A thiopeptide antibiotic
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Nosiheptide

Item No. 17094

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[1-(aminocarbonyl)ethenyl]-2-[(11S,14Z,21S,23S,29S)-14-ethylidene-9,10,11,12,13,14,19,20,21,22,23,24,26,33,35,36-hexadecahydro-3,23-dihydroxy-11-[(1R)-1-hydroxyethyl]-31-methyl-9,12,19,24,33,43-hexaoxo-30,32-imino-8,5:18,15:40,37-trinitrilo-21,36-([2,4]-endothiazolomethanimino)-4-thiazolecarboxamide
CAS Number
56377-79-8
Synonyms
  • Multhiomycin
  • NSC 307240
  • RP 9671
Molecular Formula
C51H43N13O12S6
Formula Weight
1222.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
λmax
217 nm
SMILES
OC1=C(C2=NC(C(NC(C(N)=O)=C)=O)=CS2)N=C(C3=CSC([C@](NC(C4=CSC([C@](NC(C5=CSC(/C(NC([C@](NC(C6=CSC7=N6)=O)([H])[C@@H](O)C)=O)=C/C)=N5)=O)([H])C[C@H](O)C(OC8)=O)=N4)=O)([H])CSC(C9=C(C)C(C8=CC=C%10)=C%10N9)=O)=N3)C7=C1
InChi Code
InChI=1S/C51H43N13O12S6/c1-5-23-46-60-28(14-79-46)41(70)56-25-10-33(67)50(74)76-11-21-7-6-8-24-34(21)18(2)35(54-24)51(75)82-17-31(57-42(71)29-15-80-47(25)61-29)48-58-26(12-78-48)37-22(45-59-30(13-77-45)43(72)64-36(20(4)65)44(73)55-23)9-32(66)38(63-37
InChi Key
OQAOHXRUMXWDLQ-OIHXUFRMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Nosiheptide is a thiopeptide antibiotic that inhibits bacterial protein synthesis by interfering with the function of elongation factors.1,2 It is effective against many different methicillin-resistant S. aureus strains (MICs ≤ 0.25 mg/L), Enterococcus spp (MICs ≤ 0.125 mg/L), and the BI strain of C. difficile (MIC = 0.008 mg/L) but inactive against most Gram-negative bacteria.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cundliffe, E., and Thompson, J. The mode of action of nosiheptide (multhiomycin) and the mechanism of resistance in the producing organism. J. Gen. Microbiol. 126(1), 185-192 (1981).

    2. Yu, Y., Duan, L., Zhang, Q., et al. Nosiheptide biosynthesis featuring a unique indole side ring formation on the characteristic thiopeptide framework. ACS Chem. Biol. 4(10), 855-864 (2009).

    3. Haste, N.M., Thienphrapa, W., Tran, D.N., et al. Activity of the thiopeptide antibiotic nosiheptide against contemporary strains of methicillin-resistant Staphylococcus aureus. J. Antibiot. (Tokyo) 65(12), 593-598 (2012).