This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Annamycin
- DrugBank Accession Number
- DB06420
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- 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).
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- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.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 softwareArticaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Cinchocaine. Cocaine The risk or severity of methemoglobinemia can be increased when Annamycin is combined with Cocaine. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
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[C@@H]1O[C@@H](O[C@H]2C[C@@](O)(CC3=C2C(O)=C2C(=O)C4=CC=CC=C4C(=O)C2=C3O)C(=O)CO)[C@H](I)[C@H](O)[C@H]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. [Article]
- External Links
- ChemSpider
- 103088
- ZINC
- ZINC000003918134
- Wikipedia
- Annamycin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Terminated Treatment Acute Lymphocytic Leukaemia / Acute Myeloid Leukemia 1 1, 2 Completed Treatment Acute Myeloid Leukemia 2 1, 2 Completed Treatment Breast Cancer 1 1, 2 Recruiting Treatment Acute Myeloid Leukemia 1 1, 2 Recruiting Treatment Pulmonary Metastasis / Soft Tissue Sarcoma 2 1, 2 Unknown Status Treatment Acute Lymphocytic Leukaemia 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

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1. DetailsDNA topoisomerase 2-alpha
- 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
2. DetailsDNA
Unknown
Transporters
1. DetailsP-glycoprotein 1
- 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. [Article]
Drug created at March 19, 2008 16:33 / Updated at January 14, 2023 19:03