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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 of TAMIBAROTENE

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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 45.0 nM [EC50]
Agonist
2678
 235.0 nM [EC50]
Agonist
2678
 591.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Amnolake

Approved Use

Unknown
Primary
Phase II
1132
Amnolake

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
1988 Nov
The prevention of adipose differentiation of 3T3-L1 cells caused by retinoic acid is elicited through retinoic acid receptor alpha.
1994
Activation of retinoid X receptors induces apoptosis in HL-60 cell lines.
1995 Jul
Re-induction of complete remission with a new synthetic retinoid, Am-80, for relapse of acute promyelocytic leukaemia previously treated with all-trans retinoic acid.
1997 Apr
Action mechanism of retinoid-synergistic dibenzodiazepines.
1997 Apr 7
Effect of Am-80, a synthetic derivative of retinoid, on experimental arthritis in mice.
1999 Feb
Thyroid hormone regulation of apoptosis induced by retinoic acid in promyeloleukemic HL-60 cells: studies with retinoic acid receptor-specific and retinoid x receptor-specific ligands.
2000 Dec
Effect of Am-80, a retinoid derivative, on 2, 4-dinitrofluorobenzene-induced contact dermatitis in mice.
2000 May
Effect of selective IL-6 inhibitor Am-80 on experimental autoimmune encephalomyelitis in DA rats.
2000 Nov
On-line immunoaffinity extraction followed by high-performance liquid chromatography and radioimmunoassay for a novel retinobenzoic acid, AM-80, in human plasma.
2001
Promyelocytic leukemia retinoid signaling targets regulate apoptosis,tissue factor and thrombomodulin expression.
2004 Mar
A novel retinoid, 4-[3,5-bis (trimethylsilyl) benzamido] benzoic acid (TAC-101), induces apoptosis of human ovarian carcinoma cells and shows potential as a new antitumor agent for clear cell adenocarcinoma.
2004 Sep
[Retinoid therapy for autoimmune diseases].
2006 Jun
The effect of Am-80, a synthetic retinoid, on spinal cord injury-induced motor dysfunction in rats.
2009 Feb
Discovery of tetrahydrotetramethylnaphthalene analogs as adult T-cell leukemia cell-selective proliferation inhibitors in a small chemical library constructed based on multi-template hypothesis.
2009 Jul 1
Towards retinoid therapy for Alzheimer's disease.
2009 Jun
The ATRA-dependent overexpression of the glutamate transporter EAAC1 requires RARbeta induction.
2009 Sep
[Molecular remission induced by gemtuzumab ozogamicin in an elderly patient with relapsed acute promyelocytic leukemia].
2010 Apr
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
Synthetic retinoid Am80 ameliorates chronic graft-versus-host disease by down-regulating Th1 and Th17.
2012 Jan 5
Patents

Patents

WO1991014673
1

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 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:17 UTC 2023
Record UNII
08V52GZ3H9
Record Status Validated (UNII)
Record Version
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Name Type Language
TAMIBAROTENE
INN   JAN   MART.   MI   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
FDA ORPHAN DRUG 247007
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
FDA ORPHAN DRUG 596017
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
EU-Orphan Drug EU/3/09/658
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
FDA ORPHAN DRUG 861221
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
Code System Code Type Description
CHEBI
32181
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
IUPHAR
2648
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PRIMARY
NSC
608000
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
NCI_THESAURUS
C71025
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
USAN
JK-51
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
MERCK INDEX
m10449
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PRIMARY Merck Index
EPA CompTox
DTXSID5046853
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PRIMARY
EVMPD
SUB10822MIG
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PRIMARY
FDA UNII
08V52GZ3H9
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
PUBCHEM
108143
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
SMS_ID
100000083232
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PRIMARY
ChEMBL
CHEMBL25202
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
CAS
94497-51-5
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
DRUG CENTRAL
3580
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
DRUG BANK
DB04942
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
INN
7349
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
MESH
C061133
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
WIKIPEDIA
TAMIBAROTENE
Created by admin on Fri Dec 15 16:35:17 UTC 2023 , Edited by admin on Fri Dec 15 16:35:17 UTC 2023
PRIMARY
Related Record Type Details
RETINOIC ACID RECEPTOR ALPHA
TARGET -> AGONIST
Related Record Type Details
Structure of TAMIBAROTENE
ACTIVE MOIETY
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