CARUBICIN

Investigational

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

Structure Search

SMILES

C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(C=CC=C5O)C4=O)C(O)=C23)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

HIDE SMILES / InChI

Molecular Formula	C26H27NO10
Molecular Weight	513.4933
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21199801 | https://www.ncbi.nlm.nih.gov/pubmed/7083181 | https://www.ncbi.nlm.nih.gov/pubmed/7227430

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Anthracycline antibiotics and their derivatives--inhibitors of topoisomerase I].	2008-08-05	18672696
Altered expression of topoisomerase IIalpha contributes to cross-resistant to etoposide K562/MX2 cell line by aberrant methylation.	2005-04-25	15798770
Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants.	2004-02	15112963
[Cytotoxic activity of dammarane triterpenoids from birch leaves].	2003-02-04	12561324
[Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger].	2002-04-19	11962206
New TFO conjugates containing a carminomycinone-derived chromophore.	2001-07-19	11459456
Recent developments in the field of antitumour anthracyclines.	2001-06	11525839
Screening for new compounds with antiherpes activity.	1984-10	6517562
[The antiviral activity of the antibiotics beromycin and carminomycin].	1974-02	4219122

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:50:45 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:45 GMT 2025`
Record UNII	E7437K3983
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-180024

Preferred Name

English

CARUBICIN

Official Name

English

5,12-NAPHTHACENEDIONE, 8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-1,6,8,11-TETRAHYDROXY-, (8S-CIS)-

Common Name

English

(1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,10,12-TETRAHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE

Common Name

English

CARUBICIN [MI]

Common Name

English

carubicin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594