Ornidazole
- G01AF06 (WHO) J01XD03 (WHO) P01AB03 (WHO) QP51AA03 (WHO)
- 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
- 16773-42-5 Y
- 28061
- 26102 Y
- 62XCK0G93T
- D05274 Y
- CHEBI:75176 N
- ChEMBL1449676 N
- DTXSID4045420
- Interactive image
- [O-] [N+](=O)c1cnc(n1CC(O)CCl)C
- InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3 Y
- Key:IPWKIXLWTCNBKN-UHFFFAOYSA-N Y
Ornidazole is an antibiotic used to treat protozoan infections.[1]: 1368 A synthetic nitroimidazole, it is commercially obtained from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin.[2]
Antimicrobial spectrum is similar to that of metronidazole and is more well tolerated;[1]: 1368 however there are concerns of lower relative efficacy.[3]
It was first introduced for treating trichomoniasis before being recognized for its broad anti-protozoan and anti-anaerobic-bacterial capacities.[4]: 1261 has also been investigated for use in Crohn's disease after bowel resection.[5]
References
- ^ a b c d Kuhlmann FM, Fleckenstein JM (2017-01-01). "157 - Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (Fourth ed.). Elsevier. pp. 1345–1372.e2. doi:10.1016/B978-0-7020-6285-8.00157-X. ISBN 978-0-7020-6285-8.
- ^ Sharma S, Anand N (January 1997). "Chapter 17 - Nitroheterocycles". In Sharma S, Anand N (eds.). Pharmacochemistry Library. Approaches to Design and Synthesis of Antiparasitic Drugs. Vol. 25. Elsevier. p. 428. doi:10.1016/S0165-7208(97)80039-6. ISBN 9780444894762.
- ^ Nagel JL, Aronoff DM (January 2015). "28 - Metronidazole". In Bennett JE, Dolin R, Blaser MJ (eds.). Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases (Eighth ed.). Content Repository Only!. p. 356. ISBN 978-1-4557-4801-3.
- ^ Wilcox MH (January 2017), "147 - Nitroimidazoles, Metronidazole, Ornidazole and Tinidazole; and Fidaxomicin", in Cohen J, Powderly WG, Opal SM (eds.), Infectious Diseases (Fourth ed.), Elsevier, pp. 1261–1263.e1, ISBN 978-0-7020-6285-8
- ^ Rutgeerts P, Van Assche G, Vermeire S, D'Haens G, Baert F, Noman M, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–861. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.
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(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor | |||||||||
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Sulfonamides (DHPS inhibitor) |
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Combinations |
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Other DHPS inhibitors |
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
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Fluoroquinolones |
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Newer non-fluorinated | |||||||||
Related (DG) |
inhibitors
Nitroimidazole derivatives |
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Nitrofuran derivatives |
Rifamycins/ RNA polymerase | |
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Lipiarmycins |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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