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Terizidone

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From Wikipedia, the free encyclopedia

Tuberculosis medication

Pharmaceutical compound

Terizidone
Clinical data

Trade names	Terivalidin
Other names	4-[({4-[N-(3-oxo-1,2-oxazolidin-4-yl)carboximidoyl]phenyl}methylidene)amino]-1,2-oxazolidin-3-one
AHFS/Drugs.com	International Drug Names
ATC code	J04AK03 (WHO)
Identifiers
IUPAC name 4,4'-{1,4-phenylenebis[(E)methylylidene (E)azanylylidene]}bis(1,2-oxazolidin-3-one)
CAS Number	25683-71-0^N
PubChemCID	65720
ChemSpider	59144^Y
UNII	1199LEX5N8
KEGG	D07247^Y
CompTox Dashboard(EPA)	DTXSID70905098
ECHA InfoCard	100.042.882
Chemical and physical data
Formula	C₁₄H₁₄N₄O₄
Molar mass	302.290 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C3NOCC3/N=C/c2ccc(/C=N/C1C(=O)NOC1)cc2
InChI 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+^Y Key:ODKYYBOHSVLGNU-IAGONARPSA-N^Y
^NY (what is this?) (verify)

Terizidone is a drug used in the treatment oftuberculosis.^[1] Terizidone is mainly used inmulti-drug-resistant tuberculosis (MDR-TB) in conjunction with other second-line drugs. It is a derivative ofcycloserine with bacteriostatic activity.^[2]

Terizidone is a therapeutic alternative on theWorld Health Organization's List of Essential Medicines.^[3]

References

[edit]

^Galietti F, Giorgis GE, Oliaro A, Boaro D, Ardizzi A, Barberis S, et al. (1991). "[Tolerability to terizidone (TZ) in the treatment of pulmonary tuberculosis in dialyzed patients]".Minerva Medica.82 (7–8):477–81.PMID 1922892.
^Rossiter D (2012).South African Medicines Formulary. Cape Town, South Africa: Health and Medical Publishing Group of the South African Medical Association. pp. 323–325.ISBN 978-1-875098-28-6.
^World Health Organization (2025).The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization.doi:10.2471/B09474.hdl:10665/382243.

Antimycobacterials, includingtuberculosis treatment andleprostatic agents (J04)

Nucleic acid inhibitor

Rifamycins/ RNA polymerase inhibitor	Rifampicin^# Rifabutin Rifapentine Rifalazil^§
Antifolates/DSI	Dapsone^# Acedapsone Diucifon Promin Solasulfone Sulfoxone
ASA	4-Aminosalicylic acid^# (Calcium aminosalicylate Sodium aminosalicylate)
Topoisomerase inhibitors/ quinolones	Gatifloxacin Moxifloxacin

Protein synthesis inhibitor

Aminoglycosides	Amikacin^# Kanamycin Streptomycin^#
Oxazolidone	Linezolid Sutezolid
Polypeptide antibiotics	Capreomycin

Cell envelope antibiotic

Peptidoglycan layer	Alanine analogue:Cycloserine^#
Arabinogalactan layer	Ethylenediamine/arabinosyltransferase inhibitor:Ethambutol^# SQ109^†
Mycolic acid layer	Hydrazides/mycolic acid synth. inhibition:Isoniazid^# Methaniazide Thiocarbamides:Ethionamide^# Prothionamide Thiocarlide Others/unsorted:Thioacetazone (amithiozone)

Other/unknown

Phenazine (Clofazimine)^#
Pyrazine (Pyrazinamide^#,Morinamide)
Isoxazole (Terizidone)
Bedaquiline
Nitroimidazole (Delamanid,Pretomanid)

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antibacterials active on thecell wall andenvelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ /Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems /Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization:Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking:Ramoplanin^§

Intracellular

InhibitPG subunit synthesis and transport:NAM synthesis inhibition
- Fosfomycin
DADAL/AR inhibitors
- Cycloserine
- Terizidone
bactoprenol inhibitors
- Bacitracin

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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