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Merck
CN

I3377

Isoniazid

analytical standard, ≥99% (TLC)

Synonym(s):

4-Pyridinecarboxylic acid hydrazide, INH, Isonicotinic acid hydrazide, Isonicotinic hydrazide

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About This Item

Empirical Formula (Hill Notation):
C6H7N3O
CAS Number:
54-85-3
Molecular Weight:
137.14
Beilstein:
119374
EC Number:
200-214-6
MDL number:
MFCD00006426
UNSPSC Code:
41116107
PubChem Substance ID:
329815370
NACRES:
NA.24

Key Documents

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grade

analytical standard

Quality Level

100

Assay

≥99% (TLC)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

171-173 °C (lit.)

fluorescence

λex 360 nm; λem 450 nm (thiol adduct)

antibiotic activity spectrum

mycobacteria

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

SMILES string

NNC(=O)c1ccncc1

InChI

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

InChI key

QRXWMOHMRWLFEY-UHFFFAOYSA-N

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General description

Chemical structure: pyridine
Isoniazid is a type of drug possessing antimycobacterial activity.It is used in the treatment of tuberculosis.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000376808
MKCW1792
0000376808
0000241662
MKCT7593

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Ram Shankar Upadhayaya et al.
European journal of medicinal chemistry, 45(5), 1854-1867 (2010-02-09)
We have designed and synthesized both the quinoline and naphthalene based molecules influenced by the unique structural make-up of mefloquine and TMC207, respectively. These compounds were evaluated for their anti-mycobacterial activity against drug sensitive Mycobacterium tuberculosis H37Rv in vitro at
Isoniazid could be used for antibiotic-loaded bone cement for musculoskeletal tuberculosis: an in vitro study
Han DC, et al.
Clinical Orthopaedics and Related Research, 471(7), 2400-2406 (2013)
Samantha Ellis et al.
Molecular pharmacology, 85(2), 269-278 (2013-11-19)
The rise in drug-resistant strains of Mycobacterium tuberculosis is a major threat to human health and highlights the need for new therapeutic strategies. In this study, we have assessed whether high-affinity iron chelators of the pyridoxal isonicotinoyl hydrazone (PIH) class
A fresh look at the mechanism of isoniazid-induced hepatotoxicity.
I G Metushi et al.
Clinical pharmacology and therapeutics, 89(6), 911-914 (2011-03-18)
Chang Dong Han et al.
Clinical orthopaedics and related research, 471(7), 2400-2406 (2013-03-19)
Antibiotic-loaded bone cement (ALBC) has been used in serious cases of musculoskeletal tuberculosis, but the type and amount of antibiotic that should be used in ALBC have not been determined. We therefore determined the (1) elution characteristics and (2) antimycobacterial
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