Identification
- Summary
Tallimustine is an alkylating agent previously investigated for it's antitumor activity but was stopped due to severe myelotoxicity.
- Generic Name
- Tallimustine
- DrugBank Accession Number
- DB15466
- Background
Tallimustine, a benzoyl mustard derivative of distamycin A, is an alkylating agent that binds to the minor groove of DNA.1,2 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.2,3 Newer generations of DNA minor groove binding agents can more specifically recognize base pair sequences.5
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Tallimustine (DB15466)
- Weight
- Average: 697.62
Monoisotopic: 696.2454551 - Chemical Formula
- C32H38Cl2N10O4
- Synonyms
- Tallimustine
Pharmacology
- Indication
Tallimustine was being investigated for its use in treating tumors.1,2 Derivatives of tallimustine with similar DNA binding ability and reduced myelotoxicity are being investigated for their antitumor activity.2
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Not Available
- Mechanism of action
Tallimustine binds to the minor groove of DNA while avoiding targets like glutathione.2 Currently, the mechanism of DNA minor groove binding agents is poorly understood.4 Though, they may act by directly inhibiting the interaction of protein and DNA.4
Target Actions Organism UDNA binderHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Tallimustine is associated with myelotoxicity severe enough to stop its development.1,2
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Tallimustine is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Tallimustine is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Tallimustine is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Tallimustine is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Tallimustine is combined with Bupivacaine. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Tallimustine hydrochloride JWV8AC9E4V 118438-45-2 BLSOATWWAGIRGE-UHFFFAOYSA-N
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 71193OXG6S
- CAS number
- 115308-98-0
- InChI Key
- ARKYUICTMUZVEW-UHFFFAOYSA-N
- InChI
- InChI=1S/C32H38Cl2N10O4/c1-41-18-22(14-25(41)30(46)37-11-8-28(35)36)39-32(48)27-16-23(19-43(27)3)40-31(47)26-15-21(17-42(26)2)38-29(45)20-4-6-24(7-5-20)44(12-9-33)13-10-34/h4-7,14-19H,8-13H2,1-3H3,(H3,35,36)(H,37,46)(H,38,45)(H,39,48)(H,40,47)
- IUPAC Name
- 4-{4-[bis(2-chloroethyl)amino]benzamido}-N-[5-({5-[(2-carbamimidoylethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}carbamoyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-pyrrole-2-carboxamide
- SMILES
- CN1C=C(NC(=O)C2=CC(NC(=O)C3=CC(NC(=O)C4=CC=C(C=C4)N(CCCl)CCCl)=CN3C)=CN2C)C=C1C(=O)NCCC(N)=N
References
- Synthesis Reference
Cozzi P: The discovery of a new potential anticancer drug: a case history. Farmaco. 2003 Mar;58(3):213-20. doi: 10.1016/S0014-827X(03)00014-4.
- General References
- Marchini S, Broggini M, Sessa C, D'Incalci M: Development of distamycin-related DNA binding anticancer drugs. Expert Opin Investig Drugs. 2001 Sep;10(9):1703-14. doi: 10.1517/13543784.10.9.1703 . [Article]
- Cozzi P: The discovery of a new potential anticancer drug: a case history. Farmaco. 2003 Mar;58(3):213-20. doi: 10.1016/S0014-827X(03)00014-4. [Article]
- Cozzi P: Recent outcome in the field of distamycin-derived minor groove binders. Farmaco. 2000 Mar;55(3):168-73. [Article]
- Lauria A, Montalbano A, Barraja P, Dattolo G, Almerico AM: DNA minor groove binders: an overview on molecular modeling and QSAR approaches. Curr Med Chem. 2007;14(20):2136-60. [Article]
- Paul A, Guo P, Boykin DW, Wilson WD: A New Generation of Minor-Groove-Binding-Heterocyclic Diamidines That Recognize G.C Base Pairs in an AT Sequence Context. Molecules. 2019 Mar 7;24(5). pii: molecules24050946. doi: 10.3390/molecules24050946. [Article]
- External Links
- ChemSpider
- 59332
- ChEMBL
- CHEMBL89705
- ZINC
- ZINC000003921862
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0543 mg/mL ALOGPS logP 2.6 ALOGPS logP 2.41 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 15.03 Chemaxon pKa (Strongest Basic) 12.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 184.3 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 203.55 m3·mol-1 Chemaxon Polarizability 76.45 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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Unknown
Binder
References
- Marchini S, Broggini M, Sessa C, D'Incalci M: Development of distamycin-related DNA binding anticancer drugs. Expert Opin Investig Drugs. 2001 Sep;10(9):1703-14. doi: 10.1517/13543784.10.9.1703 . [Article]
Drug created at August 01, 2019 17:29 / Updated at February 21, 2021 18:55