NIZATIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H21N5O2S2
Molecular Weight	331.457
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CNC(NCCSCC1=CSC(CN(C)C)=N1)=C[N+]([O-])=O

InChI

InChIKey=SGXXNSQHWDMGGP-WDZFZDKYSA-N

InChI=1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6-

HIDE SMILES / InChI

Molecular Formula	C12H21N5O2S2
Molecular Weight	331.457
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

Nizatidine, chemically N-[2-[[[2- [(dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N’ -methyl-2-nitro-1,1-ethenediamine, is a histamine H2-receptor antagonist. Nizatidine reduced gastric acid secretion for up to 8 h suggesting that this compound could be used in with a once or twice daily dosage regime. Nizatidine was rapidly and well-absorbed orally, was widely distributed in tissues and the majority of the dose was excreted in the urine within 24 h. Nizatidine is indicated for duodenal and gastric ulcer as well as for the treatment of endoscopically diagnosed esophagitis, including erosive and ulcerative esophagitis, and associated heartburn due to gastroesophageal reflux disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H2 receptor 46	Antagonist 2,778

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42	Primary	Approved 8,429	NIZATIDINE
Gastric ulcer 67	Primary	Approved 8,429	NIZATIDINE
Gastroesophageal reflux disease 59	Primary	Approved 8,429	NIZATIDINE

C_max

Value	Dose	Analyte	Population
1422.9 ng/mL	150 mg single, oral	NIZATIDINE plasma	Homo sapiens
1480.2 ng/mL	150 mg 1 times / day steady-state, oral	NIZATIDINE plasma	Homo sapiens
1367.6 ng/mL	150 mg single, oral	NIZATIDINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3764.2 ng × h/mL	150 mg single, oral	NIZATIDINE plasma	Homo sapiens
3776.1 ng × h/mL	150 mg 1 times / day steady-state, oral	NIZATIDINE plasma	Homo sapiens
3703.1 ng × h/mL	150 mg single, oral	NIZATIDINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.2 h	150 mg single, oral	NIZATIDINE plasma	Homo sapiens
1.3 h	150 mg 1 times / day steady-state, oral	NIZATIDINE plasma	Homo sapiens
1.4 h	150 mg single, oral	NIZATIDINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
65%	150 mg single, oral		NIZATIDINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
300 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult n = 2800	Disc. AE: Peptic ulcer disease, Cough...

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AEs

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AE	Significance	Dose	Population
Cough	Disc. AE	300 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult n = 2800
Peptic ulcer disease	Disc. AE	300 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult n = 2800

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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 MATE2 263 MATE1 306 OCT1 512 OCT2 647 OAT2 145

Drug as perpetrator

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Target	Modality	Activity
OCT1 543	inhibitor 3,277	no [IC50 >115 uM]
OCT2 648	inhibitor 3,277	no [IC50 >115 uM]
CYP2C19 1,553	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no
CYP2D6 1,891	inhibitor 3,277	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7601	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7601
MolPort	MolPort-027-655-252	https://www.molport.com/shop/molecule-link/MolPort-027-655-252
eMolecules	32278146	https://www.emolecules.com/cgi-bin/more?vid=32278146

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PubMed

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Title	Date	PubMed
Nizatidine-induced delirium in a nonagenarian.	1997 Jul	9269259
Effects of different antisecretory drugs on gastric potential difference in the rat: comparison with sucralfate.	1998 Dec	9990656
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942

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Sample Use Guides

In Vivo Use Guide

Active Duodenal Ulcer: The recommended oral dosage of adults is 300 mg once daily at bedtime. An alternative dosage regimen is 150 mg twice daily. Maintenance of Healed Duodenal Ulcer: The recommended oral dosage for adults is 150 mg once daily at bedtime. Gastroesophageal Reflux Disease: The recommended oral dosage in adults for the treatment of erosions, ulcerations, and associated heartburn is 150 mg twice daily. Active Benign Gastric Ulcer: The recommended oral dosage is 300 mg given either as 150 mg twice daily or 300 mg once daily at bedtime. Prior to treatment, care should be taken to exclude the possibility of malignant gastric ulceration.

Route of Administration: Oral

In Vitro Use Guide

In guinea pig antral muscle strips nizatidine increased the amplitude of spontaneous phasic antral contractions in a concentration-dependent fashion with threshold concentrations of 5 uM. In isolated cells, nizatidine induced concentration-dependent cell shortening, with maximal shortening at 10 uM.