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
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • AR-522
Categories
UNII
SNU299M83Q
CAS number
92689-49-1
Weight
Average: 640.379
Monoisotopic: 640.04416
Chemical Formula
C26H25IO11
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

Pharmacology

Indication

Investigated for use/treatment in breast cancer and leukemia (unspecified).

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 AvailableHuman
UDNANot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Annamycin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Annamycin.Experimental
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Annamycin.Approved, Investigational, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Annamycin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Annamycin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Annamycin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Annamycin.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Annamycin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Annamycin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Annamycin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Annamycin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Annamycin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Annamycin.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Annamycin.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Annamycin.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Annamycin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Annamycin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Annamycin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Annamycin.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Annamycin.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Annamycin.Approved, Investigational
Food Interactions
Not Available

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. [PubMed:15542779]
External Links
ChemSpider
103088
Wikipedia
Annamycin

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
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. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da

Drug created on March 19, 2008 10:33 / Updated on July 02, 2018 18:32