Alcaftadine (CHEM022365)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:30:03 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022365
Identification
Common NameAlcaftadine
ClassSmall Molecule
DescriptionAn imidazobenzazepine that is 6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine substituted at position 3 by a formyl group and at position 11 by a 1-methylpiperidin-4-ylidene group. An antihistamine used for treatment of allergic conjunctivitis.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AlcaftadinaChEBI
AlcaftadinumChEBI
LastacaftChEBI
Chemical FormulaC19H21N3O
Average Molecular Mass307.390 g/mol
Monoisotopic Mass307.168 g/mol
CAS Registry Number147084-10-4
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
SMILESCN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0290000000-89e154e3d89dbad02320Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0039000000-edbab9f942994bcdc834Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2095000000-99aa3370392cde3889c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0909-4290000000-9455884b1ad78d19deb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-f9c0d18e0b95b14486ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0096000000-07fa6dab65a51dd3e0aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w5d-9030000000-4a0dbea890140ccf214eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-9cadee9fb7834616dbdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0019000000-ba6c1afcd8f5ef945287Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-1390000000-b81ba0d09cb861c5aa36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-de69c65803e567e26ceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0089000000-5b1ba00893773270529dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001u-0190000000-b417833e34387c256453Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06766
HMDB IDHMDB0015670
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlcaftadine
Chemspider ID14201635
ChEBI ID71023
PubChem Compound ID19371515
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21250860
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21314437
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21339800
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21340041
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21383667
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21752782
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22348913
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22811343
9. 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.
10. 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.
11. 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.