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MedKoo Cat#: 461320 | Name: Sisomicin free base
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Description:

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

Sisomicin (bactoCeaze, ensamycin, and initially antibiotic 6640 and rickamicin), is an aminoglycoside antibiotic, isolated from the fermentation broth of Micromonospora inositola. It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin. Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant in vitro to other aminoglycosides.

Chemical Structure

Sisomicin free base
Sisomicin free base
CAS#32385-11-8 (free base)

Theoretical Analysis

MedKoo Cat#: 461320

Name: Sisomicin free base

CAS#: 32385-11-8 (free base)

Chemical Formula: C19H37N5O7

Exact Mass: 447.2693

Molecular Weight: 447.53

Elemental Analysis: C, 50.99; H, 8.33; N, 15.65; O, 25.02

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 550.00 2 Weeks
1g USD 1,950.00 2 Weeks
2g USD 3,650.00 2 Weeks
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Related CAS #
32385-11-8 (free base) 53179-09-2 (sulfate)
Synonym
Sisomicin; Rickamicin; Siseptin; antibiotic 6640;
IUPAC/Chemical Name
(2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol
InChi Key
URWAJWIAIPFPJE-YFMIWBNJSA-N
InChi Code
InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
SMILES Code
N[C@H]1[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@@H]3[C@H](O)[C@@H](NC)[C@](O)(C)CO3)[C@H]2O)OC(CN)=CC1
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, DMF, and ethanol
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Sisomicin is active against Gram-positive and Gram-negative bacteria including B. subtilis, S. aureus, E. coli, and P. aeruginosa among others (MICs = 0.01-0.75 µg/ml) but is less active against P. multocida and V. coli (MICs = 7.5 and 2.4 µg/ml, respectively). Sisomicin is protective against Gram-positive and Gram-negative bacterial infections in mice with 50% protective dose (PD50s) values ranging from 0.5 to 6 mg/kg.
In vitro activity:
Sisomicin exhibited bactericidal efficacy against CCCP-induced P. aeruginosa persister cells with the viable cell count decreased from 9.14 log10 CFU/mL to sisomicin log10 CFU/mL, following 4 h of treatment. Furthermore, sisomicin was also effective against conventional antibiotics induced persister cells in a time-dependent manner within 24 h. Reference: Curr Microbiol. 2021 Dec 14;79(1):12. https://pubmed.ncbi.nlm.nih.gov/34905092/
In vivo activity:
In vitro, aminoglycosides (gentamicin, sisomicin, and amikacin) were tested against natural strains of the plague microbe. The MICs of gentamicin and sisomicin for 50 strains ranged from 0.2 to 1.6 micrograms/ml, with most strains at 0.4 micrograms/ml. In albino mice, these antibiotics demonstrated high efficacy in preventing and treating experimental plague infection, with optimal doses identified. Sisomicin showed advantages over gentamicin and amikacin in prophylaxis under specific conditions like short-term regimens and longer intervals. Reference: Antibiot Khimioter. 1992 May;37(5):30-1. https://pubmed.ncbi.nlm.nih.gov/1417325/
Solvent mg/mL mM comments
Solubility
DMF 25.0 55.86
DMSO 30.0 67.03
Ethanol 25.0 55.86
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 447.53 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
Formulation protocol:
1. She P, Li S, Liu Y, Xu L, Zhou L, Zeng X, Li Y, Liu S, Li Z, Hussain Z, Wu Y. Repurposing Sitafloxacin, Prulifloxacin, Tosufloxacin, and Sisomicin as Antimicrobials Against Biofilm and Persister Cells of Pseudomonas aeruginosa. Curr Microbiol. 2021 Dec 14;79(1):12. doi: 10.1007/s00284-021-02729-w. PMID: 34905092. 2. Crowe CC, Sanders E. Sisomicin: evaluation in vitro and comparison with gentamicin and tobramycin. Antimicrob Agents Chemother. 1973 Jan;3(1):24-8. doi: 10.1128/AAC.3.1.24. PMID: 4790572; PMCID: PMC444355. 3. Wang M, Wu B, Shah SN, Lu P, Lu Q. Aminoglycoside Enhances the Delivery of Antisense Morpholino Oligonucleotides In Vitro and in mdx Mice. Mol Ther Nucleic Acids. 2019 Jun 7;16:663-674. doi: 10.1016/j.omtn.2019.04.023. Epub 2019 May 2. PMID: 31121478; PMCID: PMC6529765. 4. Shcherbaniuk AI, Makarovskaia LN, Bugaeva OK, Kasatkina IV. Antibiotiki gruppy aminoglikozidov (gentamitsin, sizomitsin, amikatsin) v profilaktike i lechenii éksperimental'noĭ chumnoĭ infektsii [Antibiotics of the aminoglycoside group (gentamicin, sisomicin and amikacin) in the prevention and treatment of experimental plague]. Antibiot Khimioter. 1992 May;37(5):30-1. Russian. PMID: 1417325.
In vitro protocol:
1. She P, Li S, Liu Y, Xu L, Zhou L, Zeng X, Li Y, Liu S, Li Z, Hussain Z, Wu Y. Repurposing Sitafloxacin, Prulifloxacin, Tosufloxacin, and Sisomicin as Antimicrobials Against Biofilm and Persister Cells of Pseudomonas aeruginosa. Curr Microbiol. 2021 Dec 14;79(1):12. doi: 10.1007/s00284-021-02729-w. PMID: 34905092. 2. Crowe CC, Sanders E. Sisomicin: evaluation in vitro and comparison with gentamicin and tobramycin. Antimicrob Agents Chemother. 1973 Jan;3(1):24-8. doi: 10.1128/AAC.3.1.24. PMID: 4790572; PMCID: PMC444355.
In vivo protocol:
1. Wang M, Wu B, Shah SN, Lu P, Lu Q. Aminoglycoside Enhances the Delivery of Antisense Morpholino Oligonucleotides In Vitro and in mdx Mice. Mol Ther Nucleic Acids. 2019 Jun 7;16:663-674. doi: 10.1016/j.omtn.2019.04.023. Epub 2019 May 2. PMID: 31121478; PMCID: PMC6529765. 2. Shcherbaniuk AI, Makarovskaia LN, Bugaeva OK, Kasatkina IV. Antibiotiki gruppy aminoglikozidov (gentamitsin, sizomitsin, amikatsin) v profilaktike i lechenii éksperimental'noĭ chumnoĭ infektsii [Antibiotics of the aminoglycoside group (gentamicin, sisomicin and amikacin) in the prevention and treatment of experimental plague]. Antibiot Khimioter. 1992 May;37(5):30-1. Russian. PMID: 1417325.
1: Lin N, Sha Y, Zhang G, Song C, Zhang Y, Zhao J, Huang D, Lu J, Bao Q, Pan W. APH(3')-Ie, an aminoglycoside-modifying enzyme discovered in a rabbit-derived Citrobacter gillenii isolate. Front Cell Infect Microbiol. 2024 Jul 30;14:1435123. doi: 10.3389/fcimb.2024.1435123. PMID: 39139766; PMCID: PMC11320999. 2: Maraslioglu-Sperber A, Blanc F, Heller S, Benkafadar N. Hyperosmotic sisomicin infusion: a mouse model for hearing loss. Sci Rep. 2024 Jul 10;14(1):15903. doi: 10.1038/s41598-024-66635-4. PMID: 38987330; PMCID: PMC11237112. 3: Sato MP, Huang AP, Heller S, Benkafadar N. Protocol for in vivo elimination of avian auditory hair cells, multiplexed mRNA detection, immunohistochemistry, and S-phase labeling. STAR Protoc. 2024 Jun 21;5(2):103118. doi: 10.1016/j.xpro.2024.103118. Epub 2024 Jun 8. PMID: 38852155; PMCID: PMC11217775. 4: Öztaş S, Er DK, Dündar D, Keçeli SA. Efficacy of ceftazidime/avibactam and plazomicin on carbapenem-resistant Klebsiella pneumoniae and Escherichia coli. Acta Microbiol Immunol Hung. 2024 Jun 5;71(2):110-120. doi: 10.1556/030.2024.02292. PMID: 38837219. 5: Sękowska A. In vitro activity of plazomicin and other aminoglycosides against Klebsiella pneumoniae multidrug-resistant strains. J Antibiot (Tokyo). 2024 Aug;77(8):548-551. doi: 10.1038/s41429-024-00734-2. Epub 2024 May 8. PMID: 38720141. 6: Maraslioglu-Sperber A, Blanc F, Heller S, Benkafadar N. Hyperosmotic Sisomicin Infusion: A Mouse Model for Hearing Loss. Res Sq [Preprint]. 2024 Apr 1:rs.3.rs-4096027. doi: 10.21203/rs.3.rs-4096027/v1. Update in: Sci Rep. 2024 Jul 10;14(1):15903. doi: 10.1038/s41598-024-66635-4. PMID: 38645253; PMCID: PMC11030510. 7: Strich JR, Mishuk A, Diao G, Lawandi A, Li W, Demirkale CY, Babiker A, Mancera A, Swihart BJ, Walker M, Yek C, Neupane M, De Jonge N, Warner S, Kadri SS; National Institutes of Health Antimicrobial Resistance Outcomes Research Initiative. Assessing Clinician Utilization of Next-Generation Antibiotics Against Resistant Gram-Negative Infections in U.S. Hospitals : A Retrospective Cohort Study. Ann Intern Med. 2024 May;177(5):559-572. doi: 10.7326/M23-2309. Epub 2024 Apr 19. PMID: 38639548. 8: Sato MP, Benkafadar N, Heller S. Hair cell regeneration, reinnervation, and restoration of hearing thresholds in the avian hearing organ. Cell Rep. 2024 Mar 26;43(3):113822. doi: 10.1016/j.celrep.2024.113822. Epub 2024 Feb 22. PMID: 38393948; PMCID: PMC11068303. 9: Gross S, Herren S, Gysin M, Rominski A, Roditscheff A, Risch M, Imkamp F, Crich D, Hobbie SN. In vitro susceptibility of Neisseria gonorrhoeae to netilmicin and etimicin in comparison to gentamicin and other aminoglycosides. Eur J Clin Microbiol Infect Dis. 2024 May;43(5):821-828. doi: 10.1007/s10096-024-04782-2. Epub 2024 Feb 22. PMID: 38388739; PMCID: PMC11108870. 10: Xu J, Shen S, Hu Z, Xu G, Li H, Xu Z, Shi J. Enhanced Production of Sisomicin in Micromonospora inyoensis by Protoplast Mutagenesis and Fermentation Optimization. Appl Biochem Biotechnol. 2024 Feb 21. doi: 10.1007/s12010-024-04889-4. Epub ahead of print. PMID: 38381313. 11: Maekawa K, Sawa R, Matsui M, Konda T, Kubota Y, Matsuo A, Maeda A, Takahashi C, Tanimoto T, Nakagawa Y, Yoneda S, Mori Y, Suzuki S. Quality Evaluation of Gentamicin Sulfate Reference Standards in Japanese Pharmacopoeia Using Hydrophilic Interaction Chromatography Combined With Tandem Mass Spectrometry. J AOAC Int. 2024 Mar 1;107(2):234-241. doi: 10.1093/jaoacint/qsad135. PMID: 38070143. 12: Ngo D, Magaña AJ, Tran T, Sklenicka J, Phan K, Eykholt B, Jimenez V, Ramirez MS, Tolmasky ME. Inhibition of Enzymatic Acetylation-Mediated Resistance to Plazomicin by Silver Ions. Pharmaceuticals (Basel). 2023 Feb 3;16(2):236. doi: 10.3390/ph16020236. PMID: 37259383; PMCID: PMC9966628. 13: Jana S, Crich D. Synthesis of Gentamicin Minor Components: Gentamicin C1a and Gentamicin C2b. Org Lett. 2022 Nov 25;24(46):8564-8567. doi: 10.1021/acs.orglett.2c03616. Epub 2022 Nov 14. PMID: 36375034. 14: Tran PMH, Dong F, Kim E, Richardson KP, Tran LKH, Waugh K, Hopkins D, Cummings RD, Wang PG, Rewers MJ, She JX, Purohit S. Use of a glycomics array to establish the anti-carbohydrate antibody repertoire in type 1 diabetes. Nat Commun. 2022 Nov 1;13(1):6527. doi: 10.1038/s41467-022-34341-2. PMID: 36316364; PMCID: PMC9622713. 15: Luterbach CL, Rao GG. Use of pharmacokinetic/pharmacodynamic approaches for dose optimization: a case study of plazomicin. Curr Opin Microbiol. 2022 Dec;70:102204. doi: 10.1016/j.mib.2022.102204. Epub 2022 Sep 16. PMID: 36122516. 16: Kawauchi R, Tada T, Sherchan JB, Shrestha S, Tohya M, Hishinuma T, Kirikae T, Sherchand JB. Stenotrophomonas maltophilia from Nepal Producing Two Novel Antibiotic Inactivating Enzymes, a Class A β-Lactamase KBL-1 and an Aminoglycoside 6'-N-Acetyltransferase AAC(6')-Iap. Microbiol Spectr. 2022 Aug 31;10(4):e0114322. doi: 10.1128/spectrum.01143-22. Epub 2022 Jul 7. PMID: 35862995; PMCID: PMC9431274. 17: Demirbas Z, Ozger HS, Suzuk-Yildiz S, Bakkaloglu Z, Dizbay M. In Vitro Activity of Plazomicin Against Carbapenem Resistant Klebsiella pneumoniae Strains. Clin Lab. 2022 Jun 1;68(6). doi: 10.7754/Clin.Lab.2021.210936. PMID: 35704736. 18: Chang Z, Zheng YY, Mathivanan J, Valsangkar VA, Du J, Abou-Elkhair RAI, Hassan AEA, Sheng J. Fluorescence-Based Binding Characterization of Small Molecule Ligands Targeting CUG RNA Repeats. Int J Mol Sci. 2022 Mar 19;23(6):3321. doi: 10.3390/ijms23063321. PMID: 35328743; PMCID: PMC8955525. 19: Zhuang L, Wu K, Jang SH, Reynolds KS, Mishra S, Iarikov D. Application of Population Pharmacokinetic Modeling, Exposure-Response Analysis, and Classification and Regression Tree Analysis to Support Dosage Regimen and Therapeutic Drug Monitoring of Plazomicin in Complicated Urinary Tract Infection Patients with Renal Impairment. Antimicrob Agents Chemother. 2022 Apr 19;66(4):e0207421. doi: 10.1128/aac.02074-21. Epub 2022 Mar 8. PMID: 35258314; PMCID: PMC9017347. 20: El-Kawy OA, Abdelaziz G, Abdel-Razek AS. Radiolabeling, characterization, and preclinical evaluation of plazomicin: A potential tracer for bacterial infection. Chem Biol Drug Des. 2022 May;99(5):688-702. doi: 10.1111/cbdd.14007. Epub 2022 Jan 4. PMID: 34923759.