Sisomicin sulfate
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MedKoo CAT#: 578647

CAS#: 53179-09-2 (sulfate)

Description: 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

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Sisomicin sulfate
CAS# 53179-09-2 (sulfate)
Instruction

Theoretical Analysis

MedKoo Cat#: 578647
Name: Sisomicin sulfate
CAS#: 53179-09-2 (sulfate)
Chemical Formula: C38H84N10O34S5
Exact Mass: 1,384.38
Molecular Weight: 1,385.430
Elemental Analysis: C, 32.94; H, 6.11; N, 10.11; O, 39.26; S, 11.57

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Related CAS #: 32385-11-8 (free base)   53179-09-2 (sulfate)    

Synonym: Antibiotic 66-40 sulfate; Baymicine; Extramycin; Pathomycin; Sisomicin sulfate

IUPAC/Chemical Name: bis((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) pentakis(sulfate)

InChi Key: CIKNYWFPGZCHDL-ZHFUJENKSA-N

InChi Code: InChI=1S/2C19H37N5O7.5H2O4S/c2*1-19(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;5*1-5(2,3)4/h2*3,9-18,24-27H,4-7,20-23H2,1-2H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+;;;;;/m11...../s1

SMILES Code: CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(=CC[C@H]3N)CN)[C@@H]2O)OC[C@]1(C)O.CN[C@@H]4[C@@H](O)[C@@H](O[C@H]5[C@H](N)C[C@H](N)[C@@H](O[C@H]6OC(=CC[C@H]6N)CN)[C@@H]5O)OC[C@]4(C)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,385.43 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tansarli GS, Rafailidis PI, Papazoglou AA, Falagas ME. Antimicrobial activity and clinical effectiveness of sisomicin: an evaluation of the literature (1995-2011). Expert Rev Anti Infect Ther. 2013 Apr;11(4):421-8. doi: 10.1586/eri.13.18. Review. PubMed PMID: 23566151.

2: Wlasichuk KB, Tan L, Guo Y, Hildebrandt DJ, Zhang H, Karr DE, Schmidt DE Jr. Determination of equilibrium constant of amino carbamate adduct formation in sisomicin by a high pH based high performance liquid chromatography. J Pharm Biomed Anal. 2015;111:126-30. doi: 10.1016/j.jpba.2015.03.033. Epub 2015 Apr 3. PubMed PMID: 25880243.

3: Kondo J, Koganei M, Maianti JP, Ly VL, Hanessian S. Crystal structures of a bioactive 6'-hydroxy variant of sisomicin bound to the bacterial and protozoal ribosomal decoding sites. ChemMedChem. 2013 May;8(5):733-9. doi: 10.1002/cmdc.201200579. Epub 2013 Feb 21. PubMed PMID: 23436717.

4: Karaiskos I, Souli M, Giamarellou H. Plazomicin: an investigational therapy for the treatment of urinary tract infections. Expert Opin Investig Drugs. 2015;24(11):1501-11. doi: 10.1517/13543784.2015.1095180. Epub 2015 Sep 30. Review. PubMed PMID: 26419762.

5: García-Salguero C, Rodríguez-Avial I, Picazo JJ, Culebras E. Can Plazomicin Alone or in Combination Be a Therapeutic Option against Carbapenem-Resistant Acinetobacter baumannii? Antimicrob Agents Chemother. 2015 Oct;59(10):5959-66. doi: 10.1128/AAC.00873-15. Epub 2015 Jul 13. PubMed PMID: 26169398; PubMed Central PMCID: PMC4576036.

6: Schassan HH. [Antimicrobial effectiveness of sisomicin. I: In vitro activity of sisomicin compared with gentamicin, tobramycin, amikacin and kanamycin (author's transl)]. Infection. 1976;4(2):35-41. German. PubMed PMID: 789246.

7: Rodríguez-Avial I, Pena I, Picazo JJ, Rodríguez-Avial C, Culebras E. In vitro activity of the next-generation aminoglycoside plazomicin alone and in combination with colistin, meropenem, fosfomycin or tigecycline against carbapenemase-producing Enterobacteriaceae strains. Int J Antimicrob Agents. 2015 Dec;46(6):616-21. doi: 10.1016/j.ijantimicag.2015.07.021. Epub 2015 Sep 9. PubMed PMID: 26391381.

8: Roth S, Naber K, Scheer M, Gruenwaldt G, Lange H. Pharmacokinetics of sisomicin in patients with normal and impaired renal function; its efficacy in urinary tract infection. Eur J Clin Pharmacol. 1976 Sep 30;10(5):357-65. PubMed PMID: 789084.

9: Wilczyński S, Pilawa B, Koprowski R, Wróbel Z, Ptaszkiewicz M, Swakoń J, Olko P. EPR studies of free radicals decay and survival in gamma irradiated aminoglycoside antibiotics: sisomicin, tobramycin and paromomycin. Eur J Pharm Sci. 2012 Feb 14;45(3):251-62. doi: 10.1016/j.ejps.2011.11.009. Epub 2011 Nov 17. PubMed PMID: 22115867.

10: Davies DH, Mallams AK, Counelis M, Loebenberg D, Moss EL Jr, Waitz JA. Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C. J Med Chem. 1978 Feb;21(2):189-93. PubMed PMID: 413921.

11: Braveny I, Voeckl J, Machka K. Antimicrobial activity of netilmicin in comparison with gentamicin, sisomicin, tobramycin, and amikacin and their resistance patterns. Arzneimittelforschung. 1980;30(3):491-5. PubMed PMID: 7387761.

12: Zhanel GG, Lawson CD, Zelenitsky S, Findlay B, Schweizer F, Adam H, Walkty A, Rubinstein E, Gin AS, Hoban DJ, Lynch JP, Karlowsky JA. Comparison of the next-generation aminoglycoside plazomicin to gentamicin, tobramycin and amikacin. Expert Rev Anti Infect Ther. 2012 Apr;10(4):459-73. doi: 10.1586/eri.12.25. Review. PubMed PMID: 22512755.

13: Feld R, Valdivieso M, Bodey GP, Rodriguez V. A comparative trial of sisomicin therapy by intermittent versus continuous infusion. Am J Med Sci. 1977 Sep-Oct;274(2):179-88. PubMed PMID: 602958.

14: Walkty A, Adam H, Baxter M, Denisuik A, Lagacé-Wiens P, Karlowsky JA, Hoban DJ, Zhanel GG. In vitro activity of plazomicin against 5,015 gram-negative and gram-positive clinical isolates obtained from patients in canadian hospitals as part of the CANWARD study, 2011-2012. Antimicrob Agents Chemother. 2014 May;58(5):2554-63. doi: 10.1128/AAC.02744-13. Epub 2014 Feb 18. PubMed PMID: 24550325; PubMed Central PMCID: PMC3993217.

15: Schieker KR, Hofmann HF. Prospective double-blind controlled clinical study of sisomicin versus tobramycin. Pharmatherapeutica. 1981;2(8):499-503. PubMed PMID: 7019928.

16: Noone P. Sisomicin, netilmicin and dibekacin. A review of their antibacterial activity and therapeutic use. Drugs. 1984 Jun;27(6):548-78. Review. PubMed PMID: 6376062.

17: Sanders WE Jr, Sanders CC. Sisomicin: a review of eight years' experience. Rev Infect Dis. 1980 Mar-Apr;2(2):182-95. PubMed PMID: 6994206.

18: Kim DH, Suh JH, Ju JY, Yum SK, Shin CS. Analysis of sisomicin binding sites in Micromonospora inyoensis cell wall. FEMS Microbiol Lett. 1998 Sep 1;166(1):9-13. PubMed PMID: 9741079.

19: Olsen SC, Carlson SA. In vitro bactericidal activity of aminoglycosides, including the next-generation drug plazomicin, against Brucella spp. Int J Antimicrob Agents. 2015 Jan;45(1):76-8. doi: 10.1016/j.ijantimicag.2014.09.011. Epub 2014 Oct 18. PubMed PMID: 25459738.

20: Drusano GL, Liu W, Fikes S, Cirz R, Robbins N, Kurhanewicz S, Rodriquez J, Brown D, Baluya D, Louie A. Interaction of drug- and granulocyte-mediated killing of Pseudomonas aeruginosa in a murine pneumonia model. J Infect Dis. 2014 Oct 15;210(8):1319-24. doi: 10.1093/infdis/jiu237. Epub 2014 Apr 22. PubMed PMID: 24760199; PubMed Central PMCID: PMC4271070.