IsoniazidAn antituberculosis agent and an inhibitor/activator of CYP isoenzymes

Isoniazid (CAS 54-85-3)

Isoniazid | CAS 54-85-3 is rated 5.0 out of 5 by 1.
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Synonym: INH; Isonicotinic acid hydrazide; Isonicotinic hydrazide
Application: An antituberculosis agent and an inhibitor/activator of CYP isoenzymes
CAS Number: 54-85-3
Purity: ≥98%
Molecular Weight: 137.14
Molecular Formula: C6H7N3O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Isoniazid is a front-line antituberculosis agent. Generates nitric oxide when activated by KatG. Isoniazid is also a strong inhibitor of DPH metabolism. This compound is both an inhibitor and inducer of various isoforms of cytochrome P450, a family of enzymes extensively involved in the metabolism of xenobiotics. CYP isoforms induced by this product include CYP2E1. Isoniazid reversibly inhibits CYP2C19 and CYP3A4 and inactivates CYP1A2 and CYP2A6.


References

Timmins GS, Master S, Rusnak F et al. J Bacteriol. 186:5427-31 (2004). Kutt H. Epilepsia. 16:393-402 (1975).

Physical State :
Solid
Solubility :
Soluble in water (50 mg/ml), ethanol (27 mg/ml at 25° C), DMSO (27 mg/ml at 25° C), and methanol.
Storage :
Store at room temperature
Melting Point :
171-173° C (lit.)
Boiling Point :
329.79° C (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.55
IC50 :
Mycobacterium bovis: IC50 = 4.59 nM; Mycobacterium tuberculosis H37Rv: IC50 = 70 nM; Mycobacterium tuberculosis: IC50 = 0.36 µM; Vero: IC50 = 455.74 µM (Chlorocebus aethiops); PBMC: IC50 = 634.97 µM (human)
Ki Data :
Dihydrofolate reductase: Ki= 1 nM (Mycobacterium tuberculosis); CYP2C19: Ki= 10 µM (human); CYP3A4: Ki= 36 µM (human); CYP1A2: Ki= 56 µM (human); CYP2A6: Ki= 60 µM (human)
Fluoresence :
λex 360 nm, λem 450 nm in thiol adduct
pK Values :
pKa: 11.4 (Predicted), pKb: 3.79 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
NS1751850
PubChem CID :
3767
Merck Index :
14: 5186
MDL Number :
MFCD00006426
EC Number :
200-214-6
Beilstein Registry :
119374
SMILES :
C1=CN=CC=C1C(=O)NN

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Certificate of Analysis

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Rated 5 out of 5 by from Stettner et al Stettner et al. (PubMed ID 26355945) found that isoniazid led to polyneuropathy in tuberculosis patients caused by the acetylation of NAT2. -SCBT Publication Review
Date published: 2015-03-31
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