Synonym
7-Deoxyadriamycinol aglycone;
IUPAC/Chemical Name
5,12-Naphthacenedione, 8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (S-(R*,S*))-
InChi Key
IGJIPNOEJDYNRR-ASSNKEHSSA-N
InChi Code
InChI=1S/C21H20O8/c1-29-12-4-2-3-10-14(12)20(27)16-15(18(10)25)19(26)11-7-21(28,13(23)8-22)6-5-9(11)17(16)24/h2-4,13,22-24,26,28H,5-8H2,1H3/t13-,21+/m1/s1
SMILES Code
O=C(C1=C2C(O)=C3CC[C@@](O)([C@H](O)CO)CC3=C1O)C4=CC=CC(OC)=C4C2=O
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
Shelf Life
>2 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).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
400.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Gille L, Nohl H. Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. Free Radic Biol Med. 1997;23(5):775-82. PubMed PMID: 9296455.
2: Samuel L. Doxorubicin-induced cardiotoxicity. Postgrad Med J. 1995 May;71(835):318. PubMed PMID: 7596949; PubMed Central PMCID: PMC2398096.
3: Cummings J, Milstead R, Cunningham D, Kaye S. Marked inter-patient variation in adriamycin biotransformation to 7-deoxyaglycones: evidence from metabolites identified in serum. Eur J Cancer Clin Oncol. 1986 Aug;22(8):991-1001. PubMed PMID: 3770056.
4: Dodion P, Riggs CE Jr, Akman SR, Bachur NR. Effect of hyperthermia on the in vitro metabolism of doxorubicin. Cancer Treat Rep. 1986 May;70(5):625-9. PubMed PMID: 3708610.
5: Creagan ET, Ahmann DL, Frytak S, Long HJ, Chang MN, Itri LM. Phase II trials of recombinant leukocyte A interferon in disseminated malignant melanoma: results in 96 patients. Cancer Treat Rep. 1986 May;70(5):619-24. PubMed PMID: 3518925.
6: Vrignaud P, Londos-Gagliardi D, Robert J. Hepatic metabolism of doxorubicin in mice and rats. Eur J Drug Metab Pharmacokinet. 1986 Apr-Jun;11(2):101-5. PubMed PMID: 3770010.
7: Cummings J, Merry S, Willmott N. Disposition kinetics of adriamycin, adriamycinol and their 7-deoxyaglycones in AKR mice bearing a sub-cutaneously growing ridgway osteogenic sarcoma (ROS). Eur J Cancer Clin Oncol. 1986 Apr;22(4):451-60. PubMed PMID: 3460809.
8: Dodion P, Riggs CE Jr, Akman SR, Tamburini JM, Colvin OM, Bachur NR. Interactions between cyclophosphamide and adriamycin metabolism in rats. J Pharmacol Exp Ther. 1984 Apr;229(1):51-7. PubMed PMID: 6423814.
9: Marshall VP, McGovren JP, Richard FA, Richard RE, Wiley PF. Microbial metabolism of anthracycline antibiotics daunomycin and adriamycin. J Antibiot (Tokyo). 1978 Apr;31(4):336-42. PubMed PMID: 26650.
