Drugbank Logo

Showing drug card for Nizatidine (DB00585)

Legend: drug field target field enzyme field

for drugs
Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:16
Primary Accession Number DB00585
Secondary Accession Number
  • APRD00706
Name Nizatidine
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms Not Available
Brand Names
  1. Acinon
  2. Antizid
  3. Axid
  4. Axid Ar
  5. Calmaxid
  6. Cronizat
  7. Distaxid
  8. Galitidin
  9. Gastrax
  10. Naxidine
  11. Niatidine
  12. Nizatidina [Spanish]
  13. Nizatidine [Usan:Ban:Inn:Jan]
  14. Nizatidinum [Latin]
  15. Nizax
  16. Nizaxid
  17. Panaxid
  18. Splendil Er
  19. Tazac
  20. Ulcosol
  21. Ulxid
  22. Zanizal
  23. Zinga
Brand Mixtures Not Available
Chemical IUPAC Name (E)-N-[2-[[2-(dimethylaminomethyl)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-N'-methyl-2-nitroethene-1,1-diamine
Chemical Formula C12H21N5O2S2
Chemical Structure Structure
CAS Registry Number 76963-41-2
InChI Identifier InChI=1/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+
InChI Key SGXXNSQHWDMGGP-IZZDOVSWBC
KEGG Drug D00440 Link Image
KEGG Compound C07270 Link Image
PubChem Compound 3033637 Link Image
PubChem Substance 191384 Link Image
ChEBI ID Not Available
PharmGKB ID PA450646 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02246046 Link Image
RxList Link http://www.rxlist.com/cgi/generic/nizat.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Nizatidine Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference R. P. Pioch, U.S. Pat. 4,375,547 (1982)
Average Molecular Weight 331.4570
Monoisotopic Molecular Weight 331.1137
State Solid
Melting Point 203 oC
Experimental Water Solubility 10-33mg/mL Source: PhysProp
Predicted Water Solubility 3.86e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.1 Source: PhysProp
Predicted LogP 0.71 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.93 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN\C(NCCSCC1=CSC(CN(C)C)=N1)=C/[N+]([O-])=O
Canonical SMILES CNC(NCCSCC1=CSC(CN(C)C)=N1)=C[N+]([O-])=O
Drug Category
  • Anti-Ulcer Agents
  • Histamine H2 Antagonists
ATC Codes
AHFS Codes
  • 56:28.12
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, active benign gastric ulcer, and active duodenal ulcer.
Pharmacology 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%)
Toxicity Oral, rat LD50: 301 mg/kg. Symptoms of overdose include cholinergic-type effects including lacrimation, salivation, emesis, miosis, and diarrhea.
Protein Binding 35%
Biotransformation 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).
Half Life 1-2 hours
Dosage Forms
Form Route
Capsule Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Enoxacin The agent decreases the absorption of enoxacin
Itraconazole The anti-H2 decreases the absorption of the imidazole
Ketoconazole The anti-H2 decreases the absorption of the imidazole
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.
Pathways
Name SMPDB Link KEGG Link
Nizatidine Pathway SMP00233 Link Image
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Histamine H2 receptor
Drug Target 1 [top]
Target 1 ID 124
Target 1 Name Histamine H2 receptor
Target 1 Synonyms
  1. Gastric receptor I
  2. H2R
Target 1 Gene Name HRH2
Target 1 Protein Sequence >Histamine H2 receptor 
MAPNGTASSFCLDSTACKITITVVLAVLILITVAGNVVVCLAVGLNRRLRNLTNCFIVSL
AITDLLLGLLVLPFSAIYQLSCKWSFGKVFCNIYTSLDVMLCTASILNLFMISLDRYCAV
MDPLRYPVLVTPVRVAISLVLIWVISITLSFLSIHLGWNSRNETSKGNHTTSKCKVQVNE
VYGLVDGLVTFYLPLLIMCITYYRIFKVARDQAKRINHISSWKAATIREHKATVTLAAVM
GAFIICWFPYFTAFVYRGLRGDDAINEVLEAIVLWLGYANSALNPILYAALNRDFRTGYQ
QLFCCRLANRNSHKTSLRSNASQLSRTQSREPRQQEEKPLKLQVWSGTEVTAPQGATDR
Target 1 Number of Residues 364
Target 1 Molecular Weight 40099
Target 1 Theoretical pI 9.39
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 Specific Function 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 23-44
  • 58-81
  • 93-114
  • 135-159
  • 181-204
  • 235-258
  • 268-289
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 184088 Link Image
Target 1 UniProtKB/Swiss-Prot ID P25021 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1080 bp 
ATGGCACCCAATGGCACAGCCTCTTCCTTTTGCCTGGACTCTACCGCATGCAAGATCACC
ATCACCGTGGTCCTTGCGGTCCTCATCCTCATCACCGTTGCTGGCAATGTGGTCGTCTGT
CTGGCCGTGGGCTTGAACCGCCGGCTCCGCAACCTGACCAATTGTTTCATCGTGTCCTTG
GCTATCACTGACCTGCTCCTCGGCCTCCTGGTGCTGCCCTTCTCTGCCATCTACCAGCTG
TCCTGCAAGTGGAGCTTTGGCAAGGTCTTCTGCAATATCTACACCAGCCTGGATGTGATG
CTCTGCACAGCCTCCATTCTTAACCTCTTCATGATCAGCCTCGACCGGTACTGCGCTGTC
ATGGACCCACTGCGGTACCCTGTGCTGGTCACCCCAGTTCGGGTCGCCATCTCTCTGGTC
TTAATTTGGGTCATCTCCATTACCCTGTCCTTTCTGTCTATCCACCTGGGGTGGAACAGC
AGGAACGAGACCAGCAAGGGCAATCATACCACCTCTAAGTGCAAAGTCCAGGTCAATGAA
GTGTACGGGCTGGTGGATGGGCTGGTCACCTTCTACCTCCCGCTACTGATCATGTGCATC
ACCTACTACCGCATCTTCAAGGTCGCCCGGGATCAGGCCAAGAGGATCAATCACATTAGC
TCCTGGAAGGCAGCCACCATCAGGGAGCACAAAGCCACAGTGACACTGGCCGCCGTCATG
GGGGCCTTCATCATCTGCTGGTTTCCCTACTTCACCGCGTTTGTGTACCGTGGGCTGAGA
GGGGATGATGCCATCAATGAGGTGTTAGAAGCCATCGTTCTGTGGCTGGGCTATGCCAAC
TCAGCCCTGAACCCCATCCTGTATGCTGCGCTGAACAGAGACTTCCGCACCGGGTACCAA
CAGCTCTTCTGCTGCAGGCTGGCCAACCGCAACTCCCACAAAACTTCTCTGAGGTCCAAC
GCCTCTCAGCTGTCCAGGACCCAAAGCCGAGAACCCAGGCAACAGGAAGAGAAACCCCTG
AAGCTCCAGGTGTGGAGTGGGACAGAAGTCACGGCCCCCCAGGGAGCCACAGACAGGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH2 Link Image
Target 1 GenAtlas ID HRH2 Link Image
Target 1 HGNC ID HGNC:5183 Link Image
Target 1 Chromosome Location 5
Target 1 Locus 5q35.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Murakami H, Sun-Wada GH, Matsumoto M, Nishi T, Wada Y, Futai M: Human histamine H2 receptor gene: multiple transcription initiation and tissue-specific expression. FEBS Lett. 1999 May 28;451(3):327-31. [PubMed Link Image]
  2. Gantz I, Munzert G, Tashiro T, Schaffer M, Wang L, DelValle J, Yamada T: Molecular cloning of the human histamine H2 receptor. Biochem Biophys Res Commun. 1991 Aug 15;178(3):1386-92. [PubMed Link Image]
  3. Nishi T, Koike T, Oka T, Maeda M, Futai M: Identification of the promoter region of the human histamine H2-receptor gene. Biochem Biophys Res Commun. 1995 May 16;210(2):616-23. [PubMed Link Image]
  4. Orange PR, Heath PR, Wright SR, Pearson RC: Allelic variations of the human histamine H2 receptor gene. Neuroreport. 1996 May 17;7(7):1293-6. [PubMed Link Image]
  5. Del Valle J, Gantz I: Novel insights into histamine H2 receptor biology. Am J Physiol. 1997 Nov;273(5 Pt 1):G987-96. [PubMed Link Image]
Target 1 Drug References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  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 Link Image]
  3. 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 Link Image]
  4. 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 Link Image]
  5. 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 Link Image]
  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 Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.