≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
A-1165442 is a potent, competitive and orally available TRPV1 antagonist with an IC 50 of 9 nM for human TRPV1.
In Vitro
A-1165442 displays potent, competitive antagonism at recombinant human TRPV1 activated by capsaicin (IC 50 =9 nM) and incomplete blockade of acid-evoked response (62% block at 30 μM). A-1165442 possesses excellent selectivity (>100-fold) versus other members of the TRP family (TRPA1, TRPM8, TRPV2, TRPV3) and other receptors expressed in peripheral sensory neurons including P2X2/3, Cav2.2, Nav channels, and KCNQ2/3. A-1165442 shows minimal cross-reactivity upon evaluation (10 μM) in a broad screening panel (n=74, CEREP) of cell-surface receptors, ion channels, and enzymes. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
A-1165442 exhibits excellent pharmacological selectivity, has a favorable pharmacokinetic profile, and demonstrates good efficacy against osteoarthritis pain in rodents. Oral administration of A-1165442 prevents capsaicin-induced nocifensive behaviors in rats, with an ED 50 of 9.5 μmol/kg corresponding to plasma concentration of 420 ng/mL (970 nM). A single dose of A-1165442 produces a robust effect on grip force, with an ED 50 of 35 μmol/kg measured 1 h postdosing. Repeated dosing of A-1165442 results in an increase in potency relative to acute analgesic efficacy. No significant changes in core body temperature is observed in conscious rats dosed with A-1165442 and this temperature-neutral profile is maintained in conscious dogs . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:IC50: 9 nM (human TRPV1)
| Canonical Smiles | CC1=CC2=C(C=CC=C2NC(=O)NC3CC(OC4=C3C=CC(=C4)Cl)(CF)CF)C=N1 |
|---|---|
| IUPAC Name | 1-[(4R)-7-chloro-2,2-bis(fluoromethyl)-3,4-dihydrochromen-4-yl]-3-(3-methylisoquinolin-5-yl)urea |
| InChIKey | VJJGAJAUECQWSZ-LJQANCHMSA-N |
| INCHI | 1S/C22H20ClF2N3O2/c1-13-7-17-14(10-26-13)3-2-4-18(17)27-21(29)28-19-9-22(11-24,12-25)30-20-8-15(23)5-6-16(19)20/h2-8,10,19H,9,11-12H2,1H3,(H2,27,28,29)/t19-/m1/s1 |
| Isomeric SMILES | CC1=CC2=C(C=CC=C2NC(=O)N[C@@H]3CC(OC4=C3C=CC(=C4)Cl)(CF)CF)C=N1 |
| PubChem CID | 46191567 |
| MeSH Entry Terms | 1-(7-chloro-2,2-bis(fluoromethyl)chroman-4-yl)-3-(3-methylisoquinolin-5-yl)urea;A-1165442 |
| Molecular Weight | 431.86 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Isoquinolines and derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Isoquinolines and derivatives |
| Alternative Parents | 1-benzopyrans Alkyl aryl ethers Methylpyridines Aryl chlorides Benzenoids Heteroaromatic compounds Ureas Oxacyclic compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organochlorides Alkyl fluorides Organofluorides Organonitrogen compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Chromane - Benzopyran - Isoquinoline - 1-benzopyran - Alkyl aryl ether - Methylpyridine - Aryl chloride - Aryl halide - Benzenoid - Pyridine - Heteroaromatic compound - Urea - Oxacycle - Ether - Azacycle - Organochloride - Organohalogen compound - Alkyl halide - Alkyl fluoride - Carbonyl group - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. |
| External Descriptors | Not available |
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| Solubility | DMSO : ≥ 100 mg/mL (231.56 mM) H2O : <0.1 mg/mL (insoluble) |
|---|---|
| Molecular Weight | 431.900 g/mol |
| XLogP3 | 4.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Exact Mass | 431.121 Da |
| Monoisotopic Mass | 431.121 Da |
| Topological Polar Surface Area | 63.300 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 609.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
