Itraconazole

• CAT Number: A000258
• CAS Number: 84625-61-6
• Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
• Molecular Weight: 705.63
• Purity: ≥95%
• Target: Antibiotic
• Solubility: >8.8mg/mL in DMSO
• Storage: -20°C
• InChI: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m1/s1
• InChIKey: VHVPQPYKVGDNFY-AVQIMAJZSA-N
• SMILES: CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl

Itraconazole, invented in 1984, is a triazole antifungal agent prescribed to patients with fungal infections. It has also recently been explored as an anticancer agent for patients with basal cell carcinoma, non-small cell lung cancer, and prostate cancer. The drug may be given orally or intravenously.

Reference

1: Le T, Adenis A, Limper A, Harrison T. Itraconazole and antiretroviral therapy:
strategies for empirical dosing – Author/’s reply. Lancet Infect Dis. 2017
Nov;17(11):1123-1124. doi: 10.1016/S1473-3099(17)30582-0. PubMed PMID: 29115263.

2: Schwartz IS, Wasserman S. Itraconazole and antiretroviral therapy: strategies
for empirical dosing. Lancet Infect Dis. 2017 Nov;17(11):1122-1123. doi:
10.1016/S1473-3099(17)30568-6. PubMed PMID: 29115262.

3: Chiu HY, Chang WL, Tsai TF, Tsai YW, Shiu MN. Risk of Psoriasis Following
Terbinafine or Itraconazole Treatment for Onychomycosis: A Population-Based
Case-Control Comparative Study. Drug Saf. 2017 Nov 6. doi:
10.1007/s40264-017-0614-2. [Epub ahead of print] PubMed PMID: 29110252.

4: Solanki N, Gupta SS, Serajuddin ATM. Rheological analysis of
itraconazole-polymer mixtures to determine optimal melt extrusion temperature for
development of amorphous solid dispersion. Eur J Pharm Sci. 2017 Oct
30;111:482-491. doi: 10.1016/j.ejps.2017.10.034. [Epub ahead of print] PubMed
PMID: 29080855.

5: Zhang L, Liu Z, Yang K, Kong C, Liu C, Chen H, Huang J, Qian F. Tumor
Progression of Non-Small Cell Lung Cancer Controlled by Albumin and Micellar
Nanoparticles of Itraconazole, a Multitarget Angiogenesis Inhibitor. Mol Pharm.
2017 Nov 7. doi: 10.1021/acs.molpharmaceut.7b00855. [Epub ahead of print] PubMed
PMID: 29068216.

6: Mugheirbi NA, Marsac PJ, Taylor LS. Insights into Water-Induced Phase
Separation in Itraconazole-Hydroxypropylmethyl Cellulose Spin Coated and Spray
Dried Dispersions. Mol Pharm. 2017 Nov 8. doi: 10.1021/acs.molpharmaceut.7b00499.
[Epub ahead of print] PubMed PMID: 29053281.

7: Puls C, Johnson A, Young K, Hare J, Rosenkrans K, Young L, Moriello K.
Efficacy of itraconazole oral solution using an alternating-week pulse therapy
regimen for treatment of cats with experimental Microsporum canis infection. J
Feline Med Surg. 2017 Oct 1:1098612X17735967. doi: 10.1177/1098612X17735967.
[Epub ahead of print] PubMed PMID: 29025320.

8: Denardi LB, Keller JT, de Azevedo MI, Oliveira V, Piasentin FB, Severo CB,
Santurio JM, Alves SH. Comparison Between Etest and Broth Microdilution Methods
for Testing Itraconazole-Resistant Aspergillus fumigatus Susceptibility to
Antifungal Combinations. Mycopathologia. 2017 Oct 9. doi:
10.1007/s11046-017-0208-7. [Epub ahead of print] PubMed PMID: 28994001.

9: Giovane RA, Manhas P, Gates K. Itraconazole or Amphotericin B for
Talaromycosis. N Engl J Med. 2017 Oct 5;377(14):1402. doi: 10.1056/NEJMc1709123.
PubMed PMID: 28980793.

10: Le T, Thwaites G, Wolbers M. Itraconazole or Amphotericin B for
Talaromycosis. N Engl J Med. 2017 Oct 5;377(14):1403. doi: 10.1056/NEJMc1709123.
PubMed PMID: 28976858.