Capreomycin

Capreomycin
Clinical data
Trade namesCapastat
AHFS/Drugs.comMonograph
MedlinePlusa682860
Pregnancy
category
  • C
Routes of
administration		intramuscular
ATC code
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H44N14O8
Molar mass668.717 g·mol−1
3D model (JSmol)
SMILES
  • C[C@H]1C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)[C@H]2CCN=C(N2)N)CNC(=O)C[C@H](CCCN)N.C1CN=C(N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N2)CNC(=O)C[C@H](CCCN)N)CO)N)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 N
  • Key:VCOPTHOUUNAYKQ-WBTCAYNUSA-N N
 NY (what is this?)  (verify)

Capreomycin is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis.[1] Specifically it is a second line treatment used for active drug resistant tuberculosis.[1] It is given by injection into a vein or muscle.[1]

Common side effects include kidney problems, hearing problems, poor balance, and pain at the site of injection.[1] Other side effects include paralysis resulting in the inability to breathe.[1] It is not recommended with streptomycin or other medications that may damage the auditory vestibular nerve.[1] It is not recommended during pregnancy as it may cause kidney or hearing problems in the baby.[1] Capreomycin is commonly grouped with the aminoglycoside family of medications.[2] How it works is unclear.[1]

Capreomycin was discovered from Streptomyces capreolus in 1960.[3] It was removed from the World Health Organization's List of Essential Medicines in 2019.[4]

  1. ^ a b c d e f g h "Capreomycin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  2. ^ Navneet, Kumar (2015). Textbook of Neurology. PHI Learning Pvt. Ltd. p. 192. ISBN 9788120342439. Archived from the original on 2016-12-20.
  3. ^ Tomlinson, Catherine. "TB Online – Capreomycin". Archived from the original on 13 January 2015. Retrieved 14 September 2014.
  4. ^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.
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