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Tallimustine

Tallimustine structure

CAS No:
115308-98-0
Formula:
C32H38Cl2N10O4
Chemical Name:
Tallimustine
Synonyms:
Tallimustine;FCE-24517;N-[5-[[(3-Amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-[4-[bis(2-chloroethyl)amino]benzoylamino]-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide;Talimustine
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Tallimustine, a benzoyl mustard derivative of distamycin A, is an alkylating agent that binds to the minor groove of DNA. It's association with severe myelotoxicity lead to the end of its development in favour of α-halogenoacrylamide derivatives such as [brostallicin], which have a favourable cytotoxicity/myelotoxicity ratio. Newer generations of DNA minor groove binding agents can more specifically recognize base pair sequences.|Tallimustine is a benzoyl mustard derivative of the antiviral agent distamycin A with potential antineoplastic activity. Tallimustine selectively binds to A-T rich regions in the minor groove of DNA and alkylates at the N3 position of adenine in a highly sequence-specific manner. This prevents DNA replication, inhibits cellular proliferation and triggers apoptosis. Moreover, unlike other clinical nitrogen mustards, tallimustine does not carry out guanine-N7 alkylation in the major groove of DNA, which may lead to a high selectivity of action.

Tallimustine Basic Attributes

Molecular Weight：

697.624

Exact Mass：

696.24500

UNII：

71193OXG6S

DSSTox ID：

DTXSID40151045

NCI Thesaurus Code：

C1603

Characteristics

PSA：

184

XLogP3：

5.20880

Density：

1.41g/cm3

Refractive Index：

1.668

Toxicity

Toxicity Summary：

Tallimustine is associated with myelotoxicity severe enough to stop its development.

Drug Information

Drug Indication：

Tallimustine was being investigated for its use in treating tumors. Derivatives of tallimustine with similar DNA binding ability and reduced myelotoxicity are being investigated for their antitumor activity.

MeSH：

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Mechanism of Action：

Tallimustine binds to the minor groove of DNA while avoiding targets like glutathione. Currently, the mechanism of DNA minor groove binding agents is poorly understood. Though, they may act by directly inhibiting the interaction of protein and DNA.

MeSH Entry Terms：

FCE 24517

Computed Properties

Molecular Weight:697.6
XLogP3:1.2
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:15
Exact Mass:696.2454551
Monoisotopic Mass:696.2454551
Topological Polar Surface Area:184
Heavy Atom Count:48
Complexity:1140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes