PENTIZIDONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H12N2O3
Molecular Weight	184.1925
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)\C=C(/C)N[C@@H]1CONC1=O

InChI

InChIKey=DGYLXKOLHICICX-OHCKJTPYSA-N

InChI=1S/C8H12N2O3/c1-5(3-6(2)11)9-7-4-13-10-8(7)12/h3,7,9H,4H2,1-2H3,(H,10,12)/b5-3+/t7-/m1/s1

HIDE SMILES / InChI

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:38:47 GMT 2023` Edited by `admin` on `Fri Dec 15 18:38:47 GMT 2023`
Record UNII	0UP011P7BS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTIZIDONE

Official Name

English

pentizidone [INN]

Common Name

English

(R)-4-((1-METHYL-3-OXO-1-BUTENYL)AMINO)-3-ISOXAZOLIDINONE

Systematic Name

English

Code System Code Type Description

SMS_ID

100000082516