This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Exatecan
- DrugBank Accession Number
- DB12185
- Background
Exatecan has been used in trials studying the treatment of Sarcoma, Leukemia, Lymphoma, Lung Cancer, and Liver Cancer, among others.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Exatecan (DB12185)
- Weight
- Average: 435.455
Monoisotopic: 435.159434363 - Chemical Formula
- C24H22FN3O4
- Synonyms
- Exatecan
- External IDs
- DX-8951
- DX-8951f
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ADNA topoisomerase 1 inhibitorHumans - 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
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Exatecan is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Exatecan is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Exatecan is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Exatecan is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Exatecan is combined with Bupivacaine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Exatecan Mesylate D2VJ1CC26Q 197720-53-9 FXQZOHBMBQTBMJ-MWPGLPCQSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Camptothecins
- Sub Class
- Not Available
- Direct Parent
- Camptothecins
- Alternative Parents
- Haloquinolines / Pyranopyridines / Pyridinones / Aralkylamines / Aryl fluorides / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Amino acids and derivatives / Lactones show 11 more
- Substituents
- Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Camptothecin show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- OC71PP0F89
- CAS number
- 171335-80-1
- InChI Key
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N
- InChI
- InChI=1S/C24H22FN3O4/c1-3-24(31)14-6-18-21-12(8-28(18)22(29)13(14)9-32-23(24)30)19-16(26)5-4-11-10(2)15(25)7-17(27-21)20(11)19/h6-7,16,31H,3-5,8-9,26H2,1-2H3/t16-,24-/m0/s1
- IUPAC Name
- (10S,23S)-23-amino-10-ethyl-18-fluoro-10-hydroxy-19-methyl-8-oxa-4,15-diazahexacyclo[14.7.1.0^{2,14}.0^{4,13}.0^{6,11}.0^{20,24}]tetracosa-1(24),2(14),6(11),12,15,17,19-heptaene-5,9-dione
- SMILES
- CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=C(F)C(C)=C4CC[C@H](N)C3=C14)C2=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 151115
- PubChem Substance
- 347828471
- ChemSpider
- 133194
- ChEBI
- 135709
- ChEMBL
- CHEMBL1614650
- ZINC
- ZINC000003800855
- Wikipedia
- Exatecan
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Pancreatic Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Breast Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Cervical Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Esophageal Cancer / Gastric Cancer 1 somestatus stop reason just information to hide 2 Completed Treatment Extrahepatic Bile Duct Cancer / Gallbladder Cancer / Liver Cancer 1 somestatus stop reason just information to hide
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 0.221 mg/mL ALOGPS logP 1.67 ALOGPS logP 1.55 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 11.71 Chemaxon pKa (Strongest Basic) 9.52 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 105.75 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 115.8 m3·mol-1 Chemaxon Polarizability 45.45 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0000900000-43ddf3d33fc3300facd8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-0009000000-8c15158ce2799cef4bb0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0000900000-e47404c9adc11b8acd31 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-0109100000-321bb60fd3a42cd9cabb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-1019200000-82f57d103b57dbbad784 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0409500000-48971889ced352640cc4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.19743 predictedDeepCCS 1.0 (2019) [M+H]+ 198.59299 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.50552 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-strand break via transesterification at a target site in duplex DNA. The scissile phosphodiester is attacked by the catalytic tyrosine of the enzyme, resulting in the formation of a DNA-(3'-phosphotyrosyl)-enzyme intermediate and the expulsion of a 5'-OH DNA strand. The free DNA strand then rotates around the intact phosphodiester bond on the opposing strand, thus removing DNA supercoils. Finally, in the religation step, the DNA 5'-OH attacks the covalent intermediate to expel the active-site tyrosine and restore the DNA phosphodiester backbone (By similarity). Regulates the alternative splicing of tissue factor (F3) pre-mRNA in endothelial cells. Involved in the circadian transcription of the core circadian clock component BMAL1 by altering the chromatin structure around the ROR response elements (ROREs) on the BMAL1 promoter
- Specific Function
- ATP binding
- Gene Name
- TOP1
- Uniprot ID
- P11387
- Uniprot Name
- DNA topoisomerase 1
- Molecular Weight
- 90725.19 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at October 20, 2016 21:33 / Updated at August 26, 2024 19:23