Tìm theo
Rifaximin
Các tên gọi khác (9 ) :
  • Rifamycin L 105
  • Rifamycin L 105SV
  • Rifaxidin
  • Rifaximin
  • Rifaximina
  • Rifaximine
  • Rifaximinum
  • Rifaximinun
  • Xifaxsan
gastrointestinal agents, anti infective agents
Thuốc Gốc
Small Molecule
CAS: 80621-81-4
ATC: A07AA11, D06AX11
ĐG : Diversified Healthcare Services Inc. , http://www.dhscorp.com
CTHH: C43H51N3O11
PTK: 785.8785
Rifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used to treat diarrhea caused by E. coli.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C43H51N3O11
Phân tử khối
785.8785
Monoisotopic mass
785.352359489
InChI
InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChI Key
InChIKey=NZCRJKRKKOLAOJ-XRCRFVBUSA-N
IUPAC Name
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1^{4,7}.0^{5,35}.0^{26,34}.0^{27,32}]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate
Traditional IUPAC Name
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1^{4,7}.0^{5,35}.0^{26,34}.0^{27,32}]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C1=C(N=C5C=C(C)C=CN15)C4=C3C2=O
Độ hòa tan
7.38e-03 g/l
logP
2.6
logS
-5
pKa (strongest acidic)
3.66
pKa (Strongest Basic)
11.87
PSA
198.38 Å2
Refractivity
216.69 m3·mol-1
Polarizability
82.26 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
11
H Bond Donor Count
5
Physiological Charge
-1
Number of Rings
6
Bioavailability
0
Dược Lực Học : Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. This non-systemic property of the drug is due to the addition of a pyridoimidazole ring, which renders it non-absorbable. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. Other studies have also shown rifaximin to be an pregnane X receptor (PXR) activator. As PXR is responsible for inhibiting the proinflammatory transcription factor NF-kappa B (NF-κB) and is inhibited in inflammatory bowel disease (IBD), rifaximin may prove to be effective for the treatment of IBD.
Cơ Chế Tác Dụng : Rifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It is used to treat diarrhea caused by E. coli. Rifaximin acts by inhibiting RNA synthesis in susceptible bacteria by binding to the beta-subunit of bacterial deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase enzyme. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process.
Dược Động Học :
▧ Absorption :
Low absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast.
▧ Metabolism :
In vitro drug interactions studies have shown that rifaximin, at concentrations ranging from 2 to 200 ng/mL, did not inhibit human hepatic cytochrome P450 isoenzymes: 1A2, 2A6, 2B6, 2C9, 2C19, 2D6, 2E1, and 3A4. In an in vitro hepa-tocyte induction model, rifaximin was shown to induce cytochrome P450 3A4 (CYP3A4), an isoenzyme which rifampin is known to induce.
▧ Route of Elimination :
In a mass balance study, after administration of 400 mg 14C-rifaximin orally to healthy volunteers, of the 96.94% total recovery, 96.62% of the administered radioactivity was recovered in feces almost exclusively as the unchanged drug and 0.32% was recovered in urine mostly as metabolites with 0.03% as the unchanged drug.Rifaximin accounted for 18% of radioactivity in plasma. This suggests that the absorbed rifaximin undergoes metabolism with minimal renal excretion of the unchanged drug
▧ Half Life :
Approximately 6 hours.
Độc Tính : LD50 > 2 g/kg (orally, in rats)
Chỉ Định : For the treatment of patients (≥12 years of age) with travelers' diarrhea caused by noninvasive strains of Escherichia coli. Rifaximin is also designated an orphan drug by the Food and Drug Administration for the adjunctive treatment of hepatic encephalopathy to reduce blood ammonia concentrations and decrease severity of neurological manifestations.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Xifaxan 200 mg tablet
    Giá bán buôn : USD >8.97
    Đơn vị tính : tablet
  • Biệt dược thương mại : Xifaxan 550 mg tablet
    Giá bán buôn : USD >22.4
    Đơn vị tính : tablet
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Normix
  • Công ty :
    Sản phẩm biệt dược : Rifacol
  • Công ty :
    Sản phẩm biệt dược : Xifaxan
  • Công ty :
    Sản phẩm biệt dược : Xifaxsan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01220
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6436173
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508705
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02554
ChemSpider
http://www.chemspider.com/Chemical-Structure.4940837.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/65649-301-03
PharmGKB
http://www.pharmgkb.org/drug/PA164752443
Wikipedia
http://en.wikipedia.org/wiki/Rifaximin
RxList
http://www.rxlist.com/cgi/generic/xifaxan.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/xif1703.shtml
Drugs.com
http://www.drugs.com/cdi/rifaximin.html
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