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Identification
Name Capreomycin
Accession Number DB00314 (APRD00844)
Type small molecule
Groups approved
Description

Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Capastat
Capastat sulfate
Capreomycin sulfate
Capreomycin sulphate
Salts Not Available
Brand names
Name Company
Ogostal
Brand mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Antibiotics, Antitubercular
CAS number 11003-38-6
Weight Average: 1321.4123
Monoisotopic: 1320.698394286
Chemical Formula C50H88N28O15
InChI Key InChIKey=VCOPTHOUUNAYKQ-WBTCAYNUSA-N
InChI
InChI=1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9+;16-10+/t11-,12-,13+,14-,16-,18-;11-,12-,13-,14+,15-,18-/m00/s1
Plain Text
IUPAC Name
(3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide; (3S)-3,6-diamino-N-{[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-5-yl]methyl}hexanamide
SMILES
[H][C@@]1(CCN=C(N)N1)[C@]1([H])NC(=O)\C(NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC1=O)=C/NC(N)=O.[H][C@@]1(CCN=C(N)N1)[C@]1([H])NC(=O)\C(NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC1=O)=C/NC(N)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Pyrimidines and Derivatives
  • Polypeptides
  • Lactams
Substructures
  • Hydroxy Compounds
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Ureas and Derivatives
  • Carboxylic Acids and Derivatives
  • Carbamates and Derivatives
  • Alcohols and Polyols
  • Pyrimidines and Derivatives
  • Polypeptides
  • Heterocyclic compounds
  • Guanidines
  • Carboxamidines
  • Carboxamides and Derivatives
  • Lactams
Pharmacology
Indication Used in the treatment of tuberculosis in combination with other drugs.
Pharmacodynamics Capreomycin is a member of the aminoglycoside family of antibiotics. These antibiotics have the ability to kill a wide variety of bacteria, including bacteria responsible for causing tuberculosis (TB).
Mechanism of action Little is known about capreomycin's exact mechanism of action, but it is thought to inhibit protein synthesis by binding to the 70S ribosomal unit. Capreomycin also binds to components in the bacterial cell which result in the production of abnormal proteins. These proteins are necessary for the bacteria's survival. Therefore the production of these abnormal proteins is ultimately fatal to the bacteria.
Absorption Not absorbed in significant quantities from the gastrointestinal tract and must be administered parenterally.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination When a 1–g dose of capreomycin was given intramuscularly to normal volunteers, 52% was excreted in the urine within 12 hours.
Half life Not Available
Clearance Not Available
Toxicity Hypokalemia, hypocalcemia, hypomagnesemia, and an electrolyte disturbance resembling Bartter's syndrome have been reported to occur in patients with capreomycin toxicity. The subcutaneous median lethal dose (LD50) in mice was 514 mg/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Akorn inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Capastat sulfate 1 gm vial 25.54 USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility Soluble in water as disulfate salt. Not Available
logP -9.609 Not Available
Predicted Properties
Property Value Source
logP -11 ChemAxon
pKa (strongest acidic) 10.62 ChemAxon
pKa (strongest basic) 10.3 ChemAxon
physiological charge 4 ChemAxon
hydrogen acceptor count 14 ChemAxon
hydrogen donor count 14 ChemAxon
polar surface area 378.42 ChemAxon
rotatable bond count 19 ChemAxon
refractivity 162.2 ChemAxon
polarizability 66.56 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00135 Link_out
KEGG Compound C01790 Link_out
PubChem Compound 3000502 Link_out
PubChem Substance 46508514 Link_out
ChemSpider 2272094 Link_out
Therapeutic Targets Database DAP000892 Link_out
PharmGKB PA164746226 Link_out
Drug Product Database 2025396 Link_out
Drugs.com http://www.drugs.com/cdi/capreomycin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Capreomycin Link_out
ATC Codes
  • J04AB30
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (204 KB)
MSDS show (131 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. 16S rRNA

Pharmacological action: yes
Actions: inhibitor

In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.

Gene Sequence: FASTA

References:
  1. Johansen SK, Maus CE, Plikaytis BB, Douthwaite S: Capreomycin binds across the ribosomal subunit interface using tlyA-encoded 2’-O-methylations in 16S and 23S rRNAs. Mol Cell. 2006 Jul 21;23(2):173-82. Pubmed

2. 23S rRNA

Pharmacological action: yes
Actions: inhibitor

In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.

Gene Sequence: FASTA

References:
  1. Johansen SK, Maus CE, Plikaytis BB, Douthwaite S: Capreomycin binds across the ribosomal subunit interface using tlyA-encoded 2’-O-methylations in 16S and 23S rRNAs. Mol Cell. 2006 Jul 21;23(2):173-82. Pubmed

3. 70S ribosome

Pharmacological action: yes
Actions: inhibitor

References:
  1. Stanley RE, Blaha G, Grodzicki RL, Strickler MD, Steitz TA: The structures of the anti-tuberculosis antibiotics viomycin and capreomycin bound to the 70S ribosome. Nat Struct Mol Biol. 2010 Mar;17(3):289-93. Epub 2010 Feb 14. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19