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
- Annamycin
- DrugBank Accession Number
- DB06420
- Background
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).
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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 ADNA topoisomerase 2-alpha other/unknownHumans 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. 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 Annamycin is combined with Ambroxol. Articaine 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. - 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
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 data1 Terminated Treatment Acute Lymphocytic Leukemia (ALL) / Acute Myeloid Leukemia 1 somestatus stop reason just information to hide 1, 2 Active Not Recruiting Treatment Pulmonary Metastasis / Soft Tissue Sarcoma 1 somestatus stop reason just information to hide 1, 2 Completed Treatment Acute Myeloid Leukemia 2 somestatus stop reason just information to hide 1, 2 Completed Treatment Breast Cancer 1 somestatus stop reason just information to hide 1, 2 Recruiting Treatment Acute Myeloid Leukemia 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
- 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 216.18271 predictedDeepCCS 1.0 (2019) [M+H]+ 218.5783 predictedDeepCCS 1.0 (2019) [M+Na]+ 224.32927 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Other/unknown
- General Function
- Key decatenating enzyme that alters DNA topology by binding to two double-stranded DNA molecules, generating a double-stranded break in one of the strands, passing the intact strand through the broken strand, and religating the broken strand (PubMed:17567603, PubMed:18790802, PubMed:22013166, PubMed:22323612). May play a role in regulating the period length of BMAL1 transcriptional oscillation (By similarity)
- Specific Function
- Atp binding
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 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]
Unknown
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- Abc-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- 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 August 26, 2024 19:23