X2N

POSACONAZOLE

Created: 2010-01-14
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count93
Chiral Atom Count4
Bond Count99
Aromatic Bond Count23
2D diagram of X2N
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Chemical Component Summary

NamePOSACONAZOLE
Systematic Name (OpenEye OEToolkits)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
FormulaC37 H42 F2 N8 O4
Molecular Weight700.777
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1N(N=CN1c2ccc(cc2)N7CCN(c6ccc(OCC3CC(OC3)(c4ccc(F)cc4F)Cn5ncnc5)cc6)CC7)C(CC)C(O)C
SMILESCACTVS3.352CC[CH]([CH](C)O)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OC[CH]5CO[C](C5)(Cn6cncn6)c7ccc(F)cc7F)cc4
SMILESOpenEye OEToolkits1.6.1CCC(C(C)O)N1C(=O)N(C=N1)c2ccc(cc2)N3CCN(CC3)c4ccc(cc4)OCC5CC(OC5)(Cn6cncn6)c7ccc(cc7F)F
Canonical SMILESCACTVS3.352 CC[C@@H]([C@H](C)O)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OC[C@@H]5CO[C@@](C5)(Cn6cncn6)c7ccc(F)cc7F)cc4
Canonical SMILESOpenEye OEToolkits1.6.1 CC[C@@H]([C@H](C)O)N1C(=O)N(C=N1)c2ccc(cc2)N3CCN(CC3)c4ccc(cc4)OC[C@H]5C[C@](OC5)(Cn6cncn6)c7ccc(cc7F)F
InChIInChI1.03 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
InChIKeyInChI1.03 RAGOYPUPXAKGKH-XAKZXMRKSA-N

Drug Info: DrugBank

DrugBank IDDB01263 
NamePosaconazole
Groups
  • approved
  • vet_approved
  • investigational
DescriptionPosaconazole is a triazole antifungal drug that is used to treat invasive infections by Candida species and Aspergillus species in severely immunocompromised patients.
SynonymsPosaconazole
Brand Names
  • Gln-posaconazole
  • Posanol
  • Noxafil
  • Taro-posaconazole
  • Posaconazole Sp
IndicationFor prophylaxis of invasive <em>Aspergillus</em> and <em>Candida</em> infections in patients, 13 years of age and older, who are at high risk of developing these infections due to being severely immunocompromised as a result of procedures such as hematopoietic stem cell transplant (HSCT) recipients with graft-versus-host disease (GVHD), or due to hematologic malignancies with prolonged neutropenia from chemotherapy. Also for the treatment of oropharyngeal candidiasis, including oropharyngeal candidiasis refractory to itraconazole and/or fluconazole. Posaconazole is used as an alternative treatment for invasive aspergillosis, <em>Fusarium</em> infections, and zygomycosis in patients who are intolerant of, or whose disease is refractory to, other antifungals.
Categories
  • 14-alpha Demethylase Inhibitors
  • Anti-Infective Agents
  • Antifungal Agents
  • Antiinfectives for Systemic Use
  • Antimycotics for Systemic Use
ATC-CodeJ02AC04
CAS number171228-49-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 51MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...unknownantagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate,inhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1397
PubChem 468595
ChEMBL CHEMBL1397
ChEBI CHEBI:64355
CCDC/CSD YIMWEZ, FUBRAY