PENTIZIDONE SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C8H11N2O3.2Na.H2O
Molecular Weight	430.3639
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[Na+].[Na+].CC(=O)\C=C(/C)N[C@@H]1CO[N-]C1=O.CC(=O)\C=C(/C)N[C@@H]2CO[N-]C2=O

InChI

InChIKey=ICRREHBPONNKIP-RIONXHBJSA-L

InChI=1S/2C8H12N2O3.2Na.H2O/c2*1-5(3-6(2)11)9-7-4-13-10-8(7)12;;;/h2*3,7H,4H2,1-2H3,(H2,9,10,11,12);;;1H2/q;;2*+1;/p-2/t2*7-;;;/m11.../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

Molecular Formula	HO
Molecular Weight	17.0073
Charge	-1
Count

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

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 18:14:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:55 GMT 2025`
Record UNII	MGX3B47WI2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(R)-4-[(1-Methyl-3-oxo-1-butenyl)amino]-3-isoxazolidinone monosodium salt hemihydrate

Preferred Name

English

PENTIZIDONE SODIUM

Official Name

English

PENTIZIDONE SODIUM [USAN]

Common Name

English

3-ISOXAZOLIDINONE, 4-((1-METHYL-3-OXO-1-BUTENYL)AMINO)-, MONOSODIUM SALT, HEMIHYDRATE, (R)-

Common Name

English

PENTIZIDONE SODIUM HEMIHYDRATE

Common Name

English

3-ISOXAZOLIDINONE, 4-((1-METHYL-3-OXO-1-BUTENYL)AMINO)-, MONOSODIUM SALT, HYDRATE (2:1), (R)-

Common Name

English

Code System Code Type Description

PUBCHEM

20055527