Compounds > n-methylcolchiceinamide, (s)-isomer
Page last updated: 2024-12-06

n-methylcolchiceinamide, (s)-isomer

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

Cross-References

ID SourceID
PubMed CID17798
CHEMBL ID88059
MeSH IDM0318595

Synonyms (18)

Synonym
CHEMBL88059 ,
10-demethoxy-10-methylaminocolchicine
nsc 403149
brn 2788038
colchicine, 10-demethoxy-10-methylamino-
2826-80-4
colchicoinamide, n-methyl-
AKOS001581086
HMS1648O10
bdbm50280009
n-((s)-1,2,3-trimethoxy-10-methylamino-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
n-(1,2,3-trimethoxy-10-methylamino-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
4-14-00-00923 (beilstein handbook reference)
n-[(7s)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
(s)-n-(1,2,3-trimethoxy-10-(methylamino)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide
STL546880
DTXSID001115945
n-[(7s)-5,6,7,9-tetrahydro-1,2,3-trimethoxy-10-(methylamino)-9-oxobenzo[a]heptalen-7-yl]acetamide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A method for extracting LD50 values from antitumor test data is described."( Toxicity quantitative structure--activity relationships of colchicines.
Beisler, JA; Neiman, Z; Quinn, FR, 1981)		0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1756945Antiproliferative activity against human A549 cells assessed as inhibition of cell growth measured after 72 hrs by SRB assay2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID132966In vivo antitumor activity against P388 mouse leukemia and minimum affective dose (MED) which produced a T/C greater than the threshold value of 125 was reported.1987Journal of medicinal chemistry, Apr, Volume: 30, Issue:4
A novel synthesis of colchicide and analogues from thiocolchicine and congeners: reevaluation of colchicide as a potential antitumor agent.
AID136914In vivo antitumor activity against P388 mouse leukemia expressed as T/C (median survival time of treated animals / median survival time of untreated controls x 100) at a dose of 0.32 mg/kg1987Journal of medicinal chemistry, Apr, Volume: 30, Issue:4
A novel synthesis of colchicide and analogues from thiocolchicine and congeners: reevaluation of colchicide as a potential antitumor agent.
AID1754731Antiproliferative activity against human Lovo/DX cells assessed as inhibition of proliferation after 72 hrs by SRB assay2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID139239Logarithm of toxic activity (1/lethal dose) in mice bearing P388 leukemia on chronic regimen (Q 1-9)1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID1756944Antiproliferative activity against human LoVo cells assessed as inhibition of cell growth measured after 72 hrs by SRB assay2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID1674001Antiproliferative activity against mouse P388 cells incubated for 72 hrs by Coulter counter method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Colchicine Alkaloids and Synthetic Analogues: Current Progress and Perspectives.
AID1756947Antiproliferative activity against human Lovo/DX cells assessed as inhibition of cell growth measured after 72 hrs by SRB assay2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID1527062Antiproliferative activity against human Bel7402 cells assessed as reduction in cell viability by MTT assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Recent developments on (-)-colchicine derivatives: Synthesis and structure-activity relationship.
AID154376Antitumor activity against murine lymphocytic leukemia P388 cells1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Quantitative structure-activity relationships of colchicines against P388 leukemia in mice.
AID1756948Cytotoxicity against mouse BALB/3T3 cells assessed as inhibition of cell growth measured after 72 hrs by SRB assay2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID1754735Antiproliferative activity against mouse BALB/3T3 cells assessed as inhibition of proliferation after 72 hrs by SRB assay2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID23461Partition coefficient (logP)1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Quantitative structure-activity relationships of colchicines against P388 leukemia in mice.
AID1754732Antiproliferative activity against human MCF-7 cells assessed as inhibition of proliferation after 72 hrs by SRB assay2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID1527061Antiproliferative activity against human A549 cells assessed as reduction in cell viability by MTT assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Recent developments on (-)-colchicine derivatives: Synthesis and structure-activity relationship.
AID23448Partition coefficient (logP)1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID1754734Resistance index, ratio of IC50 for antiproliferative activity against human Lovo/DX cells to IC50 for antiproliferative activity against human LoVo cells2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID134555Compound was tested for toxicity in P388 tumored mice1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID1527063Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability by MTT assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Recent developments on (-)-colchicine derivatives: Synthesis and structure-activity relationship.
AID1754733Antiproliferative activity against human A549 cells assessed as inhibition of proliferation after 72 hrs by SRB assay2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID1527060Antiproliferative activity against human A2780 cells assessed as reduction in cell viability by MTT assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Recent developments on (-)-colchicine derivatives: Synthesis and structure-activity relationship.
AID1756949Resistance index, ratio of IC50 for antiproliferative activity against human Lovo/DX cells to IC50 for antiproliferative activity against human Lovo cells2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID1756946Antiproliferative activity against human MCF7 cells assessed as inhibition of cell growth measured after 72 hrs by SRB assay2021European journal of medicinal chemistry, Apr-05, Volume: 215An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.
AID134556Compound was tested for toxicity in non tumored mice1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID1754730Antiproliferative activity against human LoVo cells assessed as inhibition of proliferation after 72 hrs by SRB assay2021Bioorganic & medicinal chemistry letters, 09-01, Volume: 47Synthesis and antiproliferative screening of novel doubly modified colchicines containing urea, thiourea and guanidine moieties.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (33.33)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's2 (22.22)24.3611
2020's4 (44.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.65

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.65 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (22.22%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (77.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		5.0170alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
desacetamidocolchicine
desacetamidocolchicine: structure given in first source		3.3510
thiocholchicine
thiocholchicine: RN refers to (S)-isomer		4.750
colchicenamide
colchicenamide: RN given refers to (S)-isomer; structure given in first source		4.2720
trimethylcolchicinic acid methyl ether
trimethylcolchicinic acid methyl ether: RN given refers to (S)-isomer; synonyms NSC-36354 & TMCA refers to tartrate [1:1]		2.3620acetamides;
alkaloid;
carbotricyclic compound
n-deacetyl-n-formylcolchicine
N-deacetyl-N-formylcolchicine: structure given in first source		2.3620cyclic ketone
2-demethylthiocolchicine
2-demethylthiocolchicine: RN & structure given in first source; RN not in Chemline 10/85		1.9710
3-demethylthiocolchicine
3-demethylthiocolchicine: RN & structure given in first source; RN not in Chemline 10/85		1.9710
demecolcine
Demecolcine: An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.. (-)-demecolcine : A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.		2.3620alkaloid;
secondary amino compound		antineoplastic agent;
microtubule-destabilising agent
n-acetylcolchinol
N-acetylcolchinol: structure		3.3510
3-desmethylcolchicine
3-desmethylcolchicine: structure		1.9710
fosbretabulin
[no description available]		3.3510stilbenoid
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Neoplasms
[description not available]		01.9710
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9610
Experimental Leukemia
[description not available]		01.9610
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Benign Neoplasms
[description not available]		03.1710
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.1710