Page last updated: 2024-12-08

indicine-n-oxide

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Description

indicine-N-oxide: RN given refers to (1R-(1alpha,7(2R*,3S*),7abeta))-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID280564
CHEMBL ID512655
MeSH IDM0060592

Synonyms (19)

Synonym
butanoic acid,3-dihydroxy-2-(1-methylethyl)- (2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizin-7-yl) methyl ester, n-oxide, (1r-(1.alpha.,7(2r*,3s*),7a.beta))-
nsc132319 ,
indicine n-oxide
41708-76-3
indicine, n-oxide
indicine-n-oxide
[(7r,8r)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3h-pyrrolizin-4-ium-1-yl]methyl (2r)-2-hydroxy-2-[(1s)-1-hydroxyethyl]-3-methyl-butanoate
butanoic acid, (2r,3s)-dihydroxy-2-(1-methylethyl)-(2,3,5,7a-tetrahydro-(1r)-hydroxy-1h-pyrrolizin-7-yl)methyl ester, n-oxide
NCI60_000712
CHEMBL512655
[(7r,8r)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3h-pyrrolizin-4-ium-1-yl]methyl (2r)-2-hydroxy-2-[(1s)-1-hydroxyethyl]-3-methylbutanoate
bdbm50480295
indicin-n-oxid
indicine n-oxide, hplc grade
mfcd00866484
HY-105529
DTXSID101315334
CS-0026202
AKOS040758123

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" One patient with renal impairment had an abnormally long plasma elimination phase half-life (275 min) and reduced plasma clearance (17 ml/min/m2)."( Pharmacokinetic study of indicine N-oxide in pediatric cancer patients.
Ames, MM; Coccia, PF; Davis, DM; Hughes, CS; Miser, JS; Smithson, WA, 1982
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (73)

Assay IDTitleYearJournalArticle
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID151874Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 800 mg/kg (Group II)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID152021Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152044Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID339034Cytotoxicity against human A204 cells after 24 hrs by soft agar colony forming assay
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID152175Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group III); ND = no data1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151861Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 400 mg/kg (Group II)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152335Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID397122Inhibition of HIV1 RT
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID152336Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152191Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID152333Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152015Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152019Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151863Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 400 mg/kg (Group IV)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID152022Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID152334Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151736Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 200 mg/kg (Group II)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152194Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151729Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 1600 mg/kg (Group II)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID199258In vitro cytotoxicity against human A204 Rhabdomyosarcoma cell line1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID151862Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 400 mg/kg (Group III)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151875Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 800 mg/kg (Group III)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152182Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152020Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152173Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID152193Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151885Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151735Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 200 mg/kg (Group I)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID151731Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 1600 mg/kg (Group IV)(5 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID152031Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID152180Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152192Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID333842Cytotoxicity against human KB cells
AID151860Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 400 mg/kg (Group I)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152181Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152033Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151738Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 200 mg/kg (Group IV)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID151728Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 1600 mg/kg (Group I) (6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID151884Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152014Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152179Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 200 mg/kg (Group I)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID333843In vivo cytotoxicity against mouse P388 cells relative to control
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID151730Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 1600 mg/kg (Group III)(5 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID152045Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152046Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group III)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152032Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152034Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 400 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152047Weight difference observed in survivors treated for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 800 mg/kg (Group IV)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID151737Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 200 mg/kg (Group III)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID152174Survival rate of the animals determined for antitumor activity against P388 Lymphocytic Leukemia system at a dose of 1600 mg/kg (Group II)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID151876Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 800 mg/kg (Group IV)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID151873Number of Survivors determined for antitumor activity against P388 Lymphocytic Leukemia system on day 5 at a dose of 800 mg/kg (Group I)(6 out of 6)1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-199023 (82.14)18.7374
1990's3 (10.71)18.2507
2000's1 (3.57)29.6817
2010's1 (3.57)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.82

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.

MetricThis Compound (vs All)
Research Demand Index19.82 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (14.71%)5.53%
Reviews3 (8.82%)6.00%
Case Studies1 (2.94%)4.05%
Observational0 (0.00%)0.25%
Other25 (73.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]