TAMIBAROTENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H25NO3
Molecular Weight	351.4388
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C3=CC=C(C=C3)C(O)=O)=C2

InChI

InChIKey=MUTNCGKQJGXKEM-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C22H25NO3
Molecular Weight	351.4388
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB04942
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/amnolake.html | https://www.ncbi.nlm.nih.gov/pubmed/20925433 | https://www.ncbi.nlm.nih.gov/pubmed/20925433 | https://www.ncbi.nlm.nih.gov/pubmed/24559497 | https://www.ncbi.nlm.nih.gov/pubmed/27777437

Tamibarotene (brand name: Amnolake), also called retinobenzoic acid, is orally active, the synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity against acute promyelocytic leukemia (APL). Tamibarotene is a specific agonist for retinoic acid receptor alpha/beta. It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA. It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma, and Crohn's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433	Agonist 2678	45.0 nM [EC50]
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433	Agonist 2678	235.0 nM [EC50]
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433	Agonist 2678	591.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute promyelocytic leukemia 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26205361	Primary		Approved 8429	Amnolake Approved Use Unknown
Graft-versus-host disease 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27777437	Primary		Phase II 1132	Amnolake Approved Use Unknown

PubMed

Title	Date	PubMed
The prevention of adipose differentiation of 3T3-L1 cells caused by retinoic acid is elicited through retinoic acid receptor alpha.	1994	7934625
Effect of Am-80, a synthetic derivative of retinoid, on experimental arthritis in mice.	1999 Feb	9873234
Involvement of insulin-like growth factor binding protein-3 in the retinoic acid receptor-alpha-mediated inhibition of hepatocellular carcinoma cell proliferation.	2000 Apr 3	10766424
Effect of Am-80, a retinoid derivative, on 2, 4-dinitrofluorobenzene-induced contact dermatitis in mice.	2000 May	10828746
Synthetic retinoid Am80 suppresses smooth muscle phenotypic modulation and in-stent neointima formation by inhibiting KLF5.	2005 Nov 25	16224062
4- [3,5-bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) induced fas expression and activated caspase-3 and -8 in a DLD-1 colon cancer cell line.	2007 Mar-Apr	17436592
Disposition of a new tamibarotene prodrug in mice.	2009 Dec	19952418
Retinoic acid protects human breast cancer cells against etoposide-induced apoptosis by NF-kappaB-dependent but cIAP2-independent mechanisms.	2010 Jan 26	20102612
Molecular remission in advanced acute promyelocytic leukaemia after treatment with the oral synthetic retinoid Tamibarotene.	2010 Oct	20618325
All-trans retinoic acid and a novel synthetic retinoid tamibarotene (Am80) differentially regulate CD38 expression in human leukemia HL-60 cells: possible involvement of protein kinase C-delta.	2011 Aug	21393419

Patents

Sample Use Guides

In Vivo Use Guide

Tamibarotene 6 mg/m2/day oral dose for a maximum of 56 days

Route of Administration: Oral

In Vitro Use Guide

The cell viability of A549 or MRC-5 cell lines treated with Am80 or ATRA was assessed using the CellTiter-Glo Luminescent Cell Viability Assay (Promega KK, Tokyo, Japan). Cells were seeded at 625 per cm2 in 100 μL of medium in 96-welled flat-bottom plates and grown overnight at 37°C in an incubator. After exposure to Am80 for 6 d, the plates were assayed using EnVision Plate Reader (PerkinElmer, Inc. Japan Co., Ltd., Kanagawa, Japan).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:35:17 GMT 2023` Edited by `admin` on `Fri Dec 15 16:35:17 GMT 2023`
Record UNII	08V52GZ3H9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAMIBAROTENE

Official Name

English

AM80

Code

English

TAMIBAROTENE [JAN]

Common Name

English

RR-110

Code

English

OP-01

Code

English

SY-1425

Code

English

AM-80

Code

English

4-(((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)AMINO)CARBONYL)BENZOIC ACID

Systematic Name

English

BENZOIC ACID, 4-(((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)AMINO)CARBONYL)-

Systematic Name

English

TM-411

Code

English

TAMIBAROTENE [USAN]

Common Name

English

4-((5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBAMOYL)BENZOIC ACID

Systematic Name

English

NSC-608000

Code

English

tamibarotene [INN]

Common Name

English

INNO-507

Code

English

Tamibarotene [WHO-DD]

Common Name

English

TOS-80T

Code

English

AMNOID

Brand Name

English

TAMIBAROTENE [MI]

Common Name

English

TAMIBAROTENE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C804