Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H25IO11 |
Molecular Weight | 640.3746 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4)C3=O)C(O)=C12)C(=O)CO)O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5I
InChI
InChIKey=CIDNKDMVSINJCG-GKXONYSUSA-N
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
Annamycin is a highly lipophilic form of the anthracycline doxorubicin with the ability to bypass multidrug resistance mechanisms of cellular drug resistance. 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. The agent is being evaluated in separate phase 1 and phase 2 trials in the United States and Europe. Studies in animal models showed the agent to be noncardiotoxic. Trials that included patients with leukemia showed the agent was associated with fewer dose-limiting toxicities than typically experienced with doxorubicin. The FDA granted fast track designation to Annamycin for treatment of patients with relapsed or refractory acute myeloid leukemia.
Approval Year
PubMed
Title | Date | PubMed |
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Effects of liposome-entrapped annamycin in human breast cancer cells: interference with cell cycle progression and induction of apoptosis. | 2001 |
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Mechanisms of transport across cell membranes of complexes contained in antitumour drugs. | 2001 Jul 17 |
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Aronex Pharmaceuticals reports on annamycin phase I trial. | 2001 Jun |
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Phase II study of liposomal annamycin in the treatment of doxorubicin-resistant breast cancer. | 2002 Jul |
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Enhanced topoisomerase II targeting by annamycin and related 4-demethoxy anthracycline analogues. | 2004 Nov |
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Relationship between topoisomerase II-DNA cleavable complexes, apoptosis and cytotoxic activity of anthracyclines in human cervix carcinoma cells. | 2005 May-Jun |
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Emerging therapeutic options for Philadelphia-positive acute lymphocytic leukemia. | 2007 Mar |
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Effect of structural modification at the 4, 3', and 2' positions of doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity in human melanoma cells. | 2007 May-Jun |
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NFkappaB activation and drug sensitivity in human neoplastic cells treated with anthracyclines. | 2008 Mar-Apr |
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Cationic nanoparticles for delivery of amphotericin B: preparation, characterization and activity in vitro. | 2008 May 7 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23763920
Solid tumors: a total of 51 courses were administered at doses of 2.5, 5, 10, 16.5, 21, 25 and 30 mg/m(2) in one, three, one, three, six, six and one patient respectively. Grade 2 infusional hypertension, anemia, and dizziness were noted at 16.5 mg/m(2). At 25 mg/m(2), two of six evaluable patients had DLT. DLT was grade 4 constipation, neutropenia and grade 3 nausea/vomiting. At 21 mg/m(2) one of six evaluable patients had DLT (grade 3 nausea/vomiting). This dose was the MTD. The recommended phase II dose is 21 mg/m(2).
Route of Administration:
Intravenous
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FDA ORPHAN DRUG |
787720
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FDA ORPHAN DRUG |
206205
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FDA ORPHAN DRUG |
550116
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FDA ORPHAN DRUG |
206305
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Annamycin
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SNU299M83Q
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92689-49-1
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C080315
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C2632
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100000177640
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115212
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DB06420
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DTXSID901027238
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SUB193106
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ACTIVE MOIETY