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Tamibarotene

July 24, 2017
Common Name

Tamibarotene Description

Tamibarotene is only found in individuals that have used or taken this drug. It 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.Tamibarotene is a specific agonist for retinoic acid receptor alpha/beta with possible binding to retinoid X receptors (RXR). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source Am 80ChEBI Am-80ChEBI AmnoidChEBI Retinobenzoic acidChEBI TamibaroChEBI RetinobenzoateGenerator 4-((5,6,7,8-tetrahydro-5,5,8,8-Tetramethyl-2-naphthalenyl)carbamoyl)benzoic acidMeSH

Chemical Formlia

C22H25NO3 Average Molecliar Weight

351.4388 Monoisotopic Molecliar Weight

351.183443671 IUPAC Name

4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid Traditional Name

tamibarotene CAS Registry Number

94497-51-5 SMILES

CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2

InChI Identifier

InChI=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 Key

MUTNCGKQJGXKEM-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Tetralins Direct Parent

Tetralins Alternative Parents

  • Benzoic acids
  • Benzamides
  • Benzoyl derivatives
  • Secondary carboxylic acid amides
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic homopolycyclic compounds External Descriptors

  • retinoid (CHEBI:32181 )
  • dicarboxylic acid monoamide (CHEBI:32181 )
  • tetralins (CHEBI:32181 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticancer Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.75e-04 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.000575 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity104.38 m3·mol-1ChemAxon Polarizability39.16 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04942

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04942

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04942 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    97231 KEGG Compound ID

    C12864 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Tamibarotene NuGOwiki Link

    HMDB15605 Metagene Link

    HMDB15605 METLIN ID

    Not Available PubChem Compound

    108143 PDB ID

    A80 ChEBI ID

    32181

    Product: VGX-1028

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
    2. 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. [PubMed:15843826 ]
    3. Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]
    4. 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. [PubMed:9105544 ]
    5. 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. [PubMed:16531727 ]

    Enzymes

    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    This is a receptor for retinoic acid. Retinoic acid has profound effects on vertebrate development, is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression. Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing MLL5. Mediates retinoic acid-induced granulopoiesis
    Gene Name:
    RARA
    Uniprot ID:
    P10276
    Molecular weight:
    50770.8
    References
    1. Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
    2. 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. [PubMed:15843826 ]
    3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    4. Jimi S, Mashima K, Matsumoto T, Hara S, Suzumiya J, Tamura K: RARalpha is a regulatory factor for Am-80-induced cell growth inhibition of hematologic malignant cells. Int J Oncol. 2007 Aug;31(2):397-404. [PubMed:17611697 ]
    5. Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]
    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    This is a receptor for retinoic acid. This metabolite has profound effects on vertebrate development. Retinoic acid is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression
    Gene Name:
    RARB
    Uniprot ID:
    P10826
    Molecular weight:
    50488.6
    References
    1. Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [PubMed:17925887 ]
    2. 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. [PubMed:15843826 ]
    3. Jimi S, Mashima K, Matsumoto T, Hara S, Suzumiya J, Tamura K: RARalpha is a regulatory factor for Am-80-induced cell growth inhibition of hematologic malignant cells. Int J Oncol. 2007 Aug;31(2):397-404. [PubMed:17611697 ]
    4. Authors unspecified: Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [PubMed:15563242 ]

    PMID: 9801167

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