Basic information
- CAS
76963-41-2- Standard SMILES
CN/C(=C\[N+](=O)[O-])NCCSCc1csc(CN(C)C)n1- InChIKey
SGXXNSQHWDMGGP-IZZDOVSWSA-N- Molecular formula
- C12H21N5O2S2
- Average molar mass
- 331.5 g/mol
Overview
Nizatidine is a member of the class of 1,3-thiazoles having a dimethylaminomethyl substituent at position 2 and an alkylthiomethyl moiety at position 4. It has a role as a H2-receptor antagonist, a cholinergic drug and an anti-ulcer drug. It is an organic sulfide, a carboxamidine, a C-nitro compound, a member of 1,3-thiazoles and a tertiary amino compound.
Names & identifiers
- Preferred name
- Nizax
- IUPAC
- (E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
- English name
- Nizatidine
- Molecular formula
- C12H21N5O2S2
- Molecular weight
- 331.46
Names & synonyms
NizaxZanizalZE-101MFCD00865660ZL-101(E)-N-(2-(((2-((dimethylamino)methyl)thiazol-4-yl)methyl)thio)ethyl)-N'-methyl-2-nitroethene-1,1-diamineN-(2-(((2-((Dimethylamino)methyl)thiazol-4-yl)methyl)thio)ethyl)-N-methyl-2-nitroethene-1,1-diamineNCGC00016934-01C12H21N5O2S2CAS-76963-41-2(E)-N-(2-(((2-((dimethylamino)methyl)thiazol-4-yl)methyl)thio)ethyl)-N-methyl-2-nitroethene-1,1-diamine(E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
Show more names
axidNizaxiAcinongastraxnizaxidTizanon
dimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amineN'-[2-[[[2-[(Dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N-methyl-2-nitro-1,1-ethenediamineSMR000466384Acinon (TN)Axid (TN)Nizatidine (Standard)Prestwick2_000921SCHEMBL769
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 9
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Gastric and Ulcer Drugs
Pharmaceuticals -> Listed in ZINC15
LogP1.1
Solubility
10-33mg/mL
3.86e-02 g/L
>49.7 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
130-132 °C
203 °C
Physical DescriptionSolid
Collision Cross Section
168.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
168 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 130 · 130-1320C
- Boiling point
- 478.2 · 478.2±45.0 °C(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- KM6565000
- hs_code
- 29349990
- Toxicity
- LD50 in mice, rats (mg/kg): 265, >300 i.v.; 1685, 1680 orally (Pioch)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
- Hazardous Substances Data
- 76963-41-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Protein Binding35%
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-Life1-2 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).
Absorption, Distribution and Excretion
Rapid (bioavailability of nizatidine exceeds 70%)
0.8 to 1.5 L/kg
40-60 L/h
Cellular LocationsCytoplasm
Metabolite PathwaysNizatidine Action Pathway
Applications
Related reactions
5 records
Compound notes
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