Banner
Identification
Name Nizatidine
Accession Number DB00585 (APRD00706)
Type small molecule
Groups approved
Description

A histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Acinon
Antizid
Axid
Axid Ar
Calmaxid
Cronizat
Distaxid
Galitidin
Gastrax
Naxidine
Niatidine
Nizatidina [Spanish]
Nizatidine [Usan:Ban:Inn:Jan]
Nizatidinum [Latin]
Nizax
Nizaxid
Panaxid
Splendil Er
Tazac
Ulcosol
Ulxid
Zanizal
Zinga
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
CAS number 76963-41-2
Weight Average: 331.457
Monoisotopic: 331.113666321
Chemical Formula C12H21N5O2S2
InChI Key InChIKey=SGXXNSQHWDMGGP-IZZDOVSWSA-N
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/b11-6+
Plain Text
IUPAC Name
dimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine
SMILES
CN\C(NCCSCC1=CSC(CN(C)C)=N1)=C/[N+]([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Thiazoles
Substructures
  • Ethers
  • Oxoazaniums
  • Nitro compounds
  • Aliphatic and Aryl Amines
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
Pharmacology
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, active benign gastric ulcer, and active duodenal ulcer.
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 H2-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.
Absorption Rapid (bioavailability of nizatidine exceeds 70%)
Volume of distribution
  • 0.8 to 1.5 L/kg
Protein binding 35%
Metabolism
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).

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Nizatidine
    		N2-monodes-methylnizatidine Details
    Route of elimination Not Available
    Half life 1-2 hours
    Clearance
    • 40-60 L/h
    • 7 – 14 L/h [functionally anephric patients]
    Toxicity Oral, rat LD50: 301 mg/kg. Symptoms of overdose include cholinergic-type effects including lacrimation, salivation, emesis, miosis, and diarrhea.
    Affected organisms
    • Humans and other mammals
    Pathways
    Pathway Name SMPDB ID
    Smp00233 Nizatidine Pathway SMP00233
    Pharmacoeconomics
    Manufacturers
    • Smithkline beecham corp dba glaxosmithkline
    • Apotex inc
    • Dr reddys laboratories ltd
    • Genpharm inc
    • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
    • Mylan pharmaceuticals inc
    • Sandoz inc
    • Teva pharmaceuticals usa inc
    • Watson laboratories inc
    • Braintree laboratories inc
    • Amneal pharmaceuticals
    • Wyeth consumer healthcare
    Packagers
    Dosage forms
    Form Route Strength
    Capsule Oral
    Prices
    Unit description Cost Unit
    Axid 300 mg pulvule 6.0 USD each
    Nizatidine 300 mg capsule 4.97 USD capsule
    Axid 300 mg Capsule 3.98 USD capsule
    Axid 150 mg pulvule 3.62 USD each
    Nizatidine 150 mg capsule 2.48 USD capsule
    Axid 150 mg Capsule 2.06 USD capsule
    Apo-Nizatidine 300 mg Capsule 0.96 USD capsule
    Novo-Nizatidine 300 mg Capsule 0.96 USD capsule
    Pms-Nizatidine 300 mg Capsule 0.96 USD capsule
    Axid 15 mg/ml Solution 0.84 USD ml
    Nizatidine 15 mg/ml Solution 0.76 USD ml
    Apo-Nizatidine 150 mg Capsule 0.53 USD capsule
    Gen-Nizatidine 150 mg Capsule 0.53 USD capsule
    Novo-Nizatidine 150 mg Capsule 0.53 USD capsule
    Pms-Nizatidine 150 mg Capsule 0.53 USD capsule
    Axid ar 75 mg tablet 0.3 USD tablet
    First Prev Next Last
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    Patents
    Country Patent Number Approved Expires (estimated)
    United States 6930119 2002-07-17 2022-07-17
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 130-132 °C PhysProp
    water solubility 10-33mg/mL Not Available
    logP 1.1 Not Available
    Predicted Properties
    Property Value Source
    water solubility 3.86e-02 g/l ALOGPS
    logP 0.7 ALOGPS
    logP 0.76 ChemAxon
    logS -3.9 ALOGPS
    pKa (strongest basic) 6.83 ChemAxon
    physiological charge 0 ChemAxon
    hydrogen acceptor count 6 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 86.01 ChemAxon
    rotatable bond count 10 ChemAxon
    refractivity 96.84 ChemAxon
    polarizability 35.49 ChemAxon
    References
    Synthesis Reference Not Available
    General Reference Not Available
    External Links
    Resource Link
    KEGG Drug D00440 Link_out
    KEGG Compound C07270 Link_out
    PubChem Compound 3033637 Link_out
    PubChem Substance 46507554 Link_out
    ChemSpider 2298266 Link_out
    Therapeutic Targets Database DAP000339 Link_out
    PharmGKB PA164752234 Link_out
    Drug Product Database 2246046 Link_out
    RxList http://www.rxlist.com/cgi/generic/nizat.htm Link_out
    Drugs.com http://www.drugs.com/cdi/nizatidine.html Link_out
    Wikipedia http://en.wikipedia.org/wiki/Nizatidine Link_out
    ATC Codes
    • A02BA04
    AHFS Codes
    • 56:28.12
    PDB Entries Not Available
    FDA label show (380 KB)
    MSDS Not Available
    Interactions
    Drug Interactions
    Drug Interaction
    Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
    Cefditoren H2-Antagonists such as nizatidine may decrease the serum concentration of cefditoren. Cefditoren prescribing information recommends to avoid concomitant use with H2-antagonists (eg, famotidine, ranitidine) and antacids as well. Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of H2-antagonists can not be avoided.
    Enoxacin Nizatidine may decrease the absorption of enoxacin.
    Itraconazole The H2-receptor antagonist, nizatidine, may decrease the absorption of itraconazole.
    Ketoconazole The H2-receptor antagonist, nizatidine, may decrease the absorption of ketoconazole.
    Food Interactions
    • Avoid alcohol.
    • Avoid excessive quantities of coffee or tea (Caffeine).
    • Do not take Aluminum or magnesium antacids or supplements while on this medication.
    • May take Vitamin D.
    • No iron, zinc or fluoride within 2 hours of taking this medication.
    • Take without regard to meals.
    Targets

    1. Histamine H2 receptor

    Pharmacological action: yes
    Actions: antagonist

    The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway

    Organism class: human
    UniProt ID: P25021 Link_out
    Gene: HRH2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
    2. Enriz RD, Jauregui EA: [Theoretical conformation study of tiotidine and nizatidine, two strong histamine H2-receptor antagonists] Acta Cient Venez. 1991;42(2):70-6. Pubmed
    3. Meredith CG, Speeg KV Jr, Schenker S: Nizatidine, a new histamine H2-receptor antagonist, and hepatic oxidative drug metabolism in the rat: a comparison with structurally related compounds. Toxicol Appl Pharmacol. 1985 Feb;77(2):315-24. Pubmed
    4. Lin TM, Evans DC, Warrick MW, Pioch RP: Actions of nizatidine, a selective histamine H2-receptor antagonist, on gastric acid secretion in dogs, rats and frogs. J Pharmacol Exp Ther. 1986 Nov;239(2):406-10. Pubmed
    5. Okabe S, Takeuchi K, Okada M, Kumadaki Y, Nakata M, Nakata H: [Effects of nizatidine, a new histamine H2-receptor antagonist, on gastric acid secretion and various gastric and duodenal lesions in rats: comparison with cimetidine] Nippon Yakurigaku Zasshi. 1989 Mar;93(3):133-44. Pubmed
    6. Kounenis G, Koutsoviti-Papadopoulou M, Elezoglou V: The excitatory effect of the new histamine H2-receptor antagonist nizatidine (LY 139037) on the guinea pig ileum. J Pharmacobiodyn. 1987 Nov;10(11):669-72. Pubmed
    Enzymes

    1. Cholinesterase

    Actions: inhibitor

    An acylcholine + H(2)O = choline + a carboxylate

    UniProt ID: P06276 Link_out
    Gene: BCHE Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. Laine-Cessac P, Turcant A, Premel-Cabic A, Boyer J, Allain P: Inhibition of cholinesterases by histamine 2 receptor antagonist drugs. Res Commun Chem Pathol Pharmacol. 1993 Feb;79(2):185-93. Pubmed
    Transporters

    1. Multidrug resistance protein 1

    Actions: substrate

    Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

    UniProt ID: P08183 Link_out
    Gene: ABCB1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. Epub 2009 Mar 25. Pubmed
    Comments
    Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19