Trimethylcolchicinic acid methyl ether

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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	84053
ChemSpider	75836
Chemical data
Formula	C₂₄H₂₉NO₁₁
Mol. mass	507.48716
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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.

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

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.