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182760-06-1,MFCD00941002
Catalog No.:AA00241M

182760-06-1 | Ravuconazole

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1mg
≥98%
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$63.00   $44.00
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250mg
98%
in stock  
$85.00   $60.00
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1g
98%
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$242.00   $170.00
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5g
98%
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$749.00   $524.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00241M
Chemical Name:
Ravuconazole
CAS Number:
182760-06-1
Molecular Formula:
C22H17F2N5OS
Molecular Weight:
437.4651
MDL Number:
MFCD00941002
SMILES:
N#Cc1ccc(cc1)c1csc(n1)[C@@H]([C@@](c1ccc(cc1F)F)(Cn1cncn1)O)C
Properties
Computed Properties
 
Complexity:
657  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
6  
XLogP3:
3.5  

Downstream Synthesis Route

[1]Locationinpatent:experimentalpartXu,Lin;Muller,MarcR.;Yu,Xiong;Zhu,Bao-Quan[SyntheticCommunications,2009,vol.39,#9,p.1611-1625]

[2]Tamura,Keiji;Kumagai,Naoya;Shibasaki,Masakatsu[JournalofOrganicChemistry,2014,vol.79,#7,p.3272-3278]

[3]Tsuruoka,Akihiko;Kaku,Yumiko;Kakinuma,Hiroyuki;Tsukada,Itaru;Yanagisawa,Manabu;Nara,Kazumasa;Naito,Toshihiko[ChemicalandPharmaceuticalBulletin,1998,vol.46,#4,p.623-630]

[4]CurrentPatentAssignee:METROCHEMAPIPRIVATE-WO2021/245590,2021,A1Locationinpatent:Page/Pagecolumn22-23

[5]CurrentPatentAssignee:METROCHEMAPIPRIVATE-WO2021/245590,2021,A1Locationinpatent:Page/Pagecolumn22-23

[1]Tsuruoka,Akihiko;Kaku,Yumiko;Kakinuma,Hiroyuki;Tsukada,Itaru;Yanagisawa,Manabu;Nara,Kazumasa;Naito,Toshihiko[ChemicalandPharmaceuticalBulletin,1998,vol.46,#4,p.623-630]

[1]Tsuruoka,Akihiko;Kaku,Yumiko;Kakinuma,Hiroyuki;Tsukada,Itaru;Yanagisawa,Manabu;Nara,Kazumasa;Naito,Toshihiko[ChemicalandPharmaceuticalBulletin,1998,vol.46,#4,p.623-630]

45952-56-5    182760-06-1   
1-(2R,3R)-3-4-(4-Cyano-phenyl)-thiazol-2-yl-2-(2,4-difluoro-phenyl)-2-hydroxy-butyl-4-(4-hydroxy-3,5-dimethyl-benzyl)-1H-1,2,4triazol-4-ium;bromide 

[1]Ohwada,Jun;Murasaki,Chikako;Yamazaki,Toshikazu;Ichihara,Shigeyasu;Umeda,Isao;Shimma,Nobuo[BioorganicandMedicinalChemistryLetters,2002,vol.12,#19,p.2775-2780]

182760-06-1    241479-84-5   
4-{4-(<i>tert</i>-butoxycarbonyl-methyl-amino)-acetoxy-3,5-dimethyl-benzyl}-1-3-4-(4-cyano-phenyl)-thiazol-2-yl-2-(2,4-difluoro-phenyl)-2-hydroxy-butyl-1<i>H</i>-1,2,4triazol-4-ium;bromide 

[1]Ohwada,Jun;Murasaki,Chikako;Yamazaki,Toshikazu;Ichihara,Shigeyasu;Umeda,Isao;Shimma,Nobuo[BioorganicandMedicinalChemistryLetters,2002,vol.12,#19,p.2775-2780]

Literature

Title: Design, synthesis, and structure-activity relationship studies of novel fused heterocycles-linked triazoles with good activity and water solubility.

Journal: Journal of medicinal chemistry 20140508

Title: Hybrids of ravuconazole: synthesis and biological evaluation.

Journal: European journal of medicinal chemistry 20120801

Title: Newer antifungal agents.

Journal: Expert review of anti-infective therapy 20110301

Title: In vitro and in vivo antifungal susceptibilities of the Mucoralean fungus Cunninghamella.

Journal: Antimicrobial agents and chemotherapy 20101101

Title: [Recent advances in the study of new antifungal lead compounds].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100801

Title: Antifungal susceptibility profile of human-pathogenic species of Lichtheimia.

Journal: Antimicrobial agents and chemotherapy 20100701

Title: Onychomycosis.

Journal: Clinics in dermatology 20100304

Title: Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole.

Journal: Current opinion in investigational drugs (London, England : 2000) 20100201

Title: In vitro interactions between antifungals and immunosuppressive drugs against zygomycetes.

Journal: Antimicrobial agents and chemotherapy 20090801

Title: Activity of posaconazole and other antifungal agents against Mucorales strains identified by sequencing of internal transcribed spacers.

Journal: Antimicrobial agents and chemotherapy 20090401

Title: Trends in species distribution and susceptibility of bloodstream isolates of Candida collected in Monterrey, Mexico, to seven antifungal agents: results of a 3-year (2004 to 2007) surveillance study.

Journal: Journal of clinical microbiology 20080901

Title: In vitro antifungal susceptibility and molecular characterization of clinical isolates of Fusarium verticillioides (F. moniliforme) and Fusarium thapsinum.

Journal: Antimicrobial agents and chemotherapy 20080601

Title: Discovery of novel indazole-linked triazoles as antifungal agents.

Journal: Bioorganic & medicinal chemistry letters 20070615

Title: Antifungal susceptibilities of the species of the Pseudallescheria boydii complex.

Journal: Antimicrobial agents and chemotherapy 20061201

Title: Multi-azole resistance in Aspergillus fumigatus.

Journal: International journal of antimicrobial agents 20061101

Title: Triazole-polyene antagonism in experimental invasive pulmonary aspergillosis: in vitro and in vivo correlation.

Journal: The Journal of infectious diseases 20061001

Title: Newer triazole antifungal agents: pharmacology, spectrum, clinical efficacy and limitations.

Journal: Expert opinion on investigational drugs 20060601

Title: In vitro activities of new and conventional antimycotics against fluconazole-susceptible and non-susceptible Brazilian Candida spp. isolates.

Journal: Mycoses 20060501

Title: The effect of ravuconazole on the pharmacokinetics of nelfinavir in healthy male volunteers.

Journal: Journal of clinical pharmacology 20060201

Title: In vitro activity of ravuconazole against 923 clinical isolates of nondermatophyte filamentous fungi.

Journal: Antimicrobial agents and chemotherapy 20051201

Title: Compartmental pharmacokinetics and tissue distribution of the antifungal triazole ravuconazole following intravenous administration of its di-lysine phosphoester prodrug (BMS-379224) in rabbits.

Journal: The Journal of antimicrobial chemotherapy 20051101

Title: Advances in antifungal therapy.

Journal: The Pediatric infectious disease journal 20051001

Title: Antifungal agents in children.

Journal: Pediatric clinics of North America 20050601

Title: In vitro activities of new and established triazoles against opportunistic filamentous and dimorphic fungi.

Journal: Medical mycology 20050501

Title: In vitro activities of posaconazole, ravuconazole, terbinafine, itraconazole and fluconazole against dermatophyte, yeast and non-dermatophyte species.

Journal: Medical mycology 20050301

Title: Clinical evaluation of the Sensititre YeastOne colorimetric antifungal plate for antifungal susceptibility testing of the new triazoles voriconazole, posaconazole, and ravuconazole.

Journal: Journal of clinical microbiology 20041001

Title: Effects of several antifungal drug combinations against clinical and environmental isolates of Cryptococcus neoformans from China.

Journal: Mycoses 20040801

Title: In vitro susceptibilities of rare Candida bloodstream isolates to ravuconazole and three comparative antifungal agents.

Journal: Diagnostic microbiology and infectious disease 20040201

Title: In vitro interactions of licensed and novel antifungal drugs against Fusarium spp.

Journal: Diagnostic microbiology and infectious disease 20040101

Title: In vitro activity of ravuconazole against Zygomycetes, Scedosporium and Fusarium isolates.

Journal: Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20031201

Title: Phosphonooxymethyl prodrugs of the broad spectrum antifungal azole, ravuconazole: synthesis and biological properties.

Journal: Bioorganic & medicinal chemistry letters 20031103

Title: Activities of caspofungin, itraconazole, posaconazole, ravuconazole, voriconazole, and amphotericin B against 448 recent clinical isolates of filamentous fungi.

Journal: Journal of clinical microbiology 20030801

Title: New antifungal agents.

Journal: Dermatologic clinics 20030701

Title: Combination therapy in treatment of experimental pulmonary aspergillosis: synergistic interaction between an antifungal triazole and an echinocandin.

Journal: The Journal of infectious diseases 20030615

Title: In vivo pharmacodynamics of a new triazole, ravuconazole, in a murine candidiasis model.

Journal: Antimicrobial agents and chemotherapy 20030401

Title: In vitro and in vivo activities of ravuconazole on Trypanosoma cruzi, the causative agent of Chagas disease.

Journal: International journal of antimicrobial agents 20030101

Title: [Present status and future prospects of azole antifungal agents in Japan].

Journal: The Japanese journal of antibiotics 20021201

Title: Laboratory evaluation of new antifungal agents against rare and refractory mycoses.

Journal: Current opinion in infectious diseases 20021201

Title: Synthesis of novel water soluble benzylazolium prodrugs of lipophilic azole antifungals.

Journal: Bioorganic & medicinal chemistry letters 20021007

Title: In vitro activity of three new triazoles and one echinocandin against Candida bloodstream isolates from cancer patients.

Journal: The Journal of antimicrobial chemotherapy 20020701

Title: In vitro activities of ravuconazole and voriconazole compared with those of four approved systemic antifungal agents against 6,970 clinical isolates of Candida spp.

Journal: Antimicrobial agents and chemotherapy 20020601

Title: Clinical evaluation of a frozen commercially prepared microdilution panel for antifungal susceptibility testing of seven antifungal agents, including the new triazoles posaconazole, ravuconazole, and voriconazole.

Journal: Journal of clinical microbiology 20020501

Title: Antifungal activities of posaconazole, ravuconazole, and voriconazole compared to those of itraconazole and amphotericin B against 239 clinical isolates of Aspergillus spp. and other filamentous fungi: report from SENTRY Antimicrobial Surveillance Program, 2000.

Journal: Antimicrobial agents and chemotherapy 20020401

Title: Ravuconazole Eisai/Bristol-Myers Squibb.

Journal: Current opinion in investigational drugs (London, England : 2000) 20020401

Title: Efficacy of ravuconazole in treatment of systemic murine histoplasmosis.

Journal: Antimicrobial agents and chemotherapy 20020301

Title: Penetration of ravuconazole, a new triazole antifungal, into rat tissues.

Journal: Chemotherapy 20020301

Title: Efficacy of ravuconazole (BMS-207147) in a guinea pig model of disseminated aspergillosis.

Journal: The Journal of antimicrobial chemotherapy 20020201

Title: Antifungals: what's in the pipeline.

Journal: Current opinion in microbiology 20011001

Title: In vitro activities of four novel triazoles against Scedosporium spp.

Journal: Antimicrobial agents and chemotherapy 20010701

Title: Effect of ravuconazole, a new triazole antifungal, in a rat intraabdominal abscess model.

Journal: Chemotherapy 20010101

Title: Efficacies of two new antifungal agents, the triazole ravuconazole and the echinocandin LY-303366, in an experimental model of invasive aspergillosis.

Journal: Antimicrobial agents and chemotherapy 20001201

Title: In vitro activity of the new triazole BMS-207147 against Aspergillus species in comparison with itraconazole and amphotericin B.

Journal: Antimicrobial agents and chemotherapy 20000201

Title: In vitro antifungal activity of BMS-207147 and itraconazole against yeast strains that are non-susceptible to fluconazole.

Journal: Diagnostic microbiology and infectious disease 19991001

Title: In vitro susceptibilities of Candida bloodstream isolates to the new triazole antifungal agents BMS-207147, Sch 56592, and voriconazole.

Journal: Antimicrobial agents and chemotherapy 19981201

Title: New azole antifungals. 2. Synthesis and antifungal activity of heterocyclecarboxamide derivatives of 3-amino-2-aryl-1-azolyl-2-butanol.

Journal: Journal of medicinal chemistry 19980521

Title: New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones.

Journal: Journal of medicinal chemistry 19980521

Title: In vitro activity of a new oral triazole, BMS-207147 (ER-30346).

Journal: Antimicrobial agents and chemotherapy 19980201

Title: In vitro and in vivo antifungal activities of ER-30346, a novel oral triazole with a broad antifungal spectrum.

Journal: Antimicrobial agents and chemotherapy 19961001

Title: Efficacy of ER-30346, a novel oral triazole antifungal agent, in experimental models of aspergillosis, candidiasis, and cryptococcosis.

Journal: Antimicrobial agents and chemotherapy 19961001

Title: Hata K, et al. In vitro and in vivo antifungal activities of ER-30346, a novel oral triazole with a broad antifungal spectrum.Antimicrob Agents Chemother. 1996 Oct;40(10):2237-42.

Title: Fung-Tomc JC, et al. In vitro activity of a new oral triazole, BMS-207147 (ER-30346)Antimicrob Agents Chemother. 1998 Feb;42(2):313-8.

Title: Hata K, et al. Efficacy of ER-30346, a novel oral triazole antifungal agent, in experimental models of aspergillosis, candidiasis, and cryptococcosis.Antimicrob Agents Chemother. 1996 Oct;40(10):2243-7.

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