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MedKoo product information:
Annamycin
Description of Annamycin:
Annamycin liposomal is a
liposome-encapsulated form of the semi-synthetic doxorubicin analogue
annamycin with antineoplastic activity. Annamycin intercalates into DNA
and inhibits topoisomerase II, resulting in the inhibition of DNA
replication and repair and RNA and protein synthesis. This agent
circumvents multidrug-resistance (MDR) transporters, including
P-glycoprotein (P-gp). Liposomal annamycin is less toxic and shows
improved antitumor activity compared to annamycin. Check for
active clinical trials or
closed clinical trials using this agent. (NCI
Thesaurus).
Current developer:
Callisto Pharmaceuticals
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MedKoo Code#: 200240
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Name: Annamycin
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CAS#: 92689-49-1
Synonym:
Annamycin.
IUPAC/Chemical name:
(7S,9S)-7-(((2R,3R,4R,5R,6S)-4,5-dihydroxy-3-iodo-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7,8,9,10-tetrahydrotetracene-5,12-dione
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Chemical structure |
Theoretical analysis
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Chemical Formula: C26H25IO11
Exact Mass: 640.04415
Molecular Weight: 640.37
Elemental Analysis: C, 48.76; H, 3.93; I,
19.82; O, 27.48
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Availability and price:
This agent is not in stock, which may be available through custom synthesis.
To inquire quotation and lead time or to ask questions, please send email to
sales@medkoo.com to describe your needs. A representative
will respond your email shortly. We offer big discount for orders of bulk quantities.
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Information about this agent
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According to
Callisto Pharmaceuticals, Annamycin was originally developed at the
M.D. Anderson Cancer Center to address the clinical limitations
associated with current anthracycline drugs (such as doxorubicin) that
are used to treat cancer. Anthracyclines, such as doxorubicin and
daunarubicin, despite their broad use to treat a number of cancers, have
clinical drawbacks limiting their use. Generally, patients become
resistant to these drugs and once they relapse are found to be
refractory to further use. In addition, the drugs produce cumulative
cardio-toxicity (heart damage) which impedes their further use. In
animal models, L-Annamycin has shown a very favorable cardio-toxicity
profile, and an ability to circumvent the development of resistance to
the drug, as well as a very good delivery profile.
In a previous Phase I/IIa trial in refractory acute
leukemia patients, L-Annamycin showed encouraging potential in
highly-pretreated relapsed patients who were shown to have multi-drug
resistant tumors, a condition that normally predicts a lack of
anthracycline activity. L-Annamycin has been given orphan drug
designation to treat both ALL and AML by the FDA. see:
http://www.callistopharma.com/content/pipeline/l-annamycing/index.jsp.
1: Gruber BM, Anuszewska EL, Bubko I,
Kasprzycka-Guttman T, Misiewicz I, Skupińska K, Fokt I, Piebe W.
NFkappaB activation and drug sensitivity in human neoplastic cells
treated with anthracyclines. Acta Pol Pharm. 2008 Mar-Apr;65(2):267-71.
PubMed PMID: 18666436.
2: Apostolidou E, Swords R, Alvarado Y, Giles FJ. Treatment of acute
lymphoblastic leukaemia : a new era. Drugs. 2007;67(15):2153-71. Review.
PubMed PMID: 17927282.
3: Gruber BM, Anuszewska EL, Bubko I, Goździk A, Fokt I, Priebe W.
Effect of structural modification at the 4, 3', and 2' positions of
doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity
in human melanoma cells. Arch Immunol Ther Exp (Warsz). 2007
May-Jun;55(3):193-8. Epub 2007 Jun 8. PubMed PMID: 17557149; PubMed
Central PMCID: PMC2765644.
4: Gruber BM, Anuszewska EL, Roman I, Goździk A, Priebe W, Fokt I.
Topoisomerase II alpha expression and cytotoxicity of anthracyclines in
human neoplastic cells. Acta Pol Pharm. 2006 Jan-Feb;63(1):15-8. Erratum
in: Acta Pol Pharm. 2006 Mar-Apr;63(2):155. PubMed PMID: 17515324.
5: Alvarado Y, Apostolidou E, Swords R, Giles FJ. Emerging therapeutic
options for Philadelphia-positive acute lymphocytic leukemia. Expert
Opin Emerg Drugs. 2007 Mar;12(1):165-79. Review. PubMed PMID: 17355221.
6: Gruber BM, Anuszewska EL, Bubko I, Gozdzik A, Priebe W, Fokt I.
Relationship between topoisomerase II-DNA cleavable complexes, apoptosis
and cytotoxic activity of anthracyclines in human cervix carcinoma
cells. Anticancer Res. 2005 May-Jun;25(3B):2193-8. PubMed PMID:
16158963.
7: 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
PMID: 15542779.
8: Aronex Pharmaceuticals reports on annamycin phase I trial. Expert Rev
Anticancer Ther. 2001 Jun;1(1):4. PubMed PMID: 12113129.
9: Booser DJ, Esteva FJ, Rivera E, Valero V, Esparza-Guerra L, Priebe W,
Hortobagyi GN. Phase II study of liposomal annamycin in the treatment of
doxorubicin-resistant breast cancer. Cancer Chemother Pharmacol. 2002
Jul;50(1):6-8. Epub 2002 May 21. PubMed PMID: 12111105.
10: Szachowicz-Petelska B, Figaszewski Z, Lewandowski W. Mechanisms of
transport across cell membranes of complexes contained in antitumour
drugs. Int J Pharm. 2001 Jul 17;222(2):169-82. Review. PubMed PMID:
11427347.
11: Orlandi L, Bertoli G, Abolafio G, Daidone MG, Zaffaroni N. Effects
of liposome-entrapped annamycin in human breast cancer cells:
interference with cell cycle progression and induction of apoptosis. J
Cell Biochem. 2001;81(1):9-22. PubMed PMID: 11180394.
12: Booser DJ, Perez-Soler R, Cossum P, Esparza-Guerra L, Wu QP, Zou Y,
Priebe W, Hortobagyi GN. Phase I study of liposomal annamycin. Cancer
Chemother Pharmacol. 2000;46(5):427-32. PubMed PMID: 11127949.
13: Kolonias D, Podona T, Savaraj N, Gate L, Cossum P, Lampidis TJ.
Comparison of annamycin to adriamycin in cardiac and MDR tumor cell
systems. Anticancer Res. 1999 Mar-Apr;19(2A):1277-83. PubMed PMID:
10368688.
14: Wasan KM, Ng S, Cassidy SM. Modifications in high-density
lipoprotein lipid composition and structure alter the plasma
distribution of free and liposomal annamycin. J Pharm Sci. 1997
Jul;86(7):872-5. PubMed PMID: 9232531.
15: Wasan KM, Kwong M. Blood and plasma lipoprotein distribution and
gender differences in the plasma pharmacokinetics of lipid-associated
annamycin. Pharmacol Toxicol. 1997 Jun;80(6):301-7. PubMed PMID:
9225368.
16: Perez-Soler R, Neamati N, Zou Y, Schneider E, Doyle LA, Andreeff M,
Priebe W, Ling YH. Annamycin circumvents resistance mediated by the
multidrug resistance-associated protein (MRP) in breast MCF-7 and
small-cell lung UMCC-1 cancer cell lines selected for resistance to
etoposide. Int J Cancer. 1997 Mar 28;71(1):35-41. PubMed PMID: 9096663.
17: Wasan KM, Lopez-Berestein G. Characteristics of lipid-based
formulations that influence their biological behavior in the plasma of
patients. Clin Infect Dis. 1996 Nov;23(5):1126-38. Review. PubMed PMID:
8922813.
18: Wasan KM. Modifications in plasma lipoprotein concentration and
lipid composition regulate the biological activity of hydrophobic drugs.
J Pharmacol Toxicol Methods. 1996 Sep;36(1):1-11. Review. PubMed PMID:
8872913.
19: Consoli U, Priebe W, Ling YH, Mahadevia R, Griffin M, Zhao S, Perez-Soler
R, Andreeff M. The novel anthracycline annamycin is not affected by
P-glycoprotein-related multidrug resistance: comparison with idarubicin
and doxorubicin in HL-60 leukemia cell lines. Blood. 1996 Jul
15;88(2):633-44. PubMed PMID: 8695811.
20: Wasan KM, Morton RE. Differences in lipoprotein concentration and
composition modify the plasma distribution of free and liposomal
annamycin. Pharm Res. 1996 Mar;13(3):462-8. PubMed PMID: 8692743.
21: Zou Y, Priebe W, Perez-Soler R. Lyophilized preliposomal formulation
of the non-cross-resistant anthracycline annamycin: effect of surfactant
on liposome formation, stability and size. Cancer Chemother Pharmacol.
1996;39(1-2):103-8. PubMed PMID: 8995506.
22: Zou Y, Priebe W, Stephens LC, Perez-Soler R. Preclinical toxicity of
liposome-incorporated annamycin: selective bone marrow toxicity with
lack of cardiotoxicity. Clin Cancer Res. 1995 Nov;1(11):1369-74. PubMed
PMID: 9815933.
23: Wasan KM, Perez-Soler R. Distribution of free and liposomal
annamycin within human plasma is regulated by plasma triglyceride
concentrations but not by lipid transfer protein. J Pharm Sci. 1995
Sep;84(9):1094-100. PubMed PMID: 8537888.
24: Zou Y, Ling YH, Reddy S, Priebe W, Perez-Soler R. Effect of vesicle
size and lipid composition on the in vivo tumor selectivity and toxicity
of the non-cross-resistant anthracycline annamycin incorporated in
liposomes. Int J Cancer. 1995 May 29;61(5):666-71. PubMed PMID: 7768640.
25: Ling YH, Zou Y, Priebe W, Perez-Soler R. Partial circumvention of
multi-drug resistance by annamycin is associated with comparable
inhibition of DNA synthesis in the nuclear matrix of sensitive and
resistant cells. Int J Cancer. 1995 May 4;61(3):402-8. PubMed PMID:
7729954.
26: Zou Y, Ling YH, Van NT, Priebe W, Perez-Soler R. Antitumor activity
of free and liposome-entrapped annamycin, a lipophilic anthracycline
antibiotic with non-cross-resistance properties. Cancer Res. 1994 Mar
15;54(6):1479-84. PubMed PMID: 8137251.
27: Perez-Soler R, Ling YH, Zou Y, Priebe W. Cellular pharmacology of
the partially non-cross-resistant anthracycline annamycin entrapped in
liposomes in KB and KB-V1 cells. Cancer Chemother Pharmacol.
1994;34(2):109-18. PubMed PMID: 8194162.
28: Zou Y, Hayman A, Priebe W, Perez-Soler R. Quantitative analysis of
the lipophilic doxorubicin analogue annamycin in plasma and tissue
samples by reversed-phase chromatography. J Pharm Sci. 1993
Nov;82(11):1151-4. PubMed PMID: 8289131.
29: Priebe W, Perez-Soler R. Design and tumor targeting of
anthracyclines able to overcome multidrug resistance: a double-advantage
approach. Pharmacol Ther. 1993 Nov;60(2):215-34. Review. PubMed PMID:
8022858.
30: Ling YH, Priebe W, Perez-Soler R. Apoptosis induced by anthracycline
antibiotics in P388 parent and multidrug-resistant cells. Cancer Res.
1993 Apr 15;53(8):1845-52. PubMed PMID: 8467504.
31: Ling YH, Priebe W, Yang LY, Burke TG, Pommier Y, Perez-Soler R. In
vitro cytotoxicity, cellular pharmacology, and DNA lesions induced by
annamycin, an anthracycline derivative with high affinity for lipid
membranes. Cancer Res. 1993 Apr 1;53(7):1583-9. PubMed PMID: 8453627.
32: Zou Y, Priebe W, Ling YH, Perez-Soler R. Organ distribution and
tumor uptake of annamycin, a new anthracycline derivative with high
affinity for lipid membranes, entrapped in multilamellar vesicles.
Cancer Chemother Pharmacol. 1993;32(3):190-6. PubMed PMID: 8500223.
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