You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCapreomycin
Accession NumberDB00314  (APRD00844)
Typesmall molecule
Groupsapproved
Description

Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem]

Structure
Thumb
SynonymsNot Available
Salts
Name/CAS Structure Properties
Capreomycin sulfate
Thumb
  • InChI Key: AJQVUIHGEOLMDY-SOCRLDLMNA-N
  • Monoisotopic Mass: 766.314033696
  • Average Mass: 766.784
DBSALT000443
Brand names
NameCompany
CapastatAkorn Incorporated
CapreomycinBristol-Myers Squibb
HelpomycinUnifarm
KapocinMacleods
LykocinLyka Labs Ltd.
Brand mixturesNot Available
CategoriesNot Available
CAS number11003-38-6
WeightAverage: 1321.4123
Monoisotopic: 1320.698394286
Chemical FormulaC50H88N28O15
InChI KeyVCOPTHOUUNAYKQ-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
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
Mass SpecNot Available
Taxonomy
KingdomNot Available
SuperclassNot Available
ClassNot Available
SubclassNot Available
Direct parentNot Available
Alternative parentsNot Available
SubstituentsNot Available
Classification descriptionNot Available
Pharmacology
IndicationUsed in the treatment of tuberculosis in combination with other drugs.
PharmacodynamicsCapreomycin 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 actionLittle 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.
AbsorptionNot absorbed in significant quantities from the gastrointestinal tract and must be administered parenterally.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationWhen a 1–g dose of capreomycin was given intramuscularly to normal volunteers, 52% was excreted in the urine within 12 hours.
Half lifeNot Available
ClearanceNot Available
ToxicityHypokalemia, 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.6871
Blood Brain Barrier - 0.9287
Caco-2 permeable - 0.6762
P-glycoprotein substrate Substrate 0.8642
P-glycoprotein inhibitor I Non-inhibitor 0.742
P-glycoprotein inhibitor II Non-inhibitor 0.9864
Renal organic cation transporter Non-inhibitor 0.7924
CYP450 2C9 substrate Non-substrate 0.6651
CYP450 2D6 substrate Non-substrate 0.8065
CYP450 3A4 substrate Non-substrate 0.5716
CYP450 1A2 substrate Non-inhibitor 0.9053
CYP450 2C9 substrate Non-inhibitor 0.8828
CYP450 2D6 substrate Non-inhibitor 0.9196
CYP450 2C19 substrate Non-inhibitor 0.881
CYP450 3A4 substrate Non-inhibitor 0.9435
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9907
Ames test Non AMES toxic 0.6035
Carcinogenicity Non-carcinogens 0.894
Biodegradation Not ready biodegradable 0.991
Rat acute toxicity 2.5199 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8741
hERG inhibition (predictor II) Non-inhibitor 0.671
Pharmacoeconomics
Manufacturers
  • Akorn inc
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Capastat sulfate 1 gm vial25.54USDvial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilitySoluble in water as disulfate salt.Not Available
logP-9.609Not Available
Predicted Properties
PropertyValueSource
logP-11ChemAxon
pKa (strongest acidic)10.62ChemAxon
pKa (strongest basic)10.3ChemAxon
physiological charge4ChemAxon
hydrogen acceptor count14ChemAxon
hydrogen donor count14ChemAxon
polar surface area378.42ChemAxon
rotatable bond count19ChemAxon
refractivity162.2ChemAxon
polarizability66.56ChemAxon
number of rings4ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Michael George Thomas, Elizabeth Anne Felnagle, Michelle Renee Rondon, Andrew David Berti, “Heterologous Production of Capreomycin and Generation of New Capreomycin Derivatives Through Metabolic Engineering.” U.S. Patent US20090104658, issued April 23, 2009.

US20090104658
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00135
KEGG CompoundC01790
PubChem Compound3000502
PubChem Substance46508514
ChemSpider2272094
ChEBI3371
ChEMBLCHEMBL2303634
Therapeutic Targets DatabaseDAP000892
PharmGKBPA164746226
Drug Product Database2025396
Drugs.comhttp://www.drugs.com/cdi/capreomycin.html
WikipediaCapreomycin
ATC CodesJ04AB30
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(204 KB)
MSDSshow(131 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 70S ribosome

Kind: protein group

Organism: Mycobacterium tuberculosis

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

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
  2. 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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09