| 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 |
|
| Name |
Capreomycin |
| Drug Type |
|
| Description |
Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem] |
| Synonyms |
- Capastat
- Capastat sulfate
- Capreomycin
- Capreomycin sulfate
- Capreomycin sulphate
|
| Brand Names |
- Caprocin
- 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 |
 |
| 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  |
| KEGG Compound |
C01790  |
| PubChem Compound |
3000502  |
| PubChem Substance |
4918  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA448773  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02025396  |
| RxList Link |
Not Available |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Capreomycin  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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 |
- Wikipedia

|
| Organisms Affected |
- Enteric bacteria and other eubacteria
|
| Targets |
- 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 |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Essential |
| Target 1 GenBank ID Protein |
24054563  |
| Target 1 UniProtKB/Swiss-Prot ID |
P0A7J6  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
RL10_SHIFL  |
| 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  |
| Target 1 General References |
- 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
]
- 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
]
|
| Target 1 Drug References |
- 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
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|