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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:13 UTC
HMDB IDHMDB0014723
Secondary Accession Numbers
  • HMDB14723
Metabolite Identification
Common NameNizatidine
DescriptionNizatidine is only found in individuals that have used or taken this drug. It is a histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers. [PubChem]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.
Structure
Data?1582753213
Synonyms
ValueSource
AcinonKegg
AxidKegg
N-(2-(((2-((Dimethylamino)methyl)-4-thiazolyl)methyl)thio)ethyl)-n'-methyl-2-nitro-1,1-ethenediamineHMDB
Chemical FormulaC12H21N5O2S2
Average Molecular Weight331.457
Monoisotopic Molecular Weight331.113666321
IUPAC Namedimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine
Traditional Namenizatidine
CAS Registry Number76963-41-2
SMILES
CN\C(NCCSCC1=CSC(CN(C)C)=N1)=C/[N+]([O-])=O
InChI Identifier
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+
InChI KeySGXXNSQHWDMGGP-IZZDOVSWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,4-disubstituted thiazoles. 2,4-Disubstituted thiazoles are compounds containing a thiazole ring substituted at the positions 2 and 3.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent2,4-disubstituted thiazoles
Alternative Parents
Substituents
  • 2,4-disubstituted 1,3-thiazole
  • Aralkylamine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • C-nitro compound
  • Tertiary amine
  • Organic nitro compound
  • Azacycle
  • Secondary amine
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Sulfenyl compound
  • Secondary aliphatic amine
  • Thioether
  • Organic nitrogen compound
  • Organic zwitterion
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP1.1Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM168.430932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP10(0.7) g/LALOGPS
logP10(0.76) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Basic)6.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.01 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.84 m³·mol⁻¹ChemAxon
Polarizability35.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nizatidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2910000000-18ba48a4b120dcbf820a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nizatidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine , positive-QTOFsplash10-001i-0349000000-2a6088cb0e1eb80f3f6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 35V, Positive-QTOFsplash10-053r-2962000000-af0953b53762d684a7f92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 40V, Negative-QTOFsplash10-0006-3900000000-194e7cece27e534ee61b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 10V, Positive-QTOFsplash10-001i-1259000000-fe59bd6bf47122b6de6f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 40V, Positive-QTOFsplash10-0a4i-9400000000-38b4f191ddd33fdb149f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 20V, Positive-QTOFsplash10-0a4i-7940000000-5e405e100f346c41156c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 35V, Negative-QTOFsplash10-000f-0900000000-b4517e52ff4ebfbbc12c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 20V, Negative-QTOFsplash10-000l-0900000000-fbe98f72fa4e7270b72c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nizatidine 10V, Negative-QTOFsplash10-000l-0901000000-57d963e7abc0488ae2952021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 10V, Positive-QTOFsplash10-0a4i-9503000000-d9c4ae72a0bbee2430782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 20V, Positive-QTOFsplash10-0a4i-7910000000-ded6129af58d4061283e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 40V, Positive-QTOFsplash10-0a4i-9300000000-dda35ba52715412d6edc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 10V, Negative-QTOFsplash10-0159-1913000000-011577e2edf7864fa5052017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 20V, Negative-QTOFsplash10-004i-1900000000-234387ab1482c0848d2e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nizatidine 40V, Negative-QTOFsplash10-0kfx-8900000000-742126cc2ddd91b34cd32017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00585 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00585 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2298266
KEGG Compound IDC07270
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNizatidine
METLIN IDNot Available
PubChem Compound3033637
PDB IDNot Available
ChEBI ID127604
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
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:8095733 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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:1843561 ]
  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:2858133 ]
  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:2877081 ]
  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]. Nihon Yakurigaku Zasshi. 1989 Mar;93(3):133-44. [PubMed:2567267 ]
  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:2895808 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
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. doi: 10.1208/s12248-009-9092-5. Epub 2009 Mar 25. [PubMed:19319690 ]