apaziquone: structure given in first source; RN given refers to (E)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
ID Source | ID |
---|---|
PubMed CID | 5813717 |
CHEMBL ID | 73822 |
CHEBI ID | 177558 |
SCHEMBL ID | 367965 |
SCHEMBL ID | 367964 |
MeSH ID | M0507513 |
Synonym |
---|
nsc-382456 |
CHEMBL73822 |
CHEBI:177558 |
5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(e)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione |
e-85/050 |
eo9 , |
nor-701 |
neoquin |
e-85/053 |
apaziquone |
eoquin |
eo-9 |
nsc 382456 |
1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-, (e)- |
apaziquonum |
apaziquonum [inn-latin] |
1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-((1e)-3-hydroxy-1-propenyl)-1-methyl- |
(e)-5-(1-azirinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione |
e 09 |
eo 9 (pharmaceutical) |
5-(azridin-1-yl)-3-(hydroxymethyl)-2-((1e)-3-hydroxyprop-1-enyl)-methyl-1h-indole-4,7-dione |
apaziquone [usan:inn] |
nsc 382459 |
apaziquone (usan/inn) |
D02965 |
114560-48-4 |
eoquin (tn) |
1h-indole-4, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl- |
nsc382459 |
E09 , |
nsc-382459 |
antineoplastic-382459 |
qapzola |
5-(aziridin-1-yl)-3-(hydroxymethyl)-2-(3-hydroxyprop-1-enyl)-1-methylindole-4,7-dione |
BCP9000309 |
h464zo600o , |
unii-h464zo600o |
apaziquone [inn] |
apaziquone [mi] |
apaziquone [usan] |
5-(azridin-1-yl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxyprop-1-enyl]-methyl-1h-indole-4,7-dione |
SCHEMBL367965 |
SCHEMBL367964 |
141304-51-0 |
5-aziridin-1-yl-3-hydroxymethyl-2-((e)-3-hydroxy-propenyl)-1-methyl-1h-indole-4,7-dione |
1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl- |
DB12593 |
CS-0006128 |
Q4779259 |
5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione; |
n1,n6-diethyl-3-methylhexanediamide |
(e)-5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione |
5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione |
DTXSID90869587 |
AKOS040744809 |
Apaziquone is a promising local agent for the treatment and prevention of recurrent urothelial carcinoma of the bladder. More research is needed to prove its actual benefit.
Excerpt | Reference | Relevance |
---|---|---|
"Apaziquone is an interesting drug for intravesical use in patients with nonmuscle invasive bladder cancer; however, more research is needed to prove its actual benefit. " | ( Apaziquone for Nonmuscle Invasive Bladder Cancer: Where Are We Now? Alfred Witjes, J; Arends, TJH, 2020) | 3.44 |
"Apaziquone is a promising drug for intravesical use in patients with NMIBC." | ( Apaziquone for non-muscle invasive bladder cancer: a critical review. Kolli, PS; Witjes, JA, 2008) | 3.23 |
"Apaziquone is a promising local agent for the treatment and prevention of recurrent urothelial carcinoma of the bladder. " | ( Apaziquone as an intravesical therapeutic agent for urothelial non-muscle-invasive bladder cancer. Chin, J; Yutkin, V, 2012) | 3.26 |
"EO9 (Apaziquone) is a bioreductive drug that has a chequered history. " | ( EO9 (Apaziquone): from the clinic to the laboratory and back again. Hendriks, HR; Peters, GJ; Phillips, RM, 2013) | 1.42 |
"EO9 (apaziquone) is a novel, promising anticancer agent, which is currently being investigated for the intravesical treatment of bladder cancer. " | ( Stability experiments in human urine with EO9 (apaziquone): a novel anticancer agent for the intravesical treatment of bladder cancer. Beijnen, JH; Lenaz, L; Mirejovsky, D; Rosing, H; Schellens, JH; Vainchtein, LD, 2007) | 1.11 |
Excerpt | Reference | Relevance |
---|---|---|
"Apaziquone treatment inhibited cell proliferation and induced apoptosis in OSCC cells in vitro." | ( Anticancer Activity of Apaziquone in Oral Cancer Cells and Xenograft Model: Implications for Oral Cancer Therapy. Ralhan, R; Somasundaram, RT; Srivastava, G; Walfish, PG, 2015) | 1.45 |
Excerpt | Reference | Relevance |
---|---|---|
" In all cases, considerable effort has gone into detailed pharmacokinetic studies conducted before and during the clinical phase I studies." | ( Pharmacokinetics and early clinical studies of selected new drugs. Cassidy, J; Graham, MA; Jodrell, D; Kaye, SB; Workman, P, 1993) | 0.29 |
" Pharmacokinetic studies were performed with the first and third dose of therapy and nine blood samples were obtained over 30 min postinfusion." | ( Phase I pharmacokinetics and limited sampling strategies for the bioreductive alkylating drug EO9. EORTC Early Clinical Trials Group. Aamdal, S; Graham, MA; Groot, Y; Lund, B; McLeod, HL; Setanoians, A, 1996) | 0.29 |
"Population pharmacokinetic-dynamic analysis was prospectively integrated in the clinical phase II programme of EO9 to determine the population pharmacokinetic profile in a larger population of patients, to estimate individual patient pharmacokinetic parameters, and to investigate relationships between drug exposure and clinical outcome." | ( Population pharmacokinetics and dynamics in phase II studies of the novel bioreductive alkylating cytotoxic indoloquinone EO9. Calabresi, F; Cassidy, J; Cox, EH; Dirix, L; Dombernowsky, P; Epelbaum, R; Hanauske, AR; Loos, WJ; Monfardini, S; Paridaens, R; Pavlidis, N; Schellens, JH; Verweij, J; Wanders, J; Wolff, J, 2001) | 0.31 |
Excerpt | Relevance | Reference |
---|---|---|
"The aim of this study was to design a stable parenteral dosing form of the investigational cytotoxic drug, encoded EO9." | ( Pharmaceutical development of a parenteral lyophilized formulation of the novel indoloquinone antitumor agent EO9. Beijnen, JH; Bult, A; Henrar, RE; Jonkman-de Vries, JD; Kettenes-van den Bosch, JJ; Talsma, H, 1994) | 0.29 |
Class | Description |
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indoles | Any compound containing an indole skeleton. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID217040 | In vitro concentration required to kill 50% of the aerobic cells | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | 2-Cyclopropylindoloquinones and their analogues as bioreductively activated antitumor agents: structure-activity in vitro and efficacy in vivo. |
AID233456 | Selectivity ratio of IC50 of BE and HT-29 cells | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID212880 | Hypoxic cytotoxic ratios of the concentration required to kill 50% of the aerobic cells and concentration required to kill hypoxic cells | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | 2-Cyclopropylindoloquinones and their analogues as bioreductively activated antitumor agents: structure-activity in vitro and efficacy in vivo. |
AID300737 | Cytotoxicity against high NQO1 protein expressing human H460 cells by MTT assay | 2007 | Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19 | Synthesis of cryptolepine analogues as potential bioreducible anticancer agents. |
AID217041 | In vitro concentration required to kill hypoxic cells V79-379A cells | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | 2-Cyclopropylindoloquinones and their analogues as bioreductively activated antitumor agents: structure-activity in vitro and efficacy in vivo. |
AID144376 | Substrate specificity towards human NAD(P)H quinone reductase | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID300739 | Activity of recombinant human NQO1 assessed as specific activity | 2007 | Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19 | Synthesis of cryptolepine analogues as potential bioreducible anticancer agents. |
AID144375 | Inhibitory activity against human NAD(P)H quinone reductase at 50 uM | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID80648 | Chemosensitivity against DT-diaphorase rich H29 cell lines | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID8478 | Chemosensitivity against DT-diaphorase rich A549 cell lines | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID233455 | Selectivity ratio of IC50 of BE and A549 cells | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID41359 | Chemosensitivity against DT-diaphorase deficient BEcell lines | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID226464 | Hypoxic cytotoxicity ratio determined in V79-379A cells | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID300738 | Cytotoxicity against low NQO1 protein expressing human BE cells by MTT assay | 2007 | Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19 | Synthesis of cryptolepine analogues as potential bioreducible anticancer agents. |
AID300741 | Selectivity ratio of IC50 for human H460 cells IC50 for human BE cells | 2007 | Bioorganic & medicinal chemistry, Oct-01, Volume: 15, Issue:19 | Synthesis of cryptolepine analogues as potential bioreducible anticancer agents. |
AID144374 | Ability to serve as substrate for human NAD(P)H quinone reductase determined by measuring reduction of cytochrome C at 550 nM | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID233084 | Ratio of IC50 of BE to IC50 of A549 | 1999 | Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20 | Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships. |
AID1347411 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (1.00) | 18.7374 |
1990's | 58 (58.00) | 18.2507 |
2000's | 27 (27.00) | 29.6817 |
2010's | 10 (10.00) | 24.3611 |
2020's | 4 (4.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (25.49) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 12 (11.65%) | 5.53% |
Reviews | 23 (22.33%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 68 (66.02%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
---|---|---|---|---|---|---|---|
A Randomized, Multicenter, Two-Arm, Single-Dose, Double-Blind, Placebo-CONtrolled Phase 3 Study of Intravesical Qapzola™ (Apaziquone) as a Chemotherapy Adjuvant to TransUrEthral Resection of Bladder Tumors in Patients With Low- to Intermediate-Risk Non-Mu [NCT03224182] | Phase 3 | 118 participants (Actual) | Interventional | 2017-08-04 | Terminated(stopped due to Suspended development) | ||
Phase I Clinical Trial to Evaluate the Safety and Pharmacokinetics of Intravesical Instillation of EO9 in Patients With Non-muscle Invasive Bladder Cancer(NMIBC) [NCT01373398] | Phase 1 | 11 participants (Actual) | Interventional | 2011-05-31 | Completed | ||
A Multicenter, Randomized, Placebo-Controlled, Double-Blind, Phase 3 Trial of Single-Dose Intravesical Apaziquone (EOquin®) as a Surgical Adjuvant Instilled in the Early Postoperative Period in Patients Undergoing Transurethral Resection for Noninvasive B [NCT00598806] | Phase 3 | 812 participants (Actual) | Interventional | 2007-08-31 | Completed | ||
Phase II Study of Intravesical Instillation of EOQUIN™ in High Risk Superficial Bladder Cancer [NCT00141531] | Phase 2 | 53 participants (Actual) | Interventional | 2005-07-31 | Completed | ||
Randomized, Placebo-controlled, Double-blinded Study of Single Immediate Instillation of EO9 After TURBT in Patients With NMIBC [NCT01475266] | Phase 2/Phase 3 | 51 participants (Actual) | Interventional | 2011-11-30 | Terminated(stopped due to Sponsor's decision) | ||
A Multicenter, Randomized, Placebo-Controlled, Double-Blind, Phase 3 Trial of Single Dose Intravesical Apaziquone (EOquin®) as a Surgical Adjuvant Instilled in the Early Postoperative Period in Patients Undergoing Transurethral Resection for Noninvasive B [NCT00461591] | Phase 3 | 802 participants (Actual) | Interventional | 2007-04-30 | Completed | ||
A Phase 3 International, Multicenter, Double-Blind, Placebo-Controlled, Randomized Trial Evaluating the Efficacy and Safety of Multiple Instillations of Intravesical Apaziquone vs. Placebo in Patients With Low-Intermediate Risk Non-Muscle Invasive Bladder [NCT01410565] | Phase 3 | 66 participants (Actual) | Interventional | 2011-07-31 | Terminated(stopped due to Business reason) | ||
A Phase 3 International, Double-Bind Trial Evaluating Efficacy and Safety of Multiple Instillations of Intravesical Apaziquone vs. Placebo in Patients With Low-Intermediate Risk Non-Muscle Invasive Bladder Cancer (NMIBC) [NCT01469221] | Phase 3 | 47 participants (Actual) | Interventional | 2012-01-31 | Terminated(stopped due to Business reason) | ||
A Multicenter, Multi-Arm, Randomized, Multi-Dose, Placebo-Controlled, Double-Blind, Phase 3 Study of Intravesical Apaziquone (EOquin®) as a Surgical Adjuvant in the Immediate Postoperative Period in Patients Undergoing Transurethral Resection for Non- Mus [NCT02563561] | Phase 3 | 62 participants (Actual) | Interventional | 2015-10-09 | Terminated | ||
[information is prepared from clinicaltrials.gov, extracted Sep-2024] |