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Substance Name: Posaconazole [USAN:INN:BAN]
RN: 171228-49-2
UNII: 6TK1G07BHZ
InChIKey: RAGOYPUPXAKGKH-XAKZXMRKSA-N

Note

  • NCI: A broad-spectrum, second generation, triazole compound with antifungal activity. Posaconazole strongly inhibits 14-alpha demethylase, a cytochrome P450-dependent enzyme. Inhibition of 14-alpha-demethylase prevents the conversion of lanosterol to ergosterol, an important component of the fungal cell wall. Inhibition of ergosterol synthesis changes the fungal cell membrane composition and integrity, alters membrane permeability and eventually leads to fungal cell lysis. Compared to other azole antifungals, posaconazole is a significantly more potent inhibitor of sterol 14-alpha demethylase. Check for active clinical trials using this agent. (NCI Thesaurus)

Molecular Formula

  • C37-H42-F2-N8-O4

Molecular Weight

  • 700.7868
 

Classification Codes

  • 14-alpha Demethylase Inhibitors
  • Anti-Infective Agents
  • Antibiotics, Antifungal
  • Antifungal
  • Antifungal (alpha-Demethylase Fungal P450 Cytochrome System Inhibitor)
  • Antifungal Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Cytochrome P-450 Enzyme Inhibitors
  • Enzyme Inhibitors
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Steroid Synthesis Inhibitors
  • Trypanocidal Agents

Names and Synonyms

Name of Substance

  • Posaconazole
  • Posaconazole [USAN:INN:BAN]

Synonyms

  • 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-(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
  • HSDB 7421
  • Noxafil
  • Posaconazole
  • Posaconazole SP
  • Sch 56592
  • UNII-6TK1G07BHZ

Systematic Name

  • 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)-

Mixture Name

  • Posatex

Registry Numbers

CAS Registry Number

  • 171228-49-2

FDA UNII

  • 6TK1G07BHZ

Other Registry Number

  • 177571-33-4

System Generated Number

  • 0171228492

Structure Descriptors

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

Smiles

CC[C@@H]([C@H](C)O)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OC[C@@H]5CO[C@](Cn6cncn6)(C5)c7ccc(F)cc7F)cc4