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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21NO7.ClH
Molecular Weight 447.866
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CETOCYCLINE HYDROCHLORIDE

SMILES

Cl.[H][C@@]12CC3=C(C(=O)[C@]1(O)C(=O)C(C(C)=O)=C(O)[C@@H]2N)C(O)=C4C(O)=C(C)C=CC4=C3C

InChI

InChIKey=BXIBTMOWCBKWEX-JKPGXYSKSA-N
InChI=1S/C22H21NO7.ClH/c1-7-4-5-10-8(2)11-6-12-16(23)19(27)13(9(3)24)20(28)22(12,30)21(29)15(11)18(26)14(10)17(7)25;/h4-5,12,16,25-27,30H,6,23H2,1-3H3;1H/t12-,16+,22+;/m0./s1

HIDE SMILES / InChI
Cetocycline (formerly chelocardin or cetotetrine) is tetracycline derivative with potent antibacterial activity against a number of Gram-positive and Gram-negative multi-resistant pathogens. Cetocycline was found to be more active than tetracycline against many clinical isolates of aerobic gram-negative bacilli, but is less active against staphylococci, and has no activity against Pseudomonas. At low concentrations, like classical tetracyclines, chelocardin induces the proteomic signature for peptidyl transferase inhibition demonstrating that protein biosynthesis inhibition is the dominant physiological challenge. At higher concentrations B. subtilis mainly responds to membrane stress indicating that at clinically relevant concentrations the membrane is the main antibiotic target of chelocardin.

Originator

Sources: Antimicrobial Agents and Chemotherapy (1961-70) (1963), 1962, 592-5.

Approval Year

PubMed

PubMed

TitleDatePubMed
Identification of the chelocardin biosynthetic gene cluster from Amycolatopsis sulphurea: a platform for producing novel tetracycline antibiotics.
2013 Dec
Patents

Patents

Name Type Language
CETOCYCLINE HYDROCHLORIDE
USAN  
USAN  
Official Name English
CHELOCARDIN MONOHYDROCHLORIDE
Common Name English
CETOCYCLINE HYDROCHLORIDE [USAN]
Common Name English
ABBOTT-40728
Code English
CETOTETRINE HYDROCHLORIDE
Common Name English
.BETA.-CHELOCARDIN HYDROCHLORIDE
Common Name English
CHELOCARDIN HYDROCHLORIDE
Common Name English
1,12(4H,5H)-NAPHTHACENEDIONE, 2-ACETYL-4-AMINO-4A,12A-DIHYDRO-3,10,11,12A-TETRAHYDROXY-6,9-DIMETHYL-, HYDROCHLORIDE, (4R-(4A,4A.BETA.,12A.BETA.))-
Systematic Name English
(4R,4aS,12aS)-2-Acetyl-4-amino-4a,12a-dihydro-3,10,11,12a-tetrahydroxy-6,9-dimethyl-1,12-(4H,5H)-naphthacenedione hydrochloride
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C98041
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
CAS
56433-46-6
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110884
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
FDA UNII
535KJI966J
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY