Acetylspiramycin (Spiramycin II; Spiramycin B; Foromacidin B), an acetylated analog of Spiramycin, is an orally bioactive macrolide antibiotic found in various Streptomyces species. It has antimicrobial activity against gram-positive organisms such as Streptococcus pyogenes, S. viridans, Corynebacterium diphtheriae and methicillin-sensitive Staphylococcus aureus. Acetylspiramycin also exhibits antiprotozoal activity against parasitic infections caused by Cryptosporidium spp.
Physicochemical Properties
| Molecular Formula | C45H76N2O15 |
| Molecular Weight | 885.0894 |
| Exact Mass | 884.524 |
| CAS # | 24916-51-6 |
| PubChem CID | 5282173 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 916.7±65.0 °C at 760 mmHg |
| Melting Point | 130-133ºC |
| Flash Point | 508.2±34.3 °C |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.543 |
| LogP | 3.6 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 17 |
| Rotatable Bond Count | 13 |
| Heavy Atom Count | 62 |
| Complexity | 1480 |
| Defined Atom Stereocenter Count | 19 |
| SMILES | O1[C@]([H])(C([H])([H])[H])[C@]([H])([C@@]([H])([C@]([H])([C@]1([H])O[C@]1([H])[C@]([H])([C@@]([H])(C([H])([H])C(=O)O[C@]([H])(C([H])([H])[H])C([H])([H])C([H])=C([H])C([H])=C([H])[C@@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])[C@]1([H])C([H])([H])C([H])=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]([H])([C@@]([H])(C([H])([H])[H])O1)N(C([H])([H])[H])C([H])([H])[H])OC(C([H])([H])[H])=O)OC([H])([H])[H])O[H])N(C([H])([H])[H])C([H])([H])[H])O[C@@]1([H])C([H])([H])[C@](C([H])([H])[H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])O[H] |c:39,43| |
| InChi Key | ZPCCSZFPOXBNDL-RSMXASMKSA-N |
| InChi Code | InChI=1S/C45H76N2O15/c1-25-22-31(20-21-48)41(62-44-39(51)38(47(10)11)40(28(4)58-44)61-37-24-45(7,53)43(52)29(5)57-37)42(54-12)34(59-30(6)49)23-35(50)55-26(2)16-14-13-15-17-33(25)60-36-19-18-32(46(8)9)27(3)56-36/h13-15,17,21,25-29,31-34,36-44,51-53H,16,18-20,22-24H2,1-12H3/b14-13+,17-15+/t25-,26-,27+,28-,29+,31+,32+,33+,34-,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-/m1/s1 |
| Chemical Name | [(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2R,5S,6S)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] acetate |
| 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) |
Biological Activity
| References | :Therapeutic effects of acetylspiramycin and garlicin on cryptosporidiosis among drug users. Int J Parasitol Drugs Drug Resist. 2015 Dec;5(3):185-90. |
| Additional Infomation |
Spiramycin II is a macrolide antibiotic produced by various Streptomyces species. It has a role as an antibacterial drug, an antimicrobial agent and a bacterial metabolite. It is an aldehyde, a disaccharide derivative, an ether, a macrolide, a tertiary amino compound and an acetate ester. Spiramycin II has been reported in Streptomyces ambofaciens with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 50 mg/mL (~56.49 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.82 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 (2.82 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1298 mL | 5.6491 mL | 11.2983 mL | |
| 5 mM | 0.2260 mL | 1.1298 mL | 2.2597 mL | |
| 10 mM | 0.1130 mL | 0.5649 mL | 1.1298 mL |