Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H11N2O3.Na |
| Molecular Weight | 206.1743 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC(=O)\C=C(/C)N[C@@H]1CO[N-]C1=O
InChI
InChIKey=RNZYSARTHBLHQB-OGFXRTJISA-M
InChI=1S/C8H12N2O3.Na/c1-5(3-6(2)11)9-7-4-13-10-8(7)12;/h3,7H,4H2,1-2H3,(H2,9,10,11,12);/q;+1/p-1/t7-;/m1./s1
Pentizidone is a prodrug which is hydrolyzed spontaneously and converted to D-cycloserine. Merck selected pentizidone as a companion product for D-fluoroalanine with the anticipation that it would be better tolerated than cycloserine itself. The expectation was that D-fluoroalanine and pentizidone would be synergistic in killing bacteria. The combination of the two enzyme inhibitors proved to have potent antibiotic activity in animal studies and abolished the self-reversal phenomenon. D-cycloserine acts on D-alanyl-D-alanine synthetase.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro activity of fludalanine combined with pentizidone compared with those of other agents. | 1984 May |
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| Experimental pneumonia due to Haemophilus influenzae: observations on pathogenesis and treatment. | 1984 May |
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| Simultaneous quantification of cycloserine and its prodrug acetylacetonylcycloserine in plasma and urine by high-performance liquid chromatography using ultraviolet absorbance and fluorescence after post-column derivatization. | 1987 Feb 20 |
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259-759-3
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55694-87-6
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VSM253T8YI
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DTXSID50971059
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23684615
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ACTIVE MOIETY
SUBSTANCE RECORD
