Isoniazid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Isoniazid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Isoniazid?

The molecule Isoniazid presents a molecular formula of C6H7N3O and its IUPAC name is pyridine-4-carbohydrazide.

Isoniazid is an organic compound with the molecular formula C6H7N3O. It is an isonicotinic acid hydrazide, a first-line antituberculosis medication. It works by inhibiting the mycobacterial enzyme InhA, which is required for the synthesis of mycolic acids. Mycolic acids are a key component of the mycobacterial cell wall..

Isoniazid was first synthesized in 1952 by Hoffmann-La Roche. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about US$0.60–1.30 per month. In the United States, it costs more than US$100 per month..

Isoniazid is generally well-tolerated. The most common side effects are gastrointestinal upset, such as nausea and vomiting. More serious side effects include liver damage, which can lead to liver failure, and neuropathy..

Isoniazid is contraindicated in people with active tuberculosis, as it can worsen the disease. It is also contraindicated in people with severe liver impairment..

Isoniazid is an important part of treatment for latent tuberculosis infection (LTBI). It is recommended for people who are at high risk of developing active tuberculosis, such as people with HIV/AIDS, people who are immunocompromised, and people who have been in close contact with someone with active tuberculosis..

Isoniazid is also used to prevent active tuberculosis in people who have been exposed to the bacteria, such as healthcare workers..

Isoniazid is a prodrug that is converted to its active form, isonicotinic acid, by the enzyme catalase. Isonicotinic acid inhibits mycolic acid synthesis by inhibiting InhA. Mycolic acids are a key component of the mycobacterial cell wall..

Isoniazid is bactericidal against Mycobacterium tuberculosis. It is generally used in combination with other antituberculosis medications..

The recommended dose of isoniazid for latent tuberculosis infection is 900 mg once daily for 3 months. The recommended dose for active tuberculosis is 9 mg/kg/day (up to a maximum of 300 mg/day) for 2 months, followed by 4 mg/kg/day (up to a maximum of 300 mg/day) for 7 months..

Isoniazid is generally well-tolerated. The most common side effects are gastrointestinal upset, such as nausea and vomiting. More serious side effects include liver damage, which can lead to liver failure, and neuropathy..

Isoniazid is contraindicated in people with active tuberculosis, as it can worsen the disease. It is also contraindicated in people with severe liver impairment..

Isoniazid is an important part of treatment for latent tuberculosis infection (LTBI). It is recommended for people who are at high risk of developing active tuberculosis, such as people with HIV/AIDS, people who are immunocompromised, and people who have been in close contact with someone with active tuberculosis..

Isoniazid is also used to prevent active tuberculosis in people who have been exposed to the bacteria, such as healthcare workers..

3D structure

Cartesian coordinates

Geometry of Isoniazid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Isoniazid QRXWMOHMRWLFEY-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Isoniazid

 

Molecule descriptors

 
IUPAC namepyridine-4-carbohydrazide
InChI codeInChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
InChI KeyQRXWMOHMRWLFEY-UHFFFAOYSA-N
SMILESNNC(=O)c1ccncc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 4-(Hydrazinocarbonyl)pyridine
  • 4-Pyridinecarbonylhydrazine
  • 4-Pyridinecarboxylic acid hydrazide
  • 4-Pyridinecarboxylic acid, hydrazide
  • 4-Pyridinecarboxylic hydrazide
  • 4-Pyridylcarbonyl hydrazide
  • 4-Pyridylcarbonylhydrazide
  • 4-pyridinecarbohydrazide
  • 4-pyridinecarbohydrazide(Isoniazid)
  • 5015 R.P.
  • 5015 RP
  • 54-85-3
  • A830384
  • AB00052025
  • AB00052025-20
  • AB00052025-21
  • AB00052025_22
  • AB00052025_23
  • AB00052025_24
  • AB00052025_25
  • AE-641/02310003
  • AI3-23936
  • AZT + Isoniazid
  • Abdizide
  • Andrazide
  • Anidrasona
  • Anti-TNF monoclonal antibody & INH
  • Antimicina
  • Antituberkulosum
  • Armacide
  • Armazid
  • Armazide
  • Atcotibine
  • Azuren
  • BB 0240534
  • BBL008409
  • BCP13791
  • BDBM50336507
  • BIDD:GT0140
  • BP 5015
  • BPBio1_000025
  • BPBio1_001322
  • BSPBio_000021
  • BSPBio_002204
  • Bacillin
  • Biomol-NT_000288
  • C07054
  • CCG-39710
  • CCRIS 351
  • Cedin
  • Cedin (Aerosol)
  • Cemidon
  • Continazine
  • Cortinazine
  • Cotinazin
  • Cotinizin
  • Chemiazid
  • Chemidon
  • D00346
  • D70582
  • DB00951
  • DSSTox_CID_755
  • DSSTox_GSID_20755
  • DSSTox_RID_75771
  • Defonin
  • Dianicotyl
  • Dibutin
  • Diforin
  • Dinacrin
  • Ditubin
  • DivK1c_000070
  • Dow-Isoniazid
  • Ebidene
  • Epitope ID:141801
  • Eralon
  • Ertuban
  • Eutizon
  • Evalon
  • F0391-0007
  • FRS-3
  • FSR 3
  • FSR-3
  • FT-0627424
  • FT-0670476
  • Fetefu
  • Fimalene
  • GINK
  • HIA
  • HMS1568B03
  • HMS1920H09
  • HMS2089I16
  • HMS2091N19
  • HMS2095B03
  • HMS2234G04
  • HMS3259E19
  • HMS3373O01
  • HMS3655L03
  • HMS3712B03
  • HMS500D12
  • HSDB 1647
  • HY-B0329
  • Hidranizil
  • Hidrasonil
  • Hidrulta
  • Hidrun
  • Hycozid
  • Hydra
  • Hydrazid
  • Hydrazide
  • Hyozid
  • Hyzyd
  • I.A.I.
  • I0138
  • IDI1_000070
  • INH
  • INHd20
  • ISONIAZID COMPONENT OF RIFAMATE
  • ISONIAZID COMPONENT OF RIFATER
  • ISONICOTINIC ACID HYDRAZIDE(ISONIAZIDE)
  • Ido-tebin
  • Idrazide dell'acido isonicotinico
  • Idrazil
  • In-73
  • Inah
  • Inh-Burgthal
  • Inizid
  • Ipcazide
  • Iscotin
  • Isidrina
  • Ismazide
  • Isobicina
  • Isocid
  • Isocidene
  • Isocotin
  • Isohydrazide
  • Isokin
  • Isolyn
  • Isonerit
  • Isonex
  • Isoniacid
  • Isoniazid
  • Isoniazid (JP17/USP/INN)
  • Isoniazid (Tubizid)
  • Isoniazid SA
  • Isoniazid(Tubizid)
  • Isoniazid/INH
  • Isoniazida
  • Isoniazide
  • Isoniazidum
  • Isonicazide
  • Isonicid
  • Isonico
  • Isonicotan
  • Isonicotil
  • Isonicotinhydrazid
  • Isonicotinic acid hydrazide
  • Isonicotinic acid hydrazide (Isoniazid)
  • Isonicotinic acid hydrazide(Isoniazid)
  • Isonicotinic hydrazide
  • Isonicotinicacidhydrazide
  • Isonicotinohydrazide
  • Isonicotinoyl hydrazide
  • Isonicotinoylhydrazine
  • Isonicotinsaeurehydrazid
  • Isonicotinyl hydrazide
  • Isonicotinylhydrazide
  • Isonicotinylhydrazine
  • Isonide
  • Isonidrin
  • Isonikazid
  • Isonilex
  • Isonin
  • Isonindon
  • Isonirit
  • Isoniton
  • Isonizida
  • Isonizide
  • Isotamine
  • Isotebe
  • Isotebezid
  • Isotinyl
  • Isozid
  • Isozide
  • Isozyd
  • KBio1_000070
  • KBio2_001333
  • KBio2_003901
  • KBio2_006469
  • KBio3_001424
  • KBioGR_000423
  • KBioSS_001333
  • KSC-27-048
  • KUC109571N
  • L 1945
  • LANIZID
  • Laniazid
  • Laniozid
  • MFCD00006426
  • MLS000069444
  • MLS001055327
  • Mayambutol
  • Mybasan
  • NC00513
  • NCGC00016244-01
  • NCGC00016244-02
  • NCGC00016244-03
  • NCGC00016244-04
  • NCGC00016244-05
  • NCGC00016244-06
  • NCGC00016244-07
  • NCGC00016244-08
  • NCGC00016244-09
  • NCGC00016244-10
  • NCGC00016244-11
  • NCGC00016244-12
  • NCGC00016244-14
  • NCGC00016244-15
  • NCGC00022648-03
  • NCGC00022648-04
  • NCGC00022648-05
  • NCGC00022648-06
  • NCGC00022648-07
  • NCGC00254094-01
  • NCGC00258919-01
  • NINDS_000070
  • NIZ
  • NSC 9659
  • NSC-757078
  • NSC-9659
  • NSC757078
  • NSC9659
  • Neo-Tizide
  • Neoteben
  • Neoxin
  • Neumandin
  • Nevin
  • Niadrin
  • Nicazide
  • Nicetal
  • Nicizina
  • Niconyl
  • Nicotibina
  • Nicotibine
  • Nicotisan
  • Nicozide
  • Nidaton
  • Nidrazid
  • Nikozid
  • Niplen
  • Nitadon
  • Niteban
  • Nitebannsc 9659
  • Nydrazid
  • Nyscozid
  • Opera_ID_454
  • Oprea1_396155
  • PS-4129
  • Pelazid
  • Percin
  • Pharmakon1600-01500355
  • Phthisen
  • Preparation 6424
  • Prestwick0_000161
  • Prestwick1_000161
  • Prestwick2_000161
  • Prestwick3_000161
  • Prestwick_578
  • Pycazide
  • Pyreazid
  • Pyricidin
  • Pyridicin
  • Pyrizidin
  • Q423169
  • RIFAMATE COMPONENT ISONIAZID
  • RIFATER COMPONENT ISONIAZID
  • RP 5015
  • RP-5015
  • RU-EF-Tb
  • RY-EF-Tb
  • Raumanon
  • Razide
  • Retozide
  • Rimicid
  • Rimifon
  • Rimiphone
  • Rimitsid
  • Robiselin
  • Robisellin
  • Roxifen
  • SBI-0051419.P003
  • SMR000059082
  • SPECTRUM1500355
  • SR-01000003025
  • SR-01000003025-2
  • SR-01000003025-3
  • STK086288
  • STR00210
  • SW196752-3
  • SY010614
  • Sanohidrazina
  • Sauterazid
  • Sauterzid
  • Soniazid,(S)
  • Stanozide
  • TB-Phlogin
  • TB-Razide
  • TB-Vis
  • Tebecid
  • Tebenic
  • Tebexin
  • Tebilon
  • Tebos
  • Teebaconin
  • Tekazin
  • Tibazide
  • Tibemid
  • Tibiazide
  • Tibinide
  • Tibison
  • Tibivis
  • Tibizide
  • Tibusan
  • Tisin
  • Tisiodrazida
  • Tizide
  • Tubazid
  • Tubazide
  • Tubeco
  • Tubecotubercid
  • Tuberian
  • Tubicon
  • Tubilysin
  • Tubizid
  • Tubomel
  • Tyvid
  • UPCMLD0ENAT5791176:001
  • Unicocyde
  • Unicozyde
  • Usaf cb-2
  • V83O1VOZ8L
  • Vazadrine
  • Vederon
  • WLN: T6NJ DVMZ
  • Z58981801
  • Zidafimia
  • Zinadon
  • Zonazide
  • [(4-Pyridinylcarbonyl)oxy]hydrazine
  • bacillen
  • isoniazid
  • isoniazid (inh)
  • isonicotinate hydrazide
  • isonicotinhydrazide
  • isonicotinic acid hydrazid
  • isonicotinic acid hydrazone
  • isonicotinicacid hydrazide
  • isonicotinoylhydrazide
  • pyridine-4-carbohydrazide
  • pyridine-4-carboxylic acid hydrazide
  • s1937
  • tebemid
  • tubercid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1590
  • CAS-54-85-3
  • UNII-V83O1VOZ8L
  • AKOS000119062
  • BRD-K87202646-001-26-8
  • DTXSID8020755
  • CHEMBL64
  • CHEBI:6030
  • Tox21_113640
  • Tox21_201367
  • Tox21_300193
  • Tox21_113640_1
  • EINECS 200-214-6
  • SPBio_000094
  • SPBio_001942
  • SCHEMBL228
  • SCHEMBL2998929
  • Spectrum_000853
  • Spectrum2_000107
  • Spectrum3_000472
  • Spectrum4_000022
  • Spectrum5_000876

Physico-Chemical properties

IUPAC namepyridine-4-carbohydrazide
Molecular formulaC6H7N3O
Molecular weight137.139
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity35.13
LogP0.8
Topological polar surface area68.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.