Annamycin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200240

CAS#: 92689-49-1

Description: 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.


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Annamycin, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200240
Name: Annamycin
CAS#: 92689-49-1
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


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

InChi Key: CIDNKDMVSINJCG-GKXONYSUSA-N

InChi Code: 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

SMILES Code: O=C1C2=C(O)C([C@@H](O[C@H]3[C@H](I)[C@H](O)[C@@H](O)[C@H](C)O3)C[C@@](C(CO)=O)(O)C4)=C4C(O)=C2C(C5=C1C=CC=C5)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

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 .
  


References

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.