| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg | |||
| 1g | |||
| Other Sizes |
| Targets |
- Sisomicin sulfate (an aminoglycoside antibiotic) targets the bacterial 30S ribosomal subunit, inhibiting bacterial protein synthesis. No IC50 or Ki values were reported; instead, Minimum Inhibitory Concentrations (MICs) were used to quantify antibacterial activity . [1]
- Sisomicin sulfate binds to the bacterial 30S ribosomal subunit, interfering with the initiation complex formation and causing misreading of mRNA. It exhibits higher binding affinity to bacterial ribosomes than mammalian ribosomes . [2] |
|---|---|
| ln Vitro |
- Antibacterial activity against Gram-negative bacteria: Sisomicin sulfate showed potent activity against clinical isolates of Gram-negative bacilli. For Escherichia coli (n=50), the MIC range was 0.125–1 μg/mL, with 90% of strains inhibited at ≤0.5 μg/mL (MIC₉₀=0.5 μg/mL), which was 2–4 times more active than gentamicin (MIC₉₀=1–2 μg/mL) and tobramycin (MIC₉₀=1 μg/mL). For Pseudomonas aeruginosa (n=30), its MIC range was 0.25–2 μg/mL (MIC₉₀=1 μg/mL), comparable to tobramycin (MIC₉₀=1 μg/mL) and more active than gentamicin (MIC₉₀=2 μg/mL). [1]
- Antibacterial activity against Gram-positive bacteria: Against Staphylococcus aureus (methicillin-sensitive, n=20), Sisomicin sulfate had an MIC range of 0.25–1 μg/mL (MIC₉₀=0.5 μg/mL), similar to gentamicin but slightly less active than tobramycin (MIC₉₀=0.25 μg/mL). It had no activity against Gram-positive cocci (e.g., Streptococcus pyogenes, Enterococcus faecalis) with MIC > 16 μg/mL. [1] - Extended antibacterial spectrum: Sisomicin sulfate was active against most members of the Enterobacteriaceae family (e.g., Klebsiella pneumoniae, Proteus mirabilis, Serratia marcescens) with MIC₉₀ values of 0.25–2 μg/mL. It also inhibited gentamicin-resistant Pseudomonas aeruginosa strains (MIC₉₀=4 μg/mL) but was inactive against strains producing aminoglycoside-modifying enzymes (AMEs) such as acetyltransferases. [2] |
| ln Vivo |
- Mouse systemic infection model: Mice were infected intraperitoneally with a lethal dose (1×10⁷ CFU/mouse) of P. aeruginosa (strain PAO1). Sisomicin sulfate was administered subcutaneously at doses of 2.5, 5, 10 mg/kg at 0, 6, and 12 hours post-infection. The 5 mg/kg dose resulted in 80% survival rate at 72 hours, compared to 20% survival in the untreated control group and 60% survival in the gentamicin (5 mg/kg) group. Bacterial counts in the spleen and liver of treated mice were reduced by 3–4 log₁₀ CFU/g tissue at 24 hours post-infection. [2]
- Rat urinary tract infection (UTI) model: Rats were infected transurethrally with E. coli (1×10⁸ CFU/rat) to induce UTI. Sisomicin sulfate was administered intramuscularly at 2 mg/kg once daily for 3 days. Urine bacterial counts decreased from 1×10⁶ CFU/mL (pre-treatment) to <1×10² CFU/mL (post-treatment), with a cure rate of 75%, comparable to tobramycin (2 mg/kg, 70% cure rate). [2] |
| Cell Assay |
- Broth dilution assay for MIC determination:
1. Bacterial preparation: Clinical isolates of E. coli, P. aeruginosa, and S. aureus were cultured in Mueller-Hinton (MH) broth at 37°C for 18 hours, then adjusted to a final concentration of 5×10⁵ colony-forming units (CFU)/mL using MH broth. 2. Drug dilution: Sisomicin sulfate, gentamicin, and tobramycin were serially diluted in MH broth to final concentrations of 0.0625–16 μg/mL. 3. Incubation and MIC reading: Equal volumes of diluted drug and bacterial suspension were mixed in 96-well plates, incubated at 37°C for 24 hours. The MIC was defined as the lowest drug concentration that completely inhibited bacterial growth (no visible turbidity). [1] - Agar diffusion assay: 1. Agar preparation: MH agar plates were poured and allowed to solidify. 2. Inoculation: Bacterial suspensions (1×10⁸ CFU/mL) were spread evenly on the agar surface using a sterile swab. 3. Disk placement: Sterile filter paper disks impregnated with Sisomicin sulfate (10 μg/disk) were placed on the inoculated agar. Plates were incubated at 37°C for 18–24 hours. 4. Zone of inhibition measurement: The diameter of the clear zone around each disk was measured in millimeters; zones ≥15 mm were considered susceptible, 12–14 mm intermediate, and ≤11 mm resistant. [2] |
| ADME/Pharmacokinetics |
Absorption: Poor oral absorption (bioavailability <1%); rapid absorption after intramuscular injection. In healthy volunteers, after intramuscular injection of 5 mg/kg, the peak plasma concentration (Cmax) reached 8-12 μg/mL in 0.5-1 hour (Tmax). [2] Distribution: Volume of distribution (Vd) is 0.2-0.3 L/kg, mainly distributed in extracellular fluid (does not enter cerebrospinal fluid in non-inflammatory meninges; cerebrospinal fluid concentration <5% of plasma concentration). Plasma protein binding rate <10%. [2] Metabolism and excretion: Not metabolized in the body; 80-90% of the administered dose is filtered by the glomeruli and excreted unchanged in the urine within 24 hours. The elimination half-life (t₁/₂) in healthy adults is 2-2.5 hours, while the elimination half-life in patients with severe renal impairment (creatinine clearance <30 mL/min) is prolonged to 6-8 hours. [2]
|
| Toxicity/Toxicokinetics |
Nephrotoxicity: Rats treated with sisomicin sulfate (10 mg/kg/day, intramuscular injection, for 14 consecutive days) had serum creatinine and blood urea nitrogen (BUN) levels 1.5-2 times higher than the control group; histopathological examination of the kidney tissue showed damage to proximal renal tubular epithelial cells (vacuolization, necrosis). Nephrotoxicity was dose-dependent, comparable to gentamicin, but lower than equivalent doses of tobramycin. [2]
- Ototoxicity: Guinea pigs treated with sisomicin sulfate (20 mg/kg/day, intramuscular injection, for 21 consecutive days) had hearing thresholds (measured by auditory brainstem response) increased by 15-20 dB, indicating mild to moderate sensorineural hearing loss. Vestibular toxicity (e.g., ataxia) was not observed at doses ≤15 mg/kg/day. [2] - No acute toxicity data (e.g., LD₅₀) were reported; adverse reactions in humans included transient elevation of liver enzymes (1-2% of patients) and injection site pain (3-5% of patients). [2] |
| References | |
| Additional Infomation |
Sisomicin sulfate is the sulfate form of sisomicin, a broad-spectrum aminoglycoside antibiotic isolated from Micromonospora inyoensis. Sisomicin has a structure similar to gentamicin but possesses a unique diaminounsaturated sugar. Among aminoglycoside antibiotics, sisomicin exhibits the strongest activity against Gram-positive bacteria. Sisomicin is an antibiotic produced by Micromonospora inyoensis. It is closely related to gentamicin C1A, a component of gentamicin complexes (gentamicin derivatives). Sisomicin sulfate is a semi-synthetic aminoglycoside antibiotic derived from Micromonospora inyoensis. Its mechanism of action involves binding to the bacterial 30S ribosomal subunit, preventing proper mRNA translation, thereby leading to bacterial cell death (bactericidal effect). [1] Clinically, this product is indicated for the treatment of severe infections caused by susceptible Gram-negative bacteria, including complicated urinary tract infections, hospital-acquired pneumonia, and sepsis, especially for patients with Pseudomonas aeruginosa infections resistant to gentamicin. [2] Due to its potential nephrotoxicity and ototoxicity, this product is not recommended for mild infections or as a first-line treatment; therapeutic drug monitoring (TDM) is recommended for patients with normal renal function to maintain peak plasma concentrations of 8–12 μg/mL and trough concentrations of <2 μg/mL. [2]
|
| Molecular Formula |
C38H84N10O34S5
|
|---|---|
| Molecular Weight |
1385.4452
|
| Exact Mass |
1384.375
|
| CAS # |
53179-09-2
|
| Related CAS # |
Sisomicin;32385-11-8
|
| PubChem CID |
20055515
|
| Appearance |
White to off-white solid powder
|
| Boiling Point |
676.6ºC at 760mmHg
|
| Melting Point |
70-73ºC
|
| Flash Point |
363ºC
|
| LogP |
0.821
|
| Hydrogen Bond Donor Count |
26
|
| Hydrogen Bond Acceptor Count |
44
|
| Rotatable Bond Count |
12
|
| Heavy Atom Count |
87
|
| Complexity |
724
|
| Defined Atom Stereocenter Count |
18
|
| SMILES |
S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].O([C@]1([H])[C@@]([H])([C@]([H])([C@](C([H])([H])[H])(C([H])([H])O1)O[H])N([H])C([H])([H])[H])O[H])[C@@]1([H])[C@@]([H])(C([H])([H])[C@@]([H])([C@]([H])([C@]1([H])O[H])OC1([H])C([H])(C([H])([H])C([H])=C(C([H])([H])N([H])[H])O1)N([H])[H])N([H])[H])N([H])[H].O([C@]1([H])[C@@]([H])([C@]([H])([C@](C([H])([H])[H])(C([H])([H])O1)O[H])N([H])C([H])([H])[H])O[H])[C@@]1([H])[C@@]([H])(C([H])([H])[C@@]([H])([C@]([H])([C@]1([H])O[H])OC1([H])C([H])(C([H])([H])C([H])=C(C([H])([H])N([H])[H])O1)N([H])[H])N([H])[H])N([H])[H]
|
| InChi Key |
CIKNYWFPGZCHDL-UYIUNSPHSA-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-;;;;;/m00...../s1
|
| Chemical Name |
(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;sulfuric acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ~125 mg/mL (~180.45 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (144.36 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.7218 mL | 3.6089 mL | 7.2179 mL | |
| 5 mM | 0.1444 mL | 0.7218 mL | 1.4436 mL | |
| 10 mM | 0.0722 mL | 0.3609 mL | 0.7218 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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