Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H27NO10 |
Molecular Weight | 513.4933 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C2C(O)=C4C(=O)C5=C(C=CC=C5O)C(=O)C4=C3O)C(C)=O
InChI
InChIKey=XREUEWVEMYWFFA-CSKJXFQVSA-N
InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1
Carubicin (also known as Carminomycin) is an anthracycline antineoplastic antibiotic isolated from the bacterium Actinomadura carminata. Carubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. The drug is active against a variety of experimental tumors. Pharmacology studies in animals revealed that the drug bound largely to serum proteins and that it was widely distributed. In clinical trials The main toxic effect was myelosuppression but gastrointestinal intolerance and alopecia were also reported. Objective partial responses were seen in two of seven previously untreated patients with non-small cell lung cancer and one of three patients with squamous cell carcinoma of the head and neck previously untreated with chemotherapy.
Approval Year
PubMed
Title | Date | PubMed |
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[The antiviral activity of the antibiotics beromycin and carminomycin]. | 1974 Feb |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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New TFO conjugates containing a carminomycinone-derived chromophore. | 2001 Jul-Aug |
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Recent developments in the field of antitumour anthracyclines. | 2001 Jun |
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[Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger]. | 2002 Mar-Apr |
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[Cytotoxic activity of dammarane triterpenoids from birch leaves]. | 2002 Nov-Dec |
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Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants. | 2004 Feb |
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Altered expression of topoisomerase IIalpha contributes to cross-resistant to etoposide K562/MX2 cell line by aberrant methylation. | 2005 Apr 25 |
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[Anthracycline antibiotics and their derivatives--inhibitors of topoisomerase I]. | 2008 May-Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7227430
Initial clinical trials in the USSR used a twice weekly schedule for 3 weeks (total dose 27-40 mg/m 2) or daily x 5 courses repeated at 21-30-day intervals (1.5-5mg/m 2 per day)
Route of Administration:
Intravenous
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NCI_THESAURUS |
C1594
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CARUBICIN
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)