5-{3-[(2-carboxy-4-oxo-4H-chromen-6-yl)oxy]-2-hydroxypropoxy}-4-oxo-4H-chromene-2-carboxylic acid

• ChemBase ID: 876
• Molecular Formular: C23H16O11
• Molecular Mass: 468.36654
• Monoisotopic Mass: 468.06926133
• SMILES: O(CC(O)COc1cc2c(oc(cc2=O)C(=O)O)cc1)c1c2c(oc(cc2=O)C(=O)O)ccc1
• Canonical SMILES: OC(COc1cccc2c1c(=O)cc(o2)C(=O)O)COc1ccc2c(c1)c(=O)cc(o2)C(=O)O
• InChI: InChI=1S/C23H16O11/c24-11(9-31-12-4-5-16-13(6-12)14(25)7-19(33-16)22(27)28)10-32-17-2-1-3-18-21(17)15(26)8-20(34-18)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)
• InChIKey: FSINDHDHRQZTPH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{3-[(2-carboxy-4-oxo-4H-chromen-6-yl)oxy]-2-hydroxypropoxy}-4-oxo-4H-chromene-2-carboxylic acid
• IUPAC Traditional name: 5-{3-[(2-carboxy-4-oxochromen-6-yl)oxy]-2-hydroxypropoxy}-4-oxochromene-2-carboxylic acid
• Brand Name: Aarane; Alercom; Alerion; Allergocrom; Apo-Cromolyn; Children's Nasalcrom; Colimune; Crolom; Cromolyn Nasal Solution; Cromoptic; Cromovet; Fivent; Gastrocrom; Gastrofrenal; Gen-Cromoglycate; Inostral; Intal; Intal Inhaler; Intal Syncroner; Introl; Irtan; Lomudal; Lomupren; Lomusol; Lomuspray; Nalcrom; Nalcron; Nasalcrom; Nasmil; Opticrom; Opticron; Rynacrom; Sofro; Vistacrom; Vividrin
• Synonyms: Acide Cromoglicique [INN-French]; Acido Cromoglicico [INN-Spanish]; Acidum Cromoglicicum [INN-Latin]; Cromoglicic Acid; Cromoglycic Acid; Cromolyn; Cromoglycate; Cromoglicate

Database IDs

• CAS Number: 16110-51-3
• PubChem SID: 160964339
• PubChem CID: 27686

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7642059
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -4.92321
• LogD (pH = 7.4): -5.5695944
• Log P: 1.4770117
• Molar Refractivity: 114.1067 cm^3
• Polarizability: 42.951942 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.94
• LOG S: -4.2
• Solubility (Water): 2.98e-02 g/l

PROPERTIES

Physical Property

• Solubility: 210 mg/L
• Hydrophobicity(logP): 1.6

DETAILS

DrugBank - DB01003

• Drug Groups: approved
• Description: A chromone complex that acts by inhibiting the release of chemical mediators from sensitized mast cells. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack. [PubChem]
• Indication: For the management of patients with bronchial asthma. Also used in the treatment of vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.
• Pharmacology: Cromoglicate or cromolyn (USAN), a synthetic compound, inhibits antigen-induced bronchospasms and, hence, is used to treat asthma and allergic rhinitis. Cromoglicate is used as an ophthalmic solution to treat conjunctivitis and is taken orally to treat systemic mastocytosis and ulcerative colitis.
• Toxicity: Symptoms of overdose include cough, nasal congestion, nausea, sneezing and wheezing.
• Affected Organisms: Humans and other mammals
• Absorption: 1%
• Half Life: 1.3 hours
• References: Heinke S, Szucs G, Norris A, Droogmans G, Nilius B: Inhibition of volume-activated chloride currents in endothelial cells by chromones. Br J Pharmacol. 1995 Aug;115(8):1393-8. [Pubmed]
• External Links: Wikipedia; RxList

REFERENCES

• Heinke S, Szucs G, Norris A, Droogmans G, Nilius B: Inhibition of volume-activated chloride currents in endothelial cells by chromones. Br J Pharmacol. 1995 Aug;115(8):1393-8. Pubmed