Nizatidine

HCID 4513CAS 76963-41-2

Grundinformationen

Standard-SMILES
CNC(=C[N+](=O)[O-])NCCSCc1csc(CN(C)C)n1
InChIKey
SGXXNSQHWDMGGP-UHFFFAOYSA-N
Summenformel
C12H21N5O2S2
Durchschnittliche Molmasse
331,5 g/mol
Monoisotopische Masse
331,11366691

Überblick

A histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers.

Namen und Bezeichner

Bevorzugter Name
Nizatidine
IUPAC
1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
Englischer Name
Nizatidine
Summenformel
C12H21N5O2S2
Molmasse
331.46

Namen und Synonyme

AcinonNizatidinaAxidAxid ArNizatidinumDTXSID5023376P41PML4GHRLY 139037NSC-7592891,1-Ethenediamine, N-(2-(((2-((dimethylamino)methyl)-4-thiazolyl)methyl)thio)ethyl)-N'-methyl-2-nitro-LY-139037N-(2-(((2-((Dimethylamino)methyl)-4-thiazolyl)methyl)thio)ethyl)-N'-methyl-2-nitro-1,1-ethenediamine
Weitere Namen anzeigen
nizaxze-101NizaxiZL-101gastraxnizaxidzanizalTizanon
N-(4-(6-Methylamino-7-nitro-2-thia-5-aza-6-hepten-1-yl)-2-thiazolylmethyl)-N,N-dimethylaminCHEBI:7601DTXCID403376n-[2-[[[2-[(dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-n'-methyl-2-nitro-1,1-ethenediamineZinga 150Zinga 300LY139037RefChem:55724

Datenbank-Bezeichner

CAS
76963-41-2
PubChem CID
4513
DTXSID
DTXSID5023376
ChEMBL
CHEMBL3183075
UNII
P41PML4GHR
EC Number
627-310-4

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,6
Polarare Oberfläche (TPSA)
140 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
9
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

Chemical ClassesPharmaceutical
OdorMild, sulfur-like odor
TasteBitter
Color/Form · 2 Einträge

Crystals from ethanol-ethyl acetate

Off-white to buff crystalline solid

Solubility · 2 Einträge

10-33mg/mL

Soluble in water

Human Drugs · 3 Einträge

Breast Feeding; Lactation; Anti-Ulcer Agents; Histamine H2 Antagonists; Gastrointestinal Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
130 · 130-1320C
Siedepunkt
478.2 · 478.2±45.0 °C(Predicted)
Dichte
1.249 · 1.249±0.06 g/cm3(Predicted)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
Sparingly soluble in water, soluble in methanol.
pka
2.1 · 2.1, 6.8(at 25℃)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Other Safety InformationIMAP assessments - 1,1-Ethenediamine, N-[2-[[[2-[(dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N'-methyl-2-nitro-: Environment tier I assessment
FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Hazard Classes and CategoriesAcute Tox. 4 (97.6%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Interactions · 5 Einträge

Concurrent use /of antacids/ with histamine H2-receptor antagonists in the treatment of peptic ulcer may be indicated for the relief of pain; however, simultaneous administration of antacids of medium to high potency (80 mmol to 150 mmol HCl) is not recommended since absorption of histamine H2-receptor antagonists may be decreased; patients should be advised not to take any antacids within 1/2 to 1 hour of histamine H2-receptor antagonists. /Histamine H2-receptor antagonists/

Concurrent use /of bone marrow depressants/ with H2-receptor antagonists may increase the risk of neutropenia or other blood dyscrasias. /Histamine H2-receptor antagonists/

Histamine H2-receptor antagonists may increase gastrointestinal pH; concurrent administration of ketoconazole with histamine H2-receptor antagonists may result in a marked reduction in absorption of ketoconazole; patients should be advised to take histamine H2-receptor antagonists at least 2 hours after ketoconazole. /Histamine H2-receptor antagonists/

Although a decrease in absorption is only reported in the literature for cimetidine and ranitidine, concurrent use with sucralfate may decrease the absorption of any H2-receptor antagonist; patients should be advised to take an H2-receptor antagonist 2 hours before sucralfate. /Histamine H2-receptor antagonists/

No drug interactions were reported when nizatidine and theophylline, lidocaine, warfarin, chlordiazepoxide, diazepam, or lorazepam were used together.

Hepatotoxicity · 1 Eintrag

Chronic therapy with nizatidine and other H2 blockers is associated with minor elevations in serum aminotransferase levels in 1% to 4% of patients, but similar rates have been reported in placebo recipients. The ALT elevations are usually asymptomatic and transient and may resolve without dose modification. Rare instances of clinically apparent liver injury have been reported in patients receiving nizatidine, but too few cases have been reported to characterize a typical time to onset or pattern of injury. More information is available on the hepatotoxicity of other H2 blockers such as ranitidine and cimetidine which have been implicated in causing clinically apparent liver injury in 1:20,000 to 1:100,000 users. The time to onset of H2 blocker induced liver injury tends to be short, between 1 and 6 weeks of starting. The typical pattern of serum enzyme elevations varies from hepatocellular to cholestatic, most cases being “mixed”. The injury can be severe, but is typically mild-to- moderate in severity and self-limited in course, resolving within 4 to 12 weeks of stopping. Immunoallergic features (rash, fever, eosinophilia) are uncommon, as is autoantibody formation. Liver biopsy histology often shows centrolobular (zone 3) necrosis with mixed cellular infiltrates and mild cholestasis.

Human Toxicity ExcerptsNizatidine may inhibit alcohol dehydrogenase in the gastric mucosa and produce higher serum levels of alcohol, but this does not appear to be clinically significant.
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nizatidine

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 5 Einträge

Studies in rats and mice with oral doses many times the recommended human dose showed no evidence of carcinogenicity.

Studies in rats and rabbits with oral doses up to 300 and 55 times the human dose, respectively, have not shown that nizatidine impairs fertility.

Rabbits treated with a dose equivalent to 300 times the human dose had abortions, a decreased number of live fetuses, and depressed fetal weights.

Nizatidine is distributed into milk in rats, and growth depression has occurred in the offspring of lactating rats treated with the drug.

For more Non-Human Toxicity Excerpts (Complete) data for NIZATIDINE (9 total), please visit the HSDB record page.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Sicherheitsdaten

wgk
3
hs_code
29349990
RTECS-Nr.
KM6565000
risk_code
22
Toxizität
LD50 in mice, rats (mg/kg): 265, >300 i.v.; 1685, 1680 orally (Pioch)
hazard_code
Xn

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding35%
Pharmacodynamics · 1 Eintrag

Nizatidine is a competitive, reversible inhibitor of histamine at the histamine H2-receptors, particularly those in the gastric parietal cells. By inhibiting the action of histamine on stomach cells, nizatidine reduces stomach acid production. Nizatidine had no demonstrable antiandrogenic action. Full-dose therapy for the problems treated by nizatidine lasts no longer than 8 weeks. It has been demonstrated that treatment with a reduced dose of nizatidine is effective as maintenance therapy following healing of active duodenal ulcers.

Mechanism of Action · 1 Eintrag

Nizatidine competes with histamine for binding at the H<sub>2</sub>-receptors on the gastric basolateral membrane of parietal cells. Competitive inhibition results in reduction of basal and nocturnal gastric acid secretions. The drug also decreases the gastric acid response to stimuli such as food, caffeine, insulin, betazole, or pentagastrin.

Biological Half-Life · 2 Einträge

1-2 hours

Half life is 10 hours.

Metabolism/Metabolites · 2 Einträge

Hepatic. Less than 7% of an oral dose is metabolized as N2-monodes-methylnizatidine, an H2-receptor antagonist, which is the principal metabolite excreted in the urine. Other likely metabolites are the N2-oxide (less than 5% of the dose) and the S-oxide (less than 6% of the dose).

Nizatidine is metabolized in the liver to N-desmethylnizatidine, nizatidine N-oxide, and nizatidine sulfoxide. Of these metabolites, only N-desmethylnizatidine has histamine H2-receptor blocking activity; studies in animals indicate that this metabolite is approximately 60% as active as nizatidine in blocking gastric acid secretion. Orally administered nizatidine undergoes minimal metabolism on first pass through the liver.

Verwendung und Herstellung

UsesMEDICATION
Methods of ManufacturingRP Pioch, Eur Pat Appl 49618; Idem, US Pat 4,375547 (1982, 1983 both to Eli Lilly)
Formulations/PreparationsEach Pulvule (capsule) contains for oral administration gelatin, pregelatinized starch, silicone, titanium dioxide, yellow iron oxide and 150 mg or 300 mg nizatidine.
Anwendungen · 2 Einträge

BeschreibungNizatidine is the fifth H2-antagonist introduced to the world market as an antiulcer agent. It is reported to be effective in the treatment of both duodenal and gastric ulcers or the prevention of their recurrences. Given once-daily, nizatidine’s bioavailability is not diminished by the concurrent administration of an antacid.

VerwendenNizatidine is used for treating stomach and duodenum ulcers and other conditions accompanied by elevated acidity of the gastrointestinal tract.

Anbieter50 Anbieter

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Ergänzende Hinweise

DefinitionChEBI: A member of the class of 1,3-thiazoles having a dimethylaminomethyl substituent at position 2 and an alkylthiomethyl moiety at position 4.

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