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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 349
Experimentelle und physikochemische Eigenschaften
Color/Form
Crystals from ethanol-ethyl acetate
Off-white to buff crystalline solid
Solubility
10-33mg/mL
Soluble in water
Human Drugs
Breast Feeding; Lactation; Anti-Ulcer Agents; Histamine H2 Antagonists; Gastrointestinal Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
130-132 °C
130-132 °C
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℃)
- Aggregatzustand
- Solid
- Farbe
- Off-White to Pale Yellow
- Wasserlöslichkeit
- 21.4 g/L · 21.4g/L(temperature not stated)
- Merck
- 14 · 14,6660
- InChI
- 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
- InChIKey
- SGXXNSQHWDMGGP-UHFFFAOYSA-N
- SMILES
- C(NCCSCC1=CSC(CN(C)C)=N1)(NC)=C[N+]([O-])=O
- CAS Datenbank
- 76963 · 76963-41-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
FDA Requirements
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).
Sicherheit und Schutzausrüstung
Disposal Methods
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
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
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.
Drug Induced Liver Injury
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
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.
USGS Health-Based Screening Levels for Evaluating Water-Quality
Nizatidine
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Regulatorische Informationen
FDA Requirements
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
- safety_code
- 36
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 76963-41-2(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
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
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
1-2 hours
Half life is 10 hours.
Metabolism/Metabolites
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.
FDA Pharmacological Classification
P41PML4GHR
NIZATIDINE
Mechanisms of Action [MoA] - Histamine H2 Receptor Antagonists
Established Pharmacologic Class [EPC] - Histamine-2 Receptor Antagonist
Nizatidine is a Histamine-2 Receptor Antagonist. The mechanism of action of nizatidine is as a Histamine H2 Receptor Antagonist.
NIZATIDINE
MeSH Pharmacological Classification
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of histamine. Their clinically most important action is the inhibition of acid secretion in the treatment of gastrointestinal ulcers. Smooth muscle may also be affected. Some drugs in this class have strong effects in the central nervous system, but these actions are not well understood.
Absorption, Distribution and Excretion
Rapid (bioavailability of nizatidine exceeds 70%)
0.8 to 1.5 L/kg
40-60 L/h
Nizatidine has a duration of action of up to 10 hours. It is eliminated primarily by the kidneys; 90% of the administered dose (65% as unchanged drug) is recovered in the urine within 16 hours.
Distribution of nizatidine into human body tissues and fluids has not been fully characterized. The apparent volume of distribution of the drug is reported to be 0.8-1.5 l/kg in adults and does not appear to be altered substantially in patients with renal dysfunction.
In one study, the oral bioavailability of nizatidine exceeded 70% and was not affected by food or the anticholinergic drug, propantheline. Its apparent volume of distribution is 1.2 l/kg. Systemic clearance (10 ml/min/kg) is decreased in uremic patients and in the elderly.
Verwendung und Herstellung
Anwendungen
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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
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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