Trimethylcolchicinic acid methyl ether
From DrugPedia: A Wikipedia for Drug discovery
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| PubChem = 84053 | | PubChem = 84053 | ||
| DrugBank = | | DrugBank = | ||
| - | | ChemSpiderID = | + | | ChemSpiderID = 75836 |
| chemical_formula =C<sub>2</sub><sub>4</sub>H<sub>2</sub><sub>9</sub>NO<sub>1</sub><sub>1</sub> | | chemical_formula =C<sub>2</sub><sub>4</sub>H<sub>2</sub><sub>9</sub>NO<sub>1</sub><sub>1</sub> | ||
| molecular_weight = 507.48716 | | molecular_weight = 507.48716 | ||
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==Description== | ==Description== | ||
RN given refers to (S)-isomer; synonyms NSC-36354 and TMCA refers to tartrate [1:1] | RN given refers to (S)-isomer; synonyms NSC-36354 and TMCA refers to tartrate [1:1] | ||
| + | |||
| + | A colchicine analog with potential antineoplastic activity. Trimethylcolchicinic acid binds to tubulin, inhibiting its polymerization into microtubules and preventing cell division. | ||
==General Properties== | ==General Properties== | ||
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195 | 195 | ||
| + | ==Toxicity== | ||
| + | organism Test Type Route Reported Dose (Normalized Dose) Effect Source | ||
| + | |||
| + | dog LD50 parenteral 9500ug/kg (9.5mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973. | ||
| + | |||
| + | human TDLo oral 200ug/kg/7D-I (0.2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING,BLOOD: LEUKOPENIA,BLOOD: THROMBOCYTOPENIA Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 263, 1972. | ||
| + | |||
| + | mouse LD50 intraperitoneal 70520ug/kg (70.52mg/kg) National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | ||
| + | |||
| + | mouse LD50 parenteral 8mg/kg (8mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973. | ||
| + | |||
| + | rat LD50 parenteral 3mg/kg (3mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973. | ||
==External Links== | ==External Links== | ||
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[http://crdd.osdd.net/raghava/biadb/detail.php?id=2115 Link to BIAdb Database] | [http://crdd.osdd.net/raghava/biadb/detail.php?id=2115 Link to BIAdb Database] | ||
| + | [[Category:BIAdb_old]] | ||
Current revision
| Trimethylcolchicinic acid methyl ether
| |
| Systematic (IUPAC) name | |
| (7S)-7-amino-1,2,3,10-tetramethoxy-6,7-dihydro-5H-benzo[g]heptalen-9-one; (2R,3R)-2,3-dihydroxybutanedioicacid | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| ChemSpider | |
| Chemical data | |
| Formula | C24H29NO11 |
| Mol. mass | 507.48716 |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Contents |
[edit] Description
RN given refers to (S)-isomer; synonyms NSC-36354 and TMCA refers to tartrate [1:1]
A colchicine analog with potential antineoplastic activity. Trimethylcolchicinic acid binds to tubulin, inhibiting its polymerization into microtubules and preventing cell division.
[edit] General Properties
*Molecular Weight
507.48716
*Molecular Formula
C24H29NO11
*IUPAC NAME
(7S)-7-amino-1,2,3,10-tetramethoxy-6,7-dihydro-5H-benzo[g]heptalen-9-one; (2R,3R)-2,3-dihydroxybutanedioicacid
*Canonical Smiles
COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)OC)N.C(C(C(=O)O)O)(C(=O)O)O
*Isomeric Smiles
COC1=CC=C2C(=CC1=O)[C@H](CCC3=CC(=C(C(=C32)OC)OC)OC)N.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
*XLogP
N/A
*Topological Polar Surface Area
195
[edit] Toxicity
organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 parenteral 9500ug/kg (9.5mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973.
human TDLo oral 200ug/kg/7D-I (0.2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING,BLOOD: LEUKOPENIA,BLOOD: THROMBOCYTOPENIA Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 263, 1972.
mouse LD50 intraperitoneal 70520ug/kg (70.52mg/kg) National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 parenteral 8mg/kg (8mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973.
rat LD50 parenteral 3mg/kg (3mg/kg) Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973.
