MedKoo Cat#: 328068 | Name: Terizidone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Terizidone is a drug used in the treatment of tuberculosis. Terizidone is used mainly used in multi-drug-resistant tuberculosis (MDR-TB) in conjunction with other second-line drugs. It is a derivate of cycloserine and it is bacteriostatic.

Chemical Structure

Terizidone
Terizidone
CAS#25683-71-0

Theoretical Analysis

MedKoo Cat#: 328068

Name: Terizidone

CAS#: 25683-71-0

Chemical Formula: C14H14N4O4

Exact Mass: 302.1015

Molecular Weight: 302.29

Elemental Analysis: C, 55.63; H, 4.67; N, 18.53; O, 21.17

Price and Availability

Size Price Availability Quantity
100mg USD 450.00
200mg USD 650.00
500mg USD 950.00
1g USD 1,450.00
2g USD 2,150.00
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Related CAS #
No Data
Synonym
Terizidone
IUPAC/Chemical Name
4,4'-(((1E,1'E)-1,4-phenylenebis(methanylylidene))bis(azanylylidene))bis(isoxazolidin-3-one)
InChi Key
ODKYYBOHSVLGNU-IAGONARPSA-N
InChi Code
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+
SMILES Code
O=C1NOCC1/N=C/C2=CC=C(/C=N/C3C(NOC3)=O)C=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 302.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Optimizing dosing of the cycloserine pro-drug terizidone in children with rifampicin-resistant tuberculosis. Antimicrob Agents Chemother. 2023 Dec 14;67(12):e0061123. doi: 10.1128/aac.00611-23. Epub 2023 Nov 16. PMID: 37971239; PMCID: PMC10720412. 6: Algharably EA, Kreutz R, Gundert-Remy U. Infant Exposure to Antituberculosis Drugs via Breast Milk and Assessment of Potential Adverse Effects in Breastfed Infants: Critical Review of Data. Pharmaceutics. 2023 Apr 13;15(4):1228. doi: 10.3390/pharmaceutics15041228. PMID: 37111713; PMCID: PMC10143885. 7: Pietersen E, Anderson K, Cox H, Dheda K, Bian A, Shepherd BE, Sterling TR, Warren RM, van der Heijden YF. Variation in missed doses and reasons for discontinuation of anti-tuberculosis drugs during hospital treatment for drug- resistant tuberculosis in South Africa. PLoS One. 2023 Feb 13;18(2):e0281097. doi: 10.1371/journal.pone.0281097. PMID: 36780443; PMCID: PMC9925007. 8: Gausi K, Chirehwa M, Ignatius EH, Court R, Sun X, Moran L, Hafner R, Wiesner L, Rosenkranz SL, de Jager V, de Vries N, Harding J, Gumbo T, Swindells S, Diacon A, Dooley KE, McIlleron H, Denti P. Pharmacokinetics of standard versus high-dose isoniazid for treatment of multidrug-resistant tuberculosis. J Antimicrob Chemother. 2022 Aug 25;77(9):2489-2499. doi: 10.1093/jac/dkac188. PMID: 35678468; PMCID: PMC10146925. 9: Ndjeka N, Campbell JR, Meintjes G, Maartens G, Schaaf HS, Hughes J, Padanilam X, Reuter A, Romero R, Ismail F, Enwerem M, Ferreira H, Conradie F, Naidoo K, Menzies D. Treatment outcomes 24 months after initiating short, all-oral bedaquiline-containing or injectable-containing rifampicin-resistant tuberculosis treatment regimens in South Africa: a retrospective cohort study. Lancet Infect Dis. 2022 Jul;22(7):1042-1051. doi: 10.1016/S1473-3099(21)00811-2. Epub 2022 May 2. PMID: 35512718; PMCID: PMC9217754. 10: Tomar LR, Pandita N, Arya S, Agrawal CS. Linezolid-Associated Posterior Reversible Leuco-encephalopathy Syndrome in a Patient with Disseminated Tuberculosis. Trop Doct. 2022 Jan;52(1):196-198. doi: 10.1177/00494755211053194. Epub 2021 Dec 6. PMID: 34866511. 11: van der Laan LE, Garcia-Prats AJ, Schaaf HS, Winckler JL, Draper H, Norman J, Wiesner L, McIlleron H, Denti P, Hesseling AC. Pharmacokinetics and Drug-Drug Interactions of Abacavir and Lamuvudine Co-administered With Antituberculosis Drugs in HIV-Positive Children Treated for Multidrug-Resistant Tuberculosis. Front Pharmacol. 2021 Oct 8;12:722204. doi: 10.3389/fphar.2021.722204. PMID: 34690765; PMCID: PMC8531271. 12: Rodionova OY, Titova AV, Demkin NA, Balyklova KS, Pomerantsev AL. Influence of the quality of capsule shell on the non-invasive monitoring of medicines using Terizidone as an example. J Pharm Biomed Anal. 2021 Sep 10;204:114245. doi: 10.1016/j.jpba.2021.114245. Epub 2021 Jul 6. PMID: 34256326. 13: Sonnenkalb L, Strohe G, Dreyer V, Andres S, Hillemann D, Maurer FP, Niemann S, Merker M. Microevolution of Mycobacterium tuberculosis Subpopulations and Heteroresistance in a Patient Receiving 27 Years of Tuberculosis Treatment in Germany. Antimicrob Agents Chemother. 2021 Jun 17;65(7):e0252020. doi: 10.1128/AAC.02520-20. Epub 2021 Jun 17. PMID: 33903103; PMCID: PMC8218629. 14: Court R, Centner CM, Chirehwa M, Wiesner L, Denti P, de Vries N, Harding J, Gumbo T, Maartens G, McIlleron H. Neuropsychiatric toxicity and cycloserine concentrations during treatment for multidrug-resistant tuberculosis. Int J Infect Dis. 2021 Apr;105:688-694. doi: 10.1016/j.ijid.2021.03.001. Epub 2021 Mar 5. PMID: 33684562; PMCID: PMC8126338. 15: van der Walt ML, Shean K, Becker P, Keddy KH, Lancaster J. Treatment Outcomes and Adverse Drug Effects of Ethambutol, Cycloserine, and Terizidone for the Treatment of Multidrug-Resistant Tuberculosis in South Africa. 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Surveillance of adverse events in the treatment of drug- resistant tuberculosis: first global report. Eur Respir J. 2019 Dec 19;54(6):1901522. doi: 10.1183/13993003.01522-2019. PMID: 31601711. 19: Mulubwa M, Mugabo P. Amount of Cycloserine Emanating from Terizidone Metabolism and Relationship with Hepatic Function in Patients with Drug- Resistant Tuberculosis. Drugs R D. 2019 Sep;19(3):289-296. doi: 10.1007/s40268-019-00281-4. PMID: 31396892; PMCID: PMC6738357. 20: Pinheiro PYM, Setúbal S, Oliveira SA. Post-surgical atypical mycobacteriosis in 125 patients in Rio de Janeiro. Rev Soc Bras Med Trop. 2019 Jul 18;52:e20190039. doi: 10.1590/0037-8682-0039-2019. PMID: 31340363.