Details of the Drug

General Information of Drug (ID: DMU6NBO)

Drug Name

APX3330

Synonyms

E3330; 136164-66-4; E-3330; E 3330; CHEMBL578390; UNII-11267UI968; 11267UI968; (2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid; (E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid; (2E)-3-(5-(2,3-Dimethoxy-6-methyl-1,4-benzoquinoyl))-2-nonyl-2-propenoic acid; SCHEMBL3758716; SCHEMBL3758719; HMS3886N15; APX 3330; EX-A2212; BDBM50303955; s7445; ZINC14252145; CCG-268389; HY-19357; B5875; CS-0015424; E3330, >=98% (HPLC); A14440; (E)-3-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)-2-nonylpropenoic acid; (E)-3-(5,6-Dimethoxy-3-methyl-14-dioxocyclohexa-25-dienyl)-2-nonylpropenoic Acid; Undecanoic acid, 2-((4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)-, (E)-

Indication

Disease Entry	ICD 11	Status	REF
Diabetic retinopathy	9B71.0	Phase 2	[1]
Solid tumour/cancer	2A00-2F9Z	Phase 1	[2]
------------------------------------------------------------------------------------

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

378.5

Logarithm of the Partition Coefficient (xlogp)

5.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C21H30O6
IUPAC Name: (2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid
Canonical SMILES: CCCCCCCCC/C(=C\\C1=C(C(=O)C(=C(C1=O)OC)OC)C)/C(=O)O
InChI: InChI=1S/C21H30O6/c1-5-6-7-8-9-10-11-12-15(21(24)25)13-16-14(2)17(22)19(26-3)20(27-4)18(16)23/h13H,5-12H2,1-4H3,(H,24,25)/b15-13+
InChIKey: AALSSIXXBDPENJ-FYWRMAATSA-N

Cross-matching ID

PubChem CID: 6439397
CAS Number: 136164-66-4
TTD ID: D9YG4P

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
AP endonuclease 1 (APEX1)	TTHGL48	APEX1_HUMAN	Inhibitor	[3]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[4]
Glucocorticoid receptor (NR3C1)	OTCI2YDI	GCR_HUMAN	Protein Interaction/Cellular Processes	[5]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[6]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[6]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT04692688) Study of the Safety and Efficacy of APX3330 in Diabetic Retinopathy (ZETA-1). U.S. National Institutes of Health.
2	ClinicalTrials.gov (NCT03375086) A Study of APX3330 in Patients With Advanced Solid Tumors (APX3330). U.S. National Institutes of Health.
3	Exploiting the Ref-1-APE1 node in cancer signaling and other diseases: from bench to clinic. NPJ Precis Oncol. 2017;1:19.
4	APE1/Ref-1 redox-specific inhibition decreases survivin protein levels and induces cell cycle arrest in prostate cancer cells. Oncotarget. 2017 Dec 13;9(13):10962-10977. doi: 10.18632/oncotarget.23493. eCollection 2018 Feb 16.
5	Potentiation of glucocorticoid-mediated gene expression by the novel benzoquinone derivative (2E)-3-[5-(2,3-dimethoxy-o-methyl-1, 4-benzoquinoyl)]-2-nonyl-2-propenoic acid (E3330). Eur J Pharmacol. 1995 Oct 15;291(2):121-7. doi: 10.1016/0922-4106(95)90133-7.
6	APE1/Ref-1 prevents oxidative inactivation of ERK for G1-to-S progression following lead acetate exposure. Toxicology. 2013 Mar 8;305:120-9. doi: 10.1016/j.tox.2013.01.010. Epub 2013 Jan 28.