Basic information
- CAS
88678-31-3- Standard SMILES
COc1cccc(N(C)C(=S)Oc2ccc3c(c2)CCCC3)n1- InChIKey
VPHPQNGOVQYUMG-UHFFFAOYSA-N- Molecular formula
- C18H20N2O2S
- Average molar mass
- 328.4 g/mol
- Monoisotopic mass
- 328.12454906
Overview
Liranaftate is a member of tetralins.
Names & identifiers
- Preferred name
- Liranaftate
- IUPAC
- O-(5,6,7,8-tetrahydronaphthalen-2-yl) N-(6-methoxy-2-pyridinyl)-N-methylcarbamothioate
- English name
- Liranaftate
- Molecular formula
- C18H20N2O2S
- Molecular weight
- 328.43
Names & synonyms
Liranaftate88678-31-3LiranaftatoZefnartLiranaftatumM-732DTXSID60464705253IGO5X3DTXCID4026470RefChem:799366O-(5,6,7,8-tetrahydro-2-naphthyl)-6-methoxy-N-methylthio-2-pyridinecarbamate(6-Methoxy-2-pyridinyl)methylcarbamothioic acid O-(5,6,7,8-tetrahydro-2-naphthalenyl) ester
Show more names
LNFLIRANAFATELIANAFTATEPIRITETRATEphthalenyl)ester
834-254-6Liranaftate [INN]MFCD00865576Liranaftato [INN-Spanish]PiritetateO-(5,6,7,8-tetrahydronaphthalen-2-yl) (6-methoxypyridin-2-yl)(methyl)carbamothioateUNII-5253IGO5X3Piritetrate;M-732
Database identifiers
- CAS
88678-31-3- PubChem CID
- 3936
- DTXSID
DTXSID6046470- ChEMBL
CHEMBL1591365- ChEBI
CHEBI:31775
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 66.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 406
Physicochemical properties
- Melting point
- 98.5 · 98.5-99.5°C
- Boiling point
- 462.5 · 462.5±55.0 °C(Predicted)
- Density
- 1.24 · 1.240±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 1.24 · 1.24±0.10(Predicted)
- color
- Off-White
- Merck
- 14 · 14,5515
- InChI
- InChI=1S/C18H20N2O2S/c1-20(16-8-5-9-17(19-16)21-2)18(23)22-15-11-10-13-6-3-4-7-14(13)12-15/h5,8-12H,3-4,6-7H2,1-2H3
- InChIKey
- VPHPQNGOVQYUMG-UHFFFAOYSA-N
- SMILES
- C(=S)(OC1=CC=C2C(=C1)CCCC2)N(C1=NC(OC)=CC=C1)C
- FDA UNII
- 5253 IGO5X3 · 5253IGO5X3
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- rtecs
- FD3890000
- hs_code
- 2933.39.4100
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H319-H315-H317
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
QD - Dermatologicals
Applications
UsesBroad-spectrum antifungal
DescriptionLiranaftate was launched in Japan as a new topical antifungal for the treatment of dermatophycoses. This compound belonging to the thiocarbamate class of antifungals can be prepared by condensation of 5,6，7,8-tetrahydro-2-naphthol with the corresponding Npyridylthiocarbamoyl chloride. It is a potent and specific inhibitor of squalene epoxidase and consequently a blocker of ergosterol biosynthesis in fungi, without any detectable effect on mammalian cholesterol biosynthesis in rat liver at therapeutic dose levels. Liranaftate was found to be significantly more active than the other thiocarbamate tolnaftate against several dermatophytes, including Trichophyton mentagrophyfes, and against certain yeasts, such as Crypfococcus neoformans. On the other hand, it was inactive against a variety of Gram-positive and negative bacteria. When applicated as a 1 or 2% cream during clinical trials, it was well tolerated and no systemic absorption was observed.
UsesA squalene epoxidase inhibitor. Used as an antifungal.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
1 records
Compound notes
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