ISONIAZID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H7N3O
Molecular Weight	137.1393
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NNC(=O)C1=CC=NC=C1

InChI

InChIKey=QRXWMOHMRWLFEY-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H7N3O
Molecular Weight	137.1393
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Isoniazid is a bactericidal agent active against organisms of the genus Mycobacterium, specifically M. tuberculosis, M. bovis and M. kansasii. Isoniazid is recommended for all forms of tuberculosis in which organisms are susceptible. Isoniazid is a prodrug and must be activated by bacterial catalase. Isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. The most frequent adverse reactions to isoniazid are those affecting the nervous system and the liver.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Enoyl-[acyl-carrier-protein] reductase 5	Binding Agent 1,064		0.75 nM [Ki]
Catalase-peroxidase 3	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83	Curative		Approved 8,429	Isoniazid

C_max

Value	Dose	Analyte	Population
8.7 mg/L	15 mg/kg bw 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
7.7 mg/L	15 mg/kg 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
2.1 mg/L	5 mg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens
2.8 mg/L	5 μg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens
16.6 mg/L	15 mg/kg bw 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
3.1 mg/L	5 mg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
37.81 mg × h/L	15 mg/kg bw 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
53.17 mg × h/L	15 mg/kg 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
6.96 mg × h/L	5 mg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens
9.71 mg × h/L	5 μg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens
71.52 mg × h/L	15 mg/kg bw 2 times / week multiple, oral	ISONIAZID plasma	Homo sapiens
11.06 ng × h/L	5 mg/kg bw 1 times / day multiple, oral	ISONIAZID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
86%	unknown, unknown		ISONIAZID plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
20 g single, oral Overdose	healthy, 16 n = 1	Disc. AE: Nausea, Vomiting...
20 g single, oral Overdose	healthy, 16 n = 1	Disc. AE: Nystagmus, Hyperreflexia...
112 mg/kg single, oral (max) Overdose	unhealthy, 17 n = 1	Disc. AE: Lethargy, Seizures...
25 g single, oral Overdose	healthy, 20 n = 1	Disc. AE: Generalized tonic-clonic seizure...
900 mg 1 times / week multiple, oral Recommended	unhealthy, 25–47 n = 3986	Disc. AE: Hepatotoxicity, Hypersensitivity...

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AEs

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AE	Significance	Dose	Population
Coma	Disc. AE	20 g single, oral Overdose	healthy, 16 n = 1
Grand mal seizure	Disc. AE	20 g single, oral Overdose	healthy, 16 n = 1
Lethargy	Disc. AE	20 g single, oral Overdose	healthy, 16 n = 1
Nausea	Disc. AE	20 g single, oral Overdose	healthy, 16 n = 1
Vomiting	Disc. AE	20 g single, oral Overdose	healthy, 16 n = 1

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 CYP3A 214 CYP2E1 882 CYP1A2 1,524 CYP2A6 707		CYP2E1 128

Drug as perpetrator

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Target	Modality	Activity
CYP2C9 1,819	inhibitor 3,277	yes [Ki 102 uM]
CYP2E1 970	inhibitor 3,277	yes [Ki 110 uM]
CYP2D6 1,891	inhibitor 3,277	yes [Ki 126 uM]
CYP2C19 1,553	inhibitor 3,277	yes [Ki 13 uM]
CYP3A 298	inhibitor 3,277	yes [Ki 51.8 uM]

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY445177	https://www.001chemical.com/chem/54-85-3
3B Scientific (Wuhan) Corp	3B1-00315	http://www.3bsc.com/index/pro_info.php?id=20527
3B Scientific (Wuhan) Corp	3B3-029741	http://www.3bsc.com/index/pro_info.php?id=50998
AA Blocks	AA00I9KA	http://www.aablocks.com/goods/Goods/detail?id=AA00I9KA
AEchem Scientific Corp., USA	AE065418	https://www.aechemsc.com/info_products/AE065418.php

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PubMed

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Title	Date	PubMed
Optic neuritis due to INH complicating tuberculous meningitis.	1976 Apr	1010830
[A case of transient isoniazid-induced myoclonic seizures].	1999 Aug	10478357
Comparative in vitro antimicrobial activities of the newly synthesized quinolone HSR-903, sitafloxacin (DU-6859a), gatifloxacin (AM-1155), and levofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.	1999 Dec	10582897
Minimal change nephrotic syndrome associated with rifampicin treatment.	2000 Jul	10862648
Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids.	2001 Apr 25	11339291

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Patents

Sample Use Guides

In Vivo Use Guide

Adults: 5 mg/kg up to 300 mg daily in a single dose; or 15 mg/kg up to 900 mg/day, two or three times/week Children: 10 mg/kg to15 mg/kg up to 300 mg daily in a single dose; or 20 mg/kg to 40 mg/kg up to 900 mg/day, two or three times/week

Route of Administration: Oral

In Vitro Use Guide

1.56 μg/ml

Substance Class	Chemical
Record UNII	V83O1VOZ8L
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ISONIAZID

Official Name

English

HYDRAZID

Common Name

English

ISONIAZID COMPONENT OF RIFATER

Common Name

English

ISOBICINA

Common Name

English

ERALON

Common Name

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175483

Antibacterials

WHO-ESSENTIAL MEDICINES LIST

6.2.4 (ETH/ISO)

Combinations of drugs for treatment of tuberculosis

WHO-ATC

J04AM01

Antibacterials

WHO-ESSENTIAL MEDICINES LIST

6.2.4

Hydrazides

WHO-ATC

J04AC01

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Code System

Code

Type

Description

HSDB

1647

PRIMARY

FDA UNII

V83O1VOZ8L

PRIMARY

DRUG CENTRAL

1497

PRIMARY

RXCUI

6038

PRIMARY

RxNorm

NSC

9659

PRIMARY

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Show entries

Related Record

Type

Details


					6TC6NN0876

STEVIA REBAUDIUNA LEAF

PARENT -> CONSTITUENT ALWAYS PRESENT

Comments:

MIC value of the in vitro growth of Mycobacterium Tuberculosis (H37RV strain) of the new anti-tuberculosis terpenoid derived agent tested was 0.02?0.04 ug/ml.