Identification
- Summary
Capreomycin is an aminoglycoside antibiotic used as an adjunct drug in tuberculosis.
- Brand Names
- Capastat
- Generic Name
- Capreomycin
- DrugBank Accession Number
- DB00314
- Background
Cyclic peptide antibiotic similar to viomycin. It is produced by Streptomyces capreolus.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Capreomycin (DB00314)
- Weight
- Average: 1321.4123
Monoisotopic: 1320.698394286 - Chemical Formula
- C50H88N28O15
- Synonyms
- Capreomicina
- Capreomycin
Pharmacology
- Indication
Used in the treatment of tuberculosis in combination with other drugs.
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism A16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA inhibitorMycobacterium tuberculosis (strain ATCC 25618 / H37Rv) - Absorption
Not absorbed in significant quantities from the gastrointestinal tract and must be administered parenterally.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
When a 1–g dose of capreomycin was given intramuscularly to normal volunteers, 52% was excreted in the urine within 12 hours.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Capreomycin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Capreomycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Capreomycin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Capreomycin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Capreomycin which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Capreomycin which could result in a lower serum level and potentially a reduction in efficacy. Acetylcholine The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Capreomycin. Acetyldigitoxin The risk or severity of adverse effects can be increased when Capreomycin is combined with Acetyldigitoxin. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Capreomycin which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Capreomycin which could result in a higher serum level. 
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- No interactions found.
Products
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Ingredient UNII CAS InChI Key Capreomycin sulfate 9H8D3J7V21 1405-37-4 TUATYNXRYJTQTQ-RIQUSILOSA-N - International/Other Brands
- Capastat (Akorn Incorporated) / Capreomycin (Bristol-Myers Squibb) / Helpomycin (Unifarm) / Kapocin (Macleods) / Lykocin (Lyka Labs Ltd.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Capastat Pws Im 1g Vial Powder, for solution 1 g / vial Intramuscular Eli Lilly & Co. Ltd. 1994-12-31 1997-08-13 Canada 
Capastat Sulfate Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Akorn 2009-08-01 Not applicable US 
Capastat sulfate Injection, powder, for solution 1 g/2mL Intramuscular; Intravenous Eli Lilly & Co. Ltd. 1971-10-01 2011-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Capreomycin Sulfate Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Hisun Pharmaceuticals Usa, Inc. 2018-10-18 2020-03-13 US
Categories
- ATC Codes
- J04AB30 — Capreomycin
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Amino Acids, Peptides, and Proteins
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibiotics, Antitubercular
- Antiinfectives for Systemic Use
- Antimycobacterials
- Drugs for Treatment of Tuberculosis
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Enzyme Inhibitors
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- Peptides
- Peptides, Cyclic
- Protein Synthesis Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / Macrolactams / Alpha amino acid amides / Beta amino acids and derivatives / N-acyl amines / Hydropyrimidines / Vinylogous amides / Secondary carboxylic acid amides / Ureas / Guanidines show 10 more
- Substituents
- 1,4,5,6-tetrahydropyrimidine / Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Azacycle / Beta amino acid or derivatives show 28 more
- Molecular Framework
- Not Available
- External Descriptors
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 232HYX66HC
- CAS number
- 11003-38-6
- InChI Key
- VCOPTHOUUNAYKQ-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
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014459
- KEGG Drug
- D00135
- KEGG Compound
- C01790
- PubChem Compound
- 3000502
- PubChem Substance
- 46508514
- ChemSpider
- 2272094
- 78903
- ChEBI
- 3371
- ChEMBL
- CHEMBL2303634
- Therapeutic Targets Database
- DAP000892
- PharmGKB
- PA164746226
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Capreomycin
- FDA label
- Download (204 KB)
- MSDS
- Download (131 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Terminated Treatment Osteomyelitis 1 Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections 1 Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Tuberculosis (TB) 1 Not Available Recruiting Not Available Tuberculosis (TB) 1
Pharmacoeconomics
- Manufacturers
- Akorn inc
- Packagers
- Akorn Inc.
- Eli Lilly & Co.
- Dosage Forms
Form Route Strength Powder, for solution Intramuscular 1 g / vial Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 1 g/2mL - Prices
Unit description Cost Unit Capastat sulfate 1 gm vial 25.54USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble in water as disulfate salt. Not Available logP -9.609 Not Available - Predicted Properties
Property Value Source Water Solubility 1.48 mg/mL ALOGPS logP -3.2 ALOGPS logP -11 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 10.62 Chemaxon pKa (Strongest Basic) 10.3 Chemaxon Physiological Charge 3 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 14 Chemaxon Polar Surface Area 378.42 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 162.2 m3·mol-1 Chemaxon Polarizability 65.97 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.8828 CYP450 2D6 inhibitor Non-inhibitor 0.9196 CYP450 2C19 inhibitor Non-inhibitor 0.881 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Acts as a host evasion factor, that significantly contributes to the pathogenesis of M.tuberculosis by modulating adaptive immune responses by inhibiting host-protective Th1 and Th17 cytokine responses as well as autophagy (PubMed:25847237). Catalyzes the 2'-O-methylation at nucleotides C1409 in 16S rRNA and C1920 in 23S rRNA (PubMed:16857584, PubMed:20854656). Is likely involved in ribosomal biogenesis (PubMed:21443791). Also exhibits hemolytic activity in vitro, by binding with and oligomerizing into host cell membranes (PubMed:20854656, PubMed:9611795).
- Specific Function
- Rna binding
- Gene Name
- tlyA
- Uniprot ID
- P9WJ63
- Uniprot Name
- 16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA
- Molecular Weight
- 28073.885 Da
References
- Fu LM, Shinnick TM: Genome-wide exploration of the drug action of capreomycin on Mycobacterium tuberculosis using Affymetrix oligonucleotide GeneChips. J Infect. 2007 Mar;54(3):277-84. doi: 10.1016/j.jinf.2006.05.012. Epub 2006 Jul 5. [Article]
- 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. [Article]
- Akbergenov R, Shcherbakov D, Matt T, Duscha S, Meyer M, Wilson DN, Bottger EC: Molecular basis for the selectivity of antituberculosis compounds capreomycin and viomycin. Antimicrob Agents Chemother. 2011 Oct;55(10):4712-7. doi: 10.1128/AAC.00628-11. Epub 2011 Jul 18. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:14