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|...

基本信息

化学结构

分子式

C₆H₇N₃O

分子量

137.13928

精确质量

137.05891186

电荷

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

计算属性

JChem

LogD (pH = 7.4)

-0.69

LogD (pH = 5.5)

-0.69

Log P

-0.69

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

3.26

极化表面积

68.01

极化性

13.21

摩尔折射率

37.46

LOG S

-0.41

数据来源

名称和标识

商标名

DinacrinRimicidLaniazidIsocotinAzurenNiplenFimaleneTB-PhloginTebilonDiforinPycazideArmacideTibazideNicozideHidranizilTubazidePyrizidinIscotinIsonicazideTibisonIsonicotilStanozideHidrunTuberianIsozydCedinNicizinaIsopyrinIsozideTebosNidrazidNeumandinIsonindonTubomelIsotebeFSR 3VederonDitubinIsonicotanEbideneIsotebezidIdrazilNicazideIsoniacidVazadrineNeotebenZonazideIsotamineIsonexRimifonNidatonIsonitonEvalonTekazinNiconylRaumanonNikozidIsotinylIsonidrinIsidrinaChemidonZinadonPyreazidPelazidIsonicidPercinIsoniazid SARifamateRobisellinIsonikazidHidrultaTubecotubercidPhthisenIsmazideAntituberkulosumTubiconArmazidArmazideTB-VisSauterzidIdo-tebinHidrasonilTubilysinNiadrinGINKDibutinUnicocydeEralonSanohidrazinaDefoninRetozideNeo-TizideInahSauterazidNicotibineMybasanIsobicinaIsonilexTebenicRazideInizidNydrazidAntimicinaCotinazinNevinIsocideneTubazidNicotibinaIsoneritCemidonLaniozidZidafimiaPyricidinAtcotibineTebecidEutizonTB-RazideHycozidTyvidTibusanRobiselinNitadonIsonicoIsolynPyridicinNicotisanNyscozidTebexinIsoniritIsonideRimitsidBacillinHyzydUnicozydeTibivisRimiphoneIsocidNicetalHyozidIsoniazideChemiazidCortinazineIsonizideNeoxinRoxifenTibemidCotinizinIsoninTubecoTeebaconinErtubanAndrazide

IUPAC传统名

isoniazid

别名

IsonicotinohydrazideINHIsohydrazideIsoniazidIsonicotinoyl hydrazideHydrazidHIAIsonicotinyl hydrazideIsonicotinyl hydrazineIsonicotinhydrazidIsonicotinic acid hydrazideHydrazideIsonicotinylhydrazineIsonicotinic hydrazidePyridine-4-carbohydrazideLaniazidTubizidNydrazidISONIACIDIsoniazidISONICOTINIC ACID HYDRAZIDEisonicotinohydrazide雷米封异烟肼异烟酸肼Isoniazid4-Pyridinecarboxylic HydrazideArmazide5015 R.P.ArmazidIsotebezidSauterazid4-PyridinecarbonylhydrazineRobisellin4-PyridylcarbonylhydrazideIsozide4-Pyridinecarboxylic Acid HydrazideIsonizideAtcotibineZonazide4-(Hydrazinocarbonyl)pyridineZinadonTubazidIsonicotinic acid hydrazidePyridine-4-carboxylic hydrazideisoniazideisonicotinohydrazideIsonicotinsaeurehydrazidpyridine-4-carboxylic acid hydrazideisonicotinic acid hydrazide4-pyridinecarbohydrazideIsoniazidisonicotinic hydrazideisonicotinoylhydrazideisoniazid

IUPAC标准名

pyridine-4-carbohydrazide

API名称

Isoniazid

名称和标识

数据登录号

PubChem SID

24896031465060391609642908145964

CAS号

MDL号

Beilstein号

EC号

PubChem CID

默克索引号

Chemspider ID

KEGG ID

CHEMBL

ATC码

美国药典/FDA物质标识码

CHEBI ID

Medline Plus

维基百科标题

DrugBank ID

MetaboLights数据库

MTBLS867MTBLS606MTBLS926MTBLS2945MTBLS601MTBLS615MTBLS379MTBLS2878

专利号

WO2008151303US2004198669US2007190067WO2007121963EP1839648US2007166276US2005080087US2002127577WO2008117079WO2006005112EP1803463US2007269539EP1757314WO2005037199

UniProt数据库

P9WJI4P9WJ96P73911A0R1V9P42829P84887P9WIE5Q9XBQ8P84888P05181A0QXX7P9WGR1P9WJ94P9WF09P9WJI5

BRENDA数据库

4.1.1.172.3.1.1182.3.1.1801.4.3.222.6.1.24.1.1.151.4.3.82.6.1.132.3.1.351.3.1.93.2.2.62.3.1.371.1.98.31.13.12.32.7.1.35

Gmelin ID

SureChEMBL数据库

EnzymePortal数据库

SABIO-RK数据库

ACToR数据库

BRENDA Ligand数据库

PubMed文献链接

182205651501378644530319183459

PDB数据库

5ksn5kt85syi5sxt6cdq5sxq5ksg3wxo4pae6cfq5syj5sxs

BKMS React数据库

NMRShiftDB数据库

BindingDB数据库

Reaxys Registry

MetaCyc数据库

CompTox数据库

Drug Central Database

LINCS数据库

KEGG DRUG Database

Reactom Database

数据登录号

化合物性质

药理学性质

urine (primarily), feces

oral, intramuscular, intravenous

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

Very low (0-10%)

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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
用于 HPLC 荧光检测烯-3-甾酮1
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。

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.

描述信息

参考文献

PubChem文献

数据源提供

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

• J. Chromatog. , 168 : 526, (1979).

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

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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

IUPAC传统名

isoniazid

别名

IUPAC标准名

pyridine-4-carbohydrazide

API名称

Isoniazid

描述信息

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