Tamibarotene (CHEM019304)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:00:02 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019304
Identification
Common NameTamibarotene
ClassSmall Molecule
DescriptionTamibarotene is a novel synthetic retinoid for acute promyelocytic leukaemia (APL). Tamibarotene is currently approved in Japan for treatment of recurrent APL, and is undergoing clinical trials in the United States.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Am 80ChEBI
Am-80ChEBI
AmnoidChEBI
Retinobenzoic acidChEBI
TamibaroChEBI
RetinobenzoateGenerator
4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acidHMDB
Chemical FormulaC22H25NO3
Average Molecular Mass351.439 g/mol
Monoisotopic Mass351.183 g/mol
CAS Registry Number94497-51-5
IUPAC Name4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid
Traditional Nametamibarotene
SMILESCC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2
InChI IdentifierInChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChI KeyMUTNCGKQJGXKEM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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 Solubility0.00058 g/LALOGPS
logP4.99ALOGPS
logP5.35ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.38 m³·mol⁻¹ChemAxon
Polarizability39.16 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0926000000-4e20d564460f24f3bee6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3195400000-2f9ea0b192db22b23e34Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-8077c73aa7a0b3a0493fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-1119000000-0596ca0316feae6135e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-9621000000-472a8ced02b76b7e0310Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-3ef35313b76eb3af9c7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-986ece158863bf5eb6b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2090000000-faa1fb3b6d57e52a9c4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0009000000-dbfed4dced06a8666457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1239000000-eb277707477e13926eb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kii-4930000000-87f3d164d219001d818bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-d9e09ce3c5ade8ebd024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gwb-0369000000-6c232cbaf08e18c9b277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-3921000000-fbd8a12bd61c31548a10Spectrum
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 IDDB04942
HMDB IDHMDB0015605
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDA80
Wikipedia LinkTamibarotene
Chemspider ID97231
ChEBI ID32181
PubChem Compound ID108143
Kegg Compound IDC12864
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mizojiri K, Okabe H, Sugeno K, Misaki A, Ito M, Kominami G, Esumi Y, Takaichi M, Harada T, Seki H, Inaba A: Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl] benzoic acid. 4th communication: absorption, metabolism, excretion and plasma protein binding in various animals and man. Arzneimittelforschung. 1997 Mar;47(3):259-69.
2. Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62.
3. Sanda T, Kuwano T, Nakao S, Iida S, Ishida T, Komatsu H, Shudo K, Kuwano M, Ono M, Ueda R: Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis. Leukemia. 2005 Jun;19(6):901-9.
4. Takeuchi M: [Clinical experience with a new synthetic retinoid, tamibarotene (Am-80) for relapsed or refractory acute promyelocytic leukemia]. Gan To Kagaku Ryoho. 2006 Mar;33(3):397-401.
5. Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16531727
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17925887
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19182380
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19389933
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19514122
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22014829
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22863914
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23404745
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25448496