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Identification
NameCapreomycin
Accession NumberDB00314  (APRD00844)
TypeSmall Molecule
GroupsApproved
DescriptionCyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Capastat PWS IM 1g VialPowder, for solution1 gIntramuscularEli Lilly Canada Inc1994-12-311997-08-13Canada
Capastat SulfateInjection, powder, for solution1 g/1Intramuscular; IntravenousAkorn2009-08-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CapastatAkorn Incorporated
CapreomycinBristol-Myers Squibb
HelpomycinUnifarm
KapocinMacleods
LykocinLyka Labs Ltd.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Capreomycin sulfate
1405-37-4
Thumb
  • InChI Key: AJQVUIHGEOLMDY-SOCRLDLMNA-N
  • Monoisotopic Mass: 766.314033696
  • Average Mass: 766.784
DBSALT000443
Categories
UNII232HYX66HC
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)[[email protected]](CNC(=O)C[C@@H](N)CCCN)NC(=O)[[email protected]](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)[[email protected]](CNC(=O)C[C@@H](N)CCCN)NC(=O)[[email protected]](CO)NC(=O)[C@@H](N)CNC1=O)=C/NC(N)=O
Pharmacology
IndicationUsed in the treatment of tuberculosis in combination with other drugs.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
70S ribosomeProtein groupyes
inhibitor
Mycobacterium tuberculosisnot applicabledetails
Related Articles
AbsorptionNot absorbed in significant quantities from the gastrointestinal tract and must be administered parenterally.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug Interactions
DrugInteractionDrug group
AclarubicinCapreomycin may increase the neuromuscular blocking activities of Aclarubicin.Investigational
AmikacinCapreomycin may increase the neuromuscular blocking activities of Amikacin.Approved, Vet Approved
AmrubicinCapreomycin may increase the neuromuscular blocking activities of Amrubicin.Approved, Investigational
annamycinCapreomycin may increase the neuromuscular blocking activities of annamycin.Investigational
ApramycinCapreomycin may increase the neuromuscular blocking activities of Apramycin.Experimental, Vet Approved
ArbekacinCapreomycin may increase the neuromuscular blocking activities of Arbekacin.Approved
Atracurium besylateCapreomycin may increase the neuromuscular blocking activities of Atracurium besylate.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Capreomycin.Investigational
Cisatracurium besylateCapreomycin may increase the neuromuscular blocking activities of Cisatracurium besylate.Approved
ColistimethateCapreomycin may increase the neuromuscular blocking activities of Colistimethate.Approved, Vet Approved
DaunorubicinCapreomycin may increase the neuromuscular blocking activities of Daunorubicin.Approved
DecamethoniumCapreomycin may increase the neuromuscular blocking activities of Decamethonium.Approved
DihydrostreptomycinCapreomycin may increase the neuromuscular blocking activities of Dihydrostreptomycin.Vet Approved
Domoic AcidCapreomycin may increase the neuromuscular blocking activities of Domoic Acid.Experimental
Doxacurium chlorideCapreomycin may increase the neuromuscular blocking activities of Doxacurium chloride.Approved
DoxorubicinCapreomycin may increase the neuromuscular blocking activities of Doxorubicin.Approved, Investigational
EpirubicinCapreomycin may increase the neuromuscular blocking activities of Epirubicin.Approved
FramycetinCapreomycin may increase the neuromuscular blocking activities of Framycetin.Approved
Gallamine TriethiodideCapreomycin may increase the neuromuscular blocking activities of Gallamine Triethiodide.Approved
GeneticinCapreomycin may increase the neuromuscular blocking activities of Geneticin.Experimental
GentamicinCapreomycin may increase the neuromuscular blocking activities of Gentamicin.Approved, Vet Approved
GENTAMICIN C1ACapreomycin may increase the neuromuscular blocking activities of GENTAMICIN C1A.Experimental
Hygromycin BCapreomycin may increase the neuromuscular blocking activities of Hygromycin B.Vet Approved
IdarubicinCapreomycin may increase the neuromuscular blocking activities of Idarubicin.Approved
INNO-206Capreomycin may increase the neuromuscular blocking activities of INNO-206.Investigational
KanamycinCapreomycin may increase the neuromuscular blocking activities of Kanamycin.Approved, Vet Approved
MecamylamineCapreomycin may increase the neuromuscular blocking activities of Mecamylamine.Approved
MetocurineCapreomycin may increase the neuromuscular blocking activities of Metocurine.Approved
Metocurine IodideCapreomycin may increase the neuromuscular blocking activities of Metocurine Iodide.Withdrawn
MetrizamideCapreomycin may increase the neuromuscular blocking activities of Metrizamide.Approved
MivacuriumCapreomycin may increase the neuromuscular blocking activities of Mivacurium.Approved
NeamineCapreomycin may increase the neuromuscular blocking activities of Neamine.Experimental
NeomycinCapreomycin may increase the neuromuscular blocking activities of Neomycin.Approved, Vet Approved
NeosaxitoxinCapreomycin may increase the neuromuscular blocking activities of Neosaxitoxin.Investigational
NetilmicinCapreomycin may increase the neuromuscular blocking activities of Netilmicin.Approved
PancuroniumCapreomycin may increase the neuromuscular blocking activities of Pancuronium.Approved
ParomomycinCapreomycin may increase the neuromuscular blocking activities of Paromomycin.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Capreomycin.Approved
PipecuroniumCapreomycin may increase the neuromuscular blocking activities of Pipecuronium.Approved
PirarubicinCapreomycin may increase the neuromuscular blocking activities of Pirarubicin.Investigational
PlicamycinCapreomycin may increase the neuromuscular blocking activities of Plicamycin.Approved, Withdrawn
Polymyxin B SulfateCapreomycin may increase the neuromuscular blocking activities of Polymyxin B Sulfate.Approved, Vet Approved
PuromycinCapreomycin may increase the neuromuscular blocking activities of Puromycin.Experimental
PyrantelCapreomycin may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
RapacuroniumCapreomycin may increase the neuromuscular blocking activities of Rapacuronium.Withdrawn
RibostamycinCapreomycin may increase the neuromuscular blocking activities of Ribostamycin.Approved
RocuroniumCapreomycin may increase the neuromuscular blocking activities of Rocuronium.Approved
SisomicinCapreomycin may increase the neuromuscular blocking activities of Sisomicin.Investigational
SP1049CCapreomycin may increase the neuromuscular blocking activities of SP1049C.Investigational
SpectinomycinCapreomycin may increase the neuromuscular blocking activities of Spectinomycin.Approved, Vet Approved
StreptomycinCapreomycin may increase the neuromuscular blocking activities of Streptomycin.Approved, Vet Approved
StreptozocinCapreomycin may increase the neuromuscular blocking activities of Streptozocin.Approved
SuccinylcholineCapreomycin may increase the neuromuscular blocking activities of Succinylcholine.Approved
TobramycinCapreomycin may increase the neuromuscular blocking activities of Tobramycin.Approved, Investigational
TubocurarineCapreomycin may increase the neuromuscular blocking activities of Tubocurarine.Approved
ValrubicinCapreomycin may increase the neuromuscular blocking activities of Valrubicin.Approved
VecuroniumCapreomycin may increase the neuromuscular blocking activities of Vecuronium.Approved
ZorubicinCapreomycin may increase the neuromuscular blocking activities of Zorubicin.Experimental
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesJ04AB30
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (204 KB)
MSDSDownload (131 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6871
Blood Brain Barrier-0.9287
Caco-2 permeable-0.6762
P-glycoprotein substrateSubstrate0.8642
P-glycoprotein inhibitor INon-inhibitor0.742
P-glycoprotein inhibitor IINon-inhibitor0.9864
Renal organic cation transporterNon-inhibitor0.7924
CYP450 2C9 substrateNon-substrate0.6651
CYP450 2D6 substrateNon-substrate0.8065
CYP450 3A4 substrateNon-substrate0.5716
CYP450 1A2 substrateNon-inhibitor0.9053
CYP450 2C9 inhibitorNon-inhibitor0.8828
CYP450 2D6 inhibitorNon-inhibitor0.9196
CYP450 2C19 inhibitorNon-inhibitor0.881
CYP450 3A4 inhibitorNon-inhibitor0.9435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9907
Ames testNon AMES toxic0.6035
CarcinogenicityNon-carcinogens0.894
BiodegradationNot ready biodegradable0.991
Rat acute toxicity2.5199 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8741
hERG inhibition (predictor II)Non-inhibitor0.671
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Akorn inc
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionIntramuscular1 g
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Prices
Unit descriptionCostUnit
Capastat sulfate 1 gm vial25.54USD vial
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 Area378.42 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity162.2 m3·mol-1ChemAxon
Polarizability66.56 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Macrolactam
  • Alpha-amino acid amide
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • 1,4,5,6-tetrahydropyrimidine
  • Hydropyrimidine
  • Fatty amide
  • Vinylogous amide
  • Urea
  • Secondary carboxylic acid amide
  • Lactam
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available

Targets

1. 70S ribosome
Kind
Protein group
Organism
Mycobacterium tuberculosis
Pharmacological action
yes
Actions
inhibitor
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. doi: 10.1038/nsmb.1755. Epub 2010 Feb 14. [PubMed:20154709 ]
  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:16857584 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:11