TERIZIDONE

Details

Stereochemistry	UNKNOWN
Molecular Formula	C14H14N4O4
Molecular Weight	302.2854
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NOCC1\N=C\C2=CC=C(C=C2)\C=N\C3CONC3=O

InChI

InChIKey=ODKYYBOHSVLGNU-IAGONARPSA-N

InChI=1S/C14H14N4O4/c19-13-11(7-21-17-13)15-5-9-1-2-10(4-3-9)6-16-12-8-22-18-14(12)20/h1-6,11-12H,7-8H2,(H,17,19)(H,18,20)/b15-5+,16-6+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23735593 | https://www.ncbi.nlm.nih.gov/pubmed/26381514 | https://www.ncbi.nlm.nih.gov/pubmed/21085831

TERIZIDONE, a structural analog of cycloserine, is a broad spectrum antibiotic used in the treatment of multidrug-resistant tuberculosis. However, its effectiveness is widely debated. Terizidone acts by inhibiting cell wall synthesis by competitively inhibiting two enzymes, L-alanine racemase and D-alanine ligase, thereby impairing peptidoglycan formation necessary for bacterial cell wall synthesis.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase 1 Target ID: CHEMBL2540 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21085831	Inhibitor 8297
Alanine racemase 2 Target ID: CHEMBL2031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21085831	Inhibitor 8297

PubMed

Title	Date	PubMed
[Results of clinical trials of a new antitubercular agent, terizidone (Terivalidine)].	1972 Apr-Jun	4565191
Safety of cycloserine and terizidone for the treatment of drug-resistant tuberculosis: a meta-analysis.	2013 Oct	23735593
Steady state pharmacokinetics of cycloserine in patients on terizidone for multidrug-resistant tuberculosis.	2018 Jan 1	29297422

Name

Type

Language

TERIZIDONE

Official Name

English

terizidone [INN]

Common Name

English

Terizidone [WHO-DD]

Common Name

English

4,4'-(P-PHENYLENEBIS(METHYLENEAMINO))DI-(ISOXAZOLIDIN-3-ONE)

Common Name

English

TERIZIDONE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C280