Fenretinide

Summary

Fenretinide (CHEMBL7301) is a phase-3 clinical-stage small-molecule antineoplastic agent; indicated across 28 conditions including neoplasm and schizoaffective disorder.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 28 conditions
• Clinical trials: 41
• Chemistry: 391.5 Da · C26H33NO2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL7301
Name	Fenretinide
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	5288209
ChEBI	CHEBI:42588
Molecular formula	C26H33NO2
Molecular weight	391.5
InChIKey	AKJHMTWEGVYYSE-FXILSDISSA-N

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

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

ChEBI definition: A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of ‘classical’ retinoids.

Pharmacological roles (ChEBI): antineoplastic agent, antioxidant.

Also known as: All-trans-4’-hydroxyretinanilide, Fenretinida, Fenretinide, MCN-R-1967, NSC-760419, Rii retinamide, Retinoic acid p-hydroxyanilide, SID17389243, SID26752780, SID26752781, SID26752782, SID49718105

Patent coverage: 5,560 distinct patent families (23,935 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 33 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Indoleamine 2,3-dioxygenase 1, Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, RecQ-like DNA helicase BLM, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Thrombopoietin, Geminin, Ras-related protein Rab-9A, Peripheral myelin protein 22, Sphingolipid delta(4)-desaturase DES1, Menin/Histone-lysine N-methyltransferase MLL, Indoleamine 2,3-dioxygenase 2, Serine/threonine-protein kinase mTOR, Polyunsaturated fatty acid lipoxygenase ALOX15.

Bioactivity

ChEMBL activities: 19 potent at pChembl ≥ 5 of 64 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
DEGS1	7	IC50	100	nM	CHEMBL_ACT_24982854
RBP4	6.81	Kd	156	nM	CHEMBL_ACT_6276120
Q5XIF5	5.63	IC50	2320	nM	CHEMBL_ACT_24982846
RBP4	5.62	EC50	2372	nM	CHEMBL_ACT_6276196
MEN1	5.45	Potency	3548	nM	CHEMBL_ACT_4557576
P51450	5.35	Potency	4467	nM	CHEMBL_ACT_4760329
P51450	5.3	Potency	5012	nM	CHEMBL_ACT_4095760
NFKB1	5.2	Potency	6310	nM	CHEMBL_ACT_3672790
NFKB1	5.2	Potency	6310	nM	CHEMBL_ACT_4586071
PSAP	5.16	Kd	6900	nM	CHEMBL_ACT_22754485
PSAP	5.16	Kd	6900	nM	CHEMBL_ACT_22754487
TDP1	5.15	Potency	7080	nM	CHEMBL_ACT_3940894
MAPT	5.15	Potency	7080	nM	CHEMBL_ACT_4056328
Q5XIF5	5.08	Ki	8280	nM	CHEMBL_ACT_24982845
MAPT	5.05	Potency	8912	nM	CHEMBL_ACT_3963116
ALOX15	5	Potency	10000	nM	CHEMBL_ACT_4455066
P15917	5	Potency	10000	nM	CHEMBL_ACT_4635079
THPO	5	Potency	10000	nM	CHEMBL_ACT_4813400
THPO	5	Potency	10000	nM	CHEMBL_ACT_5074353

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

21 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
neoplasm	3	MONDO:0005070	EFO:0000616
schizoaffective disorder	3	MONDO:0005487	EFO:0005411
breast neoplasm	3	MONDO:0021100	MONDO:0007254
peripheral T-cell lymphoma, not otherwise specified	2	MONDO:0004964	EFO:0000211
prostate adenocarcinoma	2	MONDO:0005082	EFO:0000673
neuroblastoma	2	MONDO:0005072	EFO:0000621
gliosarcoma	2	MONDO:0016681	EFO:1001465
cutaneous melanoma	2	MONDO:0005012	EFO:0000389
head and neck cancer	2	MONDO:0005627	EFO:0006859
central nervous system neoplasm	2	MONDO:0006130	EFO:1000158
kidney cancer	2	MONDO:0002367	MONDO:0002367
lung neoplasm	2	MONDO:0021117	MONDO:0008903
brain neoplasm	2	MONDO:0021211	EFO:0003833
glioblastoma	2	MONDO:0018177	MONDO:0020690
leukemia	1	MONDO:0005059	EFO:0000565
lymphoma	1	MONDO:0005062	EFO:0000574
plasma cell myeloma	1	MONDO:0009693	EFO:0001378
myeloproliferative neoplasm	1	MONDO:0020076	EFO:0002428
acute lymphoblastic leukemia	1	MONDO:0004967	EFO:0000220
acute myeloid leukemia	1	MONDO:0018874	EFO:0000222
cystic fibrosis	1	MONDO:0009061	MONDO:0009061

7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 41.

Phase distribution

Phase	Trials
PHASE2	16
PHASE1	16
PHASE3	5
PHASE1/PHASE2	2
Not specified	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00002646	PHASE3	COMPLETED	Hormone Therapy in Treating Postmenopausal Women With Receptor-Positive Breast Cancer
NCT00003075	PHASE3	COMPLETED	Fenretinide in Treating Patients With Cervical Neoplasia
NCT00004154	PHASE3	COMPLETED	Fenretinide in Treating Patients Who Have Undergone Surgery for Bladder Cancer
NCT00534898	PHASE3	WITHDRAWN	Bexarotene and Fenretinide as Addition to Antipsychotic Treatment in Schizophrenia Patients
NCT01479192	PHASE3	TERMINATED	Fenretinide in Healthy Young Women at Genetic and Familial Risk
NCT00003099	PHASE2	COMPLETED	Chemoprevention Therapy Plus Surgery in Treating Women With Breast Cancer
NCT00003223	PHASE2	TERMINATED	SWOG-9507, Fenretinide in Treating Patients With Neoplasia of the Mouth
NCT00003601	PHASE2	COMPLETED	Tretinoin With or Without Fenretinide in Treating Patients With Dysplastic Nevus Syndrome
NCT00004161	PHASE2	COMPLETED	Fenretinide in Treating Patients With Leukoplakia of the Mouth
NCT00006080	PHASE2	COMPLETED	Fenretinide in Treating Patients With Recurrent Malignant Glioma
NCT00006471	PHASE2	COMPLETED	Fenretinide in Treating Patients With Recurrent or Metastatic Head and Neck Cancer
NCT00009971	PHASE2	COMPLETED	Fenretinide in Treating Patients With Recurrent Small Cell Lung Cancer
NCT00011973	PHASE2	COMPLETED	Chemotherapy in Treating Patients With Advanced Kidney Cancer
NCT00026091	PHASE2	COMPLETED	Fenretinide in Treating Patients With Recurrent or Metastatic Ovarian Epithelial or Primary Peritoneal Cancer
NCT00053326	PHASE2	COMPLETED	Fenretinide in Treating Children With Recurrent or Resistant Neuroblastoma
NCT00075491	PHASE2	TERMINATED	Neoadjuvant and Adjuvant Fenretinide Compared With Adjuvant Fenretinide Alone in Treating Patients Who Are Undergoing Surgical Resection For Recurrent Glioblastoma Multiforme
NCT00077402	PHASE2	COMPLETED	Fenretinide In Treating Patients With Advanced or Metastatic Hormone-Refractory Prostate Cancer
NCT00080899	PHASE2	COMPLETED	Fenretinide in Treating Patients With Biochemically Recurrent Hormone-Naïve Prostate Cancer
NCT00288067	PHASE1/PHASE2	TERMINATED	Fenretinide and Rituximab in Treating Patients With B-Cell Non-Hodgkin Lymphoma
NCT00429936	PHASE2	COMPLETED	Study of Fenretinide in the Treatment of Geographic Atrophy Associated With Dry Age-Related Macular Degeneration
NCT00546455	PHASE2	SUSPENDED	A Randomized, Double-blind Study of the Effects of Fenretinide Administered in Subjects With Obesity
NCT01535157	PHASE1/PHASE2	TERMINATED	Fenretinide/LXS Oral Powder Plus Ketoconazole in Recurrent Ovarian Cancer
NCT02495415	PHASE2	UNKNOWN	Trial of Intravenous Fenretinide Emulsion for Patients With Relapsed/Refractory Peripheral T-cell Lymphomas
NCT04234048	PHASE1	RECRUITING	Phase 1 Trial of ST-001 nanoFenretinide in Relapsed/Refractory T-cell Non-Hodgkin Lymphoma
NCT06922539	PHASE1	RECRUITING	ST-001 nanoFenretinide in Relapsed/ Refractory Small Cell Lung Cancer
NCT00001378	PHASE1	COMPLETED	A Pilot Trial of Tamoxifen and 4-HPR (4-N-Hydroxyphenyl Retinamide) in Persons at High Risk for Developing Breast Cancer
NCT00003191	PHASE1	COMPLETED	Fenretinide in Treating Children With Solid Tumors
NCT00003250	PHASE1	COMPLETED	Fenretinide in Treating Patients With Solid Tumors
NCT00005819	PHASE1	COMPLETED	Combination Chemotherapy in Treating Patients With Advanced Solid Tumors
NCT00009932	PHASE1	UNKNOWN	Combination Chemotherapy in Treating Patients With Solid Tumors
NCT00102635	PHASE1	TERMINATED	4-HPR and FTI in Head and Neck Squamous Cell Carcinoma (HNSCC)
NCT00104923	PHASE1	COMPLETED	Fenretinide in Treating Patients With Refractory or Relapsed Hematologic Cancer
NCT00387504	PHASE1	COMPLETED	Fenretinide in Treating Patients With Metastatic or Unresectable Malignant Solid Tumors
NCT00646230	PHASE1	COMPLETED	N2004-03: Intravenous Fenretinide in Treating Young Patients With Recurrent or Resistant Neuroblastoma
NCT01187810	PHASE1	TERMINATED	Fenretinide in Children With Recurrent/Resistant ALL, AML, and NHL
NCT01553071	PHASE1	TERMINATED	Phase I Trial of IV Fenretinide (4-HPR) Plus IV Safingol for Patients With Relapsed Malignancies
NCT02141958	PHASE1	COMPLETED	Safety Study of Fenretinide in Adult Patients With Cystic Fibrosis
NCT02163356	PHASE1	TERMINATED	Fenretinide Lym-X-Sorb + Ketoconazole + Vincristine for Recurrent or Resistant Neuroblastoma
NCT06181760	PHASE1	COMPLETED	A Study to Evaluate the Safety of Fenretinide in Healthy Volunteers
NCT00017134	Not specified	TERMINATED	Fenretinide Followed by Surgery Compared With Surgery Alone in Preventing Ovarian Cancer in Patients at Increased Risk
NCT00098800	Not specified	COMPLETED	Fenretinide in Preventing Ovarian Cancer in Participants Who Are at High Risk for Developing Ovarian Cancer and Planning to Undergo Surgery to Remove the Ovaries

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).