pyridine-4-carbohydrazide

• ChemBase编号: 827
• 分子式: C6H7N3O
• 平均质量: 137.13928
• 单一同位素质量: 137.05891186
• SMILES: O=C(NN)c1ccncc1
• Canonical SMILES: NNC(=O)c1ccncc1
• 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

名称和登记号

名称

• IUPAC标准名: pyridine-4-carbohydrazide
• IUPAC传统名: isoniazid
• 商标名: Andrazide; Antimicina; Antituberkulosum; Armacide; Armazid; Armazide; Atcotibine; Azuren; Bacillin; Cedin; Cemidon; Chemiazid; Chemidon; Cortinazine; Cotinazin; Cotinizin; Defonin; Dibutin; Diforin; Dinacrin; Ditubin; Ebidene; Eralon; Ertuban; Eutizon; Evalon; FSR 3; Fimalene; GINK; Hidranizil; Hidrasonil; Hidrulta; Hidrun; Hycozid; Hyozid; Hyzyd; Ido-tebin; Idrazil; Inah; Inizid; Iscotin; Isidrina; Ismazide; Isobicina; Isocid; Isocidene; Isocotin; Isolyn; Isonerit; Isonex; Isoniacid; Isoniazid SA; Isoniazide; Isonicazide; Isonicid; Isonico; Isonicotan; Isonicotil; Isonide; Isonidrin; Isonikazid; Isonilex; Isonin; Isonindon; Isonirit; Isoniton; Isonizide; Isopyrin; Isotamine; Isotebe; Isotebezid; Isotinyl; Isozide; Isozyd; Laniazid; Laniozid; Mybasan; Neo-Tizide; Neoteben; Neoxin; Neumandin; Nevin; Niadrin; Nicazide; Nicetal; Nicizina; Niconyl; Nicotibina; Nicotibine; Nicotisan; Nicozide; Nidaton; Nidrazid; Nikozid; Niplen; Nitadon; Nydrazid; Nyscozid; Pelazid; Percin; Phthisen; Pycazide; Pyreazid; Pyricidin; Pyridicin; Pyrizidin; Raumanon; Razide; Retozide; Rifamate; Rimicid; Rimifon; Rimiphone; Rimitsid; Robiselin; Robisellin; Roxifen; Sanohidrazina; Sauterazid; Sauterzid; Stanozide; TB-Phlogin; TB-Razide; TB-Vis; Tebecid; Tebenic; Tebexin; Tebilon; Tebos; Teebaconin; Tekazin; Tibazide; Tibemid; Tibison; Tibivis; Tibusan; Tubazid; Tubazide; Tubeco; Tubecotubercid; Tuberian; Tubicon; Tubilysin; Tubomel; Tyvid; Unicocyde; Unicozyde; Vazadrine; Vederon; Zidafimia; Zinadon; Zonazide
• 别名: 异烟酸肼; 雷米封; 异烟肼; Pyridine-4-carboxylic hydrazide; Isonicotinic acid hydrazide; Isoniazid; ISONICOTINIC ACID HYDRAZIDE; Tubizid; Laniazid; Nydrazid; Pyridine-4-carbohydrazide; Isonicotinohydrazide; Isonicotinoyl hydrazide; Isonicotinyl hydrazide; Isonicotinylhydrazine; Isohydrazide; Isonicotinyl hydrazine; INH; Hydrazide; Hydrazid; HIA; Isoniazid; Isonicotinhydrazid; Isonicotinic acid hydrazide; Isonicotinic hydrazide; isonicotinohydrazide; Isoniazid; ISONIACID; 4-Pyridinecarboxylic Acid Hydrazide; 4-(Hydrazinocarbonyl)pyridine; 4-Pyridinecarbonylhydrazine; 4-Pyridinecarboxylic Hydrazide; 4-Pyridylcarbonylhydrazide; 5015 R.P.; Armazid; Armazide; Atcotibine; Isonizide; Isotebezid; Isozide; Robisellin; Sauterazid; Zinadon; Zonazide; Tubazid

登记号

• CAS号: 54-85-3
• EC号: 200-214-6
• MDL号: MFCD00006426
• Beilstein号: 119374
• 默克索引号: 145186
• PubChem SID: 24896031; 46506039; 160964290
• PubChem CID: 3767
• CHEBI ID: 6030
• ATC码: J04AC01
• CHEMBL: 64
• Chemspider ID: 3635
• DrugBank ID: DB00951
• KEGG ID: D00346
• 美国药典/FDA物质标识码: V83O1VOZ8L
• 维基百科标题: Isoniazid
• Medline Plus: a682401

理论计算性质

JChem

• Acid pKa: 13.605502
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.69309795
• LogD (pH = 7.4): -0.6902981
• Log P: -0.690262
• 摩尔折射率: 37.4636 cm^3
• 极化性: 13.709231 Å^3
• 极化表面积: 68.01 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.71
• LOG S: -0.59
• 溶解度: 3.49e+01 g/l

分子性质

理化性质

• 溶解度: 140 mg/mL; DMSO; Methanol
• 外观: White Solid
• 熔点: 167-169°C; 168-171°C; 169-174°C; 170-173 °C; 171.4; 171.4°C; 171-173 °C(lit.)
• 疏水性(logP): -0.8
• 荧光: λex 360 nm; λem 450 nm (thiol adduct); λex 433 nm; λem 500 nm in methanol (after derivatization with progesterone and as complex with Al3+)

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: Air Sensitive; Irritant
• RTECS编号: NS1751850
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22-36/37/38-40; 22-38; R:22
• 安全公开号: 26-36/37; 37; S:36/37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H301-H315-H319-H335-H351; H302-H315
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: oral, intramuscular, intravenous
• 排泄: urine (primarily), feces
• 半衰期: 0.5-1.6h (fast acetylators), 2-5h (slow acetylators)
• 代谢: liver; CYP450: 2C19, 3A4 inhibitor
• 蛋白结合率: Very low (0-10%)
• 法定药品分级: prescription only (US)
• 妊娠期药物分类: C

产品相关信息

• 纯度: ≥99% (TLC); ≥99.0% (NT); 98%; 98+%
• 级别: for fluorescence; purum
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C6H7N3O

详细说明

MP Biomedicals - 05207836

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102096

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

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]

Sigma Aldrich - 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。

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

Toronto Research Chemicals - 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

参考文献

• J. Chromatog. , 168 : 526, (1979).
• http://www.drugbank.ca/drugs/DB00951
• Brewer, G.A., et al.: Anal. Profiles Drug Subs., 6, 183 (1977)
• Weber, W.W., et al.: Clin. Pharmacokinet., 4, 401 (1979)