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
• #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: CHEBI:42588
  CAS Number: 65646-68-6
  DrugBank ID: DB05076
  TTD ID: D08JAC
  INTEDE ID: DR1893
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

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]
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[8]
Acyl carrier protein, mitochondrial (NDUFAB1)	OTF906UR	ACPM_HUMAN	Gene/Protein Processing	[9]
Alanine--glyoxylate aminotransferase (AGXT)	OTIPTH3Q	AGT1_HUMAN	Gene/Protein Processing	[7]
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]
Aminopeptidase N (ANPEP)	OTP3WYFD	AMPN_HUMAN	Gene/Protein Processing	[8]
Apolipoprotein C-IV (APOC4)	OTE8ZUXY	APOC4_HUMAN	Gene/Protein Processing	[7]

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] The transforming growth factor-beta family members bone morphogenetic protein-2 and macrophage inhibitory cytokine-1 as mediators of the antiangiogenic activity of N-(4-hydroxyphenyl)retinamide. Clin Cancer Res. 2005 Jun 15;11(12):4610-9.
• [9] 4-HPR modulates gene expression in ovarian cells. Int J Cancer. 2006 Sep 1;119(5):1005-13. doi: 10.1002/ijc.21797.