NAV

Annamycin

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
Thumb
3D
Similar Structures
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).

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
UDNA topoisomerase 2-alphaNot AvailableHumans
UDNANot AvailableHumans
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
Adverseeffects
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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.
DrugInteraction
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Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Annamycin.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Annamycin.
MargetuximabThe risk or severity of cardiotoxicity can be increased when Margetuximab is combined with Annamycin.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Annamycin.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Annamycin.
TrastuzumabThe risk or severity of cardiotoxicity can be increased when Trastuzumab is combined with Annamycin.
Interactions
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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
  1. 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]
ChemSpider
103088
ZINC
ZINC000003918134
Wikipedia
Annamycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentAcute Lymphoblastic Leukemia (ALL) / Acute Myeloid Leukemia (AML)1
1, 2CompletedTreatmentAcute Myeloid Leukemia (AML)1
1, 2CompletedTreatmentBreast Cancer1
1, 2RecruitingTreatmentAcute Myeloid Leukemia (AML)1
1, 2RecruitingTreatmentPulmonary Metastasis / Soft Tissue Sarcoma (STS)1
1, 2Unknown StatusTreatmentAcute Lymphoblastic 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
PropertyValueSource
Water Solubility0.527 mg/mLALOGPS
logP2.16ALOGPS
logP2.65ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area191.05 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity139.24 m3·mol-1ChemAxon
Polarizability55.55 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Details1. DNA 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
Details2. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Transporters

Details1. P-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
  1. 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 June 12, 2020 16:52