Details of the Drug

General Information of Drug (ID: DMVY0BU)

Drug Name
Apaziquone
Synonyms
EOquin; 114560-48-4; Apaziquonum; NOR-701; EO 9 (pharmaceutical); EO-9; Apaziquone [USAN:INN]; NSC-382459; Apaziquonum [INN-Latin]; E 09; NSC 382459; UNII-H464ZO600O; E-85/053; E-09; EO9; NSC 382456; H464ZO600O; 5-(Azridin-1-yl)-3-(hydroxymethyl)-2-((1E)-3-hydroxyprop-1-enyl)-methyl-1H-indole-4,7-dione; (E)-5-(1-Azirinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1H-indole-4,7-dione; E09; 1H-Indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-, (E)-; Neoquin; Qapzola; Apaziquonum; EO 9; Eoquin (TN); Apaziquone (USAN/INN); E-85/050; 3-hydroxymethyl-5-aziridinyl-1-methyl-2-(1H-indole-4,7-dione)prop-beta-en-alpha-ol; 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione; Apaziquone/EOquin
Indication
Disease Entry ICD 11 Status REF
Bladder cancer 2C94 Phase 3 [1]
Non-muscle invasive bladder cancer 2C94 Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.3
Topological Polar Surface Area (xlogp) -0.5
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H16N2O4
IUPAC Name
5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione
Canonical SMILES
CN1C(=C(C2=C1C(=O)C=C(C2=O)N3CC3)CO)/C=C/CO
InChI
InChI=1S/C15H16N2O4/c1-16-10(3-2-6-18)9(8-19)13-14(16)12(20)7-11(15(13)21)17-4-5-17/h2-3,7,18-19H,4-6,8H2,1H3/b3-2+
InChIKey
MXPOCMVWFLDDLZ-NSCUHMNNSA-N
Cross-matching ID
PubChem CID
5813717
CAS Number
114560-48-4
DrugBank ID
DB12593
TTD ID
D0FP0R

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human Deoxyribonucleic acid (hDNA) TTUTN1I NOUNIPROTAC Modulator [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000838)
2 ClinicalTrials.gov (NCT00598806) Phase 3 Trial of Single-Dose Intravesical EOquin as a Surgical Adjuvant for Noninvasive Bladder Cancer. U.S. National Institutes of Health.
3 EO9 (Apaziquone): from the clinic to the laboratory and back again
4 Cisplatin and DNA repair in cancer chemotherapy.Trends Biochem Sci.1995 Oct;20(10):435-9.
5 Structures of oxaliplatin-oligonucleotide adducts from DNA.J Mass Spectrom.2012 Oct;47(10):1282-93.
6 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12.
7 Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35.
8 O6-methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int J Cancer. 1998 Sep 11;77(6):919-22.
9 Inhibition of carboplatin-induced DNA interstrand cross-link repair by gemcitabine in patients receiving these drugs for platinum-resistant ovarian cancer.Clin Cancer Res.2010 Oct 1;16(19):4899-905.
10 DNA intrastrand cross-link at the 5'-GA-3' sequence formed by busulfan and its role in the cytotoxic effect. Cancer Sci. 2004 May;95(5):454-8.
11 Brca2/Xrcc2 dependent HR, but not NHEJ, is required for protection against O(6)-methylguanine triggered apoptosis, DSBs and chromosomal aberrations... DNA Repair (Amst). 2009 Jan 1;8(1):72-86.
12 Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Ther. 1999 Sep;83(3):181-215.
13 Predicting the myelotoxicity of chemotherapy: the use of pretreatment O6-methylguanine-DNA methyltransferase determination in peripheral blood mono... Melanoma Res. 2011 Dec;21(6):502-8.