isoniazid (JP18/USP/INN), pyridine, 4-hydrazinocarbonyl-, BPBio1_000025, BPBio1_001322, orb1310116, orb3025438, ISONIAZID [EP IMPURITY], ISONIAZID [ORANGE BOOK], component of Niadox (Salt/Mix), ISONIAZID [EP MONOGRAPH], GTPL12761, HMS500D12, HY-B0329R, KBio1_000070, KBio2_001333, KBio2_003901, KBio2_006469, KBio3_001424, ISONIAZID [USP MONOGRAPH], NINDS_000070, RIFATER COMPONENT ISONIAZID, 4-Pyridinecarboxamide, 2'-amino-, GLXC-07773, HMS1568B03, HMS1920H09, HMS2089I16, HMS2091N19, HMS2095B03, HMS2234G04, HMS3259E19, HMS3373O01, HMS3655L03, HMS3712B03, HMS5080B07, HMS6018K15, KUC109571N, Pharmakon1600-01500355, 4-pyridinecarbohydrazide(Isoniazid), ISONIAZIDUM [WHO-IP LATIN], RIFAMATE COMPONENT ISONIAZID, HY-B0329, MSK10311, STR00210, [(4-Pyridinylcarbonyl)oxy]hydrazine, Anti-TNF monoclonal antibody & INH, Tox21_113640, Tox21_201367, Tox21_300193, BBL008409, BDBM50336507, CCG-39710, EBC-11047, NSC757078, SBB004195, STK086288, (HBD) Human beta-defensin-1 & INH, AKOS000119062, Isonicotinic acid hydrazide(Isoniazid), Tox21_113640_1, AI24685, DB00951, KSC-27-048, NC00513, NSC-757078, PS-4129, IDI1_000070, UPCMLD0ENAT5791176:001, NCGC00016244-01, NCGC00016244-02, NCGC00016244-03, NCGC00016244-04, NCGC00016244-05, NCGC00016244-06, NCGC00016244-07, NCGC00016244-08, NCGC00016244-10, NCGC00016244-11, NCGC00016244-12, NCGC00016244-14, NCGC00016244-15, NCGC00016244-17, NCGC00022648-03, NCGC00022648-04, NCGC00022648-05, NCGC00022648-06, NCGC00022648-07, NCGC00254094-01, NCGC00258919-01, ISONICOTINIC ACID HYDRAZIDE [IARC], ST078858, SY010614, Isoniazid, Vetec(TM) reagent grade, 98%, SBI-0051419.P003, AB00052025, ISONICOTINIC ACID HYDRAZIDE [WHO-IP], NS00006598, SW196752-3, EN300-18498, ISONICOTINIC ACID HYDRAZIDE(ISONIAZIDE), C07054, D00346, D70582, Isoniazid, analytical standard, >=99% (TLC), AB00052025-20, AB00052025-21, AB00052025_22, AB00052025_23, AB00052025_24, AB00052025_25, AE-641/02310003, F236758, Q423169, 4-PYRIDINECARBOXYLIC ACID HYDRAZIDE [WHO-IP], SR-01000003025-2, SR-01000003025-3, BRD-K87202646-001-26-8, BRD-K87202646-001-32-6, BRD-K87202646-001-33-4, BRD-K87202646-061-04-9, BRD-K87202646-061-05-6, Isoniazid, certified reference material, TraceCERT(R), Z58981801, F0391-0007, Isoniazid, European Pharmacopoeia (EP) Reference Standard, Isoniazid, United States Pharmacopeia (USP) Reference Standard, InChI=1/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10, Isoniazid, Pharmaceutical??Secondary??Standard;??Certified??Reference??Material
Theoretical properties:
molecular_formula: C6H7N3O
molecular_weight: 137.14 g/mol
exact_mass: 137.058911855 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 10
topological_polar_surface_area: 68 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: COLORLESS OR WHITE CRYSTALS, OR A WHITE, CRYSTALLINE POWDER
color: COLORLESS OR WHITE CRYSTALS, OR A WHITE, CRYSTALLINE POWDER
melting_point: 340.5 °F (NTP, 1992)
solubility: greater than or equal to 100 mg/mL at 77 °F (NTP, 1992)
flash_point: 374 °F (NTP, 1992)
vapor_pressure: Negligible (NTP, 1992)
Descriptions:
pubchem: Isoniazide is a carbohydrazide obtained by formal condensation between pyridine-4-carboxylic acid and hydrazine. It has a role as an antitubercular agent and a drug allergen. It is functionally related to an isonicotinic acid.
chebi: A carbohydrazide obtained by formal condensation between pyridine-4-carboxylic acid and hydrazine.
chembl: ISONIAZID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.
Isoniazid is a prodrug that, when activated by catalase-peroxidase KatG, generates adducts and radicals that inhibits the formation of the mycobacterial cell wall. Side effects in those treated with isoniazid include vitamin B6 deficiency, liver toxicity, peripheral neuropathy, and a reduction in blood cell production. Mutations in the ahpC, inhA, kasA, katG, genes of M. tuberculosis may result in isoniazid resistance.
Although first synthesized in 1912, the anti-tuberculosis activity of isoniazid was not discovered until the 1940s. It is on the World Health Organization's List of Essential Medicines and is available as a generic medication.