PENTIZIDONE SODIUM ANHYDROUS

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

Structure Search

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

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C8H12N2O3
Molecular Weight	184.1925
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6610389 | https://www.ncbi.nlm.nih.gov/pubmed/6610002 | Cordes, E.H. (2014) Hallelujah Moments: Tales of Drug Discovery, page 190, retrieved from: https://books.google.ru/books?id=lG2JAgAAQBAJ

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
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.	1987-02-20	3571377
In vitro activity of fludalanine combined with pentizidone compared with those of other agents.	1984-05	6610389
Experimental pneumonia due to Haemophilus influenzae: observations on pathogenesis and treatment.	1984-05	6610002

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:58 GMT 2025`
Record UNII	VSM253T8YI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-ISOXAZOLIDINONE, 4-((1-METHYL-3-OXO-1-BUTEN-1-YL)AMINO)-, SODIUM SALT (1:1), (4R)-

Preferred Name

English

PENTIZIDONE SODIUM ANHYDROUS

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

259-759-3