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Annamycin
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Annamycin
- Accession Number
- DB06420
- Description
- Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Annamycin (DB06420)
- Weight
- Average: 640.379
Monoisotopic: 640.04416 - Chemical Formula
- C26H25IO11
- Synonyms
- 2'-Iodo-3'-hydroxy-4'-epi-4-demethoxydoxorubicin
- External IDs
- AR-522
Pharmacology
- Indication
Investigated for use/treatment in breast cancer and leukemia (unspecified).
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Annamycin belongs to the anthracycline class of drugs, and has a pleiotropic mechanism of action where it targets topoisomerase II, causing strand breaks in DNA. Annamycin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
Target Actions Organism UDNA topoisomerase 2-alpha Not Available Humans UDNA Not Available Humans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataDarbepoetin alfa The risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Annamycin. Erythropoietin The risk or severity of Thrombosis can be increased when Erythropoietin is combined with Annamycin. Methoxy polyethylene glycol-epoetin beta The risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Annamycin. Peginesatide The risk or severity of Thrombosis can be increased when Peginesatide is combined with Annamycin. Trastuzumab The risk or severity of cardiotoxicity can be increased when Trastuzumab is combined with Annamycin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Categories
- Drug Categories
- Classification
- Not classified
Chemical Identifiers
- UNII
- SNU299M83Q
- CAS number
- 92689-49-1
- InChI Key
- CIDNKDMVSINJCG-GKXONYSUSA-N
- InChI
- InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1
- IUPAC Name
- (7S,9S)-7-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
- SMILES
- C[[email protected]@H]1O[[email protected]@H](O[[email protected]]2C[[email protected]@](O)(CC3=C2C(O)=C2C(=O)C4=CC=CC=C4C(=O)C2=C3O)C(=O)CO)[[email protected]](I)[[email protected]](O)[[email protected]]1O
References
- General References
- Trevino AV, Woynarowska BA, Herman TS, Priebe W, Woynarowski JM: Enhanced topoisomerase II targeting by annamycin and related 4-demethoxy anthracycline analogues. Mol Cancer Ther. 2004 Nov;3(11):1403-10. [PubMed:15542779]
- External Links
- ChemSpider
- 103088
- ZINC
- ZINC000003918134
- Wikipedia
- Annamycin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Terminated Treatment Acute Lymphocytic Leukemia (ALL) / Acute Myeloid Leukemia (AML) 1 1, 2 Active Not Recruiting Treatment Acute Myeloid Leukemia (AML) 1 1, 2 Completed Treatment Breast Cancer 1 1, 2 Recruiting Treatment Acute Myeloid Leukemia (AML) 1 1, 2 Unknown Status Treatment Acute Lymphocytic Leukemia (ALL) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.527 mg/mL ALOGPS logP 2.16 ALOGPS logP 2.65 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 8.05 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 191.05 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 139.24 m3·mol-1 ChemAxon Polarizability 55.55 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
Unknown
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Dewanjee S, Dua TK, Bhattacharjee N, Das A, Gangopadhyay M, Khanra R, Joardar S, Riaz M, Feo V, Zia-Ul-Haq M: Natural Products as Alternative Choices for P-Glycoprotein (P-gp) Inhibition. Molecules. 2017 May 25;22(6). pii: molecules22060871. doi: 10.3390/molecules22060871. [PubMed:28587082]
Drug created on March 19, 2008 10:33 / Updated on June 12, 2020 10:52
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