General Information of Drug (ID: DMOB01U)

Drug Name
Amsilarotene
Synonyms Am-555S; TAC-101; Anticancer retinoic acid receptor antagonist (oral), Taiho
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
0
Molecular Weight 385.6
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 5
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 3
Chemical Identifiers
Formula
C20H27NO3Si2
IUPAC Name
4-[[3,5-bis(trimethylsilyl)benzoyl]amino]benzoic acid
Canonical SMILES
C[Si](C)(C)C1=CC(=CC(=C1)C(=O)NC2=CC=C(C=C2)C(=O)O)[Si](C)(C)C
InChI
InChI=1S/C20H27NO3Si2/c1-25(2,3)17-11-15(12-18(13-17)26(4,5)6)19(22)21-16-9-7-14(8-10-16)20(23)24/h7-13H,1-6H3,(H,21,22)(H,23,24)
InChIKey
VVTNSTLJOVCBDL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
9800306
CAS Number
125973-56-0
TTD ID
D0I9HG

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor (RAR) TTOD7B3 NOUNIPROTAC Antagonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [3]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [3]
Cyclin-A2 (CCNA2) OTPHHYZJ CCNA2_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [4]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [5]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [6]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [4]
Retinoic acid receptor beta (RARB) OT367U3E RARB_HUMAN Gene/Protein Processing [6]
Thymidylate synthase OTXTG0C7 TYSY_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00687596) Study of TAC-101 as Second Line Treatment in Patients With Advanced Hepatocellular Carcinoma Who Received Sorafenib as First Line Therapy. U.S. National Institutes ofHealth.
2 Initial clinical trial of oral TAC-101, a novel retinoic acid receptor-alpha selective retinoid, in patients with advanced cancer. J Clin Oncol. 2002 Aug 15;20(16):3522-32.
3 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. In Vivo. 2007 Mar-Apr;21(2):381-7.
4 Induction of cell-cycle arrest and apoptosis by a novel retinobenzoic-acid derivative, TAC-101, in human pancreatic-cancer cells. Int J Cancer. 1999 May 17;81(4):637-44.
5 4-[3,5-Bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) inhibits the intrahepatic spread of hepatocellular carcinoma and prolongs the life-span of tumor-bearing animals. Clin Exp Metastasis. 1998 Oct;16(7):633-43. doi: 10.1023/a:1006567229929.
6 Contribution of AP-1 interference induced by TAC-101 to tumor growth suppression in a hepatocellular carcinoma model. Tumour Biol. 2009;30(1):1-7. doi: 10.1159/000189712. Epub 2009 Jan 12.