Itraconazole | CAS#84625-61-6 | antifungal agent| MedKoo

MedKoo Cat#: 318077 | Name: Itraconazole

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Itraconazole

CAS#84625-61-6

Theoretical Analysis

MedKoo Cat#: 318077

Name: Itraconazole

CAS#: 84625-61-6

Chemical Formula: C35H38Cl2N8O4

Exact Mass: 704.2393

Molecular Weight: 705.63

Elemental Analysis: C, 59.57; H, 5.43; Cl, 10.05; N, 15.88; O, 9.07

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 200.00	Ready to ship
500mg	USD 400.00	Ready to ship
1g	USD 650.00	Ready to ship
2g	USD 850.00	Ready to ship
5g	USD 1,450.00	Ready to ship

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Itraconazole, R51211, Orungal, Oriconazole, Sporanox, Itraconazolum, Itraconazol, Itrizole

IUPAC/Chemical Name

2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one

InChi Key

VHVPQPYKVGDNFY-ZPGVKDDISA-N

InChi Code

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-/m0/s1

SMILES Code

O=C1N(C(CC)C)N=CN1C2=CC=C(N3CCN(C4=CC=C(OC[C@@H]5O[C@@](CN6N=CN=C6)(C7=CC=C(Cl)C=C7Cl)OC5)C=C4)CC3)C=C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T20C06I25

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Itraconazole (R51211) is a triazole antifungal agent and Hedgehog (Hh) signaling pathway antagonist with an IC50 of ~800 nM that potently inhibits lanosterol 14α-demethylase (cytochrome P450 enzyme).

In vitro activity:

This study aimed to evaluate the effects of itraconazole on A549 and NCI-H460 human lung cancer cell stemness in vitro. Itraconazole reduced the expression of CD133 and ABCG2 in a concentration-dependent manner (Figure 1A–1C). The effects of itraconazole on ALDH1 activity in A549 and NCI-H460 human lung cancer cells were further examined. As shown in Figure 1D, ALDH1 activity was significantly reduced in A549 and NCI-H460 human lung cancer cells treated with itraconazole. Itraconazole reduced the cell sphere size of lung CSCs (Figure 2A). The cell sphere number was also reduced in A549 and NCI-H460 human lung cancer cells treated with itraconazole (Figure 2B). The expression of β-catenin and Wnt3a was reduced in A549 and NCI-H460 human lung cancer cells treated with itraconazole (Figure 3A–3C). Also, the activity of TCF/LEF reporter plasmid, a Wnt reporter plasmid, was reduced in A549 and NCI-H460 human lung cancer cells treated with itraconazole (Figure 3D, 3E). In conclusion, itraconazole altered the stemness characteristics by suppressing Wnt signaling but did not affect cell viability. Med Sci Monit. 2019; 25: 9509–9516. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6929554/

In vivo activity:

The aim of this study was to investigate the efficacy of itraconazole for MPE (malignant pleural effusion) and the mechanism of lymphangiogenesis suppression. Lewis lung carcinoma (LLC) cells were injected into the mouse pleural cavity to establish the MPE mouse model, followed by randomization of the mice into three groups. Each mice was injected with either a high dose of itraconazole (25 mg/kg, H-ITCZ), a low dose of itraconazole (8 mg/kg, L-ITCZ), or 50 μL of hydroxypropyl-β-cyclodextrin (130 mg/mL, H-β-C) into the pleural cavity four times every 3 days. As shown in Figure 1D, the mean volume of pleural effusion was 575.76±32.61 μL in the H-β-C control group, 445.64±27.75 μL in L-ITCZ group, and 311.19±27.20 μL in H-ITCZ group, respectively. The volume of pleural effusion in the L-ITCZ group was significantly different with that in control group (P<0.01). Similarly, the volume in the HITCZ group was significantly reduced when compared to both control group (P<0.01) and the L-ITCZ group (P<0.01). As shown in Figure 2A-C, tumor foci on pleural surfaces and lymph nodes were decreased in L-ITCZ and H-ITCZ groups. As shown in Figure 4, compared to the control group, the expressions of VEGF-C were reduced in the supernatants of pleural effusions from L-ITCZ group and H-ITCZ group and the expression in MPE from the H-ITCZ group was significantly lower than those from both two other groups (P<0.001). The percentage of VEGF-C expression was 65% in control group, 47% in L-ITCZ group and 36% in H-ITCZ group, respectively.A significant decrease was observed in the H-ITCZ group compared to the control group (P<0.001) and L-ITCZ group (P<0.01). Taken together, the results of this study substantiate the therapeutic effect of itraconazole on MPE in vivo, largely through inhibiting lymphangiogenesis in the generation and progression of MPE. Transl Lung Cancer Res. 2015 Feb; 4(1): 27–35. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4367708/

	Solvent	mg/mL	mM
Solubility
	DMSO	8.0	11.34

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 705.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Buczacki SJA, Popova S, Biggs E, Koukorava C, Buzzelli J, Vermeulen L, Hazelwood L, Francies H, Garnett MJ, Winton DJ. Itraconazole targets cell cycle heterogeneity in colorectal cancer. J Exp Med. 2018 Jul 2;215(7):1891-1912. doi: 10.1084/jem.20171385. Epub 2018 May 31. PMID: 29853607; PMCID: PMC6028508. 2. Chen C, Zhang W. Itraconazole Alters the Stem Cell Characteristics of A549 and NCI-H460 Human Lung Cancer Cells by Suppressing Wnt Signaling. Med Sci Monit. 2019 Dec 13;25:9509-9516. doi: 10.12659/MSM.919347. PMID: 31833479; PMCID: PMC6929554. 3. Buczacki SJA, Popova S, Biggs E, Koukorava C, Buzzelli J, Vermeulen L, Hazelwood L, Francies H, Garnett MJ, Winton DJ. Itraconazole targets cell cycle heterogeneity in colorectal cancer. J Exp Med. 2018 Jul 2;215(7):1891-1912. doi: 10.1084/jem.20171385. Epub 2018 May 31. PMID: 29853607; PMCID: PMC6028508. 4. Wang Y, Yao Y, Liu H, Ma X, Lv T, Yuan D, Xiao X, Yin J, Song Y. Itraconazole can inhibit malignant pleural effusion by suppressing lymphangiogenesis in mice. Transl Lung Cancer Res. 2015 Feb;4(1):27-35. doi: 10.3978/j.issn.2218-6751.2014.11.03. PMID: 25806344; PMCID: PMC4367708

In vitro protocol:

In vivo protocol:

1: Wahid M, Jawed A, Mandal RK, Dar SA, Khan S, Akhter N, Haque S. Vismodegib, itraconazole and sonidegib as hedgehog pathway inhibitors and their relative competencies in the treatment of basal cell carcinomas. Crit Rev Oncol Hematol. 2016 Feb;98:235-41. doi: 10.1016/j.critrevonc.2015.11.006. Epub 2015 Nov 21. Review. PubMed PMID: 26614022. 2: Agarwal R, Vishwanath G, Aggarwal AN, Garg M, Gupta D, Chakrabarti A. Itraconazole in chronic cavitary pulmonary aspergillosis: a randomised controlled trial and systematic review of literature. Mycoses. 2013 Sep;56(5):559-70. doi: 10.1111/myc.12075. Epub 2013 Mar 18. Review. PubMed PMID: 23496375. 3: Lestner J, Hope WW. Itraconazole: an update on pharmacology and clinical use for treatment of invasive and allergic fungal infections. Expert Opin Drug Metab Toxicol. 2013 Jul;9(7):911-26. doi: 10.1517/17425255.2013.794785. Epub 2013 May 6. Review. PubMed PMID: 23641752. 4: Charles M, Le Guellec C, Richard D, Libert F; Groupe Suivi Therapeutique Pharmacologique de la Societe Francaise de Pharmacologie et de Therapeutique. [Level of evidence for therapeutic drug monitoring of itraconazole]. Therapie. 2011 Mar-Apr;66(2):103-8. Epub 2011 Jun 6. Review. French. PubMed PMID: 21635856. 5: Homans JD, Spencer L. Itraconazole treatment of nonmeningeal coccidioidomycosis in children: two case reports and review of the literature. Pediatr Infect Dis J. 2010 Jan;29(1):65-7. doi: 10.1097/INF.0b013e3181b20ebd. Review. PubMed PMID: 19884875. 6: Yao M, Srinivas NR. Bioanalytical methods for the determination of itraconazole and hydroxyitraconazole: overview from clinical pharmacology, pharmacokinetic, pharmacodynamic and metabolism perspectives. Biomed Chromatogr. 2009 Jul;23(7):677-91. doi: 10.1002/bmc.1186. Review. PubMed PMID: 19309762. 7: Ishiguro T, Takayanagi N, Harasaw K, Yoshii Y, Matsushita A, Yoneda K, Miyahara Y, Kagiyama N, Tokunaga D, Aoki F, Saito H, Ubukata M, Kurashima K, Yanagisawa T, Sugita Y, Kawabata Y, Kamei K. [Mucoid impaction of the bronchi caused by Schizophyllum commune which developed after discontinuation of itraconazole administration]. Nihon Kokyuki Gakkai Zasshi. 2009 Apr;47(4):296-303. Review. Japanese. PubMed PMID: 19455959. 8: Korting HC, Schöllmann C. The significance of itraconazole for treatment of fungal infections of skin, nails and mucous membranes. J Dtsch Dermatol Ges. 2009 Jan;7(1):11-9, 11-20. doi: 10.1111/j.1610-0387.2008.06751.x. Epub 2008 May 7. Review. English, German. PubMed PMID: 18479501. 9: Savini V, Catavitello C, Manna A, Talia M, Febbo F, Balbinot A, D'Antonio F, Di Bonaventura G, Celentano C, Liberati M, Piccolomini R, D'Antonio D. Two cases of vaginitis caused by itraconazole-resistant Saccharomyces cerevisiae and a review of recently published studies. Mycopathologia. 2008 Jul;166(1):47-50. doi: 10.1007/s11046-008-9119-y. Epub 2008 Apr 29. Review. PubMed PMID: 18443923. 10: Pantazidou A, Tebruegge M. Recurrent tinea versicolor: treatment with itraconazole or fluconazole? Arch Dis Child. 2007 Nov;92(11):1040-2. Review. PubMed PMID: 17954488; PubMed Central PMCID: PMC2083600. 11: Otani H, Inoue K, Shiota T, Suzuki Y, Nomura S, Harada Y, Ishibashi H, Abe S, Uchida K, Yamaguchi H, Torii S. [Pharmacological, pharmacokinetic, and clinical profile of itraconazole oral solution (ITRIZOLE Oral Solution 1%)]. Nihon Yakurigaku Zasshi. 2007 Jul;130(1):69-76. Review. Japanese. PubMed PMID: 17634684. 12: Rufke C, Nieber K. [Long QT interval. Interaction of terfenadine and itraconazole]. Med Monatsschr Pharm. 2006 Jan;29(1):22-4. Review. German. PubMed PMID: 16463550. 13: Potter M. Strategies for managing systemic fungal infection and the place of itraconazole. J Antimicrob Chemother. 2005 Sep;56 Suppl 1:i49-i54. Review. PubMed PMID: 16120634. 14: Maertens J, Boogaerts M. The place for itraconazole in treatment. J Antimicrob Chemother. 2005 Sep;56 Suppl 1:i33-i38. Review. PubMed PMID: 16120632. 15: Prentice AG, Glasmacher A. Making sense of itraconazole pharmacokinetics. J Antimicrob Chemother. 2005 Sep;56 Suppl 1:i17-i22. Review. PubMed PMID: 16120630. 16: Bermúdez M, Fuster JL, Llinares E, Galera A, Gonzalez C. Itraconazole-related increased vincristine neurotoxicity: case report and review of literature. J Pediatr Hematol Oncol. 2005 Jul;27(7):389-92. Review. PubMed PMID: 16012330. 17: Buchkowsky SS, Partovi N, Ensom MH. Clinical pharmacokinetic monitoring of itraconazole is warranted in only a subset of patients. Ther Drug Monit. 2005 Jun;27(3):322-33. Review. PubMed PMID: 15905803. 18: Gupta AK, Cooper EA, Ginter G. Efficacy and safety of itraconazole use in children. Dermatol Clin. 2003 Jul;21(3):521-35. Review. PubMed PMID: 12956205. 19: Jain S, Sehgal VN. Itraconazole versus terbinafine in the management of onychomycosis: an overview. J Dermatolog Treat. 2003 Jan;14(1):30-42. Review. PubMed PMID: 12745853. 20: Groll AH. Itraconazole--perspectives for the management of invasive aspergillosis. Mycoses. 2002;45 Suppl 3:48-55. Review. PubMed PMID: 12690972.