A macrolide antibiotic
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Spiramycin

Item No. 20267

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-((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-dimethyltetrahydro-2H-pyran-2-yl)oxy)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-10-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-7-yl)acetaldehyde (Spiramycin I, R = H)
CAS Number
8025-81-8
Synonyms
  • Formacidine
  • NSC 55926
  • Rovamycine
Molecular Formula
C43H74N2O14 (Spiramycin I, R = H)
Formula Weight
843.1
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 25 mg/ml
λmax
226, 231 nm
SMILES
O=C1C[C@H]([C@@H]([C@H]([C@H](C[C@H]([C@H](/C=C/C=C/C[C@H](O1)C)O[C@@]2([H])CC[C@@H]([C@H](O2)C)N(C)C)C)CC=O)O[C@@]3([H])[C@@H]([C@H]([C@@H]([C@H](O3)C)O[C@]4([H])O[C@H]([C@@H]([C@@](C)(C4)O)O)C)N(C)C)O)OC)O.O=C5C[C@H]([C@@H]([C@H]([C@H](C[C@H]([C@H]
InChi Code
InChI=1S/C46H78N2O15.C45H76N2O15.C43H74N2O14/c1-13-35(50)60-34-24-36(51)56-27(3)17-15-14-16-18-33(61-37-20-19-32(47(8)9)28(4)57-37)26(2)23-31(21-22-49)42(43(34)55-12)63-45-40(52)39(48(10)11)41(29(5)59-45)62-38-25-46(7,54)44(53)30(6)58-38;1-25-22-31(2
InChi Key
YSPJBQMQEKNSDS-AHTQBDIFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Spiramycin is a polyketide synthase-derived macrolide antibiotic that has been found in Streptomyces.1,2 It inhibits the binding of tetrahydroleucomycin A3 to E. coli ribosomes (IC50 = 1 µM) and is active against S. aureus, B. subtilis, B. cereus, and M. luteus (MICs = 3.12, 1.56, 3.12, and 0.1 µg/ml, respectively).3 Spiramycin protects mice from S. aureus, S. pneumoniae, and P. berghei infections (ED50s = 116.6, 167.9, and 27 mg/kg, respectively).4,5 This product is a mixture of spiramycin I, II, and III, with spiramycin I being the major component.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wilson, D.N. The A-Z of bacterial translation inhibitors. Crit. Rev. Biochem. Mol. Biol. 44(6), 393-433 (2009).

    2. Agnoletti, F., Ferro, T., Guolo, A., et al. A survey of Clostridium spiroforme antimicrobial susceptibility in rabbit breeding. Vet. Microbiol. 136(1-2), 188-191 (2009).

    3. Sano, H., Inoue, M., and Ōmura, S. Chemical modification of spiramycins. II. Synthesis and antimicrobial activity of 4'-deoxy derivatives of neospiramycin I and their 12-(Z)-isomers. J. Antibiot. (Tokyo) 37(7), 738-749 (1984).

    4. Sano, H., Inoue, M., Yamashita, K., et al. Chemical modification of spiramycins. I. Synthesis of the acetal derivatives of neospiramycin I. J. Antibiot. (Tokyo) 36(10), 1336-1344 (1983).

    5. Chawira, A.N., Warhurst, D.C., Robinson, B.L., et al. The effect of combinations of qinghaosu (artemisinin) with standard antimalarial drugs in the suppressive treatment of malaria in mice. Trans. R. Soc. Trop. Med. Hyg. 81(4), 554-558 (1987).