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...

基本信息

化学结构

分子式

C₂₂H₂₅NO₃

分子量

351.4388

精确质量

351.18344367

电荷

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

计算属性

JChem

LogD (pH = 7.4)

2.04

LogD (pH = 5.5)

3.54

Log P

5.35

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

false

Acid pKa

3.69

极化表面积

66.40

极化性

40.19

摩尔折射率

104.38

LOG S

-6.67

数据来源

名称和标识

别名

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标准名

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

IUPAC传统名

tamibarotene

商标名

TamibaroAmnoid

名称和标识

数据登录号

CAS号

94497-51-5

PubChem CID

108143

PubChem SID

4650903916096783356352906

MDL号

CHEMBL

DrugBank ID

Beilstein号

Chemspider ID

维基百科标题

PubMed文献链接

195141221918238023404745165317272201482917925887254484962286391419389933

SABIO-RK数据库

ACToR数据库

PDBeChem数据库

Reaxys Registry

MetaboLights数据库

KEGG ID

CHEBI ID

LINCS数据库

PDB数据库

BindingDB数据库

SureChEMBL数据库

Drug Central Database

CompTox数据库

HMDB数据库

KEGG DRUG Database

数据登录号

化合物性质

产品相关信息

药理学性质

作用靶点

Others

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

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

IUPAC传统名

tamibarotene

商标名

TamibaroAmnoid

数据登录号

CAS号

94497-51-5

PubChem CID

108143

PubChem SID

4650903916096783356352906

MDL号

CHEMBL

DrugBank ID

Beilstein号

Chemspider ID

维基百科标题

PubMed文献链接

195141221918238023404745165317272201482917925887254484962286391419389933

SABIO-RK数据库

ACToR数据库

PDBeChem数据库

Reaxys Registry

MetaboLights数据库

KEGG ID

CHEBI ID

LINCS数据库

PDB数据库

BindingDB数据库

SureChEMBL数据库

Drug Central Database

CompTox数据库

HMDB数据库

KEGG DRUG Database

化合物性质

产品相关信息

药理学性质

作用靶点

Others

描述信息

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.

参考文献

PubChem文献

数据源提供

• 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)

生物活性

PubChem BioAssay

化合物信息

ID:4401