ceratamine A: an antimitotic alkaloid isolated from the sponge Pseudoceratina; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
ceratamine A : An organic heterobicyclic compound, which is imidazo[4,5-d]azepin-5(6H)-one substituted by a 3,5-dibromo-4-methoxybenzyl group at position 4, a methyl group at position 6 and a methylamino group at position 2. It is an antimitotic alkaloid isolated from the marine sponge Pseudoceratina. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 11488186 |
| CHEMBL ID | 1277687 |
| CHEBI ID | 65608 |
| SCHEMBL ID | 2228904 |
| SCHEMBL ID | 14019702 |
| SCHEMBL ID | 14019716 |
| MeSH ID | M0466195 |
| Synonym |
|---|
| FT-0664484 |
| chebi:65608 , |
| CHEMBL1277687 |
| ceratamine a |
| 4-(3,5-dibromo-4-methoxybenzyl)-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5(6h)-one |
| 634151-15-8 |
| SCHEMBL2228904 |
| SCHEMBL14019702 |
| SCHEMBL14019716 |
| DTXSID80467455 |
| Q27134074 |
| HAIJSTYZBPUVSG-UHFFFAOYSA-N |
| HY-N6997 |
| CS-0100466 |
| 4-[(3,5-dibromo-4-methoxyphenyl)methyl]-6-methyl-2-(methylamino)imidazo[4,5-d]azepin-5-one |
| AKOS040732787 |
| Role | Description |
|---|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| antimitotic | Any compound that inhibits cell division (mitosis). |
| [role 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] | |
| Class | Description |
|---|---|
| organobromine compound | A compound containing at least one carbon-bromine bond. |
| alkaloid | Any of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids. |
| organic heterobicyclic compound | |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| cyclic ketone | |
| tertiary amine | A compound formally derived from ammonia by replacing three hydrogen atoms by hydrocarbyl groups. |
| secondary amino compound | A compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups. |
| [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 |
|---|---|---|---|---|
| AID1374415 | Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by MTT assay | 2018 | Bioorganic & medicinal chemistry letters, 03-01, Volume: 28, Issue:5 | Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. |
| AID537573 | Antimitotic activity in human MCF7mp53 cells assessed as induction of mitotic arrest after 20 hrs | 2010 | Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21 | Synthetic analogues of the microtubule-stabilizing sponge alkaloid ceratamine A are more active than the natural product. |
| AID1374413 | Cytotoxicity against human HepG2 cells assessed as growth inhibition after 72 hrs by MTT assay | 2018 | Bioorganic & medicinal chemistry letters, 03-01, Volume: 28, Issue:5 | Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. |
| AID1181076 | Drug metabolism in rat liver microsomes incubated with 10 uM ceratamine A for 60 mins assessed as metabolite formation in presence of 1 mM NADPH at pH 7.4 and 37 degC by reverse phase HPLC-UV chromatography | 2014 | Journal of natural products, Jul-25, Volume: 77, Issue:7 | Structure elucidation of phase I metabolites of the microtubule perturbagens: ceratamines A and B. |
| AID1374414 | Cytotoxicity against human BGC823 cells assessed as growth inhibition after 72 hrs by MTT assay | 2018 | Bioorganic & medicinal chemistry letters, 03-01, Volume: 28, Issue:5 | Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. |
| AID537574 | Antimitotic activity in human MCF7mp53 cells assessed as cells arrested at mitotic stage at optimal concentration after 20 hrs | 2010 | Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21 | Synthetic analogues of the microtubule-stabilizing sponge alkaloid ceratamine A are more active than the natural product. |
| AID1374416 | Cytotoxicity against human A2780 cells assessed as growth inhibition after 72 hrs by MTT assay | 2018 | Bioorganic & medicinal chemistry letters, 03-01, Volume: 28, Issue:5 | Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. |
| AID1374412 | Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by MTT assay | 2018 | Bioorganic & medicinal chemistry letters, 03-01, Volume: 28, Issue:5 | Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 5 (55.56) | 29.6817 |
| 2010's | 4 (44.44) | 24.3611 |
| 2020's | 0 (0.00) | 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 weak demand-to-supply ratio for research on this compound.
| This Compound (12.07) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||