Home Imidazoles 72559-06-9
72559-06-9,MFCD00866816
Catalog No.:AA00IC7A

72559-06-9 | Spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione,16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-,[9S-(9R*,12E,14R*,15S*,16R*,17S*,18S*,19S*,20R*,21R*,22E,24Z)]-

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00IC7A
Chemical Name:
Spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione,16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-,[9S-(9R*,12E,14R*,15S*,16R*,17S*,18S*,19S*,20R*,21R*,22E,24Z)]-
CAS Number:
72559-06-9
Molecular Formula:
C46H62N4O11
Molecular Weight:
847.0047
MDL Number:
MFCD00866816
SMILES:
CO[C@H]1C=CO[C@@]2(C)Oc3c(C2=O)c2C4=NC5(NC4=C(C(=O)c2c(c3C)O)NC(=O)C(=CC=C[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)C)CCN(CC5)CC(C)C
Properties
Computed Properties
 
Complexity:
2110  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
3  
Heavy Atom Count:
61  
Hydrogen Bond Acceptor Count:
14  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
5  
XLogP3:
4.7  

Downstream Synthesis Route
72559-06-9   
25-hydroxy-rifabutin 

[1]Patent:WO2004/5298,2004,A1.Locationinpatent:Page17-19

[2]JournalofMolecularStructure,2001,vol.563-564,p.61-78

72559-06-9    108-24-7   
21-O-acetyl-rifabutin 

[1]JournalofMolecularStructure,2001,vol.563-564,p.61-78

72559-06-9    75-36-5   
N'-acetyl-rifabutin 

[1]Patent:WO2004/5298,2004,A1.Locationinpatent:Page25-26

72559-06-9   
rifabutinol 

[1]Patent:WO2004/5298,2004,A1.Locationinpatent:Page11

72559-06-9   
rifabutinN-oxide 

[1]Patent:WO2004/5298,2004,A1.Locationinpatent:Page22-24

Literature

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Title: Efficacy of rifabutin-loaded microspheres for treatment of Mycobacterium avium-infected macrophages and mice.

Journal: Drug delivery 20070301

Title: In-vitro activity of rifabutin against rifampicin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations.

Journal: Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20040701

Title: The activity of grepafloxacin in two murine models of Mycobacterium avium infection.

Journal: Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20040601

Title: New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.

Journal: The Journal of antimicrobial chemotherapy 20040101

Title: Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.

Journal: Antimicrobial agents and chemotherapy 20030101

Title: In vitro effect of short-term exposure to two synthetic peptides, alone or in combination with clarithromycin or rifabutin, on Cryptosporidium parvum infectivity.

Journal: Peptides 20020501

Title: CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit.

Journal: Biopharmaceutics & drug disposition 20010501

Title: Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium.

Journal: Antimicrobial agents and chemotherapy 20010101

Title: Activity of rifapentine and its metabolite 25-O-desacetylrifapentine compared with rifampicin and rifabutin against Mycobacterium tuberculosis, Mycobacterium africanum, Mycobacterium bovis and M. bovis BCG.

Journal: The Journal of antimicrobial chemotherapy 20001001

Title: Therapeutic efficacy of liposomal rifabutin in a Mycobacterium avium model of infection.

Journal: Antimicrobial agents and chemotherapy 20000901

Title: Activity of nitazoxanide alone and in combination with azithromycin and rifabutin against Cryptosporidium parvum in cell culture.

Journal: The Journal of antimicrobial chemotherapy 20000401

Title: Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.

Journal: Biochemical pharmacology 20000201

Title: In-vitro activity of rifabutin and albendazole singly and in combination with other clinically used antimicrobial agents against Pneumocystis carinii.

Journal: The Journal of antimicrobial chemotherapy 19991101

Title: In vitro anticryptosporidial activity of ranalexin alone and in combination with other peptides and with hydrophobic antibiotics.

Journal: European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 19991101

Title: Development of a firefly luciferase-based assay for determining antimicrobial susceptibility of Mycobacterium avium subsp. paratuberculosis.

Journal: Journal of clinical microbiology 19990201

Title: Activities of eighteen antimicrobial regimens against Mycobacterium avium infection in beige mice.

Journal: Microbial drug resistance (Larchmont, N.Y.) 19990101

Title: Relationship between antimycobacterial activities of rifampicin, rifabutin and KRM-1648 and rpoB mutations of Mycobacterium tuberculosis.

Journal: The Journal of antimicrobial chemotherapy 19981101

Title: In vitro activity of antimicrobial combinations against clinical isolates of susceptible and resistant Mycobacterium tuberculosis.

Journal: The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 19980801

Title: Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 19980701

Title: [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].

Journal: Kekkaku : [Tuberculosis] 19980201

Title: Rapid drug susceptibility of Mycobacterium avium complex using a fluorescence quenching method.

Journal: Journal of chemotherapy (Florence, Italy) 19970801

Title: Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

Journal: Antimicrobial agents and chemotherapy 19970501

Title: Metabolism of rifabutin in human enterocyte and liver microsomes: kinetic parameters, identification of enzyme systems, and drug interactions with macrolides and antifungal agents.

Journal: Clinical pharmacology and therapeutics 19970501

Title: Clinically used antimicrobial drugs against experimental pneumocystosis, singly and in combination: analysis of drug interactions and efficacies.

Journal: Antimicrobial agents and chemotherapy 19970201

Title: Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 19961201

Title: In vitro and in vivo effects of rifabutin alone or combined with atovaquone against Toxoplasma gondii.

Journal: Antimicrobial agents and chemotherapy 19960901

Title: Comparative activity of azithromycin against clinical isolates of mycobacteria.

Journal: The Journal of antimicrobial chemotherapy 19960901

Title: Susceptibility testing of Mycobacterium avium complex isolates.

Journal: Antimicrobial agents and chemotherapy 19960801

Title: Rifapentine is active in vitro and in vivo against Toxoplasma gondii.

Journal: Antimicrobial agents and chemotherapy 19960601

Title: Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.

Journal: European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 19960501

Title: Chemotherapeutic activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium tuberculosis in C57BL/6 mice.

Journal: Tubercle and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 19960401

Title: Activity of rifabutin, clarithromycin, ethambutol, sparfloxacin and amikacin, alone and in combination, against Mycobacterium avium complex in human macrophages.

Journal: The Journal of antimicrobial chemotherapy 19960301

Title: How effective is KRM-1648 in treatment of disseminated Mycobacterium avium complex infections in beige mice?

Journal: Antimicrobial agents and chemotherapy 19960201

Title: Rifamycin resistance in mycobacteria.

Journal: Research in microbiology 19960101

Title: Evaluation of the activities of rifabutin combined with atovaquone or low-dose of cotrimoxazole for prevention of pneumocystosis and toxoplasmosis in a dual infection rat model.

Journal: The Journal of eukaryotic microbiology 19960101

Title: In vitro and in vivo activities of the benzoxazinorifamycin KRM-1648 against Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 19951001

Title: New drugs for tuberculosis.

Journal: The European respiratory journal. Supplement 19950901

Title: Activity of seven antimicrobial agents, alone and in combination, against AIDS-associated isolates of Mycobacterium avium complex.

Journal: The Journal of antimicrobial chemotherapy 19950901

Title: In-vitro and intracellular activity of rifabutin on drug-susceptible and multiple drug-resistant (MDR) tubercle bacilli.

Journal: The Journal of antimicrobial chemotherapy 19950801

Title: [Extra and intracellular activity of dirithromycin against Mycobacterium avium].

Journal: Pathologie-biologie 19950401

Title: Comparison of activities of fluoroquinolones in murine macrophages infected with Mycobacterium tuberculosis.

Journal: Antimicrobial agents and chemotherapy 19950301

Title: Activities of rifabutin, clarithromycin, and ethambutol against two virulent strains of Mycobacterium avium in a mouse model.

Journal: Antimicrobial agents and chemotherapy 19950301

Title: Mutation position and type of substitution in the beta-subunit of the RNA polymerase influence in-vitro activity of rifamycins in rifampicin-resistant Mycobacterium tuberculosis.

Journal: The Journal of antimicrobial chemotherapy 19950201

Title: Clinical experience with rifabutin in the treatment of mycobacterial infections.

Journal: Scandinavian journal of infectious diseases. Supplementum 19950101

Title: [New drugs against tuberculosis and nontuberculous mycobacterial infections: a review].

Journal: Kekkaku : [Tuberculosis] 19941101

Title: Effectiveness of various antimicrobial agents against Mycobacterium avium complex in the beige mouse model.

Journal: Antimicrobial agents and chemotherapy 19941101

Title: A bone marrow-derived murine macrophage model for evaluating efficacy of antimycobacterial drugs under relevant physiological conditions.

Journal: Antimicrobial agents and chemotherapy 19941101

Title: Activity of KRM-1648, a new benzoxazinorifamycin, against Mycobacterium tuberculosis in a murine model.

Journal: Antimicrobial agents and chemotherapy 19941001

Title: In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.

Journal: Antimicrobial agents and chemotherapy 19941001

Title: Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy.

Journal: Drugs 19940601

Title: In vitro and in vivo antibacterial activities of KRM-1648 and KRM-1657, new rifamycin derivatives.

Journal: Antimicrobial agents and chemotherapy 19940501

Title: Rifabutin and sparfloxacin but not azithromycin inhibit binding of Mycobacterium avium complex to HT-29 intestinal mucosal cells.

Journal: Antimicrobial agents and chemotherapy 19940501

Title: Rifabutin is active in murine models of toxoplasmosis.

Journal: Antimicrobial agents and chemotherapy 19940301

Title: Comparative in vivo activities of rifabutin and rifapentine against Mycobacterium avium complex.

Journal: Antimicrobial agents and chemotherapy 19940201

Title: Effectiveness of rifampin, rifabutin, and rifapentine for preventive therapy of tuberculosis in mice.

Journal: The American review of respiratory disease 19931201

Title: Anti-Mycobacterium avium activity of quinolones: in vitro activities.

Journal: Antimicrobial agents and chemotherapy 19930901

Title: Azithromycin, rifabutin, and rifapentine for treatment and prophylaxis of Mycobacterium avium complex in rats treated with cyclosporine.

Journal: Antimicrobial agents and chemotherapy 19930301

Title: In vitro antimicrobial activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium avium complex, determined by the radiometric method.

Journal: Antimicrobial agents and chemotherapy 19930101

Title: Synthesis and biological activity of 3'-hydroxy-5'-aminobenzoxazinorifamycin derivatives.

Journal: Chemical & pharmaceutical bulletin 19930101

Title: Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?

Journal: Zentralblatt fur Bakteriologie : international journal of medical microbiology 19921201

Title: Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.

Journal: Antimicrobial agents and chemotherapy 19920901

Title: Activity of azithromycin against Mycobacterium avium infection in beige mice.

Journal: Antimicrobial agents and chemotherapy 19920801

Title: Chlorpromazine: a drug potentially useful for treating mycobacterial infections.

Journal: Chemotherapy 19920101

Title: Activity in vitro of rifabutin, FCE 22807, rifapentine, and rifampin against Mycobacterium microti and M. tuberculosis and their penetration into mouse peritoneal macrophages.

Journal: The American review of respiratory disease 19920101

Title: In vivo activities of newer rifamycin analogs against Mycobacterium avium infection.

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Title: [Activity of antibiotics against pigmented and unpigmented variants of Mycobacterium avium-intracellulare].

Journal: Pathologie-biologie 19910501

Title: In vitro antimycobacterial activities of newly synthesized benzoxazinorifamycins.

Journal: Antimicrobial agents and chemotherapy 19910301

Title: Oxazolidinones, a new class of synthetic antituberculosis agent. In vitro and in vivo activities of DuP-721 against Mycobacterium tuberculosis.

Journal: Diagnostic microbiology and infectious disease 19910101

Title: [In vivo activities of new rifamycin derivatives against mycobacteria].

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Title: [In vitro activities of new rifamycin derivatives against Mycobacterium tuberculosis and M. avium complex].

Journal: Kekkaku : [Tuberculosis] 19901201

Title: Effect of rifabutin on disseminated Mycobacterium avium infections in thymectomized, CD4 T-cell-deficient mice.

Journal: Antimicrobial agents and chemotherapy 19900901

Title: Activities of clarithromycin, sulfisoxazole, and rifabutin against Mycobacterium avium complex multiplication within human macrophages.

Journal: Antimicrobial agents and chemotherapy 19900801

Title: In vitro activities against mycobacteria of two long-acting rifamycins, FCE22807 and CGP40/469A (SPA-S-565).

Journal: Tubercle 19900601

Title: [Activity of azithromycin and roxithromycin alone or in combination against Mycobacterium avium and Mycobacterium xenopi].

Journal: Pathologie-biologie 19900501

Title: Bactericidal activity in vitro of various rifamycins against Mycobacterium avium and Mycobacterium tuberculosis.

Journal: The American review of respiratory disease 19900301

Title: Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.

Journal: The Journal of antimicrobial chemotherapy 19881001

Title: In vitro effectiveness of a combination of zidovudine and ansamycin against human immunodeficiency virus.

Journal: The Journal of infectious diseases 19881001

Title: Comparative in vitro and in vivo activity of rifabutin and rifampicin against Mycobacterium avium complex.

Journal: Tubercle 19880901

Title: New antibacterial drugs for the treatment of mycobacterial disease in man.

Journal: British medical bulletin 19880701

Title: Interaction between rifabutin and human immunodeficiency virus type 1: inhibition of replication, cytopathic effect, and reverse transcriptase in vitro.

Journal: Antimicrobial agents and chemotherapy 19880501

Title: Qualitative and quantitative drug-susceptibility tests in mycobacteriology.

Journal: The American review of respiratory disease 19880501

Title: Combinations of rifampin or rifabutine plus ethambutol against Mycobacterium avium complex. Bactericidal synergistic, and bacteriostatic additive or synergistic effects.

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Title: Rifabutine: minimal inhibitory and bactericidal concentrations for Mycobacterium tuberculosis.

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Title: In vitro activity of antimicrobial agents against mycobacteria.

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Title: Action of antituberculous and beta-lactam drugs (including imipenem) against extra- and intra-cellularly growing Mycobacterium avium-intracellulare.

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Title: In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.

Journal: Diagnostic microbiology and infectious disease 19871101

Title: In vitro activity of new rifamycins against rifampicin-resistant M. tuberculosis and MAIS-complex mycobacteria.

Journal: Tubercle 19870901

Title: Activity of rifabutin alone or in combination with clofazimine or ethambutol or both against acute and chronic experimental Mycobacterium intracellulare infections.

Journal: The American review of respiratory disease 19870801

Title: Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.

Journal: Drugs under experimental and clinical research 19870101

Title: Rifabutine inhibits HTLV-III.

Journal: Lancet (London, England) 19860111

Title: Determination of ansamycin MICs for Mycobacterium avium complex in liquid medium by radiometric and conventional methods.

Journal: Antimicrobial agents and chemotherapy 19851001

Title: Determination of in vitro susceptibility of mycobacteria to ansamycin.

Journal: The American review of respiratory disease 19850901

Title: Comparative in vitro activities of MDL 473, rifampin, and ansamycin against Mycobacterium intracellulare.

Journal: Antimicrobial agents and chemotherapy 19850901

Title: Activity of the spiropiperidyl rifamycin LM 427 on rifampicin resistant Mycobacterium tuberculosis.

Journal: Giornale italiano di chemioterapia 19840101

Title: LM 427, a new spiropiperidylrifamycin: in vitro and in vivo studies.

Journal: The Journal of antibiotics 19831101

Title: In vitro susceptibility of Mycobacterium avium complex and Mycobacterium tuberculosis strains to a spiro-piperidyl rifamycin.

Journal: The American review of respiratory disease 19820901

Title: Biological activity of a new class of rifamycins. Spiro-piperidyl-rifamycins.

Journal: The Journal of antibiotics 19801001

Title: Review Article: Rifabutin in the Treatment of Refractory Helicobacter pylori InfectionJ. P. Gisbert, X. Calvet Issue Alimentary Pharmacology & Therapeutics Volume 35, Issue 2, pages 209-221, January 2012

Title: Vourvahis M, Davis J, Wang R, Layton G, Choo HW, Chong CL, Tawadrous M.Effect of rifampin and rifabutin on the pharmacokinetics of lersivirine and effect of lersivirine on the pharmacokinetics of rifabutin and 25-o-desacetyl-rifabutin in healthy subjects.Antimicrob Agents Chemother. 2012 Aug;56(8):4303-9.

Title: Gisbert JP, Castro-Fernandez M, Perez-Aisa A, Cosme A, Molina-Infante J, Rodrigo L, Modolell I, Cabriada JL, Gisbert JL, Lamas E, Marcos E, Calvet X.Fourth-line rescue therapy with rifabutin in patients with three Helicobacter pylori eradication failures.Aliment Pharmacol Ther. 2012 Apr;35(8):941-7. doi: 10.1111/j.1365-2036.2012.05053.x.

Title: Gisbert JP, Calvet X.Review article: rifabutin in the treatment of refractory Helicobacter pylori infection.Aliment Pharmacol Ther. 2012 Jan;35(2):209-21. doi: 10.1111/j.1365-2036.2011.04937.x.

Title: Horne DJ, Spitters C, Narita M.Experience with rifabutin replacing rifampin in the treatment of tuberculosis.Int J Tuberc Lung Dis. 2011 Nov;15(11):1485-9, i.

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Related Products of 72559-06-9
Tags:72559-06-9 Molecular Formula|72559-06-9 MDL|72559-06-9 SMILES|72559-06-9 Spiro[9,4-(epoxypentadeca[1,11,13]trienimino)-2H-furo[2',3':7,8]naphth[1,2-d]imidazole-2,4'-piperidine]-5,10,26(3H,9H)-trione,16-(acetyloxy)-6,18,20-trihydroxy-14-methoxy-7,9,15,17,19,21,25-heptamethyl-1'-(2-methylpropyl)-,[9S-(9R*,12E,14R*,15S*,16R*,17S*,18S*,19S*,20R*,21R*,22E,24Z)]-