Tìm theo
Benzoxazinorifamycin
Các tên gọi khác (2) :
  • KRM-1648
  • RLZ
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 129791-92-0
CTHH: C49H62N2O13Si
PTK: 915.1077
Benzoxazinorifamycin (trade name rifalazil) is a derivative of the antibiotic rifamycin. It is being investigated by ActivBiotics for the treatment of various bacterial infections.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C49H62N2O13Si
Phân tử khối
915.1077
Monoisotopic mass
914.402116613
InChI
InChI=1S/C49H62N2O13Si/c1-23-17-15-18-24(2)47(58)51-38-42(56)34-33(37-45(38)62-31-19-16-20-32(36(31)50-37)64-65(13,14)48(8,9)10)35-44(28(6)41(34)55)63-49(11,46(35)57)60-22-21-30(59-12)25(3)43(61-29(7)52)27(5)40(54)26(4)39(23)53/h15-23,25-27,30,39-40,43,50,53-55H,1-14H3/b17-15+,22-21+,24-18-,51-38+/t23-,25+,26+,27+,30-,39-,40+,43+,49-/m0/s1
InChI Key
InChIKey=CRYHGQHDLPBRAY-CGRNWXITSA-N
IUPAC Name
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-32-[(tert-butyldimethylsilyl)oxy]-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.1^{4,7}.0^{5,36}.0^{26,35}.0^{28,33}]octatriaconta-1,3,5(36),9,19,21,24,26(35),28,30,32-undecaen-13-yl acetate
Traditional IUPAC Name
(7S,11S,12R,13S,14R,15R,16R,17S,18S)-32-[(tert-butyldimethylsilyl)oxy]-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.1^{4,7}.0^{5,36}.0^{26,35}.0^{28,33}]octatriaconta-1,3,5(36),9,19,21,24,26(35),28,30,32-undecaen-13-yl acetate
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(=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(=O)C)[C@@H]1C)C1=C2NC2=C(C=CC=C2O[Si](C)(C)C(C)(C)C)O1
Độ hòa tan
2.28e-03 g/l
logP
6.25
logS
-5.6
pKa (strongest acidic)
6.95
pKa (Strongest Basic)
1.14
PSA
208.74 Å2
Refractivity
245.93 m3·mol-1
Polarizability
95.82 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
14
H Bond Donor Count
4
Physiological Charge
-1
Number of Rings
6
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Benzoxazinorifamycin represents a new generation of ansamycins that contain a unique four-ring structure. Originally benzoxazinorifamycin was developed as a therapeutic agent to replace rifampin as part of a multiple drug regimen in the treatment of tuberculosis. As a result of its superior antimicrobial activity and high intracellular levels, benzoxazinorifamycin has potential to treat indications caused by the intracellular pathogen, Chlamydia trachomatis, which causes non-gonococcal urethritis and cervicitis, often leading to pelvic inflammatory disease. Benzoxazinorifamycin also has potential to treat the related microorganism, Chlamydia pneumoniae, which may be involved in chronic inflammatory processes thought to be partly responsible for atherosclerosis. Due to its favourable antimicrobial spectrum and other positive attributes, benzoxazinorifamycin may also prove valuable in the treatment of gastric ulcer disease, caused by Helicobacter pylori, and antibiotic-associated colitis, the result of toxin production following the growth of Clostridium difficile in the colon. The potential value of benzoxazinorifamycin in the treatment of these indications will be assessed in human clinical trials.
Cơ Chế Tác Dụng : Benzoxazinorifamycin (trade name rifalazil) is a derivative of the antibiotic rifamycin. It is being investigated by ActivBiotics for the treatment of various bacterial infections. The potent antimycobacterial activity of benzoxazinorifamycin is due to inhibition of bacterial RNA polymerase.
Dược Động Học :

▧ Metabolism :
The major metabolites of benzoxazinorifamycin in human are 25-deacetyl-benzoxazinorifamycin and 32-hydroxy-benzoxazinorifamycin. The enzyme responsible for the benzoxazinorifamycin-25-deacetylation is a B-esterase while the enzyme responsible for the benzoxazinorifamycin-32-hydroxylation is CYP3A4.
Chỉ Định : Investigated for use/treatment in atherosclerosis, bacterial infection, and peripheral vascular disease.
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Rifalazil
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04934
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6540558
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=17396721
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02550
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