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Isoniazid

Product Name
Isoniazid
CAS No.
54-85-3
Chemical Name
Isoniazid
Synonyms
ISONICOTINOHYDRAZIDE;INH;ISONIAZIDE;Nydrazid;PYRIDINE-4-CARBOHYDRAZIDE;ISONICOTINIC ACID HYDRAZIDE;HIA;Hyzyd;Rimifon;Laniazid
CBNumber
CB5102053
Molecular Formula
C6H7N3O
Formula Weight
137.14
MOL File
54-85-3.mol
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Isoniazid Property

Melting point:
171-173 °C (lit.)
Boiling point:
251.97°C (rough estimate)
Density 
1.2620 (rough estimate)
refractive index 
1.6910 (estimate)
Flash point:
>250°C
storage temp. 
2-8°C
solubility 
125g/l
form 
Crystals or Crystalline Powder
pka
pKa 2.00/3.60/10.8(H2O) (Uncertain)
color 
White or colorless
PH
6-8 (50g/l, H2O, 20℃)
Odor
Odorless
PH Range
5.5 - 6.5 at 10 g/l at 25 °C
Water Solubility 
14 g/100 mL (25 ºC)
Sensitive 
Air Sensitive
Merck 
14,5186
BRN 
119374
BCS Class
1,3
Stability:
Stability Stable, but may be air or light sensitive. Combustible. Incompatible with strong oxidizing agents, chloral, aldehydes, iodine, ferric salts, hypochlorites.
InChIKey
QRXWMOHMRWLFEY-UHFFFAOYSA-N
CAS DataBase Reference
54-85-3(CAS DataBase Reference)
NIST Chemistry Reference
Isoniazid(54-85-3)
IARC
3 (Vol. 4, Sup 7) 1987
EPA Substance Registry System
Isoniazid (54-85-3)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-38-40-36/37/38
Safety Statements 
37-36/37/39-26
RIDADR 
2811
WGK Germany 
3
RTECS 
NS1751850
TSCA 
Yes
PackingGroup 
III
HS Code 
29333999
Hazardous Substances Data
54-85-3(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 151 i.p., 149 i.v. (Jenney, Pfeiffer)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
BP1083
Product name
Isoniazid
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$274
Updated
2024/03/01
Sigma-Aldrich
Product number
8.06753
Product name
4-Pyridinecarboxylic acid hydrazide
Purity
for synthesis
Packaging
100G
Price
$65.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1349706
Product name
Isoniazid
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1083
Product name
Isoniazid
Purity
British Pharmacopoeia (BP) Reference Standard
Price
$226
Updated
2021/12/16
TCI Chemical
Product number
I0138
Product name
Isonicotinic Acid Hydrazide
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$29
Updated
2024/03/01
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Isoniazid Chemical Properties,Usage,Production

Description

Isoniazid, the hydrazide of isonicotinic acid was introduced into medical practice for treating tuberculosis in 1953. Isoniazid exhibits bactericidal action on Mycobacterium tuberculosis. It inhibits the synthesis of mycolic acid, an important component of the cell membrane of mycobacteria. Mycolic acid is specific only to mycobacteria, and it is the cause of the selective toxicity of the drug with respect to these microorganisms.
Mutants that are resistant to isoniazid are rarely seen in nature, and in a spontaneously growing population of tuberculous bacillus there is approximately one mutant in every 105 –106 organisms. Large populations of microorganisms of the order 109 –1010 bacilli in the pulmonary cavities contain a significant number of resistant mutants. If only isoniazid is taken during treatment, an increased number of mutants will be observed and they will eventually become the dominant phenotype. The transformation from sensitive to nonsensitive microorganisms during treatment is called secondary or acquired resistance, which can originate over the course of a few weeks. Isoniazid is the most important drug for treating pulmonary and nonpulmonary forms of tuberculosis. It is active against both intracellular and extracellular organisms. In order to prevent secondary resistance, isoniazid should be used with other effective drugs (usually rifampin). Synonyms of this drug are tubazid, andrazide, niazid, piridizin, and many others.

Description

Isoniazid is an antibiotic that acts as a prodrug, being converted by bacterial catalase-peroxidases to form isonicotinic acyl-NADH complex, which inhibits mycolic acid biosynthesis. It is effective against several species of Mycobacterium, including M. tuberculosis.

Chemical Properties

white crystalline powder

Originator

Nyrazid,Squibb,US,1952

Uses

Isoniazid is an antimicrobial used for the prevention of tuberculosis infection or used concurrently with another agent for the treatment of tuberculosis infection. Rifampin, pyrazinamide, or both of these agents are commonly used with isoniazid. Isoniazid is the only Food and Drug Administration approved drug to treat latent tuberculosis in order to prevent it from becoming active.

Uses

antibacterial, tuberculostatic

Uses

Antibiotic for treatment of Mycobacterium tuberculosis, inhibits mycolic acid biosynthesis. Metabolized by hepatic N-acetyltransferase (NAT) and cytochrome P450 2E1 (CYP2E1) to form hepatotoxins. Sele ctively induces expression of CYP2E1. Reversibly inhibits CYP2C19 and CYP3A4 activities, and mechanistically inactivates CYP1A2, CYP2A6, CYP2C19 and CYP3A4 at clinically relevant concentrations. Antib acterial (tuberculostatic).

Uses

For the treatment of all forms of tuberculosis in which organisms are susceptible.

Definition

ChEBI: A carbohydrazide obtained by formal condensation between pyridine-4-carboxylic acid and hydrazine.

Indications

Isoniazid (isonicotinic acid hydrazide, or INH) is the most active drug for the treatment of tuberculosis caused by susceptible strains. It is a synthetic agent with a structural similarity to that of pyridoxine.

Manufacturing Process

4 parts of 4-cyanopyridine in 12 parts of water were reacted with 4 parts of hydrazine hydrate in the presence of 0.08 part of sodium hydroxide at 100°C under reflux for 7 hours. The product, after filtration and evaporation to dryness, was crystallized from ethanol. The yield of isonicotinyl hydrazide amounted to 3.27 parts which is 62% of the theoretical.

brand name

Inh (Novartis); Nydrazid (Bristol-Myers Squibb); Nydrazid (Sandoz); Rimifon (Roche).

Therapeutic Function

Antitubercular

Biological Functions

Its action is bactericidal against replicating organisms, but it appears to be only bacteriostatic at best against semidormant and dormant populations. After treatment with INH, M . tuberculosis loses its acid fastness, which may be interpreted as indicating that the drug interferes with cell wall development.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 412, 1955 DOI: 10.1021/jo01122a002

Antimicrobial activity

Susceptibility to isoniazid is virtually restricted to the M. tuberculosis complex (MIC 0.01–0.2 mg/L). It is highly bactericidal against actively replicating M. tuberculosis. Other mycobacteria are resistant, except for some strains of M. xenopi (MIC 0.2 mg/L) and a few strains of M. kansasii (MIC 1 mg/L).

Acquired resistance

Mutations in the katG gene, the inhA gene or its promoter region, and in the intergenic region of the oxyR–ahpC locus confer resistance to isoniazid. The relative proportions of such mutations vary geographically and are related to the distribution of the various lineages or superfamilies of M. tuberculosis.
Isoniazid resistance is the commonest form of drug resistance worldwide and the great majority of strains resistant to another agent are also resistant to isoniazid.

General Description

Odorless colorless or white crystals or white crystalline powder. Taste is slightly sweet at first and then bitter. pH (1% aqueous solution) 5.5-6.5. pH (5% aqueous solution) 6-8.

Air & Water Reactions

Sensitive to air and light. Absorbs insignificant amounts of moisture at 77°F at relative humidities up to approximately 90%. Water soluble. Dust can be explosive when suspended in air at specific concentrations.

Reactivity Profile

Isoniazid is incompatible with chloral, aldehydes, iodine, hypochlorites and ferric salts. Isoniazid is also incompatible with oxidizers. Isoniazid may react with sugars and ketones. Isoniazid can react as a weak acid or a weak base. Isoniazid can be decomposed by oxidative and reductive reactions.

Fire Hazard

Isoniazid is combustible.

Pharmaceutical Applications

One of a number of nicotinamide analogs found to have antituberculosis activity, following the observation that nicotinamide inhibited the replication of M. tuberculosis. It is soluble in water. The dry powder is stable if protected from light. It is a prodrug requiring oxidative activation by KatG, a mycobacterial catalase–peroxidase enzyme.

Biochem/physiol Actions

Antibiotic for treatment of Mycobacterium tuberculosis, inhibits mycolic acid biosynthesis. Metabolized by hepatic N-acetyltransferase (NAT) and cytochrome P450 2E1 (CYP2E1) to form hepatotoxins. Selectively induces expression of CYP2E1. Reversibly inhibits CYP2C19 and CYP3A4 activities, and mechanistically inactivates CYP1A2, CYP2A6, CYP2C19 and CYP3A4 at clinically relevant concentrations.

Mechanism of action

Isoniazid is active against susceptible bacteria only when they are undergoing cell division. Susceptible bacteria may continue to undergo one or two divisions before multiplication is arrested. Isoniazid can inhibit the synthesis of mycolic acids, which are essential components of mycobacterial cell walls.The mycobacterial enzyme catalase– peroxidase KatG activates the administered isoniazid to its biologically active form.The target sites for the activated isoniazid action are acyl carrier protein AcpM and Kas A, a β-ketoaceyl carrier protein synthetase that blocks mycolic acid synthesis. Isoniazid exerts its lethal effects at the target sites by forming covalent complexes.

Pharmacology

Isoniazid is water soluble and is well absorbed when administered either orally or parenterally. Oral absorption is decreased by concurrent administration of aluminum-containing antacids.
Isoniazid does not bind to serum proteins; it diffuses readily into all body fluids and cells, including the caseous tuberculous lesions. The drug is detectable in significant quantities in pleural and ascitic fluids, as well as in saliva and skin. The concentrations in the central nervous system (CNS) and cerebrospinal fluid are generally about 20% of plasma levels but may reach close to 100% in the presence of meningeal inflammation.
Isoniazid is acetylated to acetyl isoniazid by N-acetyltransferase, an enzyme in liver, bowel, and kidney. Individuals who are genetically rapid acetylators will have a higher ratio of acetyl isoniazid to isoniazid than will slow acetylators. Rapid acetylators were once thought to be more prone to hepatotoxicity, but this is not proved. The slow or rapid acetylation of isoniazid is rarely important clinically, although slow inactivators tend to develop peripheral neuropathy more readily. Metabolites of isoniazid and small amounts of unaltered drug are excreted in the urine within 24 hours of administration.

Pharmacokinetics

Oral absorption: >95%
Cmax 300 mg oral: 3–5 mg/L after 1–2 h
Plasma half-life: 0.5–1.5 h (rapid acetylators)
: 2–4 h (slow acetylators)
Volume of distribution: 0.6–0.8 L/kg
Plasma protein binding: Very low
Absorption and distribution
Isoniazid is almost completely absorbed from the gut and is well distributed. Absorption is impaired by aluminum hydroxide. Therapeutic concentrations are achieved in sputum and CSF. It crosses the placenta and is found in breast milk.
Metabolism
Isoniazid is extensively metabolized to a variety of pharmacologically inactive derivatives, predominantly by acetylation. As a result of genetic polymorphism, patients are divisible into rapid and slow acetylators. About 50% of Caucasians and Blacks, but 80–90% of Chinese and Japanese, are rapid acetylators. Acetylation status does not affect the efficacy of daily administered therapy. The rate of acetylation is reduced in chronic renal failure.
Excretion
Nearly all the dose is excreted in the urine within 24 h, as unchanged drug and metabolic products.

Clinical Use

Isonicotinic acid hydrazide, isonicotinyl hydrazide, or INH(Nydrazid) occurs as a nearly colorless crystalline solid thatis very soluble in water. It is prepared by reacting the methylester of isonicotinic acid with hydrazine.
Isoniazid is a remarkably effective agent and continuesto be one of the primary drugs (along with rifampin, pyrazinamide,and ethambutol) for the treatment of tuberculosis.It is not, however, uniformly effective against all formsof the disease. The frequent emergence of strains of the tuberclebacillus resistant to isoniazid during therapy wasseen as the major shortcoming of the drug. This problemhas been largely, but not entirely, overcome with the use ofcombinations.
The activity of isoniazid is manifested on the growing tuberclebacilli and not on resting forms. Its action, which isconsidered bactericidal, is to cause the bacilli to lose lipidcontent by a mechanism that has not been fully elucidated.The most generally accepted theory suggests that the principaleffect of isoniazid is to inhibit the synthesis of mycolicacids, high–molecular-weight, branched β-hydroxyfatty acids that constitute important components of the cellwalls of mycobacteria.

Clinical Use

Isoniazid is among the safest and most active mycobactericidal agents. It is considered the primary drug for use in all therapeutic and prophylactic regimens for susceptible tuberculosis infections. It is also included in the first-line drug combinations for use in all types of tuberculous infections. Isoniazid is preferred as a single agent in the treatment of latent tuberculosis infections in high-risk persons having a positive tuberculin skin reaction with no radiological or other clinical evidence of tuberculosis. Mycobacterium kansasii is usually susceptible to isoniazid, and it is included in the standard multidrug treatment regimen.

Clinical Use

Tuberculosis (intensive and continuation phases)
Prevention of primary tuberculosis in close contacts and reactivation disease in infected but healthy persons (monotherapy)

Side effects

The incidence and severity of adverse reactions to isoniazid are related to dosage and duration of therapy. Isoniazid-induced hepatitis and peripheral neuropathy are two major untoward effects.

Side effects

Toxic effects are unusual on recommended doses and are more frequent in slow acetylators. Many side effects are neurological, including restlessness, insomnia, muscle twitching and difficulty in starting micturition. More serious but less common neurological side effects include peripheral neuropathy, optic neuritis, encephalopathy and a range of psychiatric disorders, including anxiety, depression and paranoia.
Neurotoxicity is usually preventable by giving pyridoxine (vitamin B6) 10 mg per day. Pyridoxine should be given to patients with liver disease, pregnant women, alcoholics, renal dialysis patients, HIV-positive patients, the malnourished and the elderly. Encephalopathy, which has been reported in patients on renal dialysis, may not be prevented by, or respond to, pyridoxine, but usually resolves on withdrawal of isoniazid.
Isoniazid-related hepatitis occurs in about 1% of patients receiving standard short-course chemotherapy. The incidence is unaffected by acetylator status. It is more common in those aged over 35 years and preventive isoniazid monotherapy should be used with care in older people.
Less common side effects include arthralgia, a ‘flu’-like syndrome, hypersensitivity reactions with fever, rashes and, rarely, eosinophilia, sideroblastic anemia, pellagra (which responds to treatment with nicotinic acid) and hemolysis in patients with glucose-6-phosphate dehydrogenase deficiency. It exacerbates acute porphyria and induces antinuclear antibodies, but overt systemic lupus erythematosus is rare.

Synthesis

Isoniazid, isonicotinic acid hydrazide (34.1.1), is synthesized by reacting ethyl ester of isonicotinic acid with hydrazine.

Veterinary Drugs and Treatments

Isoniazid (INH) is sometimes used for chemoprophylaxis in small animals in households having a human with tuberculosis. It potentially can be used in combination with other antimycobacterial drugs to treat infections of M. bovis or M. tuberculosis in dogs or cats. But because of the public health risks, particularly in the face of increased populations of immunocompromised people, treatment of mycobacterial (M. bovis, M. tuberculosis) infections in domestic or captive animals is controversial. In addition, INH has a narrow therapeutic index and toxicity is a concern (see Adverse Effects).
In humans, isoniazid (INH) is routinely used alone to treat latent tuberculosis infections (positive tuberculin skin test) and in combination with other antimycobacterial agents to treat active disease.

Environmental Fate

Isoniazid is a colorless, odorless, white crystalline powder that is slowly oxidized by exposure to air. It undergoes degradation upon prolonged exposure to light. Isoniazid has a solubility of 1 g per 8 ml water, 1 g per 50 ml ethanol, and it is slightly soluble in chloroform and very slightly soluble in ether. A 10% solution of isoniazid has a pH of 6.0–8.0.

Metabolism

Isoniazid is extensively metabolized to inactive metabolites. The major metabolite is N-acetylisoniazid. The enzyme responsible for acetylation, cytosolic N-acetyltransferase, is produced under genetic control in an inherited autosomal fashion. Individuals who possess high concentrations of the enzyme are referred to as rapid acetylators, whereas those with low concentrations are slow acetylators. This may result in a need to adjust the dosage for fast acetylators. The N-acetyltransferase is located primarily in the liver and small intestine. Other metabolites include isonicotinic acid, which is found in the urine as a glycine conjugate, and hydrazine. Isonicotinic acid also may result from hydrolysis of acetylisoniazid, but in this case, the second product of hydrolysis is acetylhydrazine. Acetylhydrazine is acetylated by N-acetyltransferase to the inactive diacetyl product. This reaction occurs more rapidly in rapid acetylators. The formation of acetylhydrazine is significant in that this compound has been associated with the hepatotoxicity, which may occur during INH therapy.

Purification Methods

Crystallise isoniazide from 95% EtOH and dry it in a vacuum. [Beilstein 22 III/IV 545, 22/2 V 219.]

Toxicity evaluation

Isoniazid causes toxicity by altering the metabolism of pyridoxine and creating a functional deficiency. Pyridoxine is needed for transamination, transketolization, decarboxylation, and biotransformation reactions. This occurs through three processes: (1) isoniazid metabolites form complexes with pyridoxine increasing its urinary excretion with increasing doses; (2) isoniazid metabolites disrupt the conversion of pyridoxine to its active form, pyridoxine-50-phosphokinase; and (3) metabolites directly inactivate pyridoxal-50-phosphate.
Isoniazid-induced seizures are thought to be caused by the depletion of gamma-aminobutyric acid (GABA). GABA is the primary inhibitory neurotransmitter in the central nervous system that requires the cofactor pyridoxal-50-phosphate for its synthesis from glutamate. Prolonged seizures commonly result in plasma lactic acid accumulation that can lead to an anion gap metabolic acidosis. Isoniazid may worsen the severity of acidosis by inhibiting the production of nicotinamideadensosine dinucleotide (NAD), a cofactor necessary for the conversion of lactate to pyruvate. Long-term exposure to isoniazid therapy commonly causes peripheral neuropathy due to pyridoxine deficiency, and may induce pellagra, a niacin deficiency disorder. Niacin requires the cofactor pyridoxal-50- phosphate for its production from tryptophan.
The exact mechanism of isoniazid-induced hepatotoxicity is unknown. However, it is thought to involve an idiopathic autoimmune mechanism or result from direct hepatic injury from isoniazid or its metabolites. The metabolite thought to be responsible is acetyl hydrazine, produced from isoniazid hydrolysis via cytochrome P450 (CYP)2E1. Persons with the CYP2E1c1/c1 genotype may be more susceptible to hepatotoxicity. The role acetylator status plays in hepatotoxicity continues to be debated, but it is currently thought that slow acetylators are at greater risk. Other risk factors include increasing age, chronic isoniazid overdose, comorbid conditions such as malnutrition, pregnancy, diabetes, HIV, renal dysfunction, hepatic dysfunction, alcoholism, and concomitant use of enzyme inducing drugs.
Other enzymes inhibited by isoniazid include the cytochrome P450 mixed function oxidases, monoamine oxidase, glutamate decarboxylase, and histaminase. The consequences of these extensive enzymatic disturbances are mood elevation, decreased central nervous system GABA levels, depressed catecholamine synthesis, defects in glucose and fatty acid oxidation, and impaired metabolism of other drugs. Important drug interactions include those with carbamazepine, phenytoin, rifampin, theophylline, valproate, and warfarin. Isoniazid is also a weak monoamine oxidase inhibitor, and serotonin syndrome and tyramine reactions to foods causing flushing, tachycardia, and hypertension are reported.
Isoniazid does cross the placenta and enters the fetal compartment; however, it has been determined to not be a human teratogen in studies. In acute toxicity, fetal deformities have been reported.

Precautions

High isoniazid plasma levels inhibit phenytoin metabolismand potentiate phenytoin toxicity when the twodrugs are coadministered. The serum concentrations ofphenytoin should be monitored, and the dose should beadjusted if necessary.

Isoniazid Preparation Products And Raw materials

Raw materials

Preparation Products

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Isoniazid Suppliers

Wuhan Noble Pharmaceutical&Chemical Co.Ltd.
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J & K SCIENTIFIC LTD.
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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future industrial shanghai co., ltd
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View Lastest Price from Isoniazid manufacturers

Shanghai Affida new material science and technology center
Product
Isoniazid 54-85-3
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99
Supply Ability
10 tons
Release date
2024-03-19
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Isoniazid
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2021-01-14
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Isoniazid 54-85-3
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-08

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