Tinidazole

Tinidazole
Clinical data
Trade names	Fasigyn, Simplotan, Tindamax
AHFS/Drugs.com	Monograph
MedlinePlus	a604036
Pregnancy; category	AU: B3 ; US: C (Risk not ruled out) ;
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: ℞-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;
ECHA InfoCard	100.039.089
Chemical and physical data
Formula	C8H13N3O4S
Molar mass	247.273 g/mol
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 ;
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Tinidazole is a 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 and is a prominent member of the nitroimidazole antibiotic class.^[1]

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.

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 intolerance. 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).^[2]

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.

Half-life

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

References

↑ 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

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[Ebel-1] 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

[2] 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.