Synonym
Liranaftate; M-732; Piritetrate;
IUPAC/Chemical Name
O-(5,6,7,8,-Tetrahydro-2-naphthyl) 6-methoxy-N-methylthio-2-pyridinecarbamate
InChi Key
GTLOCRWOJSGVDM-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H20N2O3S/c1-22-17-9-5-8-16(19-17)20(24-2)18(21)23-15-11-10-13-6-3-4-7-14(13)12-15/h5,8-12H,3-4,6-7H2,1-2H3
SMILES Code
O=C(OC1=CC=C2CCCCC2=C1)N(SC)C3=NC(OC)=CC=C3
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
>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
Biological target:
Liranaftate (Piritetrate) is a squalene epoxidase inhibitor with anti-fungicidal activities.
In vitro activity:
Keratinocytes were incubated with this antifungal drug (liranaftate) in the presence of beta -glucan or trichophytin. Augmented production of IL-8 was profoundly suppressed by the addition of liranaftate to the culture in a dose-dependent manner. Clinically, liranaftate an antifungal drug with IL-8-decreasing activity may reduce infiltration of neutrophils in the skin and their invasion into the epidermis.
Reference: Nihon Ishinkin Gakkai Zasshi. 2008;49(4):319-22. https://pubmed.ncbi.nlm.nih.gov/19001760/
In vivo activity:
To evaluate the anti-inflammatory activity of the thiocarbamate antifungal agent liranaftate, the edema and the neutrophil accumulation detected by the activity of neutrophil marker enzyme, myeloperoxidase (MPO), were examined following application of liranaftate to mouse ears with inflammation induced by phorbol 12-myristate 13-acetate (PMA). Topical 20 microl administration of liranaftate in a dose-range between 1-4% suppressed the increase in ear thickness 6 hr after PMA application dose-dependently. Similarly, it decreased the weight increase of an ear section after 24 hr dose-dependently. More than 1% of liranaftate also suppressed augmentation of MPO activity of the ear section. This and histological observation indicate that liranaftate treatment suppressed neutrophil accumulation in PMA-applied ear lesion.
Reference: Nihon Ishinkin Gakkai Zasshi. 2010;51(1):7-11. https://pubmed.ncbi.nlm.nih.gov/20185866/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
100.0 |
290.34 |
|
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
344.43
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. Kobayashi M, Kabashima K, Tokura Y. [Anti-fungal drug liranaftate suppresses fungal element-promoted production of IL-8 in normal human keratinocytes]. Nihon Ishinkin Gakkai Zasshi. 2008;49(4):319-22. Japanese. doi: 10.3314/jjmm.49.319. PMID: 19001760.
2. Oku Y, Takahashi N, Yokoyama K. [Fungicidal activity of liranaftate against dermatophytes]. Nihon Ishinkin Gakkai Zasshi. 2009;50(1):9-13. Japanese. doi: 10.3314/jjmm.50.9. PMID: 19194054.
3. Maruyama N, Ishijima S, Abe S. [Suppression of experimental footpad inflammatory reaction by anti-fungal agent liranaftate in mice]. Med Mycol J. 2012;53(2):129-33. Japanese. doi: 10.3314/mmj.53.129. PMID: 22728596.
4. Maruyama N, Abe Y, Hisajima T, Hayama K, Abe S. [Suppression of experimental inflammation by anti-fungal agent liranaftate in mice]. Nihon Ishinkin Gakkai Zasshi. 2010;51(1):7-11. Japanese. doi: 10.3314/jjmm.51.7. PMID: 20185866.
In vitro protocol:
1. Kobayashi M, Kabashima K, Tokura Y. [Anti-fungal drug liranaftate suppresses fungal element-promoted production of IL-8 in normal human keratinocytes]. Nihon Ishinkin Gakkai Zasshi. 2008;49(4):319-22. Japanese. doi: 10.3314/jjmm.49.319. PMID: 19001760.
2. Oku Y, Takahashi N, Yokoyama K. [Fungicidal activity of liranaftate against dermatophytes]. Nihon Ishinkin Gakkai Zasshi. 2009;50(1):9-13. Japanese. doi: 10.3314/jjmm.50.9. PMID: 19194054.
In vivo protocol:
1. Maruyama N, Ishijima S, Abe S. [Suppression of experimental footpad inflammatory reaction by anti-fungal agent liranaftate in mice]. Med Mycol J. 2012;53(2):129-33. Japanese. doi: 10.3314/mmj.53.129. PMID: 22728596.
2. Maruyama N, Abe Y, Hisajima T, Hayama K, Abe S. [Suppression of experimental inflammation by anti-fungal agent liranaftate in mice]. Nihon Ishinkin Gakkai Zasshi. 2010;51(1):7-11. Japanese. doi: 10.3314/jjmm.51.7. PMID: 20185866.
1: Maruyama N, Abe Y, Hisajima T, Hayama K, Abe S. [Suppression of experimental inflammation by anti-fungal agent liranaftate in mice]. Nihon Ishinkin Gakkai Zasshi. 2010;51(1):7-11. Japanese. PubMed PMID: 20185866.
2: Maruyama N, Ishijima S, Abe S. [Suppression of experimental footpad inflammatory reaction by anti-fungal agent liranaftate in mice]. Med Mycol J. 2012;53(2):129-33. Japanese. PubMed PMID: 22728596.
3: Oku Y, Takahashi N, Yokoyama K. [Fungicidal activity of liranaftate against dermatophytes]. Nihon Ishinkin Gakkai Zasshi. 2009;50(1):9-13. Japanese. PubMed PMID: 19194054.
4: Oku Y, Sakuma K, Yokoyama K, Miyaji M. [Fungicidal activity of liranaftate against Trichophyton rubrum]. Nihon Ishinkin Gakkai Zasshi. 2002;43(3):181-7. Japanese. PubMed PMID: 12145634.
5: Kobayashi M, Kabashima K, Tokura Y. [Anti-fungal drug liranaftate suppresses fungal element-promoted production of IL-8 in normal human keratinocytes]. Nihon Ishinkin Gakkai Zasshi. 2008;49(4):319-22. Japanese. PubMed PMID: 19001760.
6: Maeda J, Nanjoh Y, Koga H, Toga T, Makimura K, Tsuboi R. [In vitro Antifungal Activity of Luliconazole against Trichophyton spp]. Med Mycol J. 2016;57(1):J1-6. doi: 10.3314/mmj.57.J1. Japanese. PubMed PMID: 26936346.
7: Koga H, Nanjoh Y, Makimura K, Tsuboi R. In vitro antifungal activities of luliconazole, a new topical imidazole. Med Mycol. 2009;47(6):640-7. doi: 10.1080/13693780802541518. PubMed PMID: 19115136.
8: Mishra B, Sahoo S, Sahoo SK. Liranaftate loaded Xanthan gum based hydrogel for topical delivery: Physical properties and ex-vivo permeability. Int J Biol Macromol. 2017 Oct 8. pii: S0141-8130(17)33241-5. doi: 10.1016/j.ijbiomac.2017.10.039. [Epub ahead of print] PubMed PMID: 29020654.
9: Sulaiman A, Wan X, Fan J, Kasimu H, Dong X, Wang X, Zhang L, Abliz P, Upur H. Analysis on curative effects and safety of 2% liranaftate ointment in treating tinea pedis and tinea corporis & cruris. Pak J Pharm Sci. 2017 May;30(3(Special)):1103-1106. PubMed PMID: 28671089.
