U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CARUBICIN

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

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
[The antiviral activity of the antibiotics beromycin and carminomycin].
1974 Feb
Screening for new compounds with antiherpes activity.
1984 Oct
New TFO conjugates containing a carminomycinone-derived chromophore.
2001 Jul-Aug
Recent developments in the field of antitumour anthracyclines.
2001 Jun
[Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger].
2002 Mar-Apr
[Cytotoxic activity of dammarane triterpenoids from birch leaves].
2002 Nov-Dec
Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants.
2004 Feb
Altered expression of topoisomerase IIalpha contributes to cross-resistant to etoposide K562/MX2 cell line by aberrant methylation.
2005 Apr 25
[Anthracycline antibiotics and their derivatives--inhibitors of topoisomerase I].
2008 May-Jun
Patents

Sample Use Guides

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
Name Type Language
CARUBICIN
INN   MI  
INN  
Official Name English
NSC-180024
Code 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
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
Code System Code Type Description
SMS_ID
100000081350
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
NSC
180024
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
PUBCHEM
443831
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110620
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
EVMPD
SUB06151MIG
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
CHEBI
31359
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
NCI_THESAURUS
C352
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
MERCK INDEX
m3140
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3022742
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
INN
4552
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
WIKIPEDIA
CARUBICIN
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
DRUG CENTRAL
510
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
CAS
50935-04-1
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
MESH
D002360
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY
FDA UNII
E7437K3983
Created by admin on Fri Dec 15 17:42:20 GMT 2023 , Edited by admin on Fri Dec 15 17:42:20 GMT 2023
PRIMARY