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

Structure Search

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2892249

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 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18157166	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 42 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8429	NIZATIDINE Approved Use Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active duodenal ulcer. In most patients, the ulcer will heal within 4 weeks. Nizatidine capsules USP are indicated for maintenance therapy for duodenal ulcer patients at a reduced dosage of 150 mg h.s. after healing of an active duodenal ulcer. The consequences of continuous therapy with nizatidine for longer than 1 year are not known. Nizatidine capsules USP are indicated for up to 12 weeks for the treatment of endoscopically diagnosed esophagitis, including erosive and ulcerative esophagitis, and associated heartburn due to GERD. Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active benign gastric ulcer. Before initiating therapy, care should be taken to exclude the possibility of malignant gastric ulceration. Launch Date 1.31060164E12
Gastric ulcer 67 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8429	NIZATIDINE Approved Use Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active duodenal ulcer. In most patients, the ulcer will heal within 4 weeks. Nizatidine capsules USP are indicated for maintenance therapy for duodenal ulcer patients at a reduced dosage of 150 mg h.s. after healing of an active duodenal ulcer. The consequences of continuous therapy with nizatidine for longer than 1 year are not known. Nizatidine capsules USP are indicated for up to 12 weeks for the treatment of endoscopically diagnosed esophagitis, including erosive and ulcerative esophagitis, and associated heartburn due to GERD. Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active benign gastric ulcer. Before initiating therapy, care should be taken to exclude the possibility of malignant gastric ulceration. Launch Date 1.31060164E12
Gastroesophageal reflux disease 59 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8429	NIZATIDINE Approved Use Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active duodenal ulcer. In most patients, the ulcer will heal within 4 weeks. Nizatidine capsules USP are indicated for maintenance therapy for duodenal ulcer patients at a reduced dosage of 150 mg h.s. after healing of an active duodenal ulcer. The consequences of continuous therapy with nizatidine for longer than 1 year are not known. Nizatidine capsules USP are indicated for up to 12 weeks for the treatment of endoscopically diagnosed esophagitis, including erosive and ulcerative esophagitis, and associated heartburn due to GERD. Nizatidine capsules USP are indicated for up to 8 weeks for the treatment of active benign gastric ulcer. Before initiating therapy, care should be taken to exclude the possibility of malignant gastric ulceration. Launch Date 1.31060164E12

C_max

Value	Dose	Analyte	Population
1422.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
1480.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
1367.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3764.2 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
3776.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
3703.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
1.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN
1.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	NIZATIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21494s001lbl.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		NIZATIDINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/	unhealthy, adult n = 2800 Health Status: unhealthy Condition: duodenal ulcer Age Group: adult Sex: M+F Population Size: 2800 Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/	Disc. AE: Peptic ulcer disease, Cough... AEs leading to discontinuation/dose reduction: Peptic ulcer disease Cough Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/

AEs

AE	Significance	Dose	Population
Cough	Disc. AE	300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/	unhealthy, adult n = 2800 Health Status: unhealthy Condition: duodenal ulcer Age Group: adult Sex: M+F Population Size: 2800 Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/
Peptic ulcer disease	Disc. AE	300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/	unhealthy, adult n = 2800 Health Status: unhealthy Condition: duodenal ulcer Age Group: adult Sex: M+F Population Size: 2800 Sources: https://pubmed.ncbi.nlm.nih.gov/2892253/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP3A 214 MATE2 263 MATE1 306 OCT1 512 OCT2 647 OAT2 145

Drug as perpetrator

Target	Modality	Activity
OCT1 543	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	no [IC50 >115 uM]
OCT2 648	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	no [IC50 >115 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP3A 298	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
MATE1 308	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	yes [IC50 52.7 uM]
MATE2 263	inhibitor 3277 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	yes [IC50 7.81 uM]
OAT2 147	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S1347436718301113	yes [IC50 71.4 uM]

Sourcing

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

PubMed

Title	Date	PubMed
Possible nizatidine-induced subfulminant hepatic failure.	1995 Mar	7769203
Effect of anti-ulcer drugs on DNA synthesis in adult normal human hepatocytes in culture.	1995 Sep	7657287
Neurotoxic convulsions induced by histamine H2 receptor antagonists in mice.	1996 Feb	8619239
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
Aplastic anemia associated with initiation of nizatidine therapy in a hemodialysis patient.	2004 Jun	15235935
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Effect of the H2 receptor antagonist nizatidine on xerostomia in patients with primary Sjögren's syndrome.	2008	18478182
Influence of H2-receptor antagonists and proton pump inhibitors on dasatinib pharmacokinetics in Japanese leukemia patients.	2012 Apr	22147077

Patents

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.

Name

Type

Language

NIZATIDINE

Official Name

English

NIZATIDINE [HSDB]

Common Name

English

NIZATIDINE [USP-RS]

Common Name

English

NSC-759289

Code

English

ACINON

Brand Name

English

1,1-ETHENEDIAMINE, N-(2-(((2-((DIMETHYLAMINO)METHYL)-4-THIAZOLYL)METHYL)THIO)ETHYL)-N'-METHYL-2-NITRO-

Systematic Name

English

NIZATIDINE [EP MONOGRAPH]

Common Name

English

Nizatidine [WHO-DD]

Common Name

English

nizatidine [INN]

Common Name

English

NIZATIDINE [JAN]

Common Name

English

LY 139037

Code

English

NIZATIDINE [VANDF]

Common Name

English

NIZATIDINE [USP MONOGRAPH]

Common Name

English

NIZATIDINE [ORANGE BOOK]

Common Name

English

AXID

Brand Name

English

N-(2-(((2-((DIMETHYLAMINO)METHYL)-4-THIAZOLYL)METHYL)THIO)ETHYL)-N'-METHYL-2-NITRO-1,1-ETHENE DIAMINE

Common Name

English

AXID AR

Brand Name

English

NIZATIDINE [MART.]

Common Name

English

NIZATIDINE [MI]

Common Name

English

NIZATIDINE [USP IMPURITY]

Common Name

English

NIZATIDINE [USAN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548387

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

NDF-RT

N0000175784

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

WHO-VATC

QA02BA04

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

NDF-RT

N0000000151

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

NCI_THESAURUS

C29702

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

WHO-ATC

A02BA04

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

Code System Code Type Description

CHEBI

7601

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

HSDB

3574

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

LACTMED

Nizatidine

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

USAN

S-90

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

MERCK INDEX

m8017

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

Merck Index

PUBCHEM

4513

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

MESH

D016567

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

CAS

76963-41-2

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

DRUG CENTRAL

1955

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

IUPHAR

7248

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

EPA CompTox

DTXSID5023376

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

EVMPD

SUB09335MIG

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

SMS_ID

100000092426

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

DRUG BANK

DB00585

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

NCI_THESAURUS

C29295

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

RXCUI

42319

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

RxNorm

WIKIPEDIA

NIZATIDINE

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

DAILYMED

P41PML4GHR

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

RS_ITEM_NUM

1467804

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

ChEMBL

CHEMBL653

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

NSC

759289

Created by admin on Fri Dec 15 16:11:22 UTC 2023 , Edited by admin on Fri Dec 15 16:11:22 UTC 2023

PRIMARY

INN

5194

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

FDA UNII

P41PML4GHR

Created by admin on Fri Dec 15 16:11:21 UTC 2023 , Edited by admin on Fri Dec 15 16:11:21 UTC 2023

PRIMARY

ACTIVE MOIETY


					P41PML4GHR

NIZATIDINE

METABOLITE (PARENT)


					92WGS5433U

NIZATIDINE N2-OXIDE

METABOLITE (PARENT)


					5495DYZ7W0

NIZATIDINE SULFOXIDE

METABOLITE (PARENT)


					9X29GQN4HV

N2-MONODESMETHYLNIZATIDINE

Details

SMILES

InChI

DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2892249

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2892249

C_max

T_1/2

F_unbound

Drug as perpetrator