Structure via PubChem · Public domain (PubChem)
capreomycin
Sign in to saveAlso known as Capastat sulfate, Ogostal, Capromycin
Capreomycin is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis. Specifically it is a second line treatment used for active drug resistant tuberculosis. It is given by injection into a vein or muscle.
OverviewAI-generated
Capreomycin is a chemical substance identified by the NCI Thesaurus ID C72607. It is indexed in PubMed, where a query for the term yields 823 results.
In the PubChem database, capreomycin is assigned the CID 135483770. Its InChIKey is VCOPTHOUUNAYKQ-WBTCAYNUSA-N. The molecule has a topological polar surface area (TPSA) of 737. It contains 27 hydrogen bond donors and 23 hydrogen bond acceptors.
Synthesized by Vinony from 8 facts across 3 sources: Wikidata, PubMed, PubChem. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.image
- Capreomycin IA.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Capreomycin IB.svg
- Drug.image_class2
- skin-invert-image
- Drug.tradename
- Capastat
- Drug.MedlinePlus
- a682860
- Drug.routes_of_administration
- Intramuscular
- Drug.ATC_prefix
- J04
- Drug.ATC_suffix
- AB30
- Drug.CAS_number
- 11003-38-6
- Drug.PubChem
- 3000502
- Drug.DrugBank
- DB00314
- Drug.ChemSpiderID
- 2272094
- Drug.UNII
- 232HYX66HC
- Drug.KEGG
- D07607
- Drug.ChEMBL
- 2221250
- Drug.NIAID_ChemDB
- 007653
- Drug.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 | C=25 | H=44 | N=14 | O=8 | 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 | StdInChI = 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 | StdInChIKey = VCOPTHOUUNAYKQ-WBTCAYNUSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation =
via Wikipedia infobox
Chemical data
- Formula
- C50H88N28O15
- Molecular weight
- 1321.4 g/mol
- IUPAC name
- (3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-1,4,5,6-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-1,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide
- 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]2CCNC(=N2)N)CNC(=O)C[C@H](CCCN)N.C1CNC(=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
- InChIKey
- VCOPTHOUUNAYKQ-WBTCAYNUSA-N
- Polar surface area
- 737 Ų
- H-bond donors
- 27
- H-bond acceptors
- 23
- Formal charge
- 0
via PubChem
Research
823 papers- Capreomycin.2006
- Capreomycin.2012
- Capreomycin.Tuberculosis (Edinburgh, Scotland) · 2008
- Capreomycin.Journal of clinical pathology · 1967
- Aminoglycosides and Capreomycin in the Treatment of Multidrug-resistant Tuberculosis: Individual Patient Data Meta-analysis of 12 030 Patients From 25 Countries, 2009-2016.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2021
via PubMed
Wikidata facts
- Instance of
- essential medicine
Show 4 more facts
- NCI Thesaurus ID
- C72607
- defined daily dose
- 1
- medical condition treated
- tuberculosis
- natural product of taxon
- Streptomyces
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Spectrum of susceptibility
- Side effects
- Interactions
- History
- References
Capreomycin is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis. Specifically it is a second line treatment used for active drug resistant tuberculosis. It is given by injection into a vein or muscle.
Common side effects include kidney problems, hearing problems, poor balance, and pain at the site of injection. Other side effects include paralysis resulting in the inability to breathe. It is not recommended with streptomycin or other medications that may damage the auditory vestibular nerve. It is not recommended during pregnancy as it may cause kidney or hearing problems in the baby. Capreomycin is commonly grouped with the aminoglycoside family of medications. How it works is unclear.
Excerpted from Wikipedia’s “capreomycin” article, available under the CC BY-SA 4.0 licence.