Pretomanid
Pretomanid Basic information
- Product Name:
- Pretomanid
- Synonyms:
-
- PA 824
- (S)-PA 824
- (6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine
- (S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine
- 5H-IMidazo[2,1-b][1,3]oxazine, 6,7-dihydro-2-nitro-6-[[4-(trifluoroMethoxy)phenyl]Methoxy]-, (6S)-
- (S)-6-(4-(trifluoromethoxy)benzyloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
- (6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine PA-824
- EOS-60675
- CAS:
- 187235-37-6
- MF:
- C14H12F3N3O5
- MW:
- 359.26
- EINECS:
- 1533716-785-6
- Product Categories:
-
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Inhibitors
- Mol File:
- 187235-37-6.mol
Pretomanid Chemical Properties
- Melting point:
- 149-150℃
- Boiling point:
- 462.3±55.0 °C(Predicted)
- Density
- 1.58
- storage temp.
- -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- -0.67±0.40(Predicted)
- form
- powder
- color
- white to brown
- optical activity
- [α]/D -40 to -48°, c = 1 in methanol
- InChI
- 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
- InChIKey
- ZLHZLMOSPGACSZ-NSHDSACASA-N
- SMILES
- O1C[C@@H](OCC2=CC=C(OC(F)(F)F)C=C2)CN2C=C([N+]([O-])=O)N=C12
Pretomanid Usage And Synthesis
Uses
A novel anti-tuberculosis drug.
Biological Activity
pa-824, a bicyclic nitroimidazoles, is an anti-tuberculosis (tb) agent that exerts potent in vitro activity against mycobacterium tuberculosis with the minimal inhibition concentration (mic) ranging from 0.015 μg/ml to 0.25 μg/ml and remains actively against a wide range of isolates that are resistant to commonly used anti-tb agents leading to its successful application in the treatment of tb [1].pa-824 has been found to exhibit bactericidal activity against replicating bacilli and non-replicating bacilli under hypoxic or prolonged culture conditions in a dose dependent fashion through two possible mechanisms, which include pa-824 induced inhibition of ketomycolate synthesis and pa-824 mediated donation of nitric oxide during enzymatic nitro-reduction [1].
Biochem/physiol Actions
PA-824 is an anti-tuberculosis drug.
Synthesis
Pretomanid can be produced as follow
References
[1] ahmad z, peloquin ca, singh rp, derendorf h, tyagi s, ginsberg a, grosset jh, nuermberger el. pa-824 exhibits time-dependent activity in a murine model of tuberculosis. antimicrob agents chemother. 2011 jan;55(1):239-45. doi: 10.1128/aac.00849-10. epub 2010 oct 11.
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