pyridine-4-carbohydrazide

• ChemBase ID: 827
• Molecular Formular: C6H7N3O
• Molecular Mass: 137.13928
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine-4-carbohydrazide
• IUPAC Traditional name: isoniazid
• Brand Name: 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
• Synonyms: 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; 异烟酸肼; 雷米封; 异烟肼

Database IDs

• CAS Number: 54-85-3
• EC Number: 200-214-6
• MDL Number: MFCD00006426
• Beilstein Number: 119374
• Merck Index: 145186
• PubChem SID: 46506039; 24896031; 160964290
• PubChem CID: 3767
• CHEBI ID: 6030
• ATC CODE: J04AC01
• CHEMBL: 64
• Chemspider ID: 3635
• DrugBank ID: DB00951
• KEGG ID: D00346
• Unique Ingredient Identifier: V83O1VOZ8L
• Wikipedia Title: Isoniazid
• Medline Plus: a682401

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.605502
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.69309795
• LogD (pH = 7.4): -0.6902981
• Log P: -0.690262
• Molar Refractivity: 37.4636 cm^3
• Polarizability: 13.709231 Å^3
• Polar Surface Area: 68.01 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.71
• LOG S: -0.59
• Solubility (Water): 3.49e+01 g/l

PROPERTIES

Physical Property

• Solubility: 140 mg/mL; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 167-169°C; 168-171°C; 169-174°C; 170-173 °C; 171.4; 171.4°C; 171-173 °C(lit.)
• Hydrophobicity(logP): -0.8
• Fluorescence: 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+)

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Air Sensitive; Irritant
• RTECS: NS1751850
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-36/37/38-40; 22-38; R:22
• Safety Statements: 26-36/37; 37; S:36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335-H351; H302-H315
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: oral, intramuscular, intravenous
• Excretion: urine (primarily), feces
• Half Life: 0.5-1.6h (fast acetylators), 2-5h (slow acetylators)
• Metabolism: liver; CYP450: 2C19, 3A4 inhibitor
• Protein Bound: Very low (0-10%)
• Legal Status: prescription only (US)
• Pregnancy Category: C

Product Information

• Purity: ≥99% (TLC); ≥99.0% (NT); 98%; 98+%
• Grade: for fluorescence; purum
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C6H7N3O

DETAILS

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
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.

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

REFERENCES

• 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)