Details of the Drug

General Information of Drug (ID: DMRD5SP)

Drug Name
Fenretinide
Synonyms
RT-101; ST-602; SYT-101; Fenretinide (pulmonary Pseudomonas aeruginosa infections in cystic fibrosis), McGill University; LXS/4-HPR; Fenretinide (Ewing's sarcoma), Cancer Research UK; Fenretinide (ILE formulation), Children's Hospital LA; Fenretinide (intralipid emulsion formulation), Children's Hospital of Los Angeles; Fenretinide (intravenous, cancer), SciTech Development; Fenretinide (iv), Children's Hospital LA; Fenretinide (oral, AMD), Sytera; Fenretinide (soft gel capsule, AMD), ReVision Therapeutics; Fenretinide (soft gel capsule, AMD), Sirion; Fenretinide (topical, actinic keratosis and cancer), SciTech Development; N-(4-hydroxyphenyl)retinamide; Fenretinide (intravenous emulsion, lymphoma/solid tumors/pediatric neuroblastomas/pediatric leukemia), CerRx; Fenretinide (oral powder/Lym-X-Sorb, neuroblastoma), BioMolecular Products; 4-HPR
Indication
Disease Entry ICD 11 Status REF
Macular degeneration 9B78.3 Phase 3 [1]
Lymphoma 2A80-2A86 Phase 2 [2]
Peripheral T-cell lymphoma 2A90.C Phase 2 [3]
Solid tumour/cancer 2A00-2F9Z Phase 2 [2]
Tumour 2A00-2F9Z Phase 1 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 391.5
Logarithm of the Partition Coefficient (xlogp) 7.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C26H33NO2
IUPAC Name
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
Canonical SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/C
InChI
InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
InChIKey
AKJHMTWEGVYYSE-FXILSDISSA-N
Cross-matching ID
PubChem CID
5288209
ChEBI ID
CHEMBL7301
CAS Number
65646-68-6
UNII
187EJ7QEXL
DrugBank ID
DB05076
TTD ID
D08JAC
INTEDE ID
DR1893
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor (RAR) TTOD7B3 NOUNIPROTAC Modulator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C8 (CYP2C8)
Main DME 		DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein theta OTWG7F3H 1433T_HUMAN Protein Interaction/Cellular Processes [6]
6-phosphogluconate dehydrogenase, decarboxylating (PGD) OTVG296F 6PGD_HUMAN Gene/Protein Processing [7]
Acyl carrier protein, mitochondrial (NDUFAB1) OTF906UR ACPM_HUMAN Gene/Protein Processing [8]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [7]
Alpha-crystallin B chain (CRYAB) OTY4JGYU CRYAB_HUMAN Gene/Protein Processing [7]
Amino acid transporter heavy chain SLC3A2 (SLC3A2) OTBR33M9 4F2_HUMAN Gene/Protein Processing [7]
Apolipoprotein C-IV (APOC4) OTE8ZUXY APOC4_HUMAN Gene/Protein Processing [7]
Apoptosis facilitator Bcl-2-like protein 14 (BCL2L14) OT87E7HW B2L14_HUMAN Gene/Protein Processing [8]
Baculoviral IAP repeat-containing protein 2 (BIRC2) OTFXFREP BIRC2_HUMAN Gene/Protein Processing [9]
BAG family molecular chaperone regulator 1 (BAG1) OTRQNIA4 BAG1_HUMAN Protein Interaction/Cellular Processes [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00003075) Fenretinide in Treating Patients With Cervical Neoplasia. U.S. National Institutes of Health.
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 National Cancer Institute Drug Dictionary (drug id 39582).
5 Characterization of the metabolism of fenretinide by human liver microsomes, cytochrome P450 enzymes and UDP-glucuronosyltransferases. Br J Pharmacol. 2011 Feb;162(4):989-99.
6 Fenretinide-induced neuronal differentiation of ARPE-19 human retinal pigment epithelial cells is associated with the differential expression of Hsp70, 14-3-3, pax-6, tubulin beta-III, NSE, and bag-1 proteins. Mol Vis. 2006 Nov 1;12:1355-63.
7 Regulation of lipocalin-2 gene by the cancer chemopreventive retinoid 4-HPR. Int J Cancer. 2006 Oct 1;119(7):1599-606.
8 4-HPR modulates gene expression in ovarian cells. Int J Cancer. 2006 Sep 1;119(5):1005-13. doi: 10.1002/ijc.21797.
9 N-(4-hydroxyphenyl)retinamide inhibits invasion, suppresses osteoclastogenesis, and potentiates apoptosis through down-regulation of I(kappa)B(alpha) kinase and nuclear factor-kappaB-regulated gene products. Cancer Res. 2005 Oct 15;65(20):9555-65. doi: 10.1158/0008-5472.CAN-05-1585.