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Showing drug card for Capreomycin (DB00314)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:58
Primary Accession Number DB00314
Secondary Accession Number
  • APRD00844
Name Capreomycin
Drug Type
  • Approved
  • Small Molecule
Description Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem]
Synonyms
  1. Capastat
  2. Capastat sulfate
  3. Capreomycin
  4. Capreomycin sulfate
  5. Capreomycin sulphate
Brand Names
  1. Caprocin
  2. Ogostal
Brand Mixtures Not Available
Chemical 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-pentazacyclohexadec-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-pentazacyclohexadec-5-yl]methyl]hexanamide
Chemical Formula C50H88N28O15
Chemical Structure Structure
CAS Registry Number 11003-38-6
InChI Identifier InChI=1/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/f/h32-39H,29-30H2;32-39H,29-30H2
InChI Key VCOPTHOUUNAYKQ-LRONDEINDU
KEGG Drug D00135 Link Image
KEGG Compound C01790 Link Image
PubChem Compound 3000502 Link Image
PubChem Substance 4918 Link Image
ChEBI ID Not Available
PharmGKB ID PA448773 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02025396 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Capreomycin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 1321.4123
Monoisotopic Molecular Weight 1320.6984
State Solid
Melting Point Not Available
Experimental Water Solubility Soluble in water as disulfate salt. Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity -9.609 Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@@H]1NC(=O)[C@@H](N)CNC(=O)[C@@H](NC(=O)\C(NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC1=O)=C/NC(N)=O)[C@H]1CCN=C(N)N1.NCCC[C@H](N)CC(=O)NC[C@@H]1NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H](NC(=O)\C(NC1=O)=C/NC(N)=O)[C@H]1CCN=C(N)N1
Canonical SMILES CC1NC(=O)C(N)CNC(=O)C(NC(=O)C(NC(=O)C(CNC(=O)CC(N)CCCN)NC1=O)=CNC(N)=O)C1CCN=C(N)N1.NCCCC(N)CC(=O)NCC1NC(=O)C(CO)NC(=O)C(N)CNC(=O)C(NC(=O)C(NC1=O)=CNC(N)=O)C1CCN=C(N)N1
Drug Category
  • Anti-Bacterial Agents
  • Antibiotics, Antitubercular
ATC Codes
AHFS Codes Not Available
Indication Used in the treatment of tuberculosis in combination with other drugs.
Pharmacology 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.
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.
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. 50S ribosomal protein L10
Drug Target 1 [top]
Target 1 ID 818
Target 1 Name 50S ribosomal protein L10
Target 1 Synonyms Not Available
Target 1 Gene Name rplJ
Target 1 Protein Sequence >50S ribosomal protein L10 
ALNLQDKQAIVAEVSEVAKGALSAVVADSRGVTVDKMTELRKAGREAGVYMRVVRNTLLR
RAVEGTPFECLKDAFVGPTLIAYSMEHPGAAARLFKEFAKANAKFEVKAAAFEGELIPAS
QIDRLATLPTYEEAIARLMATMKEASAGKLVRTLAAVRDAKEAA
Target 1 Number of Residues 166
Target 1 Molecular Weight 17581
Target 1 Theoretical pI 9.51
Target 1 GO Classification
Function
structural molecule activity
structural constituent of ribosome
Process
metabolism
macromolecule metabolism
macromolecule biosynthesis
protein biosynthesis
physiological process
cellular physiological process
cell organization and biogenesis
organelle organization and biogenesis
ribosome biogenesis and assembly
Component
protein complex
ribonucleoprotein complex
ribosome
cell
intracellular
Target 1 General Function Translation, ribosomal structure and biogenesis
Target 1 Specific Function Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 24054563 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0A7J6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name RL10_SHIFL Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >498 bp 
ATGGCTTTAAATCTTCAAGACAAACAAGCGATTGTTGCTGAAGTCAGCGAAGTAGCCAAA
GGCGCGCTGTCTGCAGTAGTTGCGGATTCCCGTGGCGTAACTGTAGATAAAATGACTGAA
CTGCGTAAAGCAGGTCGCGAAGCTGGCGTATACATGCGTGTTGTTCGTAACACCCTGCTG
CGCCGTGCTGTTGAAGGTACTCCGTTCGAGTGCCTGAAAGACGCGTTTGTTGGTCCGACC
CTGATTGCATACTCTATGGAACACCCGGGCGCTGCTGCTCGTCTGTTCAAAGAGTTCGCG
AAAGCGAATGCAAAATTTGAGGTCAAAGCCGCTGCCTTTGAAGGTGAGCTGATCCCGGCG
TCTCAGATCGACCGCCTGGCAACTCTGCCGACCTACGAAGAAGCAATTGCACGCCTGATG
GCAACCATGAAAGAAGCTTCGGCTGGCAAACTGGTTCGTACTCTGGCTGCTGTACGCGAT
GCGAAAGAAGCTGCTTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Jin Q, Yuan Z, Xu J, Wang Y, Shen Y, Lu W, Wang J, Liu H, Yang J, Yang F, Zhang X, Zhang J, Yang G, Wu H, Qu D, Dong J, Sun L, Xue Y, Zhao A, Gao Y, Zhu J, Kan B, Ding K, Chen S, Cheng H, Yao Z, He B, Chen R, Ma D, Qiang B, Wen Y, Hou Y, Yu J: Genome sequence of Shigella flexneri 2a: insights into pathogenicity through comparison with genomes of Escherichia coli K12 and O157. Nucleic Acids Res. 2002 Oct 15;30(20):4432-41. [PubMed Link Image]
  2. Wei J, Goldberg MB, Burland V, Venkatesan MM, Deng W, Fournier G, Mayhew GF, Plunkett G 3rd, Rose DJ, Darling A, Mau B, Perna NT, Payne SM, Runyen-Janecky LJ, Zhou S, Schwartz DC, Blattner FR: Complete genome sequence and comparative genomics of Shigella flexneri serotype 2a strain 2457T. Infect Immun. 2003 May;71(5):2775-86. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.