A anti-tuberculosis agent
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PA-824

Item No. 13142

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6S)-6,7-dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine
CAS Number
187235-37-6
Synonyms
  • (S)-PA-824
Molecular Formula
C14H12F3N3O5
Formula Weight
359.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 33 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.33 mg/mlEthanol: 5 mg/ml
λmax
324 nm
SMILES
FC(F)(F)OC1=CC=C(CO[C@@H]2COC3=NC([N+]([O-])=O)=CN3C2)C=C1
InChi Code
InChI=1S/C14H12F3N3O5/c15-14(16,17)25-10-3-1-9(2-4-10)7-23-11-5-19-6-12(20(21)22)18-13(19)24-8-11/h1-4,6,11H,5,7-8H2/t11-/m0/s1
InChi Key
ZLHZLMOSPGACSZ-NSHDSACASA-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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    Cayman Chemical
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    Product Description

    PA-824 is an anti-tuberculosis (anti-TB) agent that is activated intracellularly via deazaflavin-dependent nitroreductase (Ddn) metabolism into a desnitro metabolite that kills M. tuberculosis by releasing reactive nitrogen species (RNS), including nitric oxide.1 It is active against replicating and non-replicating M. tuberculosis but exhibits little or no activity against M. avium, M. smegmatis, M. chelonae, and M. fortuitum.2 In vitro, it inhibits growth of susceptible and mono- and multi-drug resistant M. tuberculosis clinical isolates (MICs = 0.015-5 μg/ml).2,3 In vivo, PA-824 (100 mg/kg per day) decreases luminescence in the lung to background levels after 60 days of treatment in a mouse model of systemic infection with a reporter strain of M. tuberculosis.2 It also decreases M. tuberculosis burden in the lung and spleen in an aerosol challenged guinea pig model of TB when administered at a dose of 40 mg/kg per day for 30 days.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Singh, R., Manjunatha, U., Boshoff, H.I.M., et al. PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release. Science 322(5906), 1392-1395 (2008).

    2. Stover, C.K., Warrener, P., VanDevanter, D.R., et al. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 405(6789), 962-966 (2000).

    3. Lenaerts, A.J., Gruppo, V., Marietta, K.S., et al. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models. Antimicrob. Agents Chemother. 49(6), 2294-2301 (2005).