Spiramycin

Alias: HSDB-7027; Rovamycin; HSDB7027; HSDB 7027
Cat No.:V3561 Purity: ≥98%
Spiramycin (HSDB7027; HSDB-7027; Rovamycin) is naturally occurring and clinically important 16-member macrolide antibiotic isolated from Streptomyces ambofaciens.
Spiramycin Chemical Structure CAS No.: 8025-81-8
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Spiramycin:

  • Spiramycin III
  • Spiramycin Embonate
  • Spiramycin adipate
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Spiramycin (HSDB7027; HSDB-7027; Rovamycin) is naturally occurring and clinically important 16-member macrolide antibiotic isolated from Streptomyces ambofaciens. It has activity against bacteria and Toxoplasma gondii, and also has antiparasitic effect. Spiramycin is composed of a 16-member lactone ring, on which three sugars (mycaminose, forosamine, and mycarose) are attached. Biosynthetic studies have established that the earliest lactonic intermediate in spiramycin biosynthesis, the macrolactone platenolide I, is synthesized by a type I modular polyketide synthase (PKS). Platenolide I then undergoes a series of post-PKS tailoring reactions yielding the final products, spiramycins I, II, and III.

Biological Activity I Assay Protocols (From Reference)
Targets
Macrolide;Toxoplasma
ln Vitro
Treatment with spiramycin (24 hours; 1-1000 μM; T. gondii-infected HeLa cells and HeLa cells) decreases the cytotoxicity and exhibits anti-Toxoplasma gondii activity, with IC50 values of 189 μM for HeLa cells and 262 μM for T. gondii-infected HeLa cells[3].
ln Vivo
Treatment with spiramycin (100 mg/kg; intraperitoneal injection; daily; for 4 days; female KM mice) decreases tachyzoites, hepatotoxicity, and greatly increases antioxidative effects. Treatment with piramycin also lessens the liver's granulomatous inflammation[3].
Cell Assay
Cell Line: T. gondii infected HeLa cells and HeLa cells
Concentration: 1-1000 μM
Incubation Time: 24 hours
Result: Reduced the cytotoxicity.
Animal Protocol
Animal Model: 36 female KM mice with T.gondii[3]
Dosage: 100 mg/kg
Administration: Intraperitoneal injection; every day; for 4 days
Result: Tachyzoites were considerably fewer in number. decreased hepatotoxicity and markedly increased antioxidative benefits. Formation of cysts and granulomas was inhibited.
References

[1]. Post-PKS tailoring steps of the spiramycin macrolactone ring in Streptomyces ambofaciens. Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42.

[2]. Assessment of spiramycin-loaded chitosan nanoparticles treatment on acute and chronic toxoplasmosis in mice. J Parasit Dis. 2018 Mar;42(1):102-113.

[3]. Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti-Toxoplasma gondii Agents. J Agric Food Chem. 2019 Aug 28;67(34):9630-9642.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C43H74N2O14
Molecular Weight
843.0527
Exact Mass
842.51
Elemental Analysis
C, 61.26; H, 8.85; N, 3.32; O, 26.57
CAS #
8025-81-8
Related CAS #
8025-81-8;24916-52-7 (III);67724-08-7 (Embonate);68880-55-7 (adipate);
Appearance
Solid powder
SMILES
O=CC[C@@H]1[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)C(C)(O)C3)[C@H](N(C)C)[C@H]2O)[C@@H](OC)[C@H](O)CC(O[C@H](C)C/C=C/C=C/[C@H](O[C@@H]4O[C@H](C)[C@@H](N(C)C)CC4)[C@H](C)C1)=O
InChi Key
ACTOXUHEUCPTEW-AQKFJFIXSA-N
InChi Code
InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43?/m1/s1
Chemical Name
2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Synonyms
HSDB-7027; Rovamycin; HSDB7027; HSDB 7027
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

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 : 100~157 mg/mL ( 118.62~186.22 mM )
Ethanol : ~157 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.97 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 25.0 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: ≥ 2.5 mg/mL (2.97 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 25.0 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: ≥ 2.5 mg/mL (2.97 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 25.0 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: ≥ 2.5 mg/mL (2.97 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.1862 mL 5.9308 mL 11.8617 mL
5 mM 0.2372 mL 1.1862 mL 2.3723 mL
10 mM 0.1186 mL 0.5931 mL 1.1862 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

Biological Data
  • Spiramycin biosynthesis. (A) Spiramycin biosynthetic cluster with the three putative reductase genes srm26, srm42, and srm43 represented by blue arrows and srm13 represented by a red arrow. (B) Proposed biosynthetic pathway for the post-PKS tailoring steps.[1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42.
  • LC and LC-MS analyses of culture supernatants of the wild-type strain (OSC2) and the Δsrm13 deletion mutant (SPM513). [1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42.
  • Identification of the gene catalyzing the reduction of the C-9 keto group of platenolide I by LC-MS analyses. [1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42.
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