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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
Structure of PENTIZIDONE SODIUM ANHYDROUS

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

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
In vitro activity of fludalanine combined with pentizidone compared with those of other agents.
1984 May
Experimental pneumonia due to Haemophilus influenzae: observations on pathogenesis and treatment.
1984 May
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
Name Type Language
PENTIZIDONE SODIUM ANHYDROUS
Common Name English
3-ISOXAZOLIDINONE, 4-((1-METHYL-3-OXO-1-BUTEN-1-YL)AMINO)-, SODIUM SALT (1:1), (4R)-
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
259-759-3
Created by admin on Fri Dec 15 15:54:44 GMT 2023 , Edited by admin on Fri Dec 15 15:54:44 GMT 2023
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CAS
55694-87-6
Created by admin on Fri Dec 15 15:54:44 GMT 2023 , Edited by admin on Fri Dec 15 15:54:44 GMT 2023
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FDA UNII
VSM253T8YI
Created by admin on Fri Dec 15 15:54:44 GMT 2023 , Edited by admin on Fri Dec 15 15:54:44 GMT 2023
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EPA CompTox
DTXSID50971059
Created by admin on Fri Dec 15 15:54:44 GMT 2023 , Edited by admin on Fri Dec 15 15:54:44 GMT 2023
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PUBCHEM
23684615
Created by admin on Fri Dec 15 15:54:44 GMT 2023 , Edited by admin on Fri Dec 15 15:54:44 GMT 2023
PRIMARY