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Nitazoxanide

产品号 DB00507 公司名称 DrugBank
CAS号 55981-09-4 公司网站 http://www.ualberta.ca/
分子式 C12H9N3O5S 电 话 (780) 492-3111
分子量 307.28196 传 真
纯 度 电子邮件 david.wishart@ualberta.ca
保 存 Chembase数据库ID: 389

产品价格信息

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产品别名

标题
Nitazoxanide
IUPAC标准名
2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate
IUPAC传统名
nitazoxanide
商标名
Phavic-1
Fental
Alinia
别名
NTZ
Nitazoxanida [INN-Spanish]
Tizoxanide Glucuronide
Nitazoxanidum [INN-Latin]
Nitazoxanid
2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide
2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide
nitazoxanide

产品登记号

PubChem CID 41684
CAS号 55981-09-4
PubChem SID 46507813

产品性质

疏水性(logP) 1.2

产品详细信息

详细说明 (English)
Item Information
Drug Groups approved; investigational
Description Nitazoxanide, also known by the brand name Alinia, is a synthetic nitrothiazolyl-salicylamide derivative and an anti-protozoal agent. It is approved for treatment of infectious diarrhea caused by Cryptosporidium parvum and Giardia lamblia in patients 1 year of age and older. Following oral administration it is rapidly hydrolyzed to its active metabolite, tizoxanide, which is 99% protein bound. Peak concentrations are observed 1–4 hours after administration. It is excreted in the urine, bile and feces. Untoward effects include abdominal pain, vomiting and diarrhea. [Wikipedia]
Indication For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia and for the treatment of diarrhea in children caused by the protozoa Cryptosporidium parvum.
Pharmacology Nitazoxanide is an antifolate containing the pyrrolopyrimidine-based nucleus that exerts its antineoplastic activity by disrupting folate-dependent metabolic processes essential for cell replication. In vitro studies have shown that nitazoxanide inhibits thymidylate synthase (TS), dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT), all folate-dependent enzymes involved in the de novo biosynthesis of thymidine and purine nucleotides. Nitazoxanide is transported into cells by both the reduced folate carrier and membrane folate binding protein transport systems. Once in the cell, nitazoxanide is converted to polyglutamate forms by the enzyme folylpolyglutamate synthetase. The polyglutamate forms are retained in cells and are inhibitors of TS and GARFT. Polyglutamation is a time- and concentration-dependent process that occurs in tumor cells and, to a lesser extent, in normal tissues. Polyglutamated metabolites have an increased intracellular half-life resulting in prolonged drug action in malignant cells.
Toxicity In acute studies in rodents and dogs, the oral LD50 was higher than 10,000 mg/kg. Single oral doses of up to 4000 mg nitazoxanide have been administered to healthy adult volunteers without significant adverse effects.
Affected Organisms
Protozoa
Biotransformation Rapidly hydrolyzed to an active metabolite, tizoxanide (desacetyl-nitazoxanide), followed by conjugation, primarily by glucuronidation to tizoxanide glucuronide.
Absorption The relative bioavailability of the suspension compared to the tablet was 70%. When administered with food the AUC and Cmax increased by two-fold and 50%, respectively, for the tablet and 45 to 50% and ≤ 10%, respectively, for the oral suspension.
Half Life 3.5 hours in patients with normal renal function
Protein Binding Very High (greater than 99%), bound to proteins. Binding is not affected by degree of renal impairment.
Elimination Tizoxanide is excreted in the urine, bile and feces, and tizoxanide glucuronide is excreted in urine and bile. Approximately two-thirds of the oral dose of nitazoxanide is excreted in the feces and one-third in the urine.
References
Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

参考文献

  • Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. Pubmed