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MedKoo Cat#: 412270 | Name: Capreomycin free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Capreomycin is a polypeptide antibiotic originally isolated from S. capreolus. It is active against M. tuberculosis (MIC = 10 µg/ml). Capreomycin binds to both the 30S and 50S ribosomal subunits, inhibiting protein synthesis.

Chemical Structure

Capreomycin free base
Capreomycin free base
CAS#11003-38-6 (free base)

Theoretical Analysis

MedKoo Cat#: 412270

Name: Capreomycin free base

CAS#: 11003-38-6 (free base)

Chemical Formula: C50H88N28O15

Exact Mass: 1320.6984

Molecular Weight: 1321.43

Elemental Analysis: C, 45.45; H, 6.71; N, 29.68; O, 18.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
11003-38-6 (free base) 1405-37-4 (sulfate)
Synonym
Capreomycin (free base); HSDB 3211; HSDB 3211; HSDB 3211
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 Key
VCOPTHOUUNAYKQ-WBTCAYNUSA-N
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
C[C@@H]1NC([C@H](CNC([C@H]([C@H]2CCN=C(N2)N)NC(/C(NC([C@@H](NC1=O)CNC(C[C@H](CCCN)N)=O)=O)=C\NC(N)=O)=O)=O)N)=O.NCCC[C@@H](CC(NC[C@@H]3NC([C@@H](NC([C@H](CNC([C@H]([C@H]4CCN=C(N4)N)NC(/C(NC3=O)=C\NC(N)=O)=O)=O)N)=O)CO)=O)=O)N
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
>3 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,321.43 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
1: Pan YC, Wang YL, Toh SI, Hsu NS, Lin KH, Xu Z, Huang SC, Wu TK, Li TL, Chang CY. Dual-Mechanism Confers Self-Resistance to the Antituberculosis Antibiotic Capreomycin. ACS Chem Biol. 2022 Jan 21;17(1):138-146. doi: 10.1021/acschembio.1c00799. Epub 2022 Jan 7. PMID: 34994196. 2: Shao Z, Tai W, Qiu Y, Man RCH, Liao Q, Chow MYT, Kwok PCL, Lam JKW. Spray- Dried Powder Formulation of Capreomycin Designed for Inhaled Tuberculosis Therapy. Pharmaceutics. 2021 Nov 30;13(12):2044. doi: 10.3390/pharmaceutics13122044. PMID: 34959328; PMCID: PMC8706516. 3: Penn-Nicholson A, Georghiou SB, Ciobanu N, Kazi M, Bhalla M, David A, Conradie F, Ruhwald M, Crudu V, Rodrigues C, Myneedu VP, Scott L, Denkinger CM, Schumacher SG; Xpert XDR Trial Consortium. Detection of isoniazid, fluoroquinolone, ethionamide, amikacin, kanamycin, and capreomycin resistance by the Xpert MTB/XDR assay: a cross-sectional multicentre diagnostic accuracy study. Lancet Infect Dis. 2022 Feb;22(2):242-249. doi: 10.1016/S1473-3099(21)00452-7. Epub 2021 Oct 7. PMID: 34627496. 4: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Capreomycin. 2021 Sep 20. PMID: 31643953. 5: Ali W, Jamal S, Grover A, Grover S. Insights into the mutations leading to capreomycin resistance in S-adenosyl-L-methionine binding motif in TlyA from Mycobacterium tuberculosis. J Biomol Struct Dyn. 2021 Aug 31:1-9. doi: 10.1080/07391102.2021.1969284. Epub ahead of print. PMID: 34463210. 6: Hsu SH, Zhang S, Huang SC, Wu TK, Xu Z, Chang CY. Characterization of Enzymes Catalyzing the Formation of the Nonproteinogenic Amino Acid l-Dap in Capreomycin Biosynthesis. Biochemistry. 2021 Jan 12;60(1):77-84. doi: 10.1021/acs.biochem.0c00808. Epub 2020 Dec 23. PMID: 33356147. 7: Cegielski JP, Chan PC, Lan Z, Udwadia ZF, Viiklepp P, Yim JJ, Menzies D. Aminoglycosides and Capreomycin in the Treatment of Multidrug-resistant Tuberculosis: Individual Patient Data Meta-analysis of 12 030 Patients From 25 Countries, 2009-2016. Clin Infect Dis. 2021 Dec 6;73(11):e3929-e3936. doi: 10.1093/cid/ciaa621. PMID: 33124668; PMCID: PMC8653626. 8: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Capreomycin. 2020 Sep 21. PMID: 30000651. 9: Siddiqi MK, Alam P, Chaturvedi SK, Khan MV, Nusrat S, Malik S, Khan RH. Corrigendum to "Capreomycin inhibits the initiation of amyloid fibrillation and suppresses amyloid induced cell toxicity" [Biochim. Biophy. Acta 1866 (2018) 549-557]. Biochim Biophys Acta Proteins Proteom. 2020 Jun;1868(6):140407. doi: 10.1016/j.bbapap.2020.140407. Epub 2020 Mar 6. Erratum for: Biochim Biophys Acta Proteins Proteom. 2018 Apr;1866(4):549-557. PMID: 32151539. 10: Puri MM, Kumar A, Aneja P, Gupta R, Kumar L, Sarin R. Tetany in an Extensively Drug Resistant Tuberculosis (XDR-TB) Patient Treated with Capreomycin. J Assoc Physicians India. 2019 Aug;67(8):79-82. PMID: 31562727. 11: Vianna JF, S Bezerra K, I N Oliveira J, Albuquerque EL, Fulco UL. Binding energies of the drugs capreomycin and streptomycin in complex with tuberculosis bacterial ribosome subunits. Phys Chem Chem Phys. 2019 Sep 21;21(35):19192-19200. doi: 10.1039/c9cp03631h. Epub 2019 Aug 22. PMID: 31436279. 12: Chowdhury AS, Khaledian E, Broschat SL. Capreomycin resistance prediction in two species of Mycobacterium using a stacked ensemble method. J Appl Microbiol. 2019 Dec;127(6):1656-1664. doi: 10.1111/jam.14413. Epub 2019 Sep 8. PMID: 31419358. 13: Zhao J, Wei W, Yan H, Zhou Y, Li Z, Chen Y, Zhang C, Zeng J, Chen T, Zhou L. Assessing capreomycin resistance on tlyA deficient and point mutation (G695A) Mycobacterium tuberculosis strains using multi-omics analysis. Int J Med Microbiol. 2019 Nov;309(7):151323. doi: 10.1016/j.ijmm.2019.06.003. Epub 2019 Jun 24. PMID: 31279617. 14: Li G, Xu Z, Jiang Y, Liu H, Zhao LL, Li M, Xu D, Zhao X, Liu Z, Wang R, Wan K. Synergistic activities of clofazimine with moxifloxacin or capreomycin against Mycobacterium tuberculosis in China. Int J Antimicrob Agents. 2019 Nov;54(5):642-646. doi: 10.1016/j.ijantimicag.2019.06.002. Epub 2019 Jun 11. PMID: 31200023. 15: Pitner RA, Durham PG, Stewart IE, Reed SG, Cassell GH, Hickey AJ, Carter D. A Spray-Dried Combination of Capreomycin and CPZEN-45 for Inhaled Tuberculosis Therapy. J Pharm Sci. 2019 Oct;108(10):3302-3311. doi: 10.1016/j.xphs.2019.05.024. Epub 2019 May 29. PMID: 31152746; PMCID: PMC6759370. 16: Soeroto AY, Darmawan G, Supriyadi R, Bhaskara PG, Santoso P, Alisjahbana B, Parwati I. Comparison of Serum Potassium, MagnEsium, and Calcium Levels between Kanamycin and Capreomycin-BASEd Regimen-Treated MultiDrug-Resistant TuBerculosis Patients in Bandung (CEASE MDR-TB): A Retrospective Cohort Study. Int J Microbiol. 2019 Mar 14;2019:5065847. doi: 10.1155/2019/5065847. PMID: 31001341; PMCID: PMC6437726. 17: Miryala SK, Anbarasu A, Ramaiah S. Impact of bedaquiline and capreomycin on the gene expression patterns of multidrug-resistant Mycobacterium tuberculosis H37Rv strain and understanding the molecular mechanism of antibiotic resistance. J Cell Biochem. 2019 Sep;120(9):14499-14509. doi: 10.1002/jcb.28711. Epub 2019 Apr 15. PMID: 30989745. 18: Liu G, Luan B, Liang G, Xing L, Huang L, Wang C, Xu Y. Isolation and identification of four major impurities in capreomycin sulfate. J Chromatogr A. 2018 Oct 12;1571:155-164. doi: 10.1016/j.chroma.2018.08.015. Epub 2018 Aug 7. PMID: 30115387. 19: Man DK, Kanno T, Manzo G, Robertson BD, Lam JKW, Mason AJ. Rifampin- or Capreomycin-Induced Remodeling of the Mycobacterium smegmatis Mycolic Acid Layer Is Mitigated in Synergistic Combinations with Cationic Antimicrobial Peptides. mSphere. 2018 Jul 18;3(4):e00218-18. doi: 10.1128/mSphere.00218-18. PMID: 30021876; PMCID: PMC6052339. 20: Thuboy B, Kellermann T, Castel S, Norman J, Joubert A, Garcia-Prats AJ, Hesseling AC, Wiesner L. The determination of capreomycin in human plasma by LC- MS/MS using ion-pairing chromatography and solid-phase extraction. Biomed Chromatogr. 2018 May 3:e4269. doi: 10.1002/bmc.4269. Epub ahead of print. PMID: 29726023.