DrugBank: Cromoglicate (DB01003)

targets (2)

Identification

Name

Cromoglicate

Accession Number

DB01003 (APRD00336)

Type

small molecule

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]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Acide Cromoglicique [INN-French]
Acido Cromoglicico [INN-Spanish]
Acidum Cromoglicicum [INN-Latin]
Cromoglicic Acid
Cromoglycate
Cromoglycic Acid
Cromolyn

Brand names

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

Brand name mixtures

Not Available

Categories

Anti-Asthmatic Agents

CAS number

16110-51-3

Weight

Average: 468.3665
Monoisotopic: 468.069261354

Chemical Formula

C₂₃H₁₆O₁₁

InChI Key

InChIKey=FSINDHDHRQZTPH-UHFFFAOYSA-N

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)

Plain Text

IUPAC Name

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

SMILES

OC(COC1=CC2=C(OC(=CC2=O)C(O)=O)C=C1)COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Chromones

Substructures

Glycerol and Derivatives
Hydroxy Compounds
Acetates
Phenols and Derivatives
Ethers
Benzene and Derivatives
Chromones
Carboxylic Acids and Derivatives
Heterocyclic compounds
Aromatic compounds
Anisoles
Alcohols and Polyols
Phenyl Esters

Pharmacology

Indication

For the management of patients with bronchial asthma. Also used in the treatment of vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.

Pharmacodynamics

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.

Mechanism of action

Cromoglicate inhibits degranulation of mast cells, subsequently preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), mediators of type I allergic reactions. Cromoglicate also may reduce the release of inflammatory leukotrienes. Cromoglicate may act by inhibiting calcium influx.

Absorption

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

1.3 hours

Clearance

Not Available

Toxicity

Symptoms of overdose include cough, nasal congestion, nausea, sneezing and wheezing.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

King pharmaceuticals inc
Sanofi aventis us llc
Ucb inc
Genera pharmaceuticals llc
Azur pharma international ltd
Bausch and lomb pharmaceuticals inc
Akorn inc
Alcon laboratories inc
Novex pharma
Allergan inc
Actavis mid atlantic llc
Dey lp
Pharmascience inc
Roxane laboratories inc
Teva parenteral medicines inc
Watson laboratories inc
Wockhardt eu operations (swiss) ag
L perrigo co
Qpharma llc
Blacksmith brands inc

Packagers

Dosage forms

Form	Route	Strength
Aerosol, metered	Respiratory (inhalation)
Capsule	Oral
Liquid	Ophthalmic
Solution	Ophthalmic
Solution	Respiratory (inhalation)
Spray	Nasal

Prices

Unit description	Cost	Unit
Cromolyn Sodium 4% Solution 10ml Bottle	38.74 USD	bottle
Cromolyn sodium powder	9.49 USD	g
Intal inhaler	5.77 USD	g
Crolom 4% eye drops	4.46 USD	ml
Gastrocrom 100 mg/5ml Concentrate 5ml Ampule	3.92 USD	ampule
Cromolyn 4% eye drops	3.65 USD	ml
Cromolyn Sodium 20 mg/2ml Neb. Solution 2ml Plastic Container	1.73 USD	plastic
Nalcrom 100 mg Capsule	1.54 USD	capsule
Gastrocrom 100 mg/5 ml conc	0.78 USD	ml
Nasalcrom 4% spray	0.66 USD	ml
Cromolyn sodium nasal solution	0.49 USD	ml
CVS Pharmacy cromolyn sod nasal solutn	0.31 USD	ml
Pms-Sodium Cromoglycate 1 % Solution	0.27 USD	ml
Introl 75% solution	0.13 USD	ml

Patents

Not Available

Properties

State

solid

Melting point

241-242oC

Experimental Properties

Property	Value	Source
water solubility	210 mg/L	PhysProp
logP	1.6	PhysProp
pKa	1.1	Various sources

Predicted Properties

Property	Value	Source
water solubility	2.98e-02 g/l	ALOGPS
logP	1.94	ALOGPS
logP	1.48	ChemAxon Molconvert
logS	-4.20	ALOGPS
pKa	2.37	ChemAxon Molconvert
hydrogen acceptor count	11	ChemAxon Molconvert
hydrogen donor count	3	ChemAxon Molconvert
polar surface area	165.89	ChemAxon Molconvert
rotatable bond count	8	ChemAxon Molconvert
refractivity	114.11	ChemAxon Molconvert
polarizability	44.74	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

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

Resource	Link
KEGG Compound	C06928
PubChem Compound	27686
PubChem Substance	46504509
ChemSpider	25758
ChEBI	128458
ChEMBL	128458
Therapeutic Targets Database	DAP000819
PharmGKB	PA449138
Drug Product Database	2231671
RxList	http://www.rxlist.com/cgi/generic/cromolyn.htm
Wikipedia	http://en.wikipedia.org/wiki/Cromoglicate

ATC Codes

R01AC01
A07EB01
S01GX01
R03BC01

AHFS Codes

48:10.32

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (58.3 KB)

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Calcium-activated potassium channel subunit alpha 1 Pharmacological action: yes Actions: inhibitor Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX) Organism class: human UniProt ID: Q12791 Gene: KCNMA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 2. Protein S100-P Pharmacological action: unknown Actions: antagonist Organism class: human UniProt ID: P25815 Gene: S100P Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Arumugam T, Ramachandran V, Logsdon CD: Effect of cromolyn on S100P interactions with RAGE and pancreatic cancer growth and invasion in mouse models. J Natl Cancer Inst. 2006 Dec 20;98(24):1806-18. Pubmed

Targets

1. Calcium-activated potassium channel subunit alpha 1

Pharmacological action: yes
Actions: inhibitor

Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX)

Organism class: human
UniProt ID: Q12791 Link_out

Gene: KCNMA1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Protein S100-P

Pharmacological action: unknown
Actions: antagonist
Organism class: human
UniProt ID: P25815 Link_out

Gene: S100P Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Arumugam T, Ramachandran V, Logsdon CD: Effect of cromolyn on S100P interactions with RAGE and pancreatic cancer growth and invasion in mouse models. J Natl Cancer Inst. 2006 Dec 20;98(24):1806-18. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:45

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.