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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H27NO10.ClH
Molecular Weight 549.954
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARUBICIN HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)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=WYVYEIZFAUXWKW-SHUUXQFMSA-N
InChI=1S/C26H27NO10.ClH/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;1H/t9-,13-,15-,16-,21+,26-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:35:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:05 GMT 2023
Record UNII
4V3R166MB3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARUBICIN HYDROCHLORIDE
MART.   MI   USAN  
USAN  
Official Name English
CARUBICIN HCL
Common Name English
CARUBICIN HYDROCHLORIDE [MART.]
Common Name English
CARUBICIN HYDROCHLORIDE [MI]
Common 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-, HYDROCHLORIDE, (8S-CIS)-
Common Name English
NSC-275649
Code 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 HYDROCHLORIDE
Common Name English
CARUBICIN HYDROCHLORIDE [USAN]
Common Name English
CARMINOMYCIN HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2110620
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
MERCK INDEX
m3140
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY Merck Index
CAS
52794-97-5
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
NSC
275649
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
PUBCHEM
11570269
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
NCI_THESAURUS
C1582
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID30967253
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
FDA UNII
4V3R166MB3
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY