Page last updated: 2024-11-08

nsc 366140

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

NSC 366140: a 9-methoxypyrazoloacridine; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID339455
CHEMBL ID118841
SCHEMBL ID867991
SCHEMBL ID6350605
MeSH IDM0177741

Synonyms (47)

Synonym
2-[(3-n',4,5-kl]acridine, free base
pyrazolo-acridine (free base)
NSC627168 ,
nsc-627168
2-[(3-n',n'-dimethylamino)propyl]-9-methoxy-5-nitro-[6h]-pyrazolo[3,4,5-kl]acridine
NCI60_008612
NCIMECH_000572
NCI60_003371
pyrazoloacridine
nsc-366140
pd 115934
pyrazolo(3,4,5-kl)acridine-2(6h)-propanamine, n,n-dimethyl-9-methoxy-5-nitro-
pd 115,934
n,n-dimethyl-9-methoxy-5-nitropyrazolo(3,4,5-kl)acridine-2(6h)-propanamine
brn 4211902
nsc 366140
pd-115934
pyrazolo(3,4,5-kl)acridine-2(6h)-propanamine, 9-methoxy-n,n-dimethyl-5-nitro-
NEURO_000260
NEURO_000206
CHEMBL118841
99009-20-8
unii-l24xjn68ow
l24xjn68ow ,
ccris 9408
CCG-35612
SCHEMBL867991
SCHEMBL6350605
HZCWPKGYTCJSEB-UHFFFAOYSA-N
pyrazolo[3,4,5-kl]acridine-2(6h)-propanamide, 9-methoxy-n,n-dimethyl-
3-(9-methoxy-5-nitropyrazolo[3,4,5-kl]acridin-2(6h)-yl)-n,n-dimethyl-1-propanamine #
AKOS024419418
3-(9-methoxy-5-nitropyrazolo[3,4,5-kl]acridin-2(6h)-yl)-n,n-dimethyl-1-propanamine
DB12549
nsc 366140; nsc 627168; pd 115934; pza
SB17160
3-(4-methoxy-10-nitro-8,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-14-yl)-n,n-dimethylpropan-1-amine
Q27282607
MS-25883
HY-108969
DTXSID301316714
(3-{4-methoxy-10-nitro-8,14,15-triazatetracyclo[7.6.1.0?,?.0??,??]hexadeca-1(15),2,4,6,9(16),10,12-heptaen-14-yl}propyl)dimethylamine
3-(9-methoxy-5-nitropyrazolo[3,4,5-kl]acridin-2(1h)-yl)-n,n-dimethylpropan-1-amine
DTXSID50869326
CS-0033826
AKOS040749252
PD132328

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Plasma samples were obtained for pharmacokinetic analysis in 17 patients."( Phase I trial and pharmacokinetic study of pyrazoloacridine in children and young adults with refractory cancers.
Adamson, PC; Arndt, C; Balis, FM; Berg, SL; Blaney, SM; Blatt, J; O'Brien, M; Poplack, DG, 1998
)
0.3
" The pharmacokinetic results obtained here in mice have been used to facilitate the dose escalations during the Phase I trial and to determine pharmacokinetic drug exposure targets for its acute and sub-acute toxic effects."( Pharmacokinetics of 9-methoxy-N,N-dimethyl-5-nitropyrazolo [3,4, 5-kl]acridine-2(6H)-propanamine (PZA, PD 115934, NSC 366140) in mice: guidelines for early clinical trials1.
Baker, LH; Foster, BJ; LoRusso, PM; Wiegand, RA, 1995
)
0.29
" Pharmacokinetic studies to determine PZA plasma concentrations were performed."( A phase II pharmacodynamic study of pyrazoloacridine in patients with metastatic colorectal cancer.
Budd, GT; Bukowski, RM; Ganapathi, R; McLain, D; Olencki, T; Peereboom, D; Pelley, R; Rybicki, L; Wood, L, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NADHomo sapiens (human)IC50 (µMol)45.00000.00260.80763.4000AID277029
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
protein polyubiquitinationNADHomo sapiens (human)
response to ischemiaNADHomo sapiens (human)
NADH oxidationNADHomo sapiens (human)
ubiquinone metabolic processNADHomo sapiens (human)
xenobiotic metabolic processNADHomo sapiens (human)
nitric oxide biosynthetic processNADHomo sapiens (human)
response to oxidative stressNADHomo sapiens (human)
synaptic transmission, cholinergicNADHomo sapiens (human)
response to nutrientNADHomo sapiens (human)
response to toxic substanceNADHomo sapiens (human)
response to hormoneNADHomo sapiens (human)
response to carbohydrateNADHomo sapiens (human)
response to amineNADHomo sapiens (human)
removal of superoxide radicalsNADHomo sapiens (human)
protein catabolic processNADHomo sapiens (human)
response to estradiolNADHomo sapiens (human)
response to lipopolysaccharideNADHomo sapiens (human)
response to testosteroneNADHomo sapiens (human)
cellular response to oxidative stressNADHomo sapiens (human)
negative regulation of protein catabolic processNADHomo sapiens (human)
vitamin E metabolic processNADHomo sapiens (human)
vitamin K metabolic processNADHomo sapiens (human)
negative regulation of apoptotic processNADHomo sapiens (human)
response to alkaloidNADHomo sapiens (human)
positive regulation of neuron apoptotic processNADHomo sapiens (human)
innate immune responseNADHomo sapiens (human)
cell redox homeostasisNADHomo sapiens (human)
response to ethanolNADHomo sapiens (human)
response to electrical stimulusNADHomo sapiens (human)
cellular response to hydrogen peroxideNADHomo sapiens (human)
NADPH oxidationNADHomo sapiens (human)
cellular response to metal ionNADHomo sapiens (human)
negative regulation of ferroptosisNADHomo sapiens (human)
response to tetrachloromethaneNADHomo sapiens (human)
response to L-glutamineNADHomo sapiens (human)
response to hydrogen sulfideNADHomo sapiens (human)
response to flavonoidNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
RNA bindingNADHomo sapiens (human)
cytochrome-b5 reductase activity, acting on NAD(P)HNADHomo sapiens (human)
superoxide dismutase activityNADHomo sapiens (human)
protein bindingNADHomo sapiens (human)
NADPH dehydrogenase (quinone) activityNADHomo sapiens (human)
identical protein bindingNADHomo sapiens (human)
NADH:ubiquinone reductase (non-electrogenic) activityNADHomo sapiens (human)
NAD(P)H dehydrogenase (quinone) activityNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusNADHomo sapiens (human)
cytoplasmNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
dendriteNADHomo sapiens (human)
neuronal cell bodyNADHomo sapiens (human)
synapseNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID98712Growth inhibition against mouse leukemia L1210 cell line1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Comparative molecular field analysis of in vitro growth inhibition of L1210 and HCT-8 cells by some pyrazoloacridines.
AID255803In vitro cytotoxicity against murine leukemia cell line L12102005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
Design, synthesis, and antiproliferative activity of some novel aminosubstituted xanthenones, able to overcome multidrug resistance toward MES-SA/Dx5 cells.
AID432397Inhibition of human topoisomerase 1-mediated relaxation of supercoiled plasmid O6#7 DNA at 8 uM after 30 mins by gel electrophoresis2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
On the role of topoisomerase I in mediating the cytotoxicity of 9-aminoacridine-based anticancer agents.
AID277029Inhibition of human recombinant NQO12006Bioorganic & medicinal chemistry letters, Dec-15, Volume: 16, Issue:24
In silico identification and biochemical characterization of novel inhibitors of NQO1.
AID78970Growth inhibition against human colon carcinoma HCT-8 cell line1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Comparative molecular field analysis of in vitro growth inhibition of L1210 and HCT-8 cells by some pyrazoloacridines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's21 (46.67)18.2507
2000's23 (51.11)29.6817
2010's1 (2.22)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials22 (46.81%)5.53%
Reviews3 (6.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (46.81%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (8)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Phase I/II Trial of Pyrazoloacridine and Carboplatin in Patients With Recurrent Glioma [NCT00005976]Phase 260 participants (Actual)Interventional2000-05-31Completed
Phase I/II Study of Pyrazoloacridine (PZA) in Adults With Newly Diagnosed Glioblastoma Multiforme [NCT00006355]Phase 1/Phase 20 participants Interventional2000-05-31Completed
A Phase I Study of High-dose Pyrazoloacridine (PZA) (NSC 366140) Supported With Autologous Hematopoietic Stem Cell Rescue in Children With Recurrent or Resistant Neuroblastoma (IND # 36325) [NCT00053950]Phase 142 participants (Actual)Interventional2002-12-31Terminated(stopped due to Administratively complete.)
Phase II Trial of Pyrazoloacridine (PZA) in Previously Untreated Hepatocellular Carcinoma (HCC) Patients [NCT00003714]Phase 20 participants (Actual)InterventionalWithdrawn(stopped due to Withdrawn)
PHASE II CLINICAL EVALUATION OF PYRAZOLOACRIDINE IN PATIENTS WITH ADVANCED NON-SMALL CELL LUNG CARCINOMA [NCT00002656]Phase 220 participants (Actual)Interventional1995-10-31Completed
A Phase II Trial of Pyrazoloacridine (NSC 366140, IND 36325) in Metastatic Cutaneous and Ocular Melanoma [NCT00003802]Phase 20 participants Interventional1999-02-28Completed
PHASE II CLINICAL EVALUATION OF PYRAZOLOACRIDINE IN PATIENTS WITH METASTATIC BREAST CANCER [NCT00002585]Phase 220 participants (Anticipated)Interventional1994-02-28Completed
Phase II Evaluation of Pyrazoloacridine (NSC #366140) in Patients With Metastatic Breast Cancer [NCT00003041]Phase 20 participants Interventional1997-07-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]