Drug Details

General Information of the Drug (ID: DR7967)
Name
Entinostat
Synonyms
Entinostat; 209783-80-2; ms-275; SNDX-275; MS 275; MS-27-275; SNDX 275; Entinostat (MS-275); MS 27-275; pyridin-3-ylmethyl 4-((2-aminophenyl)carbamoyl)benzylcarbamate; MS275; pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate; UNII-1ZNY4FKK9H; Entinostat (MS-275,SNDX-275); 1ZNY4FKK9H; BAY 86-5274; N-(2-aminophenyl)-4-(N-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamide; CHEMBL27759; pyridin-3-ylmethyl 4-(2-aminophenylcarbamoyl)benzylcarbamate; pyridin-3-ylmethyl {4-[(2-aminophenyl)carbamoyl]benzyl}carbamate; NSC706995; BAY86-5274; NSC-706995; N-[[4-[(2-aminoanilino)-oxomethyl]phenyl]methyl]carbamic acid 3-pyridinylmethyl ester; pyridin-3-ylmethyl 4-((2-aminophenyl)carbamoyl)benzylcarbamate.; pyridin-3-ylmethyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate; Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl ester; Histone Deacetylase Inhibitor I; entinostatum; N-(2-aminophenyl)-4-[N-(pyridin-3-ylmethoxycarbonyl)aminomethyl]benzamide; Entinostat, free base; PubChem24433; Entinostat [USAN:INN]; MS-275 (Entinostat); MS-275 - Entinostat; 3-Pyridinylmethyl ((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)carbamate; benzamide-type inhibitor, 3; Carbamic acid, ((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)-, 3-pyridinylmethyl ester; cc-216; MLS006010183; Entinostat (JAN/USAN/INN); SCHEMBL148309; GTPL7007; DTXSID0041068; BDBM19410; AOB2570; EX-A038; SYN3039; CHEBI:132082; BCPP000155; HMS3426G07; HMS3648K12; HMS3654O11; HMS3744O17; ACT06782; AMY31163; BCP01824; MS-275,Entinostat,SNDX-275/; ZINC1488870; ABP000145; MFCD08272435; NSC756642; s1053; 3-pyridylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate; AKOS024262667; N-(2-Aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl)aminomethyl]benzamide; AC-8968; BCP9000967; Carbamic acid, 3-pyridinylmethyl ester; CCG-208680; CS-0511; DB11841; Entinostat (MS-275, SNDX-275); NSC 706995; NSC-756642; SB16665; Carbamic acid, [[4-[[(2-aminophenyl)carbaonyl]phenyl]methyl]-, 3-pyridinylmethyl ester; NCGC00165833-01; NCGC00165833-02; NCGC00165833-03; NCGC00165833-04; NCGC00165833-13; AK158952; AS-17906; Carbamic acid, N-((4-(((2-aminophenyl)amino)carbonyl)phenyl)methyl)-, 3- pyridinylmethyl ester; HY-12163; MS27-275; NCI60_038022; SMR004458705; MS-275, A HDAC1 and HDAC3 inhibitor; AB0021206; MS-275-27; ZK 244894; FT-0667871; SW219667-1; V2451; EC-000.2117; D09338; W-5370; 48247-EP2298768A1; 48247-EP2305643A1; 48247-EP2308868A1; 48247-EP2311494A1; 48247-EP2311840A1; 783M802; A815057; MS-275,Entinostat, SNDX-275, MS-27-275; SR-01000946382; Q1281020; SR-01000946382-1; W-201831; BRD-K77908580-001-02-1; BRD-K77908580-001-04-7; (pyridin-3-yl)methyl 4-(2-aminophenylcarbamoyl)benzylcarbamate; [4-(2-Amino-phenylcarbamoyl)-benzyl]-carbamic acid pyridin-3-ylmethyl ester; N-[[4-[[(2-Aminophenyl)amino]carbonyl]phenyl]methyl]-3-pyridinylmethyl ester, carbamic acid; N-[[4-[[(2-Aminophenyl)amino]carbonyl]phenyl]methyl]carbamic acid 3-pyridinylmethyl ester; 442532-99-2
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Molecular Type
Small molecule
Disease Breast cancer [ICD-11: 2C60] Phase 3 [1]
Structure
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2D MOL

3D MOL

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Formula
C21H20N4O3
PubChem CID
4261
Canonical SMILES
C1=CC=C(C(=C1)N)NC(=O)C2=CC=C(C=C2)CNC(=O)OCC3=CN=CC=C3
InChI
1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
InChIKey
INVTYAOGFAGBOE-UHFFFAOYSA-N
CAS Number
CAS 209783-80-2
ChEBI ID
CHEBI:132082
TTD Drug ID
D0M8FD
DrugBank ID
DB11841
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Cladribine      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
                    In-vitro Model RPMI-8226 CVCL_0014 Plasma cell myeloma Homo sapiens
U266B1 CVCL_0566 Plasma cell myeloma Homo sapiens
MM1.R CVCL_8794 Plasma cell myeloma Homo sapiens
                    Experimental
                    Result(s)		 Combinations of cladribine and entinostat exhibit potent activity to induce anti-proliferative/anti-survival effects on MM cells via induction of cell cycle G1 arrest, apoptosis, and DNA damage response.
Target and Pathway
Target(s) Histone deacetylase 1 (HDAC1)  Molecule Info  [3]
KEGG Pathway Cell cycle Click to Show/Hide
2 Notch signaling pathway
3 Thyroid hormone signaling pathway
4 Huntington's disease
5 Amphetamine addiction
6 Alcoholism
7 Epstein-Barr virus infection
8 Pathways in cancer
9 Transcriptional misregulation in cancer
10 Viral carcinogenesis
11 MicroRNAs in cancer
12 Chronic myeloid leukemia
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Wnt signaling pathway Click to Show/Hide
2 p53 pathway
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Notch signaling pathway
3 E2F transcription factor network
4 Presenilin action in Notch and Wnt signaling
5 Signaling events mediated by HDAC Class I
6 Regulation of Telomerase
7 Glucocorticoid receptor regulatory network
8 Sumoylation by RanBP2 regulates transcriptional repression
9 Regulation of Androgen receptor activity
10 IL3-mediated signaling events
11 Validated nuclear estrogen receptor alpha network
12 Retinoic acid receptors-mediated signaling
13 Hedgehog signaling events mediated by Gli proteins
14 Regulation of nuclear beta catenin signaling and target gene transcription
15 Validated targets of C-MYC transcriptional repression
16 Regulation of retinoblastoma protein
17 Notch-mediated HES/HEY network
Reactome G0 and Early G1 Click to Show/Hide
2 p75NTR negatively regulates cell cycle via SC1
3 Formation of the beta-catenin:TCF transactivating complex
4 NOTCH1 Intracellular Domain Regulates Transcription
5 SMAD2/SMAD3:SMAD4 heterotrimer regulates transcription
6 Constitutive Signaling by NOTCH1 PEST Domain Mutants
7 Constitutive Signaling by NOTCH1 HD+PEST Domain Mutants
8 HDACs deacetylate histones
9 Deactivation of the beta-catenin transactivating complex
10 NoRC negatively regulates rRNA expression
11 RNA Polymerase I Transcription Initiation
12 Factors involved in megakaryocyte development and platelet production
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Notch Signaling Pathway
3 TGF beta Signaling Pathway
4 IL-6 signaling pathway
5 Apoptosis-related network due to altered Notch3 in ovarian cancer
6 Transcriptional activity of SMAD2/SMAD3:SMAD4 heterotrimer
7 Notch Signaling Pathway
8 Retinoblastoma (RB) in Cancer
9 Neural Crest Differentiation
10 TWEAK Signaling Pathway
11 Integrated Breast Cancer Pathway
12 Signalling by NGF
13 RNA Polymerase I, RNA Polymerase III, and Mitochondrial Transcription
14 Mitotic G1-G1/S phases
15 Factors involved in megakaryocyte development and platelet production
16 Cell Cycle
17 Androgen receptor signaling pathway
References
Reference 1 ClinicalTrials.gov (NCT03538171) Ph3 Study of Exemestane With or Without Entinostat in Chinese Patients With Hormone Receptor-Positive, Locally Advanced or Metastatic Breast Cancer. U.S. National Institutes of Health.
Reference 2 Cladribine in combination with entinostat synergistically elicits anti-proliferative/anti-survival effects on multiple myeloma cells. Cell Cycle. 2018;17(8):985-996.
Reference 3 Emerging therapies for multiple myeloma. Expert Opin Emerg Drugs. 2009 Mar;14(1):99-127.
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