You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-18 08:46:24 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0001930
Secondary Accession Numbers
  • HMDB0005003
  • HMDB01930
  • HMDB05003
Metabolite Identification
Common NameRanitidine
DescriptionRanitidine (CAS: 66357-35-5) is a non-imidazole blocker of histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers (PubChem). Ranitidine is a histamine H2-receptor antagonist that inhibits stomach acid production and is commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD). It is currently marketed by GlaxoSmithKline under the trade name Zantac (Wikipedia ).
Structure
Data?1582752217
Synonyms
ValueSource
RanitidinaChEBI
RanitidinumChEBI
2-(Benzhydryloxy)-N,N-dimethylethylamineHMDB
2-Diphenylmethoxy-N,N-demthylethanamineHMDB
alpha-(2-Dimethylaminoethoxy)diphenylmethaneHMDB
beta-Dimethylaminoethanol diphenylmethyl etherHMDB
beta-Dimethylaminoethyl benzhydryl etherHMDB
DifenhidraminaHMDB
DiphenhydraminumHMDB
N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamineHMDB
O-BenzhydryldimethylaminoethanolHMDB
RestaminHMDB
a-(2-Dimethylaminoethoxy)diphenylmethaneHMDB
Α-(2-dimethylaminoethoxy)diphenylmethaneHMDB
b-Dimethylaminoethanol diphenylmethyl etherHMDB
Β-dimethylaminoethanol diphenylmethyl etherHMDB
b-Dimethylaminoethyl benzhydryl etherHMDB
Β-dimethylaminoethyl benzhydryl etherHMDB
BenadrylHMDB
DobacenHMDB
BendylateHMDB
DimedrolumHMDB
AlledrylHMDB
AllerganHMDB
AllerginaHMDB
BenzantinHMDB
DifenhydramineHMDB
DimedrolHMDB
Dimethylamine benzhydryl esterHMDB
DiphamineHMDB
DiphantineHMDB
AllerdrylHMDB
BenzhydramineHMDB
BenhydraminHMDB
Diphenhydramine citrate (1:1)HMDB
DiphenylhydramineHMDB
2-Diphenylmethoxy-N,N-dimethylethylamineHMDB
BenylinHMDB
DiphenylhydraminHMDB
Citrate, diphenhydramineHMDB
Diphenhydramine citrateHMDB
Diphenhydramine hydrochlorideHMDB
DorminHMDB
Hydrochloride, diphenhydramineHMDB
AchedosHMDB
AcidexHMDB
AturalHMDB
AxobanHMDB
CoralenHMDB
CuranHMDB
DuractinHMDB
EzoptaHMDB
GastrialHMDB
GastrosedolHMDB
IstomarHMDB
LogastHMDB
MauranHMDB
MicrotidHMDB
PtinolinHMDB
QuantorHMDB
QuicranHMDB
RadinatHMDB
RandinHMDB
RanidineHMDB
RaninHMDB
RaniogasHMDB
RanisenHMDB
RaniterHMDB
Ranitidine (form I and form II)HMDB
Ranitidine baseHMDB
Ranitidine HCL 1/2 typeHMDB
RanitigetHMDB
RantacidHMDB
RantidineHMDB
RaticHMDB
RaticinaHMDB
RNDHMDB
SampepHMDB
TauralHMDB
Ul-pepHMDB
UlceraninHMDB
UrantacHMDB
VerlostHMDB
VesycaHMDB
VizerulHMDB
WeichilinHMDB
WeidosHMDB
XanidineHMDB
ZantabHMDB
ZANTACHMDB
ZantadinHMDB
Hydrochloride, ranitidineHMDB
RanitidinHMDB
BiotidinHMDB
Ranitidine hydrochlorideHMDB
SostrilHMDB
N (2-(((5-((Dimethylamino)methyl)-2-furanyl)methyl)thio)ethyl)-n'-methyl-2-nitro-1,1-ethenediamineHMDB
ZanticHMDB
(e)-RanitidineHMDB
RanitidineHMDB
Chemical FormulaC13H22N4O3S
Average Molecular Weight314.404
Monoisotopic Molecular Weight314.14126128
IUPAC Namedimethyl[(5-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine
Traditional Nameranitidine
CAS Registry Number82530-72-1
SMILES
CN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O
InChI Identifier
InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
InChI KeyVMXUWOKSQNHOCA-UKTHLTGXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Furan
  • Heteroaromatic compound
  • C-nitro compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organic nitro compound
  • Secondary aliphatic amine
  • Organic oxoazanium
  • Secondary amine
  • Thioether
  • Sulfenyl compound
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic zwitterion
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.93Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP0.79ALOGPS
logP0.99ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)7.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.58 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity94.15 m³·mol⁻¹ChemAxon
Polarizability33.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-4920000000-0ff56d86c0b8ad4464b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ot-7906000000-d0c73cd55f0c88b5292cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004j-2900000000-72810aa2bdb337010c71Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f92-3900000000-4984706aec6a10a3a701Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0009000000-3a9ffadb8ced05c4f2f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-006x-0900000000-26410712c1d9fca3970fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-02ml-0900000000-b8d8d8a38eb5ff79811dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-2900000000-417be0cb4c8a324c3ae4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-03di-5900000000-ca80edf051507a622e91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0009000000-e8f56e6282043759674eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00vi-0933000000-aaee0f5a149286ba8834Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0059-1900000000-52e4e1bcfef85a6bafeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0faj-2900000000-e412e77b79750d8bb513Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0uea-4900000000-76d786153c89ecf65f8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00fr-0930000000-01f54848489d6a7b4da4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0970000000-49b8e0b710b97f5d5da6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00kf-0900000000-cf634d229fba340e6e3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-001i-0900000000-09008c251fc8dd33b8bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00e9-4900000000-350ded3a1f334f8103b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-052f-0900000000-14196f34248aa3cac7fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f79-0900000000-0a386c1d346e41534469Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-4296a8171c03e3b2b689Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-8f1190f23bd90f0c3b38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1549000000-af62393506f3591718fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-5900000000-95db7e388662e86b0520Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1109000000-0f5426155ce76257c4a2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.3 (0.63-16.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00863
Phenol Explorer Compound IDNot Available
FooDB IDFDB022747
KNApSAcK IDNot Available
Chemspider ID2272523
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRanitidine
METLIN IDNot Available
PubChem Compound3001055
PDB IDNot Available
ChEBI ID8776
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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