Identification

Name
Cromoglicic acid
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.

Structure
Thumb
Synonyms
  • 5-[3-(2-carboxy-4-oxo-4H-5-chromenyloxy)-2-hydroxypropoxy]-4-oxo-4H-2-chromenecarboxylic acid
  • Acide Cromoglicique
  • Acido Cromoglicico
  • Acidum Cromoglicicum
  • Cromoglicate
  • Cromoglicic acid
  • Cromoglycate
  • Cromoglycic acid
  • Cromolyn
External IDs
R03BC01
Product Ingredients
IngredientUNIICASInChI Key
Cromoglicate sodiumQ2WXR1I0PK15826-37-6VLARUOGDXDTHEH-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cromolyn SodiumSolution20 mg/mLOralWallace Pharmaceuticals Inc.2015-10-20Not applicableUs
Cromolyn SodiumConcentrate20 mg/mLOralWallace Pharmaceuticals Inc.2015-06-15Not applicableUs
Cromolyn SodiumSolution, concentrate20 mg/mLOralPrasco, Laboratories2011-12-12Not applicableUs
GastrocromLiquid20 mg/mLOralMeda Pharmaceuticals Ltd2015-05-01Not applicableUs
GastrocromSolution, concentrate20 mg/mLOralJazz Pharmaceuticals Commercial Corp.1996-11-01Not applicableUs
Gen-cromoglycate Sterinebs - Liq Inh 1%Liquid1 %Respiratory (inhalation)Genpharm Ulc1996-09-102001-08-03Canada
Intal InhalerAerosol, metered1 mgRespiratory (inhalation)Sanofi Aventis1982-12-312007-02-28Canada
Intal Nebulizer 1%Solution1 %Respiratory (inhalation)Aventis Pharma Ltd.1981-12-312004-07-30Canada
Intal Spincaps 20mgPowder20 mgRespiratory (inhalation)Aventis Pharma Ltd.1985-12-312006-06-09Canada
Intal SyncronerAerosol, metered1 mgRespiratory (inhalation)Aventis Pharma Ltd.1985-12-312004-07-30Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cromolyn SterulesSolution1 %Respiratory (inhalation)Apotex Corporation1998-06-18Not applicableCanada
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicAkorn1998-04-29Not applicableUs
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicTeva1998-05-262016-10-31Us
Cromolyn SodiumSolution20 mg/2mLIntrabronchialWoodward Pharma Services Llc2017-10-16Not applicableUs
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicBauch & Lomb Incorporated1995-01-30Not applicableUs
Cromolyn SodiumSolution, concentrate100 mg/5mLOralPack Pharmaceuticals LLC2011-12-05Not applicableUs
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicNucare Pharmaceuticals, Inc.1995-01-30Not applicableUs
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicSandoz1999-06-29Not applicableUs
Cromolyn SodiumSolution, concentrate100 mg/5mLOralWoodward Pharma Services Llc2017-10-16Not applicableUs
Cromolyn SodiumSolution / drops40 mg/mLOphthalmicA S Medication Solutions1999-06-292017-06-20Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Allergan Eye Itch ReliefSolution2 %OphthalmicAllerganNot applicableNot applicableCanada
Anti-allergy Eye DropsSolution2 %OphthalmicPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
Apo-cromolyn Nasal SpraySolution; Spray2 %NasalApotex Corporation1997-07-28Not applicableCanada
Cromolyn Eye DropsSolution2 %OphthalmicPendopharm Division Of De Pharmascience Inc1993-12-31Not applicableCanada
Cromolyn SodiumSpray, metered5.2 mg/mLNasalCardinal Health2010-07-03Not applicableUs
Cromolyn SodiumSpray, metered5.2 mg/mLNasalBauch & Lomb Incorporated2001-07-03Not applicableUs
Cromolyn SodiumSpray, metered5.2 mg/mLNasalMajor2001-07-03Not applicableUs
Cromolyn SodiumSpray, metered5.2 mg/mLNasalCVS Health2001-07-03Not applicableUs
Gen-cromolyn Nasal SprayAerosol, metered; Solution2 %NasalGenpharm Ulc1997-07-082001-08-03Canada
NasalCromSpray, metered5.2 mg/1NasalPrestige Brands Holdings, Inc.2009-10-29Not applicableUs
International/Other Brands
Aarane (Sanofi) / Allergocrom (Ursapharm) / Colimune (Sanofi) / Crolom (Crolom) / Cromo-Comod (Ursapharm) / Cromoptic (Bausch & Lomb) / Gastrofrenal (Marvecs Pharma Services) / Intal (Sanofi) / Lomudal (Sanofi) / Lomusol (Sanofi) / Opticron (Cooper) / Rynacrom (Sanofi) / Vividrin (Bausch & Lomb)
Categories
UNII
Y0TK0FS77W
CAS number
16110-51-3
Weight
Average: 468.3665
Monoisotopic: 468.069261354
Chemical Formula
C23H16O11
InChI Key
IMZMKUWMOSJXDT-UHFFFAOYSA-N
InChI
InChI=1S/C23H16O11/c24-11(9-31-14-3-1-5-16-20(14)12(25)7-18(33-16)22(27)28)10-32-15-4-2-6-17-21(15)13(26)8-19(34-17)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)
IUPAC Name
5-{3-[(2-carboxy-4-oxo-4H-chromen-5-yl)oxy]-2-hydroxypropoxy}-4-oxo-4H-chromene-2-carboxylic acid
SMILES
OC(COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O)COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O

Pharmacology

Indication

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

Structured Indications
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.

TargetActionsOrganism
ACalcium-activated potassium channel subunit alpha-1
inhibitor
Human
UProtein S100-P
antagonist
Human
Absorption

1%

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Margit Nagy, Lidia Fedina, Rita Balazs, Borbala Barta, Gizella Toth nee Gyarmati, Judit Marczis, Andras Szasz, "Antiasthmatic aerosol preparation of sodium cromoglycate." U.S. Patent US5753208, issued June, 1965.

US5753208
General References
  1. 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:8564197]
External Links
Human Metabolome Database
HMDB15138
KEGG Drug
D07753
KEGG Compound
C06928
PubChem Compound
2882
PubChem Substance
46504509
ChemSpider
2779
BindingDB
50440033
ChEBI
59773
ChEMBL
CHEMBL428880
Therapeutic Targets Database
DAP000819
PharmGKB
PA449138
RxList
RxList Drug Page
Wikipedia
Cromoglicate
ATC Codes
S01GX01 — Cromoglicic acidD11AH03 — Cromoglicic acidR01AC51 — Cromoglicic acid, combinationsS01GX51 — Cromoglicic acid, combinationsR01AC01 — Cromoglicic acidR03AK04 — Salbutamol and sodium cromoglicateR03AK05 — Reproterol and sodium cromoglicateA07EB01 — Cromoglicic acidR03BC01 — Cromoglicic acid
AHFS Codes
  • 52:02.00 — Antiallergic Agents
  • 48:10.32 — Mast-cell Stabilizers
MSDS
Download (58.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceChronic Prostatitis With Chronic Pelvic Pain Syndrome1
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers1
1RecruitingDiagnosticIdiopathic Pulmonary Fibrosis (IPF) / Reflux, Gastroesophageal / Respiratory Aspiration / Transplantation, Lung1
1, 2Unknown StatusTreatmentPapulopustular Rosacea1
2CompletedTreatmentEnd Stage Renal Disease (ESRD) / Pruritus1
2CompletedTreatmentPsoriasis1
2SuspendedTreatmentPost-stroke Cognitive Impairment / Stroke, Ischemic1
2TerminatedTreatmentUrticaria Pigmentosa1
3RecruitingTreatmentAlzheimer's Disease (AD)1
3Unknown StatusNot AvailableStroke, Acute1
4RecruitingNot AvailableIndigestion1
4RecruitingTreatmentOesophagitis, Eosinophilic1

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
FormRouteStrength
Solution; sprayNasal2 %
SolutionOphthalmic2 %
ConcentrateOral20 mg/mL
SolutionIntrabronchial20 mg/2mL
SolutionOral20 mg/mL
Solution / dropsOphthalmic40 mg/mL
Solution, concentrateOral100 mg/5mL
Solution, concentrateOral20 mg/mL
Spray, meteredNasal5.2 mg/mL
LiquidOral20 mg/mL
LiquidRespiratory (inhalation)1 %
Aerosol, metered; solutionNasal2 %
Aerosol, meteredRespiratory (inhalation)1 mg
PowderRespiratory (inhalation)20 mg
CapsuleOral100 mg
Spray, meteredNasal5.2 mg/1
SolutionRespiratory (inhalation)1 %
Liquid; sprayNasal2 %
SolutionRespiratory (inhalation)10 mg
LiquidOphthalmic2 %
SolutionOral; Respiratory (inhalation)1 %
Spray, meteredNasal2 %
Aerosol, meteredNasal2 %
OintmentOphthalmic40 mg
Prices
Unit descriptionCostUnit
Cromolyn Sodium 4% Solution 10ml Bottle38.74USD bottle
Cromolyn sodium powder9.49USD g
Intal inhaler5.77USD g
Crolom 4% eye drops4.46USD ml
Gastrocrom 100 mg/5ml Concentrate 5ml Ampule3.92USD ampule
Cromolyn 4% eye drops3.65USD ml
Cromolyn Sodium 20 mg/2ml Neb. Solution 2ml Plastic Container1.73USD plastic
Nalcrom 100 mg Capsule1.54USD capsule
Gastrocrom 100 mg/5 ml conc0.78USD ml
Nasalcrom 4% spray0.66USD ml
Cromolyn sodium nasal solution0.49USD ml
CVS Pharmacy cromolyn sod nasal solutn0.31USD ml
Pms-Sodium Cromoglycate 1 % Solution0.27USD ml
Introl 75% solution0.13USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)241 dec °CPhysProp
water solubility210 mg/LNot Available
logP1.92POMONA (1987)
pKa1.1SANGSTER,J (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0358 mg/mLALOGPS
logP1.84ALOGPS
logP1.48ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area165.89 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.11 m3·mol-1ChemAxon
Polarizability44.38 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6657
Blood Brain Barrier+0.5988
Caco-2 permeable-0.694
P-glycoprotein substrateSubstrate0.6275
P-glycoprotein inhibitor INon-inhibitor0.7152
P-glycoprotein inhibitor IINon-inhibitor0.5451
Renal organic cation transporterNon-inhibitor0.8563
CYP450 2C9 substrateNon-substrate0.8622
CYP450 2D6 substrateNon-substrate0.8862
CYP450 3A4 substrateNon-substrate0.682
CYP450 1A2 substrateNon-inhibitor0.8834
CYP450 2C9 inhibitorNon-inhibitor0.8521
CYP450 2D6 inhibitorNon-inhibitor0.8726
CYP450 2C19 inhibitorNon-inhibitor0.7856
CYP450 3A4 inhibitorNon-inhibitor0.9299
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8624
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9363
BiodegradationNot ready biodegradable0.8705
Rat acute toxicity2.5373 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9539
hERG inhibition (predictor II)Non-inhibitor0.8574
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0000900000-b29947fd1c55b6bb244e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-06r2-0090000000-14c9cd86f6f2c6066ed8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4j-0090000000-28843e4d8ab22e289734
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0390000000-3f291eddb35619c6f657
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-1970000000-3eb328adfc6464d47d0a

Taxonomy

Description
This compound belongs to the class of organic compounds known as chromones. These are compounds containing a benzopyran-4-one moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Chromones
Alternative Parents
Pyranones and derivatives / Alkyl aryl ethers / Dicarboxylic acids and derivatives / Benzenoids / Vinylogous esters / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Carboxylic acids / Organic oxides
show 1 more
Substituents
Chromone / Alkyl aryl ether / Pyranone / Dicarboxylic acid or derivatives / Pyran / Benzenoid / Heteroaromatic compound / Vinylogous ester / Secondary alcohol / Oxacycle
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid, chromones (CHEBI:59773)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
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 activati...
Gene Name
KCNMA1
Uniprot ID
Q12791
Uniprot Name
Calcium-activated potassium channel subunit alpha-1
Molecular Weight
137558.115 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Magnesium ion binding
Specific Function
May function as calcium sensor and contribute to cellular calcium signaling. In a calcium-dependent manner, functions by interacting with other proteins, such as EZR and PPP5C, and indirectly plays...
Gene Name
S100P
Uniprot ID
P25815
Uniprot Name
Protein S100-P
Molecular Weight
10399.81 Da
References
  1. 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:17179482]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34