Capreomycin Sulfate

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MedKoo CAT#: 329207

CAS#: 1405-37-4 (sulfate)

Description: Capreomycin Sulfate, also known as HSDB-3211 and Capostatin, is a ribosomal subunit inbihitor used to treat tuberculosis.

Chemical Structure

Capreomycin Sulfate
CAS# 1405-37-4 (sulfate)

Theoretical Analysis

MedKoo Cat#: 329207
Name: Capreomycin Sulfate
CAS#: 1405-37-4 (sulfate)
Chemical Formula: C25H48N14O16S2
Exact Mass:
Molecular Weight: 864.861
Elemental Analysis: C, 34.72; H, 5.59; N, 22.67; O, 29.60; S, 7.41

Price and Availability

Size Price Availability Quantity
1.0g USD 295.0 2 Weeks
2.0g USD 485.0 2 Weeks
5.0g USD 795.0 2 Weeks
10.0g USD 1650.0 2 Weeks
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Related CAS #: 11003-38-6 (free base)   1405-37-4 (sulfate)  

Synonym: Capreomycin Sulfate; Kapreomycin; Capostatin; HSDB 3211; HSDB-3211; HSDB3211

IUPAC/Chemical Name: (S)-3,6-diamino-N-(((2S,5S,11S,15S,E)-15-amino-11-((R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl)-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-8-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-5-yl)methyl)hexanamide compound with (S)-3,6-diamino-N-(((2S,5S,11S,15S,E)-15-amino-11-((R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl)-2-methyl-3,6,9,12,16-pentaoxo-8-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-5-yl)methyl)hexanamide (1:1)


InChi Code: 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

SMILES Code: O=C(NC[C@@H](C(N/C(C(N[C@@H]([C@@H]1NC(N)=NCC1)C(NC[C@@H]2N)=O)=O)=C/NC(N)=O)=O)NC([C@H](CO)NC2=O)=O)C[C@@H](N)CCCN.O=C(NC[C@@H](C(N/C(C(N[C@@H]([C@@H]3NC(N)=NCC3)C(NC[C@@H]4N)=O)=O)=C/NC(N)=O)=O)NC([C@H](C)NC4=O)=O)C[C@@H](N)CCCN

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Capreomycin sulfate is a peptide antibiotic, commonly grouped with the aminoglycosides, which is given in combination with other antibiotics for MDR-tuberculosis.
In vitro activity: Time course of insulin fibrillation in the absence and presence of capreomycin (CN) (mixture of four isoforms) was studied by a ThT fluorescence assay and shown in Fig. 1. Initially, to monitor CN's behavior towards insulin fibril formation, different concentrations of CN (from 0 to 200 μM) were tested. Drop in ThT fluorescence was observed with increase in the concentration of CN and saturated at 100 μM of CN (Fig. 1A), indicates that CN inhibits fibril formation in a concentration dependent manner, maximum at ≈100 μM of CN. ThT fluorescence spectra of free insulin and insulin incubated with CN showed that ThT fluorescence reduced from 295 to 135 and 48 in the presence of 75 and 100 μM of CN, respectively (Supplementary Fig. S1). In other words, we can say that CN inhibits the aggregation process of insulin up to 83% as compared to the control (Supplementary Fig. S2). Even at 75 μM, CN showed the delaying effect in fibrillation process (54% effective). The IC50 value of CN was also evaluated to be 69.98 μM, from the dose response curve (Fig. 2). Furthermore, we also tested whether CN would hamper the elongation phase or not. To test this hypothesis, we added the CN (100 μM) at two different points along the aggregation pathway (Fig. 3). The addition of CN at the midpoint arrested aggregation completely, but did not decrease the ThT fluorescence significantly, suggests CN may block aggregation in log phase. Similarly, adding CN at the end of lag phase reduced the yield of fibril. Ratha et. Al. also described that novel amphipathic heptapeptide inhibits insulin fibril formation, similar to action of CN. Overall these results concluded that either the premixing of CN with insulin or the addition of CN during the growing phase retards the amyloid fibril formation. Importantly, these observed results were due to the cumulative effect of different isoform of CN viz. IA, IB, IIA and IIB, since, individually these isoforms may behave differentially. Reference: Biochim Biophys Acta Proteins Proteom. 2018 Apr;1866(4):549-557.
In vivo activity: The efficacy of the intrapulmonary aerosol delivery for capreomycin and amikacin is shown in Fig. 2. Neither capreomycin nor amikacin is orally bioavailable. Mice treated by the intrapulmonary aerosol or by subcutaneous injection of capreomycin or amikacin demonstrated similar reductions of the pulmonary bacterial load after 3 weeks of treatment. During the 3 weeks of treatment, mice treated with capreomycin or amikacin received a total of 9 doses when delivered by intrapulmonary aerosol or a total of 15 doses by subcutaneous injection. Similarly, both drugs were administered at 500 μg/dose when delivered by the intrapulmonary aerosol and at 3,300 μg/dose when delivered by subcutaneous injection. The bacterial loads of controls treated with sterile phosphate-buffered saline (PBS) (diluents for the drugs) were statistically similar to those of untreated mice (P > 0.05). The bacterial load in the spleen of mice treated by either intrapulmonary aerosol or subcutaneous injection with capreomycin or amikacin did not differ significantly from that of the control mice treated with the drug diluents (P > 0.05) (data not shown). Reference: Antimicrob Agents Chemother. 2012 Jul;56(7):3957-9.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Water 37.0 49.28

Preparing Stock Solutions

The following data is based on the product molecular weight 864.861 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
In vitro protocol: 1. Siddiqi MK, Alam P, Chaturvedi SK, Khan MV, Nusrat S, Malik S, Khan RH. Capreomycin inhibits the initiation of amyloid fibrillation and suppresses amyloid induced cell toxicity. Biochim Biophys Acta Proteins Proteom. 2018 Apr;1866(4):549-557. doi: 10.1016/j.bbapap.2018.02.005. Epub 2018 Feb 26. Erratum in: Biochim Biophys Acta Proteins Proteom. 2020 Jun;1868(6):140407. PMID: 29496560.
In vivo protocol: 1. Gonzalez-Juarrero M, Woolhiser LK, Brooks E, DeGroote MA, Lenaerts AJ. Mouse model for efficacy testing of antituberculosis agents via intrapulmonary delivery. Antimicrob Agents Chemother. 2012 Jul;56(7):3957-9. doi: 10.1128/AAC.00464-12. Epub 2012 Apr 30. PMID: 22547626; PMCID: PMC3393411.

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1: Schoubben A, Giovagnoli S, Tiralti MC, Blasi P, Ricci M. Capreomycin inhalable powders prepared with an innovative spray-drying technique. Int J Pharm. 2014 Jul 20;469(1):132-9. doi: 10.1016/j.ijpharm.2014.04.042. PubMed PMID: 24747443.

2: Cambronero-Rojas A, Torres-Vergara P, Godoy R, von Plessing C, Sepúlveda J, Gómez-Gaete C. Capreomycin oleate microparticles for intramuscular administration: Preparation, in vitro release and preliminary in vivo evaluation. J Control Release. 2015 Jul 10;209:229-37. doi: 10.1016/j.jconrel.2015.05.001. PubMed PMID: 25956458.

3: Mallampati S, Huang S, Ashenafi D, Van Hemelrijck E, Hoogmartens J, Adams E. Development and validation of a liquid chromatographic method for the analysis of capreomycin sulfate and its related substances. J Chromatogr A. 2009 Mar 20;1216(12):2449-55. doi: 10.1016/j.chroma.2009.01.031. PubMed PMID: 19185869.

4: Schoubben A, Blasi P, Marenzoni ML, Barberini L, Giovagnoli S, Cirotto C, Ricci M. Capreomycin supergenerics for pulmonary tuberculosis treatment: preparation, in vitro, and in vivo characterization. Eur J Pharm Biopharm. 2013 Apr;83(3):388-95. doi: 10.1016/j.ejpb.2012.11.005. PubMed PMID: 23220041.

5: Giovagnoli S, Blasi P, Schoubben A, Rossi C, Ricci M. Preparation of large porous biodegradable microspheres by using a simple double-emulsion method for capreomycin sulfate pulmonary delivery. Int J Pharm. 2007 Mar 21;333(1-2):103-11. PubMed PMID: 17079101.

6: Ricci M, Giovagnoli S, Blasi P, Schoubben A, Perioli L, Rossi C. Development of liposomal capreomycin sulfate formulations: effects of formulation variables on peptide encapsulation. Int J Pharm. 2006 Mar 27;311(1-2):172-81. PubMed PMID: 16439072.

7: Giovagnoli S, Blasi P, Vescovi C, Fardella G, Chiappini I, Perioli L, Ricci M, Rossi C. Unilamellar vesicles as potential capreomycin sulfate carriers: preparation and physicochemical characterization. AAPS PharmSciTech. 2004 Dec 31;4(4):E69. PubMed PMID: 15198564; PubMed Central PMCID: PMC2750662.

8: Fiegel J, Garcia-Contreras L, Thomas M, VerBerkmoes J, Elbert K, Hickey A, Edwards D. Preparation and in vivo evaluation of a dry powder for inhalation of capreomycin. Pharm Res. 2008 Apr;25(4):805-11. PubMed PMID: 17657592.

9: Garcia-Contreras L, Fiegel J, Telko MJ, Elbert K, Hawi A, Thomas M, VerBerkmoes J, Germishuizen WA, Fourie PB, Hickey AJ, Edwards D. Inhaled large porous particles of capreomycin for treatment of tuberculosis in a guinea pig model. Antimicrob Agents Chemother. 2007 Aug;51(8):2830-6. PubMed PMID: 17517845; PubMed Central PMCID: PMC1932523.

10: Ianni F, Schoubben A, Montesano D, Wauthoz N, Cossignani L, Sardella R, Natalini B. Quantitative assay of capreomycin oleate levels in a drug formulation for inhalation with a fully validated HPLC method. J Pharm Biomed Anal. 2016 Feb 20;120:413-8. doi: 10.1016/j.jpba.2015.11.040. PubMed PMID: 26680112.

11: OʼDonnell MR, Pillay M, Pillay M, Werner L, Master I, Wolf A, Mathema B, Coovadia YM, Mlisana K, Horsburgh CR, Padayatchi N. Primary Capreomycin Resistance Is Common and Associated With Early Mortality in Patients With Extensively Drug-Resistant Tuberculosis in KwaZulu-Natal, South Africa. J Acquir Immune Defic Syndr. 2015 Aug 15;69(5):536-43. doi: 10.1097/QAI.0000000000000650. PubMed PMID: 25886924; PubMed Central PMCID: PMC4501864.

12: Manning T, Mikula R, Lee H, Calvin A, Darrah J, Wylie G, Phillips D, Bythell BJ. The copper (II) ion as a carrier for the antibiotic capreomycin against Mycobacterium tuberculosis. Bioorg Med Chem Lett. 2014 Feb 1;24(3):976-82. doi: 10.1016/j.bmcl.2013.12.053. PubMed PMID: 24424129.

13: Lin Y, Li Y, Zhu N, Han Y, Jiang W, Wang Y, Si S, Jiang J. The antituberculosis antibiotic capreomycin inhibits protein synthesis by disrupting interaction between ribosomal proteins L12 and L10. Antimicrob Agents Chemother. 2014;58(4):2038-44. doi: 10.1128/AAC.02394-13. PubMed PMID: 24449778; PubMed Central PMCID: PMC4023752.

14: Dharmadhikari AS, Kabadi M, Gerety B, Hickey AJ, Fourie PB, Nardell E. Phase I, single-dose, dose-escalating study of inhaled dry powder capreomycin: a new approach to therapy of drug-resistant tuberculosis. Antimicrob Agents Chemother. 2013 Jun;57(6):2613-9. doi: 10.1128/AAC.02346-12. PubMed PMID: 23529740; PubMed Central PMCID: PMC3716148.

15: Szafraniec M, Stokowa-Sołtys K, Nagaj J, Kasprowicz A, Wrzesiński J, Jeżowska-Bojczuk M, Ciesiołka J. Capreomycin and hygromycin B modulate the catalytic activity of the delta ribozyme in a manner that depends on the protonation and complexation with Cu2+ ions of these antibiotics. Dalton Trans. 2012 Aug 28;41(32):9728-36. doi: 10.1039/c2dt30794d. PubMed PMID: 22791142.

Additional Information

Related CAS#

1405-37-4(Capreomycin Sulfate)