CAS 68550-75-4 Cilostamide (HCID 2753)

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Basic information

CAS: 68550-75-4
Standard SMILES: CN(C(=O)CCCOc1ccc2[nH]c(=O)ccc2c1)C1CCCCC1
InChIKey: UIAYVIIHMORPSJ-UHFFFAOYSA-N
Molecular formula: C20H26N2O3
Average molar mass: 342.4 g/mol
Monoisotopic mass: 342.19434269

Overview

N-cyclohexyl-N-methyl-4-[(2-oxo-1H-quinolin-6-yl)oxy]butanamide is a member of quinolines.

Names & identifiers

Preferred name: Cilostamide
IUPAC: N-cyclohexyl-N-methyl-4-[(2-oxo-1H-quinolin-6-yl)oxy]butanamide
English name: CILOSTAMIDE
Molecular formula: C20H26N2O3
Molecular weight: 342.43

Names & synonyms

cilostamide68550-75-4N-Cyclohexyl-N-methyl-4-(1,2-dihydro-2-oxo-6-quinolyloxy)butyramideCilostamidumCilostamidaOPC-3689DTXSID3045140N-Cyclohexyl-N-methyl-4-((2-oxo-1,2-dihydroquinolin-6-yl)oxy)butanamideN-Cyclohexyl-4-((1,2-dihydro-2-oxo-6-quinolyl)oxy)-N-methylbutyramideN-cyclohexyl-N-methyl-4-[(2-oxo-1,2-dihydroquinolin-6-yl)oxy]butanamide45S5605Q18DTXCID1025140

Show more names

OCP 3689ciloalaMideCilostamide,OPC 3689Cilostamide, 10 mM in DMSOCilostamide, PDE3 inhibitorCilostamide - CAS 68550-75-4 - CalbiochemN-cyclohexyl-4-[(2-hydroxyquinolin-6-yl)oxy]-N-methylbutanamide6-[3-(N-Cyclohexyl-N-methylcarbamoyl)propoxy]quinolin-2[1H]-one

Butanamide, N-cyclohexyl-4-((1,2-dihydro-2-oxo-6-quinolinyl)oxy)-N-methyl-RefChem:126145Cilostamide [INN]OPC 3689N-cyclohexyl-N-methyl-4-[(2-oxo-1H-quinolin-6-yl)oxy]butanamideMFCD00673958CHEMBL34431NCGC00015269-03

Properties

Computed structural properties

XLogP: 2.9
Topological polar surface area: 58.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 6
Heavy atoms: 25
Formal charge: 0
Complexity: 499

Physicochemical properties

Melting point: 186 · 186~188℃
Boiling point: 594.3 · 594.3±50.0 °C(Predicted)
Density: 1.18 · 1.18±0.1 g/cm3(Predicted)
storage temp.: 0 · 0-6°C
solubility: Soluble in DMSO (up to 30 mg/ml).
pka: 11.12 · 11.12±0.70(Predicted)
form: White solid
color: White
Stability: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
Cosmetics Ingredients Functions: SKIN PROTECTING
InChI: 1S/C20H26N2O3/c1-22(16-6-3-2-4-7-16)20(24)8-5-13-25-17-10-11-18-15(14-17)9-12-19(23)21-18/h9-12,14,16H,2-8,13H2,1H3,(H,21,23)
InChIKey: UIAYVIIHMORPSJ-UHFFFAOYSA-N
SMILES: [nH]1c2c(cc[c]1=O)cc(cc2)OCCCC(=O)N(C3CCCCC3)C
FDA UNII: 45 S5605Q18 · 45S5605Q18

Safety & regulation

Safety data

wgk: 3
ridadr: 3249
Signal word: Warning
Symbol(GHS): GHS07
hazard_class: 6.1(b)
Storage Class: 11 - Combustible Solids
packing_group: III
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Applications · 3 items

DescriptionCilostamide (68550-75-4) is a selective inhibitor of phosphodiesterase-3 (PDE3). Displays limited selectivity for PDE3A versus PDE3B (IC50 = 27 and 50 nM).1,2 Blocks PKB/Akt signaling pathway downstream via inhibition of Akt-activated PDE3B.3 Cilostamide reverses the effect of leptin on food intake and body weight.4

UsesSerotonin receptor ligand

UsesCilostamide (OPC 3689) is a specific phosphodiesterase 3 (PDE3) inhibitor.