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

Molecular Formula	C12H21N5O2S2
Molecular Weight	331.457
Charge	0
Count

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

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 45 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18157166	Antagonist 2760

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 41 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8360	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 66 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8360	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 60 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e7e5162-a1e7-4fbe-895e-e598f5dc2bd3	Primary	Approved 8360	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 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1463 CYP3A 211 MATE2 261 MATE1 304 OCT1 506 OCT2 638 OAT2 144

Drug as perpetrator

Target	Modality	Activity
OCT1 523	inhibitor 3240 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	no [IC50 >115 uM]
OCT2 639	inhibitor 3240 Sources: https://link.springer.com/content/pdf/10.1007/s40262-015-0332-9.pdf#page=6 Page: 6.0	no [IC50 >115 uM]
CYP2C19 1537	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP2C9 1803	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP2D6 1875	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
CYP3A 295	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/11334262/	no
MATE1 306	inhibitor 3240 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 261	inhibitor 3240 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 146	inhibitor 3240 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
Neurotoxic convulsions induced by histamine H2 receptor antagonists in mice.	1996 Feb	8619239
Nizatidine-induced delirium in a nonagenarian.	1997 Jul	9269259
Comparative study of nizatidine and famotidine for maintenance therapy of erosive esophagitis.	2005 Feb	15683433
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942

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.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:38:55 UTC 2023` Edited by `admin` on `Wed Jul 05 23:38:55 UTC 2023`
Record UNII	P41PML4GHR
Record Status	`Validated (UNII)`
Record Version

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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