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
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015670
Secondary Accession Numbers
  • HMDB15670
Metabolite Identification
Common NameAlcaftadine
DescriptionAlcaftadine is only found in individuals that have used or taken this drug. It is a H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. This drug was approved in July 2010.Alcaftadine is a H1 histamine receptor antagonist and inhibitor of the release of histamine from mast cells. Decreased chemotaxis and inhibition of eosinophil activation has also been demonstrated.
Structure
Data?1582753322
Synonyms
ValueSource
AlcaftadinaChEBI
AlcaftadinumChEBI
LastacaftChEBI
Chemical FormulaC19H21N3O
Average Molecular Weight307.3895
Monoisotopic Molecular Weight307.168462309
IUPAC Name2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde
Traditional Namealcaftadine
CAS Registry Number147084-10-4
SMILES
CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3
InChI KeyMWTBKTRZPHJQLH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Azepine
  • Imidazole-4-carbonyl group
  • Aryl-aldehyde
  • N-substituted imidazole
  • Piperidine
  • Benzenoid
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic oxide
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aldehyde
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.09ALOGPS
logP2.17ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity102.88 m³·mol⁻¹ChemAxon
Polarizability34.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.40631661259
DarkChem[M-H]-171.42231661259
DeepCCS[M-2H]-203.17330932474
DeepCCS[M+Na]+178.73830932474
AllCCS[M+H]+174.232859911
AllCCS[M+H-H2O]+170.932859911
AllCCS[M+NH4]+177.332859911
AllCCS[M+Na]+178.232859911
AllCCS[M-H]-180.832859911
AllCCS[M+Na-2H]-180.232859911
AllCCS[M+HCOO]-179.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlcaftadineCN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C123848.7Standard polar33892256
AlcaftadineCN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C122592.0Standard non polar33892256
AlcaftadineCN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C122694.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alcaftadine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0290000000-89e154e3d89dbad023202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alcaftadine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alcaftadine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 10V, Positive-QTOFsplash10-0a4i-0039000000-edbab9f942994bcdc8342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 20V, Positive-QTOFsplash10-0a6r-2095000000-99aa3370392cde3889c12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 40V, Positive-QTOFsplash10-0909-4290000000-9455884b1ad78d19deb82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 10V, Negative-QTOFsplash10-0a4i-0019000000-f9c0d18e0b95b14486cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 20V, Negative-QTOFsplash10-0a4i-0096000000-07fa6dab65a51dd3e0ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 40V, Negative-QTOFsplash10-0w5d-9030000000-4a0dbea890140ccf214e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 10V, Positive-QTOFsplash10-0a4i-0009000000-9cadee9fb7834616dbdb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 20V, Positive-QTOFsplash10-0a4i-0019000000-ba6c1afcd8f5ef9452872021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 40V, Positive-QTOFsplash10-03fr-1390000000-b81ba0d09cb861c5aa362021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 10V, Negative-QTOFsplash10-0a4i-0009000000-de69c65803e567e26cea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 20V, Negative-QTOFsplash10-0a6r-0089000000-5b1ba00893773270529d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alcaftadine 40V, Negative-QTOFsplash10-001u-0190000000-b417833e34387c2564532021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06766 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06766 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06766
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID14201635
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlcaftadine
METLIN IDNot Available
PubChem Compound19371515
PDB IDNot Available
ChEBI ID71023
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 References
  1. Simons FE, Simons KJ: Histamine and H1-antihistamines: celebrating a century of progress. J Allergy Clin Immunol. 2011 Dec;128(6):1139-1150.e4. doi: 10.1016/j.jaci.2011.09.005. Epub 2011 Oct 27. [PubMed:22035879 ]
  2. Hussar DA, Samuel J: Vilazodone hydrochloride, linagliptin, and alcaftadine. J Am Pharm Assoc (2003). 2011 Jul-Aug;51(4):557-9. doi: 10.1331/JAPhA.2011.11534. [PubMed:21752782 ]
  3. Mahvan TD, Buckley WA, Hornecker JR: Alcaftadine for the prevention of itching associated with allergic conjunctivitis. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1025-32. doi: 10.1345/aph.1Q755. Epub 2012 Jul 17. [PubMed:22811343 ]

Enzymes

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