Hmdb loader
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
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 08:46:24 UTC
Update Date2022-03-07 02:49:11 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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.93Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available166.982http://allccs.zhulab.cn/database/detail?ID=AllCCS00000695
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+172.46232859911
AllCCS[M-H]-174.12832859911
DeepCCS[M+H]+167.7830932474
DeepCCS[M-H]-164.32730932474
DeepCCS[M-2H]-199.90330932474
DeepCCS[M+Na]+176.19430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RanitidineCN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O3255.4Standard polar33892256
RanitidineCN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O2113.5Standard non polar33892256
RanitidineCN\C(NCCSCC1=CC=C(CN(C)C)O1)=C/[N+]([O-])=O2692.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ranitidine,1TMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)O12760.9Semi standard non polar33892256
Ranitidine,1TMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)O12499.7Standard non polar33892256
Ranitidine,1TMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)O13560.8Standard polar33892256
Ranitidine,1TMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C2728.2Semi standard non polar33892256
Ranitidine,1TMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C2522.0Standard non polar33892256
Ranitidine,1TMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C3619.3Standard polar33892256
Ranitidine,2TMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)[Si](C)(C)C)O12684.6Semi standard non polar33892256
Ranitidine,2TMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)[Si](C)(C)C)O12683.7Standard non polar33892256
Ranitidine,2TMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C)[Si](C)(C)C)O13102.2Standard polar33892256
Ranitidine,1TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)O12941.6Semi standard non polar33892256
Ranitidine,1TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)O12722.7Standard non polar33892256
Ranitidine,1TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)O13574.5Standard polar33892256
Ranitidine,1TBDMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C(C)(C)C2921.5Semi standard non polar33892256
Ranitidine,1TBDMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C(C)(C)C2735.0Standard non polar33892256
Ranitidine,1TBDMS,isomer #2CN/C(=C\[N+](=O)[O-])N(CCSCC1=CC=C(CN(C)C)O1)[Si](C)(C)C(C)(C)C3604.8Standard polar33892256
Ranitidine,2TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O13099.3Semi standard non polar33892256
Ranitidine,2TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O13006.0Standard non polar33892256
Ranitidine,2TBDMS,isomer #1CN(C)CC1=CC=C(CSCCN(/C(=C/[N+](=O)[O-])N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O13217.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ranitidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-4920000000-0ff56d86c0b8ad4464b82017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ranitidine 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 - Ranitidine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-01ot-7906000000-d0c73cd55f0c88b5292c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004j-2900000000-72810aa2bdb337010c712012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0f92-3900000000-4984706aec6a10a3a7012012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-03di-0009000000-3a9ffadb8ced05c4f2f12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-006x-0900000000-26410712c1d9fca3970f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-02ml-0900000000-b8d8d8a38eb5ff79811d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-03di-2900000000-417be0cb4c8a324c3ae42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-03di-5900000000-ca80edf051507a622e912012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-014i-0009000000-e8f56e6282043759674e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00vi-0933000000-aaee0f5a149286ba88342012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0059-1900000000-52e4e1bcfef85a6bafea2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0faj-2900000000-e412e77b79750d8bb5132012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0uea-4900000000-76d786153c89ecf65f8c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00fr-0930000000-01f54848489d6a7b4da42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0970000000-49b8e0b710b97f5d5da62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00kf-0900000000-cf634d229fba340e6e3b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-001i-0900000000-09008c251fc8dd33b8bf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00e9-4900000000-350ded3a1f334f8103b12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-052f-0900000000-14196f34248aa3cac7fc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0f79-0900000000-0a386c1d346e415344692012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ranitidine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0udi-0900000000-4296a8171c03e3b2b6892012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ranitidine 10V, Positive-QTOFsplash10-014i-0009000000-8f1190f23bd90f0c3b382017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ranitidine 20V, Positive-QTOFsplash10-0a4i-1549000000-af62393506f3591718fb2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ranitidine 40V, Positive-QTOFsplash10-03fr-5900000000-95db7e388662e86b05202017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ranitidine 10V, Negative-QTOFsplash10-03di-1109000000-0f5426155ce76257c4a22017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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