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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/09/13 15:44:02」(JST)
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Tinidazole
|
Systematic (IUPAC) name |
1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole
|
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 |
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 |
CAS Number |
19387-91-8 Y |
ATC code |
J01XD02 (WHO) P01AB02 (WHO) QP51AA02 (WHO) |
PubChem |
CID 5479 |
DrugBank |
DB00911 Y |
ChemSpider |
5279 Y |
UNII |
033KF7V46H Y |
KEGG |
D01426 Y |
ChEMBL |
CHEMBL1220 Y |
NIAID ChemDB |
007940 |
Chemical data |
Formula |
C8H13N3O4S |
Molar mass |
247.273 g/mol |
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 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 Pharmacology
- 2 Uses
- 3 Side effects
- 4 Half-life
- 5 References
- 6 External links
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).[2]
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
- ^ 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
- 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
Related Links
- Tindamax (tinidazole) is used to treat certain infections caused by bacteria, such as infections of the intestines or vagina. Includes Tindamax side effects, interactions and indications. ... Tindamax side effects Get emergency medical ...
- Find patient medical information for Tindamax oral on WebMD including its uses, side effects and safety, interactions, pictures, warnings and user ratings. ... Tinidazole is used to treat certain types of vaginal infections (bacterial ...
Related Pictures
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[★]
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[★]
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