9-ethyl-4,6-dioxo-10-propyl-4H,6H,9H-chromeno[7,6-b]pyridine-2,8-dicarboxylic acid

• ChemBase ID: 597
• Molecular Formular: C19H17NO7
• Molecular Mass: 371.34078
• Monoisotopic Mass: 371.10050189
• SMILES: o1c2c(c3n(CC)c(cc(=O)c3cc2c(=O)cc1C(=O)O)C(=O)O)CCC
• Canonical SMILES: CCCc1c2oc(cc(=O)c2cc2c1n(CC)c(cc2=O)C(=O)O)C(=O)O
• InChI: InChI=1S/C19H17NO7/c1-3-5-9-16-10(13(21)7-12(18(23)24)20(16)4-2)6-11-14(22)8-15(19(25)26)27-17(9)11/h6-8H,3-5H2,1-2H3,(H,23,24)(H,25,26)
• InChIKey: RQTOOFIXOKYGAN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-ethyl-4,6-dioxo-10-propyl-4H,6H,9H-chromeno[7,6-b]pyridine-2,8-dicarboxylic acid
• IUPAC Traditional name: nedocromil
• Brand Name: Alocril; Nedocromil [USAN:BAN:INN]; Nedocromilo [Spanish]; Nedocromilum [Latin]; Tilade
• Synonyms: Nedocromil

Database IDs

• CAS Number: 69049-73-6
• PubChem SID: 160964060; 46507587
• PubChem CID: 50294

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.2765472
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.950341
• LogD (pH = 7.4): -4.4912534
• Log P: 2.4967167
• Molar Refractivity: 98.086 cm^3
• Polarizability: 35.33119 Å^3
• Polar Surface Area: 121.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -3.91
• Solubility (Water): 4.59e-02 g/l

PROPERTIES

Physical Property

• Solubility: 145 mg/L
• Hydrophobicity(logP): 2.6

DETAILS

DrugBank - DB00716

• Drug Groups: approved
• Description: A pyranoquinolone derivative that inhibits activation of inflammatory cells which are associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets. [PubChem]
• Indication: For the treatment of mild to moderate asthma
• Pharmacology: Nedocromil is a anti-inflammatory agent and can be administered directly to the bronchial mucosa. It has significant inhibitory effect on allergen-induced early and late asthmatic reactions and on bronchial hyperresponsiveness.
• Toxicity: Side effects include headache, nasal congestion, ocular burning, irritation and stinging, unpleasant taste, cough, difficulty breathing, noisy breathing, shortness of breath, tightness in chest, wheezing, conjunctivitis, blurred vision, change in color vision, difficulty seeing at night, increased sensitivity of eyes to sunlight.
• Affected Organisms: Humans and other mammals
• Biotransformation: Nedocromil is not metabolized after IV administration and is excreted unchanged.
• Absorption: Low
• Half Life: ~3.3 hours
• Protein Binding: approximately 89% protein bound in human plasma over a concentration range of 0.5 to 50 µg/mL
• Elimination: It is not metabolized and is eliminated primarily unchanged in urine (70%) and feces (30%).
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com