Basic information
- CAS
153168-05-9- Standard SMILES
Cc1cc(CCCOc2c(C)cc(-c3noc(C(F)(F)F)n3)cc2C)on1- InChIKey
KQOXLKOJHVFTRN-UHFFFAOYSA-N- Molecular formula
- C18H18F3N3O3
- Average molar mass
- 381.3 g/mol
- Monoisotopic mass
- 381.13002593
Overview
Pleconaril is an antiviral drug from viral capsid inhibitor class, manufactured by Schering-Plough and intended for the prevention of acute asthma exacerbations and common cold symptoms in asthmatic patients who have had exposure to picornavirus. It acts by inhibiting viral replication. The use of pleconaril has not gained approval by the U.S. Food and Drug Administration (FDA) due to the fact that it has been found to induce CYP3A enzyme activity, therefore increasing the risk for serious drug interactions.
Names & identifiers
- Preferred name
- Pleconaril
- IUPAC
- 3-[3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
- English name
- PLECONARIL
- Molecular formula
- C18H18F3N3O3
- Molecular weight
- 381.35
Names & synonyms
Pleconaril153168-05-9PicovirWin-63843VP-63843Win 63843WIN63843PleconariloDTXSID8057649VP 63843VP638433-[3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole
Show more names
RimiducidPleconarilisPleconaril-d4PLECONARIL USP/EP/BPPleconaril - Bio-X ?Pleconaril, 10 mM in DMSO
9H4570Q89D3-[3,5-Dimethyl-4-[3-(3-methyl-5-isoxazolyl)propoxy]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazoleDTXCID90314383-(3,5-Dimethyl-4-(3-(3-methyl-5-isoxazolyl)propoxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole3-(3,5-dimethyl-4((3-(3-methyl-5-isoxazolyl)propyl)phenyl)-5-trifluoromethyl)-1,2,4-oxadiazole3-{3,5-dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]phenyl}-5-(trifluoromethyl)-1,2,4-oxadiazole3-(3,5-dimethyl-4-(3-(3-methyl-1,2-oxazol-5-yl)propoxy)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazolepleconarilum
Database identifiers
- CAS
153168-05-9- PubChem CID
- 1684
- DTXSID
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 74.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 471
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.63
Physicochemical properties
- Melting point
- 61 · 61-62°
- Boiling point
- 481.2 · 481.2±55.0 °C(Predicted)
- Density
- 1.271 · 1.271
- storage temp.
- room temp
- solubility
- 10 mg/mL · DMSO: ≥10mg/mL (warmed)
- pka
- -1.33 · -1.33±0.10(Predicted)
- form
- powder
- color
- white to beige
- InChI
- 1S/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3
- InChIKey
- KQOXLKOJHVFTRN-UHFFFAOYSA-N
- SMILES
- Cc1cc(CCCOc2c(C)cc(cc2C)-c3noc(n3)C(F)(F)F)on1
- FDA UNII
- 9 H4570Q89D · 9H4570Q89D
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- risk_code
- 25
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301-H413
- Hazard Classifications
- Acute Tox. 3 OralAquatic Chronic 4
- Precautionary statements
- P273-P301+P310+P330
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding>99%
Mechanism of Action
Pleconaril binds to a hydrophobic pocket in viral protein 1, the major protein which makes up the capsid (shell) of picornaviruses. This renders the viral capsid rigid and compressed and prevents the uncoating of its RNA. As a result, the virus is stopped from attaching to the host cell and causing infection.
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Absorption, Distribution and Excretion70% (oral)
Applications
UsesPleconaril has been used as a control or reference compound to assess the antiviral activities of the benzothiophene and other heteroaromatic derivatives against hRV-B14, hRV-A21 and hRV-A71.
UsesPicornavirus replication inhibitor. Antiviral.
General DescriptionPleconaril is a drug, that has antiviral activity.
Suppliers82 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
陕西缔都新材料有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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