WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H462585
CAS#: 14222-60-7
Description: Protionamide (or prothionamide) is a drug used in the treatment of tuberculosis. Protionamide has also been tested for use in the treatment of leprosy.
Hodoodo Cat#: H462585
Name: Protionamide
CAS#: 14222-60-7
Chemical Formula: C9H12N2S
Exact Mass: 180.07
Molecular Weight: 180.269
Elemental Analysis: C, 59.97; H, 6.71; N, 15.54; S, 17.78
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Synonym: 2-Propyl-4-pyridinecarbothioamide; 2-Propyl-4-thiocarbamoylpyridine
IUPAC/Chemical Name: 2-propylpyridine-4-carbothioamide
InChi Key: VRDIULHPQTYCLN-UHFFFAOYSA-N
InChi Code: InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)
SMILES Code: CCCc1cc(ccn1)C(=S)N
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: >3 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 180.27 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Prothionamide. Tuberculosis (Edinb). 2008 Mar;88(2):139-40. doi: 10.1016/S1472-9792(08)70020-9. PMID: 18486054.
2: Scardigli A, Caminero JA, Sotgiu G, Centis R, D'Ambrosio L, Migliori GB. Efficacy and tolerability of ethionamide versus prothionamide: a systematic review. Eur Respir J. 2016 Sep;48(3):946-52. doi: 10.1183/13993003.00438-2016. Epub 2016 Jun 10. PMID: 27288034.
3: Hasanuzzaman M, Yi M, Cho M, Parvez MM, Lee SJ, Shin JG. Rifampin Induces Expression of P-glycoprotein on the THP1 Cell-Derived Macrophages, Causing Decrease Intramacrophage Concentration of Prothionamide. J Pharm Sci. 2019 Sep;108(9):3106-3111. doi: 10.1016/j.xphs.2019.04.009. Epub 2019 Apr 13. PMID: 30991038.
4: Islam MM, Tan Y, Hameed HMA, Liu Z, Chhotaray C, Liu Y, Lu Z, Cai X, Tang Y, Gao Y, Surineni G, Li X, Tan S, Guo L, Cai X, Yew WW, Liu J, Zhong N, Zhang T. Detection of novel mutations associated with independent resistance and cross- resistance to isoniazid and prothionamide in Mycobacterium tuberculosis clinical isolates. Clin Microbiol Infect. 2019 Aug;25(8):1041.e1-1041.e7. doi: 10.1016/j.cmi.2018.12.008. Epub 2018 Dec 22. PMID: 30583053.
5: Thee S, Garcia-Prats AJ, Donald PR, Hesseling AC, Schaaf HS. A review of the use of ethionamide and prothionamide in childhood tuberculosis. Tuberculosis (Edinb). 2016 Mar;97:126-36. doi: 10.1016/j.tube.2015.09.007. Epub 2015 Oct 19. PMID: 26586647.
6: Trivedi V, Upadhyay V, Shah G, Yadav M, Shrivastav PS, Sanyal M. Ex vivo conversion of prodrug prothionamide to its metabolite prothionamide sulfoxide with different extraction techniques and their estimation in human plasma by LC- MS/MS. Bioanalysis. 2013 Jan;5(2):185-200. doi: 10.4155/bio.12.301. PMID: 23330561.
7: Debnath SK, Saisivam S, Debanth M, Omri A. Development and evaluation of Chitosan nanoparticles based dry powder inhalation formulations of Prothionamide. PLoS One. 2018 Jan 25;13(1):e0190976. doi: 10.1371/journal.pone.0190976. PMID: 29370192; PMCID: PMC5784924.
8: Hicks ND, Carey AF, Yang J, Zhao Y, Fortune SM. Bacterial Genome-Wide Association Identifies Novel Factors That Contribute to Ethionamide and Prothionamide Susceptibility in Mycobacterium tuberculosis. mBio. 2019 Apr 23;10(2):e00616-19. doi: 10.1128/mBio.00616-19. PMID: 31015328; PMCID: PMC6479004.
9: Hsu HL, Bai KJ, Chiang YC, Lin SJ, Yu MC. Hepatitis associated with prothionamide for treatment of multidrug-resistant tuberculosis. J Formos Med Assoc. 2010 Dec;109(12):923-7. doi: 10.1016/S0929-6646(10)60141-6. PMID: 21195892.
10: Tan Y, Su B, Zheng H, Wang Y, Pang Y. Prothionamide susceptibility testing of Mycobacterium tuberculosis using the resazurin microtitre assay and the BACTECMGIT 960 system. Eur J Clin Microbiol Infect Dis. 2017 May;36(5):779-782. doi: 10.1007/s10096-016-2859-6. Epub 2016 Dec 20. PMID: 28000029.
11: Tan Y, Su B, Zheng H, Song Y, Wang Y, Pang Y. Molecular Characterization of Prothionamide-Resistant Mycobacterium tuberculosis Isolates in Southern China. Front Microbiol. 2017 Nov 30;8:2358. doi: 10.3389/fmicb.2017.02358. PMID: 29250048; PMCID: PMC5714880.
12: Mugweru J, Liu J, Makafe G, Chiwala G, Wang B, Wang C, Li X, Tan Y, Yew WW, Tan S, Zhang T. Mutation EthAW21R confers co-resistance to prothionamide and ethionamide in both Mycobacterium bovis BCG and Mycobacterium tuberculosis H37Rv. Infect Drug Resist. 2018 Jun 13;11:891-894. doi: 10.2147/IDR.S163965. PMID: 29942141; PMCID: PMC6005328.
13: Lee JH, Jo KW, Shim TS. Correlation between GenoType MTBDRplus Assay and Phenotypic Susceptibility Test for Prothionamide in Patients with Genotypic Isoniazid Resistance. Tuberc Respir Dis (Seoul). 2019 Apr;82(2):143-150. doi: 10.4046/trd.2018.0027. Epub 2018 Sep 28. PMID: 30302956; PMCID: PMC6435929.
14: García-García JM, González-Martín J; Coordinadores del Consenso por parte de SEPAR y SEIMC, respectivamente, en nombre de todos los autores. Dosis de protionamida y PAS. Corrección al «Documento de Consenso sobre diagnóstico, tratamiento y prevención de la tuberculosis» [Prothionamide and PAS doses. Correction to «Consensus document on the diagnosis, treatment and prevention of tuberculosis»]. Enferm Infecc Microbiol Clin. 2016 Aug-Sep;34(7):466. Spanish. doi: 10.1016/j.eimc.2015.07.008. Epub 2015 Aug 19. PMID: 26298096.
15: Lee HW, Kim DW, Park JH, Kim SD, Lim MS, Phapale PB, Kim EH, Park SK, Yoon YR. Pharmacokinetics of prothionamide in patients with multidrug-resistant tuberculosis. Int J Tuberc Lung Dis. 2009 Sep;13(9):1161-6. PMID: 19723408.
16: Matsuo Y, Tatsukawa H, Murray JF Jr, Peters JH. Prothionamide and prothionamide-S-oxide in experimental leprosy. Int J Lepr Other Mycobact Dis. 1981 Sep;49(3):302-6. PMID: 6459296.
17: Miotto P, Tessema B, Tagliani E, Chindelevitch L, Starks AM, Emerson C, Hanna D, Kim PS, Liwski R, Zignol M, Gilpin C, Niemann S, Denkinger CM, Fleming J, Warren RM, Crook D, Posey J, Gagneux S, Hoffner S, Rodrigues C, Comas I, Engelthaler DM, Murray M, Alland D, Rigouts L, Lange C, Dheda K, Hasan R, Ranganathan UDK, McNerney R, Ezewudo M, Cirillo DM, Schito M, Köser CU, Rodwell TC. A standardised method for interpreting the association between mutations and phenotypic drug resistance in Mycobacterium tuberculosis. Eur Respir J. 2017 Dec 28;50(6):1701354. doi: 10.1183/13993003.01354-2017. PMID: 29284687; PMCID: PMC5898944.
18: Fajardo TT, Guinto RS, Cellona RV, Abalos RM, Dela Cruz EC, Gelber RH. A clinical trial of ethionamide and prothionamide for treatment of lepromatous leprosy. Am J Trop Med Hyg. 2006 Mar;74(3):457-61. PMID: 16525107.
19: Borisov S, Danila E, Maryandyshev A, Dalcolmo M, Miliauskas S, Kuksa L, Manga S, Skrahina A, Diktanas S, Codecasa LR, Aleksa A, Bruchfeld J, Koleva A, Piubello A, Udwadia ZF, Akkerman OW, Belilovski E, Bernal E, Boeree MJ, Cadiñanos Loidi J, Cai Q, Cebrian Gallardo JJ, Dara M, Davidavičienė E, Forsman LD, De Los Rios J, Denholm J, Drakšienė J, Duarte R, Elamin SE, Escobar Salinas N, Ferrarese M, Filippov A, Garcia A, García-García JM, Gaudiesiute I, Gavazova B, Gayoso R, Gomez Rosso R, Gruslys V, Gualano G, Hoefsloot W, Jonsson J, Khimova E, Kunst H, Laniado-Laborín R, Li Y, Magis-Escurra C, Manfrin V, Marchese V, Martínez Robles E, Matteelli A, Mazza-Stalder J, Moschos C, Muñoz- Torrico M, Mustafa Hamdan H, Nakčerienė B, Nicod L, Nieto Marcos M, Palmero DJ, Palmieri F, Papavasileiou A, Payen MC, Pontarelli A, Quirós S, Rendon A, Saderi L, Šmite A, Solovic I, Souleymane MB, Tadolini M, van den Boom M, Vescovo M, Viggiani P, Yedilbayev A, Zablockis R, Zhurkin D, Zignol M, Visca D, Spanevello A, Caminero JA, Alffenaar JW, Tiberi S, Centis R, D'Ambrosio L, Pontali E, Sotgiu G, Migliori GB. 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.
20: Lee SH, Seo KA, Lee YM, Lee HK, Kim JH, Shin C, Ghim JR, Shin JG, Kim DH. Low Serum Concentrations of Moxifloxacin, Prothionamide, and Cycloserine on Sputum Conversion in Multi-Drug Resistant TB. Yonsei Med J. 2015 Jul;56(4):961-7. doi: 10.3349/ymj.2015.56.4.961. PMID: 26069117; PMCID: PMC4479863.
