Tinidazole

Tinidazole
Clinical data
Trade names	Fasigyn, Simplotan, Tindamax
AHFS/Drugs.com	Monograph
MedlinePlus	a604036
Pregnancy; category	AU: B3; ;
Routes of; administration	Oral
ATC code	J01XD02 (WHO) P01AB02 (WHO) QP51AA02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Protein binding	12%
Metabolism	Hepatic (CYP3A4)
Elimination half-life	12–14 hours
Excretion	Urine (20–25%), faeces (12%)
Identifiers
	IUPAC name 1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole;
CAS Number	19387-91-8 ;
PubChem CID	5479;
DrugBank	DB00911 ;
ChemSpider	5279 ;
UNII	033KF7V46H;
KEGG	D01426 ;
ChEMBL	ChEMBL1220 ;
NIAID ChemDB	007940;
CompTox Dashboard (EPA)	DTXSID4023676 ;
ECHA InfoCard	100.039.089
Chemical and physical data
Formula	C8H13N3O4S
Molar mass	247.273 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1cnc(n1CCS(=O)(=O)CC)C;
	InChI 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 ; Key:HJLSLZFTEKNLFI-UHFFFAOYSA-N ;
	(verify)

Tinidazole is an anti-parasitic drug used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of amoebic and parasitic infections. It was developed in 1972. A derivative of 2-methylimidazole, it is a prominent member of the nitroimidazole antibiotics.^[2]

Tinidazole is marketed by Mission Pharmacal under the brand name Tindamax, by Pfizer under the names Fasigyn and Simplotan, and in some Asian countries as Sporinex.

Pharmacology

It is chemically similar to metronidazole—a drug with some unpleasant side effects that is used in the United States as first-line therapy for amoebae. Tinidazole has similar side effects but has a shorter treatment course.

Uses

A large body of clinical data exists to support use of tinidazole for infections from amoebae, giardia, and trichomonas, just like metronidazole. Tinidazole may be a therapeutic alternative in the setting of metronidazole tolerance. Tinidazole may also be used to treat a variety of other bacterial infections (e.g., as part of combination therapy for Helicobacter pylori eradication protocols).^[3]

Side effects

The most common side effects reported with tinidazole are upset stomach, bitter taste and itchiness. Other side effects include headache, physical fatigue, and dizziness. Anecdotally, people who have taken both metronidazole and tinidazole report toxicity is much the same except the side effects don't last as long with the latter.

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

Half-life

Elimination half-life is 13.2 ± 1.4 hours. Plasma half-life is 12 to 14 hours.

References

^ "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.
^ Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. “Imidazole and Derivatives.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a13_661
^ Edwards, David I. "Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action" Journal of Antimicrobial Chemotherapy 1993, volume 31, pp. 9-20. doi:10.1093/jac/31.1.9.

External links

[FDA-AllBoxedWarnings-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.

[Ebel-2] Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. “Imidazole and Derivatives.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a13_661

[3] Edwards, David I. "Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action" Journal of Antimicrobial Chemotherapy 1993, volume 31, pp. 9-20. doi:10.1093/jac/31.1.9.

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