Delamanid
 | |
|---|---|
| Systematic (IUPAC) name | |
| (2R)-2-Methyl-6-nitro-2-[(4-{4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl}phenoxy)methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole | |
| Clinical data | |
| Legal status | Investigational |
| Identifiers | |
| CAS number | 681492-22-8 |
| ATC code | J04AK06 |
| PubChem | CID 6480466 |
| ChemSpider | 4981055 |
| ChEMBL | CHEMBL218650 |
| Synonyms | OPC-67683 |
| Chemical data | |
| Formula | C25H25F3N4O6 |
| Mol. mass | 534.48 g/mol |
| SMILES
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Delamanid (USAN, codenamed OPC-67683) is an experimental drug for the treatment of multi-drug-resistant tuberculosis. It works by blocking the synthesis of mycolic acids in Mycobacterium tuberculosis, the organism which causes tuberculosis, thus destabilising its cell membrane.[1][2][3]
In phase II clinical trials, the drug was used in combination with standard treatments, such as four or five of the drugs ethambutol, isoniazid, pyrazinamide, rifampicin, aminoglycoside antibiotics, and quinolones. Healing rates (measured as sputum culture conversion) were significantly better in patients who additionally took delamanid.[3][4]
The European Medicines Agency (EMA) recommended conditional marketing authorization for delamanid in adults with multidrug-resistant pulmonary tuberculosis without other treatment options because of resistance or tolerability. The EMA considered the data show that the benefits of delamanid outweigh the risks, but that additional studies were needed on the long-term effectiveness.[5]
See also
- PA 824, a related drug
References
- ↑ Matsumoto, M.; Hashizume, H.; Tomishige, T.; Kawasaki, M.; Tsubouchi, H.; Sasaki, H.; Shimokawa, Y.; Komatsu, M. (2006). "OPC-67683, a Nitro-Dihydro-Imidazooxazole Derivative with Promising Action against Tuberculosis in Vitro and in Mice". PLoS Medicine 3 (11): e466. doi:10.1371/journal.pmed.0030466. PMC 1664607. PMID 17132069.
- ↑ Skripconoka, V.; Danilovits, M.; Pehme, L.; Tomson, T.; Skenders, G.; Kummik, T.; Cirule, A.; Leimane, V.; Kurve, A.; Levina, K.; Geiter, L. J.; Manissero, D.; Wells, C. D. (2012). "Delamanid Improves Outcomes and Reduces Mortality for Multidrug-Resistant Tuberculosis". European Respiratory Journal 41 (6): 1393–1400. doi:10.1183/09031936.00125812. PMC 3669462. PMID 23018916.
- ↑ 3.0 3.1 H. Spreitzer (18 February 2013). "Neue Wirkstoffe – Bedaquilin und Delamanid". Österreichische Apothekerzeitung (in German) (4/2013): 22.
- ↑ Gler, M. T.; Skripconoka, V.; Sanchez-Garavito, E.; Xiao, H.; Cabrera-Rivero, J. L.; Vargas-Vasquez, D. E.; Gao, M.; Awad, M.; Park, S. K.; Shim, T. S.; Suh, G. Y.; Danilovits, M.; Ogata, H.; Kurve, A.; Chang, J.; Suzuki, K.; Tupasi, T.; Koh, W. J.; Seaworth, B.; Geiter, L. J.; Wells, C. D. (2012). "Delamanid for Multidrug-Resistant Pulmonary Tuberculosis". New England Journal of Medicine 366 (23): 2151–2160. doi:10.1056/NEJMoa1112433. PMID 22670901.
- ↑ Drug Discovery & Development. EMA Recommends Two New Tuberculosis Treatments. November 22, 2013.
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