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Showing metabocard for Diphenhydramine (HMDB0001927)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-18 08:39:36 UTC
Update Date2020-02-26 21:23:37 UTC
HMDB IDHMDB0001927
Secondary Accession Numbers
  • HMDB0004997
  • HMDB01927
  • HMDB04997
Metabolite Identification
Common NameDiphenhydramine
DescriptionDiphenhydramine is a histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. -- Pubchem; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been successful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder. Despite being one of the oldest antihistamines on the market, it is by and large the most effective antihistamine available, either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs. Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the (often dangerous) effects of a massive histamine release. However, it is not always the drug of choice for treating allergies. Like many other first generation antihistamines, is also a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment (ataxia), dry mouth and throat, flushed skin, rapid or irregular heartbeat (tachycardia), blurred vision at near point due to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), pupil dilatation, urinary retention, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, confusion, erectile dysfunction, and delirium. -- Wikipedia ;.
Structure
Data?1582752217
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(Benzhydryloxy)-N,N-dimethylethylamineChEBI
2-Diphenylmethoxy-N,N-demthylethanamineChEBI
alpha-(2-Dimethylaminoethoxy)diphenylmethaneChEBI
beta-Dimethylaminoethanol diphenylmethyl etherChEBI
beta-Dimethylaminoethyl benzhydryl etherChEBI
DifenhidraminaChEBI
DiphenhydraminumChEBI
N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamineChEBI
O-BenzhydryldimethylaminoethanolChEBI
RestaminKegg
a-(2-Dimethylaminoethoxy)diphenylmethaneGenerator
Α-(2-dimethylaminoethoxy)diphenylmethaneGenerator
b-Dimethylaminoethanol diphenylmethyl etherGenerator
Β-dimethylaminoethanol diphenylmethyl etherGenerator
b-Dimethylaminoethyl benzhydryl etherGenerator
Β-dimethylaminoethyl benzhydryl etherGenerator
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
Chemical FormulaC17H21NO
Average Molecular Weight255.3547
Monoisotopic Molecular Weight255.162314299
IUPAC Name[2-(diphenylmethoxy)ethyl]dimethylamine
Traditional Namediphenhydramine
CAS Registry Number147-24-0
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
InChI KeyZZVUWRFHKOJYTH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP3.44ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.93 m³·mol⁻¹ChemAxon
Polarizability29.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b6062Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-7b9eb1f702c76f6b6062Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-6900000000-84b4a2c53eae448ca1bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-0090000000-a71e531b49571f09ab25Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00kk-0980000000-cce91896f34562beeffaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-001i-1900000000-4c29bd5e0eab94596eaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a4i-9100000000-ab642e8f86de11af896cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000t-0910000000-3576ca5ec77ab87354ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-0ccd6de9ca58593fd490Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3568aae4c27ffe333c0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-22e0c745355c836f1535Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-6bb69a66a343440c64f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-1b87d83415d22bb17f1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0900000000-50251362d768cd1b1c4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-0900000000-9f37a733a05f5b01d313Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-7d73b95ed09ea2d72260Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-2900000000-1666a8ab5a6d81c0bd01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3f31841d858381760f03Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-de872e048c7e12cef490Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-de872e048c7e12cef490Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-789a4a3fe118d5bf2456Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-8ef94659f614b9ff24caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1190000000-b33f7871c289d81b8648Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-6690000000-814b7cb7faf094058c00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9500000000-98351e9c274a79fda2d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1290000000-3911d08f3498d2ef857fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-4890000000-3d0fdfdee0fffe9f228fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9500000000-41b5f1e1a6122e43b285Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9200000000-b9014c8fc8ccbba24163Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30 (0.034-0.65) uMAdult (>18 years old)BothFatally injured drivers details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01075
Phenol Explorer Compound IDNot Available
FooDB IDFDB022744
KNApSAcK IDNot Available
Chemspider ID2989
KEGG Compound IDC06960
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiphenhydramine
METLIN ID2312
PubChem Compound3100
PDB IDNot Available
ChEBI ID4636
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Enzyme Details
2. Cytochrome P450 2D6
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
Enzyme Details
3. Histamine H1 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6