Lanoconazole | CAS#101530-10-3 | antifungal agent

MedKoo Cat#: 598304 | Name: Lanoconazole

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Description:

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

Lanoconazole is a topical antifungal agent.

Chemical Structure

Lanoconazole

CAS#101530-10-3

Theoretical Analysis

MedKoo Cat#: 598304

Name: Lanoconazole

CAS#: 101530-10-3

Chemical Formula: C14H10ClN3S2

Exact Mass: 319.0005

Molecular Weight: 319.83

Elemental Analysis: C, 52.58; H, 3.15; Cl, 11.08; N, 13.14; S, 20.05

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250.00	2 Weeks
25mg	USD 450.00	2 Weeks

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Synonym

Lanoconazole; Astat; NND-318; TJN-318;

IUPAC/Chemical Name

(E)-2-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1H-imidazol-1-yl)acetonitrile

InChi Key

ZRTQSJFIDWNVJW-WYMLVPIESA-N

InChi Code

InChI=1S/C14H10ClN3S2/c15-11-4-2-1-3-10(11)13-8-19-14(20-13)12(7-16)18-6-5-17-9-18/h1-6,9,13H,8H2/b14-12+

SMILES Code

N#C/C(N1C=CN=C1)=C2SCC(C3=CC=CC=C3Cl)S/2

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

Shelf Life

>3 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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lanoconazole is a potent and orally active imidazole antifungal agent, shows a broad spectrum of activity against fungi in vitro and in vivo.

In vitro activity:

LCZ (lanoconazole) dose-dependently suppressed 12-O-tetradecanoylphorbol-13-acetate-induced irritant dermatitis, suppressed the production of neutrophil chemotactic factors such as keratinocyte-derived chemokine and macrophage inflammatory protein-2, and inhibited neutrophil infiltration to the inflammation site. Reference: Mycoses. 2020 Feb;63(2):189-196. https://pubmed.ncbi.nlm.nih.gov/31724251/

In vivo activity:

Whereas lanoconazole inhibited the growth of C. neoformans in the brains and lungs of MAIDS mice, the pathogen grew in the brains of MAIDS mice treated with fluconazole. Lanoconazole reduced the number of C. neoformans in the brains of normal mice treated with a type 2 cytokine mixture, whereas fluconazole did not. Reference: J Antimicrob Chemother. 2000 Sep;46(3):443-50. https://pubmed.ncbi.nlm.nih.gov/10980172/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	312.67

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 319.83 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. Nakamura A, Uratsuji H, Yamada Y, Hashimoto K, Nozawa N, Matsumoto T. Anti-inflammatory effect of lanoconazole on 12-O-tetradecanoylphorbol-13-acetate- and 2,4,6-trinitrophenyl chloride-induced skin inflammation in mice. Mycoses. 2020 Feb;63(2):189-196. doi: 10.1111/myc.13034. Epub 2019 Nov 27. PMID: 31724251; PMCID: PMC7003819. 2. Uratsuji H, Nakamura A, Yamada Y, Hashimoto K, Matsumoto T, Ikeda F, Ishii R. Anti-inflammatory activity of lanoconazole, a topical antifungal agent. Mycoses. 2015 Apr;58(4):197-202. doi: 10.1111/myc.12297. Epub 2015 Feb 10. PMID: 25675966. 3. Uratsuji H, Nakamura A, Yamada Y, Hashimoto K, Matsumoto T, Ikeda F, Ishii R. Anti-inflammatory activity of lanoconazole, a topical antifungal agent. Mycoses. 2015 Apr;58(4):197-202. doi: 10.1111/myc.12297. Epub 2015 Feb 10. PMID: 25675966. 4. Furukawa K, Sasaki H, Pollard RB, Suzuki F. Lanoconazole, a new imidazole antimycotic compound, protects MAIDS mice against encephalitis caused by Cryptococcus neoformans. J Antimicrob Chemother. 2000 Sep;46(3):443-50. doi: 10.1093/jac/46.3.443. PMID: 10980172.

In vitro protocol:

In vivo protocol:

1. Uratsuji H, Nakamura A, Yamada Y, Hashimoto K, Matsumoto T, Ikeda F, Ishii R. Anti-inflammatory activity of lanoconazole, a topical antifungal agent. Mycoses. 2015 Apr;58(4):197-202. doi: 10.1111/myc.12297. Epub 2015 Feb 10. PMID: 25675966. 2. Furukawa K, Sasaki H, Pollard RB, Suzuki F. Lanoconazole, a new imidazole antimycotic compound, protects MAIDS mice against encephalitis caused by Cryptococcus neoformans. J Antimicrob Chemother. 2000 Sep;46(3):443-50. doi: 10.1093/jac/46.3.443. PMID: 10980172.

1: Uratsuji H, Nakamura A, Yamada Y, Hashimoto K, Matsumoto T, Ikeda F, Ishii R. Anti-inflammatory activity of lanoconazole, a topical antifungal agent. Mycoses. 2015 Apr;58(4):197-202. doi: 10.1111/myc.12297. Epub 2015 Feb 10. PubMed PMID: 25675966. 2: Abastabar M, Rahimi N, Meis JF, Aslani N, Khodavaisy S, Nabili M, Rezaei-Matehkolaei A, Makimura K, Badali H. Potent Activities of Novel Imidazoles Lanoconazole and Luliconazole against a Collection of Azole-Resistant and -Susceptible Aspergillus fumigatus Strains. Antimicrob Agents Chemother. 2016 Oct 21;60(11):6916-6919. doi: 10.1128/AAC.01193-16. Print 2016 Nov. PubMed PMID: 27572389; PubMed Central PMCID: PMC5075107. 3: Ghannoum MA, Long L, Kim HG, Cirino AJ, Miller AR, Mallefet P. Efficacy of terbinafine compared to lanoconazole and luliconazole in the topical treatment of dermatophytosis in a guinea pig model. Med Mycol. 2010 May;48(3):491-7. doi: 10.3109/13693780903373811. PubMed PMID: 20370362. 4: Ghannoum MA, Welshenbaugh A, Imamura Y, Isham N, Mallefet P, Yamaguchi H. Comparison of the in vitro activity of terbinafine and lanoconazole against dermatophytes. Mycoses. 2010 Jul;53(4):311-3. doi: 10.1111/j.1439-0507.2009.01723.x. Epub 2009 May 5. PubMed PMID: 19422522. 5: Niwano Y, Koga H, Kanai K, Hamaguchi H, Yamaguchi H. Wound healing effect of the new imidazole antimycotic lanoconazole in rats. Arzneimittelforschung. 1996 Feb;46(2):218-23. PubMed PMID: 8720319. 6: Niwano Y, Matsui M, Tabuchi T, Kanai K, Hamaguchi H, Miyazaki T, Uchida K, Yamaguchi H. Studies on the antifungal activity of the new imidazole antimycotic lanoconazole in infected sites. Distribution in the skin and in vitro activity in the presence of stratum corneum. Arzneimittelforschung. 1997 Sep;47(9):1056-60. PubMed PMID: 9342423. 7: Baghi N, Shokohi T, Badali H, Makimura K, Rezaei-Matehkolaei A, Abdollahi M, Didehdar M, Haghani I, Abastabar M. In vitro activity of new azoles luliconazole and lanoconazole compared with ten other antifungal drugs against clinical dermatophyte isolates. Med Mycol. 2016 Oct 1;54(7):757-63. doi: 10.1093/mmy/myw016. Epub 2016 Apr 26. PubMed PMID: 27118804. 8: Furukawa K, Sasaki H, Pollard RB, Suzuki F. Lanoconazole, a new imidazole antimycotic compound, protects MAIDS mice against encephalitis caused by Cryptococcus neoformans. J Antimicrob Chemother. 2000 Sep;46(3):443-50. PubMed PMID: 10980172. 9: Kumar AP, Ganesh VR, Rao DV, Anil C, Hariharakrishnan VS. Separation and quantitation of Z-isomer in lanoconazole by normal phase HPLC. J Pharm Biomed Anal. 2009 Oct 15;50(3):535-7. doi: 10.1016/j.jpba.2009.05.004. Epub 2009 May 15. PubMed PMID: 19487097. 10: Niwano Y, Tabuchi T, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. [Therapeutic efficacy of lanoconazole ointment in guinea pig model of tinea corporis, a comparative study with ointment and cream preparations]. Jpn J Antibiot. 1995 Jan;48(1):150-4. Japanese. PubMed PMID: 7699840. 11: Tanaka N, Kawada A, Hiruma M, Tajima S, Ishibashi A. Contact dermatitis from lanoconazole. Contact Dermatitis. 1996 Oct;35(4):256-7. PubMed PMID: 8957656. 12: Nishiyama Y, Nakaoka C, Hiratani T, Abe S, Uchida K, Yamaguchi H. Synergy of lysozyme and lanoconazole on the morphology of Candida albicans. J Electron Microsc (Tokyo). 2001;50(1):41-9. PubMed PMID: 11291959. 13: Umebayashi Y, Ito S. Allergic contact dermatitis due to both lanoconazole and neticonazole ointments. Contact Dermatitis. 2001 Jan;44(1):48-9. PubMed PMID: 11156023. 14: Nakano R, Miyoshi H, Kanzaki T. Allergic contact dermatitis from lanoconazole. Contact Dermatitis. 1996 Jul;35(1):63. PubMed PMID: 8896974. 15: Tanuma H, Tanuma M, Abe M, Kume H. Usefulness of lanoconazole (Astat) cream in the treatment of hyperkeratotic type tinea pedis. Comparative study of monotherapy and combination therapy with 10% urea ointment (Pastaron). Mycoses. 2001;44(5):181-90. PubMed PMID: 11486456. 16: Niwano Y, Tabuchi T, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. [Therapeutic efficacy of lanoconazole ointment in guinea pig model of tinea pedis, in comparison with that of cream preparations]. Jpn J Antibiot. 1994 Sep;47(9):1192-5. Japanese. PubMed PMID: 7990259. 17: Niwano Y, Seo A, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. Therapeutic efficacy of lanoconazole, a new imidazole antimycotic agent, for experimental cutaneous candidiasis in guinea pigs. Antimicrob Agents Chemother. 1994 Sep;38(9):2204-6. PubMed PMID: 7811048; PubMed Central PMCID: PMC284713. 18: Niwano Y, Ohmi T, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. [In vitro antifungal activities of lanoconazole against stock cultures and clinical isolates of Candida albicans]. Jpn J Antibiot. 1995 Jan;48(1):140-5. Japanese. PubMed PMID: 7699837. 19: Taniguchi S, Kono T. Allergic contact dermatitis due to lanoconazole with no cross-reactivity to other imidazoles. Dermatology. 1998;196(3):366. PubMed PMID: 9621155. 20: Mitsuya M, Wada K, Ishibashi H, Tansho S, Abe S, Yamaguchi H. [Suppressive effects of lanoconazole on arthus phenomenon in vivo and on production and functions of TNF in vitro]. Nihon Ishinkin Gakkai Zasshi. 2000;41(2):97-102. Japanese. PubMed PMID: 10777820.