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Sultamicillin tosylate

Alias: Sultamicillin tosilate; Sultamicillin tosylate hydrate; Sultamicillin; CP-49,952; CP 49,952; CP49,952; CP-49952; CP 49952; CP49952. VD 1827; Bacimex; p-Toluenesulfonate Sbtpc; Unacid PD oral; acim orale.
Cat No.:V3711 Purity: ≥98%
Sultamicillin Tosylate, the tosylate salt form of Sultamicillin which is a double ester of sulbactam and ampicillin.
Sultamicillin tosylate
Sultamicillin tosylate Chemical Structure CAS No.: 83105-70-8
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes

Other Forms of Sultamicillin tosylate:

  • Sultamicillin
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Sultamicillin Tosylate, the tosylate salt form of Sultamicillin which is a double ester of sulbactam and ampicillin. Sultamicillin (formerly known as CP-49952 and VD 1827) is an orally available, mutual prodrug form of ampicillin and sulbactam. As an antibiotic combination (co-drug or mutual prodrug) of ampicillin/sulbactam, it contains esterified ampicillin and sulbactam and is marketed under a number of trade names, e. g. Unasyn from Pfizer. Ampicillin is a semi-synthetic orally active broad spectrum antibiotic which is linked via a methylene group with a beta-lactamase inhibitor. Sultamicillin is chemically oxymethyl penicillinate sulfone ester of ampicillin. After absorption, sultamicillin releases ampicillin and sulbactam into the system, so all the antibacterial efficacy of sultamicillin is due to ampicillin and sulbactam. Ampicillin exerts antibacterial activity against sensitive organisms by inhibiting biosynthesis of cell wall mucopeptide where as sulbactam irreversibly inhibits most important beta-lactamases that occur in resistant strains.

Biological Activity I Assay Protocols (From Reference)
Targets
β-lactam
ln Vitro
Sultamicillin tosylate shows antibacterial activity against MRSA with a MIC value of 25 μg/mL[4].
ln Vivo
Sultamicillin tosylate is hydrolyzed to yield Sulbactam (HY-B0334) and Ampicillin (HY-B0522) after oral absorption[2].
When combined with an immunosuppressive medication (such as mycophenolate mofetil (HY-B0199) and methylprednisolone (HY-B0260), streptomycin (oral gavage, every 12 hours) significantly increases the survival of experimental polymicrobial sepsis in mice and improves bacterial clearance[3].
Animal Protocol


References

[1]. Sultamicillin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1989 Apr;37(4):491-522.

[2]. Pharmacokinetics of sultamicillin in mice, rats, and dogs. Antimicrob Agents Chemother. 1984 May;25(5):599-602.

[3]. Combined immunosuppressive and antibiotic therapy improves bacterial clearance and survival of polymicrobial septic peritonitis. Shock. 2010 Feb;33(2):155-61.

[4]. Indole-based derivatives as potential antibacterial activity against methicillin-resistance Staphylococcus aureus (MRSA). Eur J Med Chem. 2020 May 15;194:112245.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C32H38N4O12S3
Molecular Weight
766.86
Elemental Analysis
C, 47.87; H, 5.27; N, 6.98; O, 27.90; S, 11.98
CAS #
83105-70-8
Related CAS #
76203-99-1 (HCl);76497-13-7 (free);83105-70-8;
Appearance
Solid powder
SMILES
O=S(C1=CC=C(C)C=C1)(O)=O.O=C([C@@H](C(C)(C)S([C@]2([H])C3)(=O)=O)N2C3=O)OCOC([C@@H](C(C)(C)S[C@]4([H])[C@@H]5NC([C@H](N)C6=CC=CC=C6)=O)N4C5=O)=O.[H]O[H].[H]O[H]
InChi Key
KNVDAMRBJYZXRW-ZAKZIJIGSA-N
InChi Code
InChI=1S/C25H30N4O9S2.C7H8O3S/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18;1-6-2-4-7(5-3-6)11(8,9)10/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31);2-5H,1H3,(H,8,9,10)/t14-,15-,16-,17+,18+,21-;/m1./s1
Chemical Name
[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;4-methylbenzenesulfonic acid
Synonyms
Sultamicillin tosilate; Sultamicillin tosylate hydrate; Sultamicillin; CP-49,952; CP 49,952; CP49,952; CP-49952; CP 49952; CP49952. VD 1827; Bacimex; p-Toluenesulfonate Sbtpc; Unacid PD oral; acim orale.
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 (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 100~125 mg/mL ( 130.4~163.00 mM )
Ethanol : ~100 mg/mL
Water : ~9 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (2.71 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (2.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (2.71 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3040 mL 6.5201 mL 13.0402 mL
5 mM 0.2608 mL 1.3040 mL 2.6080 mL
10 mM 0.1304 mL 0.6520 mL 1.3040 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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