CAS 94497-51-5|retinobenzoic acid|Am 80|4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid|tamibarotene|Tamibarotene|Tamibarotene|Tamibaro|Amnoid|4-((5,5,8,8-Tetramethy...

General Information

Structure

Molecular Formula

C₂₂H₂₅NO₃

Molecular Mass

351.4388

Exact Mass

351.18344367

Charge

InChI

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)

InChIKey

MUTNCGKQJGXKEM-UHFFFAOYSA-N

Canonic Smiles

O=C(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C

Isomeric Smiles

O=C(Nc1cc2C(CCC(c2cc1)(C)C)(C)C)c1ccc(cc1)C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

2.04

LogD (pH = 5.5)

3.54

Log P

5.35

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

3.69

Polar Surface Area

66.40

Polarizability

40.19

Molar Refractivity

104.38

LOG S

-6.67

Data Source

Names and Identifiers

Synonyms

retinobenzoic acidAm 80TamibaroteneTamibarotene4-((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthale n-2-yl)carbamoyl)benzoic acidN-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl)-2-naphthyl)terephthalamic acid-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acidAM80N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)terephthalamic acid4-(((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino)carbonyl)-benzoic acidUNII-08V52GZ3H9AMNOLAKEAmnoidNSC 608000TamibaroteneRetinoid AM 804-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic AcidAm 80 (pharmaceutical)4-((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl)benzoic acidretinobenzoic acidtamibaroteneAm-80Am 80Tamibarotene

IUPAC name

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

IUPAC Traditional name

tamibarotene

Brand Name

TamibaroAmnoid

Names and Identifiers

Registration numbers

CAS Number

94497-51-5

PubChem CID

108143

PubChem SID

4650903916096783356352906

MDL Number

CHEMBL

DrugBank ID

Chemspider ID

Beilstein Number

Wikipedia Title

PubMed Citation Links

195141221918238023404745165317272544849622014829179258872286391419389933

ACToR Database

SABIO-RK Database

PDBeChem Database

KEGG ID

MetaboLights Database

CHEBI ID

Reaxys Registry

Protein Data Bank

Drug Central Database

BindingDB Database

CompTox Database

LINCS Database

SureChEMBL Database

HMDB Database

KEGG DRUG Database

Registration numbers

Properties

Product Information

Physical Property

Pharmacology Properties

Target

Others

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Tamibarotene

DrugBank

DB04942

Drug Groups

approved; investigational

Description

Tamibarotene 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.

Indication

Investigated for use/treatment in leukemia (unspecified).

Pharmacology

Tamibarotene is a new synthetic retinoid drug recently approved for relapsed or refractory acute promyelocytic leukemia (APL) in Japan. It is a specific agonist for retinoic acid receptor alpha/beta. Compared to all-trans retinoic acid (ATRA), a natural retinoid indicated for a first-line treatment of APL, tamibarotene is chemically more stable and several times more potent as an inducer of differentiation in promyelocytic leukemia cells. In contrast to ATRA, whose plasma concentration declines considerably during daily administration, tamibarotene sustains plasma level probably due to a lower affinity for cellular retinoic acid binding protein. Furthermore, adverse side effects were milder than those of ATRA in clinical trials.

Affected Organisms

Humans and other mammals

Protein Binding

Over 99%, predominantly to serum albumin.

References

• Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [Pubmed]

• Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [Pubmed]

• 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]

• 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]

• 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]

External Links

• [Wikipedia]

Sigma Aldrich

T3205

Biochem/physiol Actions
Tamibarotene (Am80) is a RAR α agonist. Tamibarotene was developed to overcome resistance to ATRA and is currently approved in Japan for treatment of recurrent acute promyelocytic leukemia (APL). The compound induces HL-60 cells differentiation and apoptosis. Similarly to TTNPB, the compound neither binds to nor transactivates the RXRs. In contrast to TTNPB (pan RAR agonist), Tamibarotene is rather specific toward RAR α. The compound is approximate 10 times more potent than ATRA.

TRC

T005800

Synthetic retinoic acid receptor-α/β-selective retinoid. Antineoplastic.

ChEBI

CHEBI:32181

A dicarboxylic acid monoamide resulting from the condensation of one of the carboxy groups of terephthalic acid with the amino group of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine.

Molecule Details

References

PubChem Literature

From Data Sources

• Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. Pubmed

• Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. Pubmed

• 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

• Shinjo, K., et al.: Int. J. Hematol., 72, 470 (1988)

• Hashimoto, Y., et al.: Jpn. J. Cancer Res., 79, 473 (1988)

• Sanda, T., et al.: Leukemia, 19, 901 (1988)

• Mizojiri, K., et al.: Arzneim.-Forsch., 47, 59 (1988)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

tamibarotene

Brand Name

TamibaroAmnoid

Registration numbers

CAS Number

94497-51-5

PubChem CID

108143

PubChem SID

4650903916096783356352906

MDL Number

CHEMBL

DrugBank ID

Chemspider ID

Beilstein Number

Wikipedia Title

PubMed Citation Links

195141221918238023404745165317272544849622014829179258872286391419389933

ACToR Database

SABIO-RK Database

PDBeChem Database

KEGG ID

MetaboLights Database

CHEBI ID

Reaxys Registry

Protein Data Bank

Drug Central Database

BindingDB Database

CompTox Database

LINCS Database

SureChEMBL Database

HMDB Database

KEGG DRUG Database

Properties

Product Information

Physical Property

Pharmacology Properties

Target

Others

Molecule Details

Wikipedia

Tamibarotene

DrugBank

DB04942

Drug Groups

approved; investigational

Description

Indication

Investigated for use/treatment in leukemia (unspecified).

Pharmacology

Affected Organisms

Humans and other mammals

Protein Binding

Over 99%, predominantly to serum albumin.

References

• Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. [Pubmed]

• Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. [Pubmed]

• 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]

External Links

• [Wikipedia]

Sigma Aldrich

T3205

TRC

T005800

Synthetic retinoic acid receptor-α/β-selective retinoid. Antineoplastic.

ChEBI

CHEBI:32181

A dicarboxylic acid monoamide resulting from the condensation of one of the carboxy groups of terephthalic acid with the amino group of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine.

References

PubChem Literature

From Data Sources

• Tamibarotene: AM 80, retinobenzoic acid, Tamibaro. Drugs R D. 2004;5(6):359-62. Pubmed

• Miwako I, Kagechika H: Tamibarotene. Drugs Today (Barc). 2007 Aug;43(8):563-8. Pubmed

• 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

• Shinjo, K., et al.: Int. J. Hematol., 72, 470 (1988)

• Hashimoto, Y., et al.: Jpn. J. Cancer Res., 79, 473 (1988)

• Sanda, T., et al.: Leukemia, 19, 901 (1988)

• Mizojiri, K., et al.: Arzneim.-Forsch., 47, 59 (1988)

Bioactivity

PubChem BioAssay

Molecule

ID:4401