Tinidazole

Tinidazole
Names
Trade namesFasigyn, Simplotan, Tindamax, others
IUPAC name
  • 1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole
Clinical data
Main usesBacterial vaginosis, amoebiasis, giardiasis, trichomoniasis[1]
Side effectsUpset stomach, brownish urine, headache, allergic reaction[1]
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Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
    Routes of
    use    		By mouth
    Typical dose2 gm once daily[1]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa604036
    Legal
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    Pharmacokinetics
    Protein binding12%
    MetabolismLiver (CYP3A4)
    Elimination half-life12–14 hours
    ExcretionUrine (20–25%), faeces (12%)
    Chemical and physical data
    FormulaC8H13N3O4S
    Molar mass247.27 g·mol−1
    3D model (JSmol)
    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 checkY
    • Key:HJLSLZFTEKNLFI-UHFFFAOYSA-N checkY

    Tinidazole, sold under the brand name Tindamax among others, is a medication used to treat a number of infections including amebiasis, giardiasis, trichomoniasis, bacterial vaginosis, and nongonococcal urethritis.[2] It is taken by mouth.[2]

    Common side effects include nausea, tiredness, and headaches.[2] Other side effects may include brownish urine, peripheral neuropathy, and allergic reactions.[1][2] Use is not recommended during the initial part of pregnancy.[2] It is a member of the nitroimidazole class and is believed to work by affecting DNA.[2]

    Tinidazole was developed in 1969.[3] It is on the World Health Organization's List of Essential Medicines as an alternative to metronidazole.[4] It is available as a generic medication.[5] In the United Kingdom 16 tablets of 500 mg costs the NHS about £11 as of 2021.[6] This amount in the United States costs about 35 USD.[5]

    Medical uses

    Tinidazole is used 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).[7]

    Dosage

    The dose in adults is typically 2 grams once per day; while in children 50 mg/kg is used.[1] For amoebiasis 3 days is used if the intestines are affected and 5 days if the liver is affected.[1] For giardiasis, trichomoniasis, and bacterial vaginosis a single dose is used.[1]

    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.[1]

    Chemistry

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

    Society and culture

    Names

    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.

    References

    1. 1 2 3 4 5 6 7 8 "TINIDAZOLE oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on 29 August 2021. Retrieved 25 August 2020.
    2. 1 2 3 4 5 6 "Tinidazole Monograph for Professionals". Drugs.com. Archived from the original on 16 April 2021. Retrieved 4 October 2021.
    3. ↑ Greenwood, David (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 315. ISBN 978-0-19-953484-5. Archived from the original on 4 October 2021. Retrieved 4 October 2021.
    4. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
    5. 1 2 "Tinidazole Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 5 October 2021. Retrieved 4 October 2021.
    6. ↑ BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 574. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
    7. ↑ 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.
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