A semisynthetic glycopeptide antibiotic
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Oritavancin (phosphate)

Item No. 24091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4"R)-22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-N3"-[(4'-chloro[1,1'-biphenyl]-4-yl)methyl]-vancomycin, diphosphate
CAS Number
192564-14-0
Synonyms
  • LY 333328
Molecular Formula
C86H97Cl3N10O26 • 2H3PO4
Formula Weight
1989.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.1 mg/mlDMSO: 0.1 mg/ml
λmax
273 nm
SMILES
OP(O)(O)=O.OP(O)(O)=O.O[C@@H]1[C@@H](O[C@@](O[C@@H](C)[C@@H]2O)([H])C[C@]2(C)NCC3=CC=C(C4=CC=C(Cl)C=C4)C=C3)[C@@H](O[C@H](CO)[C@H]1O)OC5=C(OC6=CC=C([C@H]([C@H]7NC([C@H](NC)CC(C)C)=O)O)C=C6Cl)C=C([C@](NC([C@@H](NC7=O)CC(N)=O)=O)([H])C(N[C@](C8=O)([H])C9=CC%10=C(O)C=C9)=O)C=C5OC%11=CC=C([C@H]([C@](C(N[C@@](C(O)=O)([H])C%12=C%10C(O)=CC(O)=C%12)=O)([H])N8)O[C@]%13([H])O[C@@H](C)[C@H](O)[C@@](C)(N)C%13)C=C%11Cl
InChi Code
InChI=1S/C86H97Cl3N10O26.2H3O4P/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114;2*1-5(2,3)4/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117);2*(H3,1,2,3,4)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-;;/m0../s1
InChi Key
PWTROOMOPLCZHB-BHYQHFGMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Oritavancin is a semisynthetic glycopeptide antibiotic that inhibits the growth of Gram-positive bacteria.1 It inhibits transglycosylation and transpeptidation in the bacterial cell wall to disrupt membrane integrity.2,3 Oritavancin inhibits the growth of clinical isolates from skin and soft-tissue infections, including methicillin-resistant and -susceptible S. aureus (MRSA, MSSA), vancomycin-resistant and -susceptible E. faecium (VREF, VSRF), as well as other staphylococci, streptococci, and enterococci (MIC90s = ≤0.008-0.5 mg/L).4 Oritavancin inhibits growth of S. aureus in a neutropenic-mouse thigh model of infection (ED50 = 0.95 mg/kg for a single dose).5 It improves survival in a mouse inhalation model of B. anthracis Ames anthrax when administered prophylactically pre- and postexposure and when administered post symptom development.6 Formulations containing oritavancin have been used to treat bacterial skin infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jones, R.N., Barrett, M.S., and Erwin, M.E. In vitro activity and spectrum of LY333328, a novel glycopeptide derivative. Antimicrob. Agents Chemother. 41(2), (1997).

    2. Zhanel, G.G., Schweizer, F., and Karlowsky, J.A. Oritavancin: Mechanism of action. Clin. Infect. Dis. 54(Suppl 3), S214-S219 (2012).

    3. Belley, A., McKay, G.A.A., F.F., Sarmiento, I., et al. Oritavancin disrupts membrane integrity of Staphylococcus aureus and vancomycin-resistant enterococci to effect rapid bacterial killing. Antimicrob. Agents Chemother. 54(12), 5369-5371 (2010).

    4. Mendes, R.E., Farrell, D.J., Sader, H.S., et al. Activity of oritavancin against Gram-positive clinical isolates responsible for documented skin and soft-tissue infections in European and US hospitals (2010-13). J. Antimicrob. Chemother. 70(2), 498-504 (2015).

    5. Boylan, C.J., Campanale, K., Iversen, P.W., et al. Pharmacodynamics of oritavancin (LY333328) in a neutropenic-mouse thigh model of Staphylococcus aureus infection. Antimicrob. Agents Chemother. 47(5), 1700-1706 (2003).

    6. Heine, H.S., Bassett, J., Miller, L., et al. Efficacy of oritavancin in a murine model of Bacillus anthracis spore inhalation anthrax. Antimicrob. Agents Chemother. 52(9), 3350-3357 (2008).