CAS 54-85-3|Dinacrin|isoniazid|Rimicid|Laniazid|Isocotin|Azuren|Isonicotinohydrazide|Niplen|Fimalene|TB-Phlogin|INH|Tebilon|Diforin|Pycazide|Armacide|Tibazide|Nicozide|Hidranizil|Tubazide|Pyrizidin|...

General Information

Structure

Molecular Formula

C₆H₇N₃O

Molecular Mass

137.13928

Exact Mass

137.05891186

Charge

InChI

InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)

InChIKey

QRXWMOHMRWLFEY-UHFFFAOYSA-N

Canonic Smiles

NNC(=O)c1ccncc1

Isomeric Smiles

O=C(NN)c1ccncc1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.69

LogD (pH = 5.5)

-0.69

Log P

-0.69

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.26

Polar Surface Area

68.01

Polarizability

13.21

Molar Refractivity

37.46

LOG S

-0.41

Data Source

Names and Identifiers

Brand Name

IsonitonStanozideNicozideIsotebezidIsonicazideHidrunTuberianIsopyrinIsozideTibazideIscotinNicazideArmacideVazadrineIsonicotilIsozydTubomelRimicidNidatonEvalonZonazideTB-PhloginNidrazidNeotebenDitubinTebosIsonicotanNeumandinTebilonPycazideHidranizilPyrizidinIsocotinEbideneAzurenNicizinaFimaleneTubazideCedinFSR 3IdrazilTibisonIsoniacidDinacrinIsonexDiforinIsotamineLaniazidIsonindonNiplenIsotebeVederonRimifonInizidHidrultaAntituberkulosumRetozideEralonDefoninArmazideTB-VisChemidonSanohidrazinaNydrazidTubecotubercidNicotibineIsobicinaTebenicInahIsonikazidPyreazidArmazidNikozidNiadrinIsonidrinGINKNiconylSauterzidRaumanonHidrasonilRifamateMybasanIsonicidPhthisenIsotinylIsoniazid SAIsidrinaUnicocydeIdo-tebinNeo-TizideDibutinZinadonIsonilexPelazidTekazinTubilysinTubiconSauterazidRobisellinPercinRazideIsmazideTibemidIsolynCotinizinCemidonPyricidinErtubanNicetalTebexinRoxifenTibivisHyozidRobiselinNicotibinaNitadonIsonicoChemiazidTeebaconinIsoniritEutizonIsoninAtcotibineTebecidTibusanUnicozydeIsonideRimiphoneHyzydAntimicinaIsocidCortinazineAndrazideTubecoNeoxinIsoniazideRimitsidIsocideneNicotisanIsonizideCotinazinNevinZidafimiaNyscozidIsoneritTyvidLaniozidTubazidTB-RazideHycozidBacillinPyridicin

IUPAC Traditional name

isoniazid

Synonyms

HydrazidIsohydrazideIsonicotinohydrazideINHIsonicotinoyl hydrazideIsoniazidIsonicotinyl hydrazineIsonicotinhydrazidIsonicotinyl hydrazideHIAIsonicotinic hydrazideIsonicotinic acid hydrazideIsonicotinylhydrazineHydrazidePyridine-4-carbohydrazideLaniazidNydrazidTubizidISONIACIDISONICOTINIC ACID HYDRAZIDEIsoniazidisonicotinohydrazide雷米封异烟肼异烟酸肼Isoniazid4-Pyridinecarboxylic HydrazideArmazidIsozide4-Pyridylcarbonylhydrazide5015 R.P.Isotebezid4-PyridinecarbonylhydrazineArmazideSauterazidRobisellin4-(Hydrazinocarbonyl)pyridine4-Pyridinecarboxylic Acid HydrazideTubazidZonazideAtcotibineZinadonIsonizidePyridine-4-carboxylic hydrazideIsonicotinic acid hydrazidepyridine-4-carboxylic acid hydrazideisonicotinic acid hydrazideisoniazideIsonicotinsaeurehydrazidisonicotinohydrazide4-pyridinecarbohydrazideisoniazidisonicotinoylhydrazideisonicotinic hydrazideIsoniazid

IUPAC name

pyridine-4-carbohydrazide

API Name

Isoniazid

Names and Identifiers

Registration numbers

Properties

Pharmacology Properties

Excretion

urine (primarily), feces

Admin Routes

oral, intramuscular, intravenous

Half Life

0.5-1.6h (fast acetylators), 2-5h (slow acetylators)

Pregnancy Category

Protein Bound

Very low (0-10%)

prescription only (US)

liver; CYP450: 2C19, 3A4 inhibitor

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00951

Drug Groups

approved

Description

Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. [PubChem]

Indication

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

Pharmacology

Isoniazid is a bactericidal agent active against organisms of the genus Mycobacterium, specifically M. tuberculosis, M. bovis and M. kansasii. It is a highly specific agent, ineffective against other microorganisms. Isoniazid is bactericidal to rapidly-dividing mycobacteria, but is bacteriostatic if the mycobacterium is slow-growing.

Toxicity

LD₅₀ 100 mg/kg (Human, oral). Adverse reactions include rash, abnormal liver function tests, hepatitis, peripheral neuropathy, mild central nervous system (CNS) effects. In vivo, Isoniazid reacts with pyridoxal to form a hydrazone, and thus inhibits generation of pyridoxal phosphate. Isoniazid also combines with pyridoxal phosphate; high doses interfere with the coenzyme function of the latter.

Affected Organisms

Mycobacteria

Biotransformation

Primarily hepatic. Isoniazid is acetylated by N -acetyl transferase to N -acetylisoniazid; it is then biotransformed to isonicotinic acid and monoacetylhydrazine. Monoacetylhydrazine is associated with hepatotoxicity via formation of a reactive intermediate metabolite when N-hydroxylated by the cytochrome P450 mixed oxidase system. The rate of acetylation is genetically determined. Slow acetylators are characterized by a relative lack of hepatic N -acetyltransferase.

Absorption

Readily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food.

Half Life

Fast acetylators: 0.5 to 1.6 hours. Slow acetylators: 2 to 5 hours.

Protein Binding

Very low (0-10%)

Elimination

From 50 to 70 percent of a dose of isoniazid is excreted in the urine within 24 hours.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1937

Research Area: Infection
Biological Activity:
Isoniazid(Tubizid) is a prodrug and must be activated by bacterial catalase. Specficially, activation is associated with reduction of the mycobacterial ferric KatG catalase-peroxidase by hydrazine and reaction with oxygen to form an oxyferrous enzyme complex. Once activated, isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. At therapeutic levels isoniazid is bacteriocidal against actively growing intracellular and extracellular Mycobacterium tuberculosis organisms. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA. [1]

MP Biomedicals

02102096

Crystalline
Used for fluorescent HPLC detection of Δ-3-Ketosteroids.

05207836

MP Biomedicals Rare Chemical collection

Wikipedia

Isoniazid

Sigma Aldrich

I3377

Biochem/physiol Actions
针对结核菌的抗生素，抑制分枝菌酸的生物合成。由肝脏 N-乙酰转移酶 (NAT) 和细胞色素 P450 2E1 (CYP2E1) 代谢形成肝毒素。选择性诱导 CYP2E1 的表达。可逆抑制 CYP2C19 和 CYP3A4 的活性，在临床相关浓度下机械性地灭活 CYP1A2、CYP2A6、CYP2C19 和 CYP3A4。
包装
5, 50, 250 g in poly bottle

58980

Application
Used for fluorescence detection in the high-performance liquid chromatography of olefinic 3-ketosteroids1
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.

TRC

I821450

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 inhibi

ChEBI

CHEBI:6030

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

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB00951

• J. Chromatog. , 168 : 526, (1979).

• Weber, W.W., et al.: Clin. Pharmacokinet., 4, 401 (1979)

• Brewer, G.A., et al.: Anal. Profiles Drug Subs., 6, 183 (1977)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

IUPAC Traditional name

isoniazid

Synonyms

IUPAC name

pyridine-4-carbohydrazide

API Name

Isoniazid

Molecule Details

DrugBank

DB00951

Drug Groups

approved

Description

Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. [PubChem]

Indication

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

Pharmacology

Toxicity

Affected Organisms

Mycobacteria

Biotransformation

Absorption

Readily absorbed following oral administration; however, may undergo significant first pass metabolism. Absorption and bioavailability are reduced when isoniazid is administered with food.

Half Life

Fast acetylators: 0.5 to 1.6 hours. Slow acetylators: 2 to 5 hours.

Protein Binding

Very low (0-10%)

Elimination

From 50 to 70 percent of a dose of isoniazid is excreted in the urine within 24 hours.

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1937