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High purity Various Specifications Isonicotinic acid hydrazide CAS:54-85-3
Cas No: 54-85-3
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CAS:54-85-3 Isoniazid
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54-85-3 Usage

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.

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.

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.

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.

Synthesis Reference(s)

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

Definition

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

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.

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.

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.

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.

Brand name

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

Uses

antibacterial, tuberculostatic

Clinical Use

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

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.

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).

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.

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.

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.

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.

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.

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.

Purification Methods

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

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.

Uses

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

Chemical Properties

white crystalline powder

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.

Therapeutic Function

Antitubercular

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).

Originator

Nyrazid,Squibb,US,1952

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.

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.

Chemical Synthesis

Isoniazid, isonicotinic acid hydrazide (34.1.1), is synthesized by reacting ethyl ester of isonicotinic acid with hydrazine.图
InChI:InChI=1/C6H7N3O2/c7-9-11-6(10)5-1-3-8-4-2-5/h1-4,9H,7H2

54-85-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (I0138)  Isonicotinic Acid Hydrazide  >98.0%(HPLC)(T) 54-85-3 25g 130.00CNY Detail
TCI America (I0138)  Isonicotinic Acid Hydrazide  >98.0%(HPLC)(T) 54-85-3 100g 410.00CNY Detail
TCI America (I0138)  Isonicotinic Acid Hydrazide  >98.0%(HPLC)(T) 54-85-3 500g 1,290.00CNY Detail
Alfa Aesar (A10583)  Isonicotinic acid hydrazide, 98+%    54-85-3 50g 106.0CNY Detail
Alfa Aesar (A10583)  Isonicotinic acid hydrazide, 98+%    54-85-3 100g 157.0CNY Detail
Alfa Aesar (A10583)  Isonicotinic acid hydrazide, 98+%    54-85-3 500g 587.0CNY Detail
Alfa Aesar (A10583)  Isonicotinic acid hydrazide, 98+%    54-85-3 1000g 1094.0CNY Detail
Sigma-Aldrich (75182)  Isoniazid  certified reference material, TraceCERT® 54-85-3 75182-50MG 1,547.91CNY Detail
Sigma-Aldrich (I0500000)  Isoniazid  European Pharmacopoeia (EP) Reference Standard 54-85-3 I0500000 1,880.19CNY Detail
USP (1349706)  Isoniazid  United States Pharmacopeia (USP) Reference Standard 54-85-3 1349706-200MG 4,662.45CNY Detail
Sigma-Aldrich (I3377)  Isoniazid  analytical standard, ≥99% (TLC) 54-85-3 I3377-5G 157.95CNY Detail
Sigma-Aldrich (I3377)  Isoniazid  analytical standard, ≥99% (TLC) 54-85-3 I3377-50G 198.90CNY Detail

54-85-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name isoniazide

1.2 Other means of identification

Product number -
Other names HIA

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:54-85-3 SDS

54-85-3Synthetic route

butyl isonicotinate
13841-66-2

butyl isonicotinate

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate at 60℃; for 4h;99.1%
With hydrazine hydrate In ethanol for 6h; Reflux;74.1%
isonicotinamide
1453-82-3

isonicotinamide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine at 115℃; for 4h;97.34%
With hydrazine at 115℃; for 4h; Heating / reflux;97.34%
With hydrazine In methanol at 110℃; for 4h;96.03%
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 0.0333333h; Microwave irradiation;97.3%
With hydrazine hydrate In ethanol Reflux;88%
Stage #1: isonicotinic acid ethylester With hydrazine hydrate at 75 - 80℃; for 10h;
Stage #2: With pyrographite In water at 70 - 75℃; for 0.5h; Reagent/catalyst; Temperature; Solvent;
87%
4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 70℃; for 0.00111111h;95.6%
With hydrazine hydrate In ethanol at 20℃; for 3h;94.1%
With hydrazine hydrate In ethanol at 23℃; for 16h;86%
isonicotinamide
1453-82-3

isonicotinamide

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine dihydrochloride In aq. phosphate buffer at 30℃; for 1h; pH=7; Kinetics; Concentration; Time; Temperature; Enzymatic reaction;A n/a
B 90.4%
isonicotinic acid ethyl ester; hydrochloride
58827-14-8

isonicotinic acid ethyl ester; hydrochloride

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 1h; Time; Reflux;87.59%
Multi-step reaction with 2 steps
1.1: sodium carbonate / dichloromethane; water
2.1: hydrazine hydrate / 10 h / 75 - 80 °C
2.2: 0.5 h / 70 - 75 °C
View Scheme
isonicotinic acid methyl ester hydrochloride

isonicotinic acid methyl ester hydrochloride

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 2.5h; Time; Reflux;84.5%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate for 0.0527778h; Microwave irradiation;80%
With hydrazine hydrate In ethanol for 4h; Reflux;55%
With hydrazine hydrate; toluene; butan-1-ol at 130 - 160℃; Entfernen des entstehenden Wassers;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

A

isoniazid
54-85-3

isoniazid

B

isonicotinamide
1453-82-3

isonicotinamide

Conditions
ConditionsYield
With NaY zeolite; hydrazine hydrate In water at 90℃; for 2h;A 67%
B 18%
(piperidin-1-yl)(pyridin-4-yl)methanethione
88057-93-6

(piperidin-1-yl)(pyridin-4-yl)methanethione

A

isoniazid
54-85-3

isoniazid

B

3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine
31599-25-4

3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine

Conditions
ConditionsYield
With hydrazine hydrate for 24h; Ambient temperature;A n/a
B 10%
N-cyclohexylpyridine-4-carbothioamide
17332-42-2

N-cyclohexylpyridine-4-carbothioamide

A

isoniazid
54-85-3

isoniazid

B

3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine
31599-25-4

3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine

Conditions
ConditionsYield
With hydrazine hydrate for 24h; Ambient temperature;A n/a
B 10%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With sodium hydroxide; water; hydrazine hydrate at 100℃;
Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride
110925-39-8

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

isoniazid
54-85-3

isoniazid

B

daunomycin hydrochloride
23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, pH 6.80, pH 7.35, 0.01 M phosphate buffer;
{3-hydroxy-4-[(E)-(isonicotinoylhydrazono)methyl]-2-methylpyridin-5-yl}methylphosphate
53-91-8

{3-hydroxy-4-[(E)-(isonicotinoylhydrazono)methyl]-2-methylpyridin-5-yl}methylphosphate

A

isoniazid
54-85-3

isoniazid

B

pyridoxal 5'-phosphate
54-47-7

pyridoxal 5'-phosphate

Conditions
ConditionsYield
at 25℃; Equilibrium constant; Rate constant; depending on pH;
N-(5-methyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

N-(5-methyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With phosphate buffer In methanol; water at 37℃; Rate constant; var. pH, also in 80 percent human plasma or 10 percent rat liver homogenate;
N-(5-ethyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

N-(5-ethyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With phosphate buffer In methanol; water at 37℃; Rate constant; var. pH, also in 80 percent human plasma or 10 percent rat liver homogenate;
N-(5-propyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

N-(5-propyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With phosphate buffer In methanol; water at 37℃; Rate constant; var. pH, also in 80 percent human plasma or 10 percent rat liver homogenate;
N-(5-butyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

N-(5-butyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-isonicotinamide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With phosphate buffer In methanol; water at 37℃; Rate constant; var. pH, also in 80 percent human plasma or 10 percent rat liver homogenate;
3-benzyl-5-(4-pyridylcarboxamido)tetrahydro-2H-1,3,5-thiadiazine-2-thione

3-benzyl-5-(4-pyridylcarboxamido)tetrahydro-2H-1,3,5-thiadiazine-2-thione

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With phosphate buffer In methanol; water at 37℃; Rate constant; var. pH, also in 80 percent human plasma or 10 percent rat liver homogenate;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

hydrazine
302-01-2

hydrazine

A

isoniazid
54-85-3

isoniazid

B

N,N'-bis(isonicotinoyl)hydrazine
4329-75-3

N,N'-bis(isonicotinoyl)hydrazine

C

3,5-di(pyridin-4-yl)-4H-1,2,4-triazol-4-amine
38634-05-8

3,5-di(pyridin-4-yl)-4H-1,2,4-triazol-4-amine

Conditions
ConditionsYield
at 130℃;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

indolyl magnesium bromide

indolyl magnesium bromide

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / sulphur / 8 h / Heating
2: 100percent hydrazine hydrate / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 84 percent / sulphur / 8 h / Heating
2: 100percent hydrazine hydrate / 24 h / Ambient temperature
View Scheme
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

(+-)-3-<4-chloro-3-methyl-phenyl>-3-<4-chloro-phenyl>-propylamine

(+-)-3-<4-chloro-3-methyl-phenyl>-3-<4-chloro-phenyl>-propylamine

A

isoniazid
54-85-3

isoniazid

B

O2,O4;O3,O5-<(R,S)-dibenzylidene>-D-xylose

O2,O4;O3,O5-<(R,S)-dibenzylidene>-D-xylose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent Chromat. / KU-2-8 cation-exchange resin / benzene / 24 h / 110 - 115 °C
2: 99.1 percent / 99.5percent hydrazine hydrate / 4 h / 60 °C
View Scheme
isonicotinoyl chloride hydrochloride
39178-35-3

isonicotinoyl chloride hydrochloride

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: N2H4+H2O; ethanol
View Scheme
pyridine
110-86-1

pyridine

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; iron-powder / 130 °C
2: aqueous SeO2; concentrated H2SO4 / 280 °C
3: ClSO3H
4: N2H4+H2O; methanol
View Scheme
4-Ethylpyridine
536-75-4

4-Ethylpyridine

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous SeO2; concentrated H2SO4 / 280 °C
2: ClSO3H
3: N2H4+H2O; methanol
View Scheme
4-(chlorocarbonyl)pyridine
14254-57-0

4-(chlorocarbonyl)pyridine

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane
Multi-step reaction with 2 steps
1: 5 h / 0 - 20 °C
2: hydrazine hydrate / ethanol / 8.5 h / 30 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide
2: hydrazine hydrate
View Scheme
Multi-step reaction with 2 steps
1.1: 0.5 h
2.1: hydrazine hydrate / 10 h / 75 - 80 °C
2.2: 0.5 h / 70 - 75 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide
2: hydrazine hydrate / methanol
View Scheme
1-isonicotinoyl-1H-imidazole
90322-87-5

1-isonicotinoyl-1H-imidazole

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine hydrate In tetrahydrofuran at 20℃;5.25 g
picoline
108-89-4

picoline

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: β‐cyclodextrin / water / 0.5 h / 60 °C
1.2: 6 h / 40 °C
2.1: oxalyl dichloride / dichloromethane / 0 °C
3.1: 5 h / 0 - 20 °C
4.1: hydrazine hydrate / ethanol / 8.5 h / 30 - 100 °C
View Scheme
2-Acetylthiophene
88-15-3

2-Acetylthiophene

isoniazid
54-85-3

isoniazid

(E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide
91397-02-3

(E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide

Conditions
ConditionsYield
at 247℃; under 6000.6 Torr; for 0.075h; Microwave irradiation; neat (no solvent);100%
With trifluoroacetic acid In ethanol Reflux;82%
With propan-1-ol
isoniazid
54-85-3

isoniazid

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

isonicotinic acid N2-(4-chloro-3-nitrobenzylidene)hydrazide
99513-84-5

isonicotinic acid N2-(4-chloro-3-nitrobenzylidene)hydrazide

Conditions
ConditionsYield
In ethanol Reflux;100%
With ethanol
2-acetylpyridine
1122-62-9

2-acetylpyridine

isoniazid
54-85-3

isoniazid

N’-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide
93086-96-5

N’-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide

Conditions
ConditionsYield
In methanol at 20℃;100%
In methanol at 20℃; for 1h;100%
In ethanol for 0.0833333h; Concentration; Temperature; Time; Microwave irradiation; Green chemistry;86%
carbon disulfide
75-15-0

carbon disulfide

isoniazid
54-85-3

isoniazid

potassium 4-pyridinyldithiocarbazate
61019-32-7

potassium 4-pyridinyldithiocarbazate

Conditions
ConditionsYield
With potassium hydroxide In ethanol100%
With potassium hydroxide In ethanol at 20℃;100%
With potassium hydroxide In ethanol at 20℃; for 16h;99%
carbon disulfide
75-15-0

carbon disulfide

isoniazid
54-85-3

isoniazid

potassium 2-isonicotinoyl hydrazine carbothionate

potassium 2-isonicotinoyl hydrazine carbothionate

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 16h; Cooling with ice;100%
With potassium hydroxide In ethanol at 25℃; for 3h;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

isoniazid
54-85-3

isoniazid

N’-(pyridin-4-ylmethylene)isonicotinohydrazide

N’-(pyridin-4-ylmethylene)isonicotinohydrazide

Conditions
ConditionsYield
In ethanol Reflux;100%
With hydrogenchloride In ethanol Microwave irradiation;96%
In ethanol for 0.333333h; Reflux; Cooling with ice;90%
With sodium disulfite In 1,2-dimethoxyethane for 0.0166667h; microwave irradiation;
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

isoniazid
54-85-3

isoniazid

N’-(pyridin-2-ylmethylene)isonicotinohydrazide
15017-32-0

N’-(pyridin-2-ylmethylene)isonicotinohydrazide

Conditions
ConditionsYield
In ethanol Reflux;100%
In ethanol Reflux;91%
In ethanol Reflux;82%
isoniazid
54-85-3

isoniazid

2,6-difluorobenzaldehyde
437-81-0

2,6-difluorobenzaldehyde

isonicotinic acid N2-(2,6-difluorobenzylidene)hydrazide
386268-24-2

isonicotinic acid N2-(2,6-difluorobenzylidene)hydrazide

Conditions
ConditionsYield
In ethanol Reflux;100%
isoniazid
54-85-3

isoniazid

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

N'-[(Z)-(2-nitrophenyl)methylidene]pyridine-4-carbohydrazide
1262213-17-1

N'-[(Z)-(2-nitrophenyl)methylidene]pyridine-4-carbohydrazide

Conditions
ConditionsYield
In water Microwave irradiation;99.2%
With acetic acid In ethanol for 3h; Reflux;76%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

isoniazid
54-85-3

isoniazid

(E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide
79728-82-8

(E)-N’-(thiophen-2-ylmethylene)isonicotinohydrazide

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol Reflux;99%
With acetic acid In ethanol for 0.25h; Sonication;92%
In ethanol for 2h; Reflux;80%
isoniazid
54-85-3

isoniazid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(E)-N′-(4′-chlorobenzylidene)isonicotinohydrazide
6342-46-7

(E)-N′-(4′-chlorobenzylidene)isonicotinohydrazide

Conditions
ConditionsYield
In ethanol; water at 20℃; for 0.0833333h; UV-irradiation;99%
With acetic acid In ethanol Reflux;92%
In methanol for 4h; Heating;89%
isoniazid
54-85-3

isoniazid

salicylaldehyde
90-02-8

salicylaldehyde

salicylaldehyde isonicotinoylhydrazone
495-84-1

salicylaldehyde isonicotinoylhydrazone

Conditions
ConditionsYield
at 56℃; for 0.333333h;99%
at 100℃; for 0.0666667h; pH=4.5; Schiff Reaction; Aqueous acetate buffer;98%
Stage #1: salicylaldehyde In ethanol for 0.166667h;
Stage #2: isoniazid In ethanol; water at 80℃; for 0.5h; UV-irradiation;
98.7%
isoniazid
54-85-3

isoniazid

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

N'-[(E)-(3-chloro-phenyl)methylidene]isonicotinohydrazide
40108-48-3

N'-[(E)-(3-chloro-phenyl)methylidene]isonicotinohydrazide

Conditions
ConditionsYield
In ethanol; water at 20℃; for 0.0833333h; UV-irradiation;99%
With acetic acid In ethanol Reflux;85%
With ethanol
isoniazid
54-85-3

isoniazid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

isonicotinic acid (4-dimethylaminobenzylidene)hydrazide
13059-77-3

isonicotinic acid (4-dimethylaminobenzylidene)hydrazide

Conditions
ConditionsYield
at 60℃; for 0.333333h;99%
In ethanol for 1h; Reflux;95%
In ethanol for 24h; Reflux;85%
isoniazid
54-85-3

isoniazid

2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

(E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide
3477-69-8

(E)-N’-(2',4'-dihydroxybenzylidene)isonicotinohydrazide

Conditions
ConditionsYield
at 140℃; for 1h;99%
With acetic acid In ethanol Reflux;70%
With ethanol
In N,N-dimethyl-formamide at 20℃;
isoniazid
54-85-3

isoniazid

4-((methylthio)(phenyl)methylene) morpholinium iodide
31646-28-3

4-((methylthio)(phenyl)methylene) morpholinium iodide

4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine
56353-00-5

4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine

Conditions
ConditionsYield
In pyridine for 16h; Ambient temperature;99%
isoniazid
54-85-3

isoniazid

1-(α-methylsulfanyl-benzylidene)-piperidinium; iodide
61135-82-8

1-(α-methylsulfanyl-benzylidene)-piperidinium; iodide

4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine
56353-00-5

4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine

Conditions
ConditionsYield
In pyridine for 16h; Ambient temperature;99%
isoniazid
54-85-3

isoniazid

methyl thioisocyanate
556-61-6

methyl thioisocyanate

4-methyl-1-(pyridine-4-yl-carbonyl)-thiosemicarbazide
4406-96-6

4-methyl-1-(pyridine-4-yl-carbonyl)-thiosemicarbazide

Conditions
ConditionsYield
In ethanol at 90℃; for 4h;99%
In ethanol for 0.416667h; Heating;95%
In isopropyl alcohol for 3h; Heating;93%
isoniazid
54-85-3

isoniazid

(4-chlorophenoxy)acetonitrile
3598-13-8

(4-chlorophenoxy)acetonitrile

Isonicotinic acid [1-amino-2-(4-chloro-phenoxy)-eth-(E)-ylidene]-hydrazide
261363-00-2

Isonicotinic acid [1-amino-2-(4-chloro-phenoxy)-eth-(E)-ylidene]-hydrazide

Conditions
ConditionsYield
Stage #1: (4-chlorophenoxy)acetonitrile With sodium ethanolate In ethanol at 20℃; for 1h; Addition;
Stage #2: isoniazid In ethanol at 0 - 20℃; Condensation;
99%
isoniazid
54-85-3

isoniazid

(3-methoxyphenoxy)acetonitrile
50635-23-9

(3-methoxyphenoxy)acetonitrile

Isonicotinic acid [1-amino-2-(3-methoxy-phenoxy)-eth-(E)-ylidene]-hydrazide
261362-96-3

Isonicotinic acid [1-amino-2-(3-methoxy-phenoxy)-eth-(E)-ylidene]-hydrazide

Conditions
ConditionsYield
Stage #1: (3-methoxyphenoxy)acetonitrile With sodium ethanolate In ethanol at 20℃; for 1h; Addition;
Stage #2: isoniazid In ethanol at 0 - 20℃; Condensation;
99%
isoniazid
54-85-3

isoniazid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(E)-N’-(4'-(dimethylamino)benzylidene)isonicotinohydrazide

(E)-N’-(4'-(dimethylamino)benzylidene)isonicotinohydrazide

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol Reflux;99%
In ethanol for 1h; Heating;87.2%
With hydrogenchloride In ethanol at 20℃; for 0.5h; Condensation;85%
isoniazid
54-85-3

isoniazid

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

N'-((2-nitrophenyl)methylidene)pyridine-4-carbohydrazide

N'-((2-nitrophenyl)methylidene)pyridine-4-carbohydrazide

Conditions
ConditionsYield
at 57℃; for 0.25h;99%
In ethanol Reflux;97%
With hydrogenchloride In ethanol Reflux;86%
isoniazid
54-85-3

isoniazid

2,3-dihydroxybenzaldehyde
24677-78-9

2,3-dihydroxybenzaldehyde

N'-[(E)-(2,3-dihydroxy-phenyl)methylidene]isonicotinohydrazide

N'-[(E)-(2,3-dihydroxy-phenyl)methylidene]isonicotinohydrazide

Conditions
ConditionsYield
In methanol for 1.16667h; Milling;99%
In ethanol; water at 20℃; for 0.0833333h; UV-irradiation;90%
In N,N-dimethyl-formamide at 20℃;
isoniazid
54-85-3

isoniazid

2,3-dichlorobenzylaldehyde
6334-18-5

2,3-dichlorobenzylaldehyde

N'-[(E)-(2,3-dichloro-phenyl)methylidene]isonicotinohydrazide

N'-[(E)-(2,3-dichloro-phenyl)methylidene]isonicotinohydrazide

Conditions
ConditionsYield
In ethanol; water at 20℃; for 0.0833333h; UV-irradiation;99%
triethylamine In tetrahydrofuran for 6h; Heating;
isoniazid
54-85-3

isoniazid

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

(E)-N'-(3,4,5-trimethoxybenzylidene)isonicotinic hydrazide

(E)-N'-(3,4,5-trimethoxybenzylidene)isonicotinic hydrazide

Conditions
ConditionsYield
With trifluoroacetic acid In ethanol Reflux;99%
In ethanol; water at 20℃;88%
With acetic acid In ethanol Reflux;66%
isoniazid
54-85-3

isoniazid

2-isopropyl-5-methyl-hex-2-enal
35158-25-9

2-isopropyl-5-methyl-hex-2-enal

isonicotinic acid N2-(2-isopropyl-5-methyl-2-hexenylidene)hydrazide
1188539-99-2

isonicotinic acid N2-(2-isopropyl-5-methyl-2-hexenylidene)hydrazide

Conditions
ConditionsYield
In ethanol Reflux;99%
furfural
98-01-1

furfural

isoniazid
54-85-3

isoniazid

N-(2-furanylmethylene)isonicotinoylhydrazine

N-(2-furanylmethylene)isonicotinoylhydrazine

Conditions
ConditionsYield
at 60℃; for 0.25h;99%
In ethanol for 4h; Reflux;83%
With acetic acid In ethanol for 3h; Reflux;
With ammonia In water for 1h;
With acetic acid In ethanol
isoniazid
54-85-3

isoniazid

salicylaldehyde
90-02-8

salicylaldehyde

salinazid
495-84-1

salinazid

Conditions
ConditionsYield
In ethanol; water at 20℃; for 0.0833333h; UV-irradiation;98.7%
In ethanol; water Heating;95%
In methanol for 3h; Reflux;95%
isoniazid
54-85-3

isoniazid

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

N'-[(Z)-(4-fluorophenyl)methylidene]pyridine-4-carbohydrazide

N'-[(Z)-(4-fluorophenyl)methylidene]pyridine-4-carbohydrazide

Conditions
ConditionsYield
In water Microwave irradiation;98.7%

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