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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) |
Biological half-life |
12–14 hours |
Excretion |
Urine (20–25%), faeces (12%) |
Identifiers |
IUPAC name
- 1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole
|
CAS Number |
|
PubChem CID |
|
DrugBank |
|
ChemSpider |
|
UNII |
|
KEGG |
|
ChEMBL |
|
NIAID ChemDB |
|
ECHA InfoCard |
100.039.089 |
Chemical and physical data |
Formula |
C8H13N3O4S |
Molar mass |
247.273 g/mol |
3D model (Jmol) |
|
SMILES
-
[O-][N+](=O)c1cnc(n1CCS(=O)(=O)CC)C
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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 Y
-
Key:HJLSLZFTEKNLFI-UHFFFAOYSA-N Y
|
(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.[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.
Contents
- 1 Uses
- 2 Side effects
- 3 Half-life
- 4 References
- 5 External links
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).[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
- MedlinePlus Drug Information: Tinidazole
- Drug Bank Facts on Tinidazole
Antibacterials: nucleic acid inhibitors (J01E, J01M)
|
|
Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Trimethoprim#
- Brodimoprim
- Tetroxoprim
- Iclaprim†
|
|
Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
|
|
Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
|
|
Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
|
|
Other/ungrouped |
- Sulfacetamide
- Sulfadicramide
- Sulfametrole
|
|
|
Combinations |
- Trimethoprim/sulfamethoxazole#
|
|
|
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine‡
- Nalidixic acid‡
- Oxolinic acid‡
- Pipemidic acid‡
- Piromidic acid‡
- Rosoxacin‡
|
|
Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Ofloxacin
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin‡
- Nadifloxacin‡
- Norfloxacin‡
- Pefloxacin‡
- Rufloxacin‡
|
|
3rd g. |
- Levofloxacin#
- Balofloxacin‡
- Grepafloxacin‡
- Pazufloxacin‡
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin‡
|
|
4th g. |
- Besifloxacin
- Gatifloxacin
- Finafloxacin
- Gemifloxacin
- Moxifloxacin
- Clinafloxacin†
- Garenoxacin‡
- Prulifloxacin‡
- Sitafloxacin‡
- Trovafloxacin‡/Alatrofloxacin‡
|
|
Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
|
|
|
Newer non-fluorinated |
|
|
Related (DG) |
- Aminocoumarins: Novobiocin
|
|
|
Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
|
|
Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
|
|
|
RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin#
- Rifapentine#
- Rifaximin
- Rifalazil§
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
|
|
Alveo-
late |
Apicom-
plexa |
Conoidasida/
(Coccidiostats) |
Cryptosporidiosis |
- thiazolides (nitazoxanide)
|
|
Isosporiasis |
- trimethoprim/sulfamethoxazole#
|
|
Toxoplasmosis |
- pyrimethamine
- sulfadiazine
|
|
|
Aconoidasida |
Malaria |
Individual
agents |
Hemozoin
inhibitors |
Aminoquinolines |
- (4-): amodiaquine#
- chloroquine#
- hydroxychloroquine#
- (8-): primaquine#
- pamaquine‡
- tafenoquine†
|
|
4-Methanolquinolines |
- mefloquine#
- quinine#
- quinidine
|
|
Other |
|
|
|
Antifolates |
DHFR inhibitors |
- biguanides
- chlorproguanil
- proguanil#
|
|
Sulfonamides |
|
|
Co-formulation |
- sulfadoxine/pyrimethamine (SP)#
|
|
|
Sesquiterpene
lactones |
- artemether#
- artemisinin
- artemotil
- artesunate#
- dihydroartemisinin
|
|
Other |
- atovaquone (+ proguanil)
- tetracycline
- doxycycline#
- clindamycin
- mepacrine
- pyronaridine
- piperaquine
|
|
|
Combi-
nations |
Fixed-dose (co-formulated) ACTs |
- artemether/lumefantrine#
- arterolane/piperaquine
- artesunate/amodiaquine (ASAQ)
- artesunate/mefloquine (ASMQ)
- artesunate/pyronaridine
- dihydroartemisinin/piperaquine
|
|
Other combinations
(not co-formulated) |
- artesunate/mefloquine
- artesunate/SP
- quinine/clindamycin
- quinine/doxycycline
- quinine/tetracycline
|
|
|
|
Babesiosis |
|
|
|
|
Cilio-
phora |
- Balantidiasis: tetracycline
|
|
|
Hetero-
kont |
- Blastocystosis: metronidazole
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
Antiparasitics – antiprotozoal agents – Excavata antiparasitics (P01)
|
|
Discicristata |
Trypanosomiasis
|
- African trypanosomiasis: ornithine (Eflornithine#)
- arsenical (Melarsoprol#)
- benzamidine (Pentamidine#)
- naphthalenesulfonate (Suramin#)
- nitroimidazole (Fexinidazole†)
Chagas disease: nitroimidazole (Benznidazole#)
|
|
Leishmaniasis
|
- macrolide (Amphotericin B#)
Pentavalent antimonials (Meglumine antimoniate#, Sodium stibogluconate)
- benzamidine (Pentamidine#)
- phosphorylcholine (Miltefosine)
- neomycin (Paromomycin)
|
|
PAM
|
- macrolide (Amphotericin B)
|
|
|
Trichozoa |
Giardiasis
|
- nitroimidazole (Metronidazole#, Tinidazole)
- benzimidazole (Albendazole)
- thiazolide (Nitazoxanide)
- nitrofuran (Furazolidone)
- aminoacridine (Quinacrine)
|
|
Trichomoniasis
|
- nitroimidazole (Carnidazole, Metronidazole#, Tinidazole)
|
|
Dientamoebiasis
|
- nitroimidazole (Metronidazole
- Secnidazole)
- oxyquinoline (Iodoquinol)
- tetracycline (Doxycycline)
- neomycin (Paromomycin)
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
|
|
Entamoeba |
Tissue amebicides
|
Nitroimidazole derivatives
|
- Metronidazole#
- Tinidazole
- Ornidazole
- Nimorazole
- Secnidazole
- Azanidazole
- Propenidazole
|
|
Other
|
- isoquinoline (Emetine/Dehydroemetine)
|
|
|
Luminal amebicides
|
Hydroxyquinoline derivatives
|
- Cl (Chlorquinaldol)
- Br (Tilbroquinol
- Broxyquinoline)
- I (Diiodohydroxyquinoline)
- I, Cl (Clioquinol)
|
|
Dichloroacetamide derivatives
|
- Diloxanide#
- Clefamide
- Etofamide
- Teclozan
|
|
Aminoglycoside
|
|
|
|
Other/ungrouped
|
- arsenic (Arsthinol
- Difetarsone
- Glycobiarsol)
- phenanthroline (Phanquinone)
- aminoacridine (Mepacrine)
- quinazoline (Trimetrexate)
- thiazole (Tenonitrozole)
- sesquiterpene (Fumagillin)
|
|
|
Acanthamoeba |
- Propamidine
- Chlorhexidine
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
UpToDate Contents
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English Journal
- HPTLC method for Simultaneous Determination of Norfloxacin and Tinidazole in presence of Tinidazole Impurity.
- Naguib IA1, Abdelaleem EA1, Hassan ES1, Ali NW1.
- Journal of chromatographic science.J Chromatogr Sci.2019 Jan 1;57(1):81-86. doi: 10.1093/chromsci/bmy085.
- PMID 30395212
- Metronidazole-Resistant Trichomoniasis: Beneficial Pharmacodynamic Relationship With High-Dose Oral Tinidazole and Vaginal Paromomycin Combination Therapy.
- Henien M1, Nyirjesy P, Smith K.
- Sexually transmitted diseases.Sex Transm Dis.2019 Jan;46(1):e1-e2. doi: 10.1097/OLQ.0000000000000903.
- PMID 30106840
- A triazine-based conjugated microporous polymer composite for magnetic solid phase extraction of 5-nitroimidazoles coupled with UPLC-MS/MS for quantification.
- Yang W 1, Wu X , Liu T , Wang T , Hou X .
- The Analyst.Analyst.2018 Nov 19;143(23):5744-5753. doi: 10.1039/c8an01600c.
- PMID 30325370
Japanese Journal
- メトロニダゾールに対する副反応のためにチニダゾールで治療し得た後天性免疫不全症候群に併発したアメーバ性大腸炎の1例
- Stability Indicating Methods for the Determination of Norfloxacin in Mixture with Tinidazole
- Voltammetric Determination of Tinidazole Using a Glassy Carbon Electrode Modified with Single-Wall Carbon Nanotubes
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20(5), 821-824, 2004-05-10
- NAID 10012941757
Related Links
- e-world in your hands (STAR-LIN Herb Corp.,USA) 海外の個人輸入・情報サイトです。 検索結果を表示 成分: チニダゾール(Tinidazole) ... 商品No 商 品 名 / 数 量 価 格 TZ-001 チニダゾール(Tinidazole) 成分 Tinidazole ...
- Tindamax (tinidazole) is a drug for the treatment of bacterial vaginosis, trichomoniasis, giardiasis, and amebiasis. ... All BV therapies are not the same. In fact, only one combines the convenience of an easy-to-swallow pill with the ...
Related Pictures
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