Drug Details

General Information of the Drug (ID: DR2271)
Name
Posaconazole
Synonyms
Posaconazole; 171228-49-2; Noxafil; Sch 56592; SCH56592; SCH-56592; Posaconazole SP; Schering 56592; UNII-6TK1G07BHZ; 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one; 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-5-(2,4-DIFLUOROPHENYL)TETRAHYDROFURAN-3-YL)METHOXY)PHENYL)PIPERAZIN-1-YL)PHENYL)-1-((2S,3S)-2-HYDROXYPENTAN-3-YL)-1H-1,2,4-TRIAZOL-5(4H)-ONE; 6TK1G07BHZ; CHEMBL1397; CHEBI:64355; 2,5-anhydro-1,3,4-trideoxy-2-(2,4-difluorophenyl)-4-({4-[4-(4-{1-[(2S,3S)-2-hydroxypentan-3-yl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}phenyl)piperazin-1-yl]phenoxy}methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol; pasaconazole; Posaconazole [USAN:INN:BAN]; HSDB 7421; C37H42F2N8O4; 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)tetrahydrofuran-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxy-propyl]-1,2,4-triazol-3-one; Noxafil (TN); Posaconazole solution; cc-165; SCHEMBL991747; Posaconazole (JAN/USAN/INN); DTXSID6049066; GTPL11428; AMY30591; BCP01102; ZINC3938482; BDBM50181473; CP0094; MFCD00941162; MMV688774; s1257; AKOS005145917; AC-1350; ACN-040495; CCG-270387; CS-0998; DB01263; KS-1413; PB30668; NCGC00274060-02; HY-17373; M842; Posaconazole in combination with MGCD290; AB0015409; P2477; SW219391-1; D02555; P-7020; Q-4359; AB01274762-01; AB01274762_02; Posaconazole, VETRANAL(TM), analytical standard; 228P492; Q906453; Posaconazole, Antibiotic for Culture Media Use Only; Posaconazole solution, 2.0 mg/mL in methanol, ampule of 1 mL, certified reference material; 1-((1S,2S)-1-Ethyl-2-hydroxypropyl)-4-{4-[4-(4-{[(5S,3R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazolylmethyl)oxolan-3-yl]methoxy}phenyl)piperazinyl]phenyl}-1,2,4-triazolin-5-one; 2,5-anhydro-1,3,4-trideoxy-2-(2,4-difluorophenyl)-4-({4-[4-(4-{1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}phenyl)piperazin-1-yl]phenoxy}methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol; 3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl)methoxy)phenyl)-1-piperazinyl)phenyl)-2-(1-ethyl-2-hydroxypropyl)-2,4-dihydro-, (3R-(3alpha(1S*,2S*),5alpha))-; 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)-tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-((2S,3S)-2-hydroxypentan-3-yl)-2H-1,2,4-triazol-3(4H)-one; 4-(4-(4-(4-(((3R,5R)-5-(3,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-hydroxypentan-3-yl)-1H-1,2,4-triazol-5(4H)-one; 4-(4-(4-(4-(((5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)-tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-((2S,3S)-2-hydroxypentan-3-yl)-2H-1,2,4-triazol-3(4H)-one; 4-(p-(4-(p-(((3R,5R)-5-(2,4-Difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furyl)methoxy)phenyl)-1-piperazinyl)phenyl)-1-((1S,2S)-1-ethyl-2-hydroxypropyl)-delta(sup 2)-1,2,4-triazolin-5-one; 4-[4-(4-{4-[(R)-5-(2,4-difluoro-phenyl)-5-(4,5-dihydro-[1,2,4]triazol-1-ylmethyl)-tetrahydro-furan-3-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-2-((1S,2S)-1-ethyl-2-hydroxy-propyl)-2,4-dihydro-[1,2,4]triazol-3-one; D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-((4-(4-(4-(1-((1S,2S)-1-etyl-2-hydroxypropyl)-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl)phenyl)-1-piperazinyl)phenoxy)methyl)-1-(1H-1,2,4-triazol-1-yl)-; PCZ
    Click to Show/Hide
Molecular Type
Small molecule
Disease Aspergillosis [ICD-11: 1F20] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
96% of drug becomes completely available to its intended biological destination(s)
Clearance
The drug present in the plasma can be removed from the body at the rate of 4.3 mL/min/kg
Elimination
0.1% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 12;) of 35 hours
Metabolism
The drug is metabolized via UDP glucuronidation
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 16.308 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.013%
Vd
The volume of distribution (Vd) of drug is 1774 L
Water Solubility
The ability of drug to dissolve in water is measured as 0.00005 mg/mL
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C37H42F2N8O4
PubChem CID
468595
Canonical SMILES
CCC(C(C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5CC(OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F
InChI
1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
InChIKey
RAGOYPUPXAKGKH-XAKZXMRKSA-N
CAS Number
CAS 171228-49-2
ChEBI ID
CHEBI:64355
TTD Drug ID
D07ABV
DrugBank ID
DB01263
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Anidulafungin      Aspergillus nidulans     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Aspergillus fumigatus Microorganism model Aspergillus fumigatus
                    In-vivo Model Six-week-old female Swiss mice were immunosuppressed with a combination of cyclophosphamide and cortisone acetate.
                    Experimental
                    Result(s)		 The PSC and AFG combination therapy was highly effective and should be evaluated in larger-scale experiments.
Target and Pathway
Target(s) Candida Cytochrome P450 51 (Candi ERG11)  Molecule Info  [3]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 022003.
Reference 2 Evaluation of the efficacy of a posaconazole and anidulafungin combination in a murine model of pulmonary aspergillosis due to infection with Aspergillus fumigatus. Diagn Microbiol Infect Dis. 2018 Jan;90(1):40-43.
Reference 3 A new, broad-spectrum azole antifungal: posaconazole--mechanisms of action and resistance, spectrum of activity. Mycoses. 2006;49 Suppl 1:2-6.
 Download Picture         KEGG Link