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
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)
Molecular Formula | C22H25NO3 |
Molecular Weight | 351.4388 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB04942Curator'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
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 | Condition | Potency |
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Target ID: CHEMBL2055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433 |
45.0 nM [EC50] | ||
Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433 |
235.0 nM [EC50] | ||
Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433 |
591.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Amnolake Approved UseUnknown |
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Primary | Amnolake Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The prevention of adipose differentiation of 3T3-L1 cells caused by retinoic acid is elicited through retinoic acid receptor alpha. | 1994 |
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Effect of Am-80, a synthetic derivative of retinoid, on experimental arthritis in mice. | 1999 Feb |
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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 |
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Effect of Am-80, a retinoid derivative, on 2, 4-dinitrofluorobenzene-induced contact dermatitis in mice. | 2000 May |
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Synthetic retinoid Am80 suppresses smooth muscle phenotypic modulation and in-stent neointima formation by inhibiting KLF5. | 2005 Nov 25 |
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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 |
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Disposition of a new tamibarotene prodrug in mice. | 2009 Dec |
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Retinoic acid protects human breast cancer cells against etoposide-induced apoptosis by NF-kappaB-dependent but cIAP2-independent mechanisms. | 2010 Jan 26 |
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Molecular remission in advanced acute promyelocytic leukaemia after treatment with the oral synthetic retinoid Tamibarotene. | 2010 Oct |
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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20925433
Tamibarotene 6 mg/m2/day oral dose for a maximum of 56 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26934924
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
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admin
on
Edited
Fri Dec 15 16:35:17 GMT 2023
by
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Fri Dec 15 16:35:17 GMT 2023
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Record UNII |
08V52GZ3H9
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C804
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FDA ORPHAN DRUG |
247007
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FDA ORPHAN DRUG |
596017
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EU-Orphan Drug |
EU/3/09/658
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FDA ORPHAN DRUG |
861221
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32181
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2648
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608000
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C71025
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JK-51
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m10449
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DTXSID5046853
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SUB10822MIG
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108143
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100000083232
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CHEMBL25202
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94497-51-5
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3580
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DB04942
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7349
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C061133
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TAMIBAROTENE
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ACTIVE MOIETY |
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