U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of NIZATIDINE

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
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

Curator's Comment: Known to be CNS non-penetrant in human. However, also known to be CNS active in mouse: nizatidine induces clonic and/or tonic convulsion in mice when administered intracerebrally, so in vivo BBB penetration in unclear https://www.ncbi.nlm.nih.gov/pubmed/8619239

Originator

Sources: R.P. Pioch (Lilly, Eli and Co.) U.S. 4.382.090, 03 May 1983, U.S. Appl. 193.192, 02 Oct. 1980, 23 pp. Cont.- in part of U.S. 4.375.547; Chem. Abstr. 99 43548w (1983).
Curator's Comment: Reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/9260662

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

2011
Primary
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

2011
Primary
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

2011
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1422.9 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
3764.2 ng × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.2 h
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
n = 2800
Health Status: unhealthy
Condition: duodenal ulcer
Age Group: adult
Sex: M+F
Population Size: 2800
Sources:
Disc. AE: Peptic ulcer disease, Cough...
AEs leading to
discontinuation/dose reduction:
Peptic ulcer disease
Cough
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, adult
n = 2800
Health Status: unhealthy
Condition: duodenal ulcer
Age Group: adult
Sex: M+F
Population Size: 2800
Sources:
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:
unhealthy, adult
n = 2800
Health Status: unhealthy
Condition: duodenal ulcer
Age Group: adult
Sex: M+F
Population Size: 2800
Sources:
PubMed

PubMed

TitleDatePubMed
Neurotoxic convulsions induced by histamine H2 receptor antagonists in mice.
1996 Feb
Influence of H2-receptor- and proton pump inhibitors on some functions of the oxydative and conjugative drug metabolism.
1996 Jul
Nizatidine-induced delirium in a nonagenarian.
1997 Jul
Effects of different antisecretory drugs on gastric potential difference in the rat: comparison with sucralfate.
1998 Dec
Effects of histamine H(2)-receptor antagonists on human plasma levels of calcitonin gene-related peptide, substance P and vasoactive intestinal peptide.
2002 Nov
Extrapyramidal symptoms related to adjunctive nizatidine therapy in an adolescent receiving quetiapine and paroxetine.
2004 Jul
Aplastic anemia associated with initiation of nizatidine therapy in a hemodialysis patient.
2004 Jun
Comparative study of nizatidine and famotidine for maintenance therapy of erosive esophagitis.
2005 Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Effect of the H2 receptor antagonist nizatidine on xerostomia in patients with primary Sjögren's syndrome.
2008
Patents

Sample Use Guides

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 Fri Dec 15 16:11:21 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:21 GMT 2023
Record UNII
P41PML4GHR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIZATIDINE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
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 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
NDF-RT N0000175784
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
WHO-VATC QA02BA04
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
NDF-RT N0000000151
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
NCI_THESAURUS C29702
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
WHO-ATC A02BA04
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Code System Code Type Description
CHEBI
7601
Created by admin on Fri Dec 15 16:11:21 GMT 2023 , Edited by admin on Fri Dec 15 16:11:21 GMT 2023
PRIMARY
HSDB
3574
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PRIMARY
LACTMED
Nizatidine
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
PRIMARY
USAN
S-90
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PRIMARY
MERCK INDEX
m8017
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PRIMARY Merck Index
PUBCHEM
4513
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PRIMARY
MESH
D016567
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PRIMARY
CAS
76963-41-2
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PRIMARY
DRUG CENTRAL
1955
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PRIMARY
IUPHAR
7248
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PRIMARY
EPA CompTox
DTXSID5023376
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PRIMARY
EVMPD
SUB09335MIG
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PRIMARY
SMS_ID
100000092426
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PRIMARY
DRUG BANK
DB00585
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PRIMARY
NCI_THESAURUS
C29295
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PRIMARY
RXCUI
42319
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PRIMARY RxNorm
WIKIPEDIA
NIZATIDINE
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
PRIMARY
DAILYMED
P41PML4GHR
Created by admin on Fri Dec 15 16:11:21 GMT 2023 , Edited by admin on Fri Dec 15 16:11:21 GMT 2023
PRIMARY
RS_ITEM_NUM
1467804
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PRIMARY
ChEMBL
CHEMBL653
Created by admin on Fri Dec 15 16:11:21 GMT 2023 , Edited by admin on Fri Dec 15 16:11:21 GMT 2023
PRIMARY
NSC
759289
Created by admin on Fri Dec 15 16:11:22 GMT 2023 , Edited by admin on Fri Dec 15 16:11:22 GMT 2023
PRIMARY
INN
5194
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PRIMARY
FDA UNII
P41PML4GHR
Created by admin on Fri Dec 15 16:11:21 GMT 2023 , Edited by admin on Fri Dec 15 16:11:21 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
About 7% of dose
MAJOR
URINE
METABOLITE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
about 5% of dose
MINOR
URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC