Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C51H64N4O13 |
| Molecular Weight | 941.0729 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(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(C)=O)[C@@H]1C)=C5OC6=C(N=C45)C(O)=CC(=C6)N7CCN(CC(C)C)CC7)C(O)=C3C
InChI
InChIKey=UEFHFKKWYKVLDC-HTQYORAHSA-N
InChI=1S/C51H64N4O13/c1-24(2)23-54-16-18-55(19-17-54)32-21-33(57)39-35(22-32)67-48-40(52-39)36-37-44(60)30(8)47-38(36)49(62)51(10,68-47)65-20-15-34(64-11)27(5)46(66-31(9)56)29(7)43(59)28(6)42(58)25(3)13-12-14-26(4)50(63)53-41(48)45(37)61/h12-15,20-22,24-25,27-29,34,42-43,46,57-60H,16-19,23H2,1-11H3,(H,53,63)/b13-12+,20-15+,26-14-/t25-,27+,28+,29+,34-,42-,43+,46+,51-/m0/s1
Rifalazil (also known as KRM-1648) is a derivative of the antibiotic rifamycin. This orally administered ansamycin is under evaluation for treatment of various bacterial infections. Rifalazil kills bacterial cells by blocking off the β-subunit in RNA polymerase. This drug was originally developed as a therapeutic agent to replace rifampin in the treatment of tuberculosis. It also showed potential to treat indications caused by chlamydia trachomatis and chlamydia pneumoniae. Furthermore, it has been suggested as a potential drug in the treatment of gastric ulcer disease (which is caused by Helicobacter pylori) and antibiotic-associated colitis. Phase II studies evaluated the efficacy and safety of this drug in patients with chlamydia trachomatis and chlamydia seropositive patients. A phase 3 study was initiated including chlamydia seropositive patients. However, the development of rifalazil was terminated in 2013 due to severe side effects.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [In vitro activities of new rifamycin derivatives against Mycobacterium tuberculosis and M. avium complex]. | 1990 Dec |
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| In vitro antimycobacterial activities of newly synthesized benzoxazinorifamycins. | 1991 Mar |
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| Chemotherapeutic efficacy of a newly synthesized benzoxazinorifamycin, KRM-1648, against Mycobacterium avium complex infection induced in mice. | 1992 Feb |
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| Therapeutic efficacy of the benzoxazinorifamycin KRM-1648 against experimental Mycobacterium avium infection induced in rabbits. | 1993 Apr |
|
| Synthesis and biological activity of 3'-hydroxy-5'-aminobenzoxazinorifamycin derivatives. | 1993 Jan |
|
| In vitro antimicrobial activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium avium complex, determined by the radiometric method. | 1993 Jan |
|
| Activity of KRM 1648 alone or in combination with ethambutol or clarithromycin against Mycobacterium avium in beige mouse model of disseminated infection. | 1994 Aug |
|
| Activities of the benzoxazinorifamycin KRM 1648 and ethambutol against Mycobacterium avium complex in vitro and in macrophages. | 1994 Aug |
|
| In vitro and in vivo antibacterial activities of KRM-1648 and KRM-1657, new rifamycin derivatives. | 1994 May |
|
| Activity of KRM-1648, a new benzoxazinorifamycin, against Mycobacterium tuberculosis in a murine model. | 1994 Oct |
|
| In vitro and in vivo activities of the benzoxazinorifamycin KRM-1648 against Mycobacterium tuberculosis. | 1995 Oct |
|
| New drugs for tuberculosis. | 1995 Sep |
|
| Chemotherapeutic activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium tuberculosis in C57BL/6 mice. | 1996 Apr |
|
| Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis. | 1996 Dec |
|
| How effective is KRM-1648 in treatment of disseminated Mycobacterium avium complex infections in beige mice? | 1996 Feb |
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| Activity of KRM-1648 alone or in combination with both ethambutol and kanamycin or clarithromycin against Mycobacterium intracellulare infections in beige mice. | 1996 Feb |
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| In vitro bactericidal and in vivo therapeutic activities of a new rifamycin derivative, KRM-1648, against Mycobacterium tuberculosis. | 1996 Feb |
|
| Activity of KRM-1648 in combination with isoniazid against Mycobacterium tuberculosis in a murine model. | 1996 Feb |
|
| Bacteriostatic and bactericidal activities of benzoxazinorifamycin KRM-1648 against Mycobacterium tuberculosis and Mycobacterium avium in human macrophages. | 1996 Jun |
|
| Comparative antimycobacterial activities of rifampin, rifapentine, and KRM-1648 against a collection of rifampin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations. | 1996 Nov |
|
| [Preclinical study of therapeutic agents used against Mycobacterium avium complex infections--with special reference to new macrolides and new quinolones]. | 1996 Sep |
|
| [In vivo activities of benzoxazinorifamycin KRM-1648, clarithromycin, and levofloxacin, or combination of KRM-1648 with diclofenac sodium against Mycobacterium avium infection induced in mice]. | 1997 Aug |
|
| Effect of Mycobacterium avium infection on the influx, accumulation, and efflux of KRM-1648 by human macrophages. | 1997 Fall |
|
| Evaluation of in vivo therapeutic efficacy of a new benzoxazinorifamycin, KRM-1648, in SCID mouse model for disseminated Mycobacterium avium complex infection. | 1998 Apr |
|
| [Therapeutic efficacy of benzoxazinorifamycin KRM-1648 against experimental murine tuberculosis: (1). A study on the efficacy of short course treatment with the intratracheal and intravenous infection model]. | 1998 Feb |
|
| Antimicrobial activities of benzoxazinorifamycin KRM-1648, clarithromycin and levofloxacin against intracellular Mycobacterium avium complex phagocytosed by murine peritoneal macrophages. | 1998 Jan |
|
| Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis. | 1998 Jul |
|
| Relationship between antimycobacterial activities of rifampicin, rifabutin and KRM-1648 and rpoB mutations of Mycobacterium tuberculosis. | 1998 Nov |
|
| Therapeutic effects of benzoxazinorifamycin KRM-1648 administered alone or in combination with a half-sized secretory leukocyte protease inhibitor or the nonsteroidal anti-inflammatory drug diclofenac sodium against Mycobacterium avium complex infection in mice. | 1999 Feb |
|
| [MICs and MBCs of levofloxacin, clarithromycin, and KRM-1648 for Mycobacterium tuberculosis and M. avium complex residing in MONO-MAC-6 human macrophage-like cell and A-549 human type II alveolar epithelial cell lines]. | 1999 Jul |
|
| Antimicrobial activities of benzoxazinorifamycin (KRM-1648) and clarithromycin against Mycobacterium avium-intracellulare complex within murine peritoneal macrophages, human macrophage-like cells and human alveolar epithelial cells. | 1999 Mar |
|
| Evaluation of rifapentine in long-term treatment regimens for tuberculosis in mice. | 1999 Oct |
|
| Safety and bactericidal activity of rifalazil in patients with pulmonary tuberculosis. | 2001 Jul |
|
| Antimicrobial activities of clarithromycin, gatifloxacin and sitafloxacin, in combination with various antimycobacterial drugs against extracellular and intramacrophage Mycobacterium avium complex. | 2002 Feb |
|
| Fluoroquinolones: an important class of antibiotics against tuberculosis. | 2006 |
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FDA ORPHAN DRUG |
122699
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NCI_THESAURUS |
C258
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C152213
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DB04934
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m9609
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7674
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DTXSID301030497
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II-70
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RIFALAZIL
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SUB10305MIG
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S1976TE8QK
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CHEMBL236297
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129791-92-0
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100000080559
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ACTIVE MOIETY
