Tinidazole

Chemical compound
  • US DailyMed: Tinidazole
Pregnancy
category
  • AU: B3
Routes of
administrationBy mouthATC code
  • J01XD02 (WHO) G01AF21 (WHO), P01AB02 (WHO), QP51AA02 (WHO)
Legal statusLegal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-only
Pharmacokinetic dataProtein binding12%MetabolismLiver (CYP3A4)Elimination half-life12–14 hoursExcretionUrine (20–25%), feces (12%)Identifiers
  • 1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole
CAS Number
  • 19387-91-8 checkY
PubChem CID
  • 5479
DrugBank
  • DB00911 checkY
ChemSpider
  • 5279 checkY
UNII
  • 033KF7V46H
KEGG
  • D01426 checkY
ChEMBL
  • ChEMBL1220 checkY
NIAID ChemDB
  • 007940
CompTox Dashboard (EPA)
  • DTXSID4023676 Edit this at Wikidata
ECHA InfoCard100.039.089 Edit this at WikidataChemical and physical dataFormulaC8H13N3O4SMolar mass247.27 g·mol−13D model (JSmol)
  • Interactive image
  • CCS(=O)(=O)CCN1C(=NC=C1[N+](=O)[O-])C
  • InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3 checkY
  • Key:HJLSLZFTEKNLFI-UHFFFAOYSA-N checkY
  (verify)

Tinidazole, sold under the brand name Tindamax among others, is a medication used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of anaerobic amoebic and bacterial infections. It was developed in 1972 and is a prominent member of the nitroimidazole antibiotic class.[2]

It is on the World Health Organization's List of Essential Medicines.[3]

Medical uses

Tinidazole may be a therapeutic alternative in the setting of metronidazole intolerance. Tinidazole is used to treat Helicobacter pylori, Amoebic dysentery, Giardia and Trichomonas vaginalis.[4]

Side effects

Drinking alcohol while taking tinidazole causes an unpleasant disulfiram-like reaction, which includes nausea, vomiting, headache, increased blood pressure, flushing, and shortness of breath.[medical citation needed]

Half-life

Elimination half-life is 13.2 ± 1.4 hours. Plasma half-life is 12 to 14 hours.[medical citation needed]

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ Ebel K, Koehler H, Gamer AO, Jäckh R (2002). "Imidazole and Derivatives.". In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a13_661. ISBN 3527306730.
  3. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  4. ^ Edwards DI (January 1993). "Nitroimidazole drugs--action and resistance mechanisms. I. Mechanisms of action". The Journal of Antimicrobial Chemotherapy. 31 (1): 9–20. doi:10.1093/jac/31.1.9. PMID 8444678.
  • v
  • t
  • e
Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor
Sulfonamides
(DHPS inhibitor)
Short-acting
Intermediate-acting
Long-acting
Other/ungrouped
Combinations
Other DHPS inhibitors
Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
1st generation
Fluoroquinolones
2nd generation
3rd generation
4th generation
Veterinary
Newer non-fluorinated
Related (DG)
Anaerobic DNA
inhibitors
Nitroimidazole derivatives
Nitrofuran derivatives
RNA synthesis
Rifamycins/
RNA polymerase
Lipiarmycins
  • v
  • t
  • e
Alveo-
late
Apicom-
plexa
Conoidasida/
(Coccidiostats)
Cryptosporidiosis
Isosporiasis
Toxoplasmosis
Aconoidasida
Malaria
Individual
agents
Hemozoin
inhibitors
Aminoquinolines
4-Methanolquinolines
Other
Antifolates
DHFR inhibitors
Sulfonamides
Co-formulation
Sesquiterpene
lactones
Other
Combi-
nations
Fixed-dose (co-formulated) ACTs
Other combinations
(not co-formulated)
  • artesunate/mefloquine
  • artesunate/SP
  • quinine/clindamycin
  • quinine/doxycycline
  • quinine/tetracycline
Babesiosis
Cilio-
phora
Stramen-
opile
  • v
  • t
  • e
Discicristata
Trypanosomiasis
African trypanosomiasis
Chagas disease
Leishmaniasis
PAM
Trichozoa
Giardiasis
Trichomoniasis
Dientamoebiasis
  • v
  • t
  • e
Entamoeba
Tissue amebicides
Nitroimidazole derivatives
Other
Luminal amebicides
Hydroxyquinoline derivatives
Dichloroacetamide derivatives
Aminoglycoside
Other/ungrouped
Acanthamoeba
Portal:
  • icon Medicine