Cromoglicic acid

Identification

Name
Cromoglicic acid
Accession Number
DB01003
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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 468.3665
Monoisotopic: 468.069261354
Chemical Formula
C23H16O11
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

Pharmacology

Indication

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

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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
UProtein S100-P
antagonist
Humans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Take before a meal. Take cromolyn sodium 30 minutes before meals.

Products

Product Ingredients
IngredientUNIICASInChI Key
Cromoglicate sodiumQ2WXR1I0PK15826-37-6VLARUOGDXDTHEH-UHFFFAOYSA-L
Product Images
International/Other Brands
Aarane (Sanofi) / Allergocrom (Ursapharm) / Colimune (Sanofi) / Cromo-Comod (Ursapharm) / Cromoptic (Bausch & Lomb) / Gastrofrenal (Marvecs Pharma Services) / Lomudal (Sanofi) / Lomusol (Sanofi) / Opticron (Cooper) / Rynacrom (Sanofi) / Vividrin (Bausch & Lomb)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GastrocromSolution, concentrate100 mg/5mLOralCelltech Pharmaceuticals, Inc.2006-05-11Not applicableUS flag
GastrocromSolution, concentrate20 mg/1mLOralJazz Pharmaceuticals, Inc.1996-11-012019-02-28US flag
GastrocromLiquid20 mg/1mLOralMEDA Pharmaceuticals2015-05-01Not applicableUS flag
IntalInhalant1 mg/1Respiratory (inhalation)Physicians Total Care, Inc.1996-06-102009-09-30US flag
IntalInhalant1 mg/1Respiratory (inhalation)Pfizer Laboratories Div Pfizer Inc.1985-12-052009-03-31US flag60793 01120180907 15195 dm9u77
IntalInhalant1 mg/1Respiratory (inhalation)Physicians Total Care, Inc.1996-06-102009-09-30US flag
IntalInhalant20 mg/2mLRespiratory (inhalation)Pfizer Laboratories Div Pfizer Inc.1982-05-282008-09-18US flag
Intal InhalerAerosol, meteredRespiratory (inhalation)Sanofi Aventis1982-12-312007-02-28Canada flag
Intal Nebulizer 1%SolutionRespiratory (inhalation)Aventis Pharma Ltd.1981-12-312004-07-30Canada flag
Intal Spincaps 20mgPowderRespiratory (inhalation)Aventis Pharma Ltd.1985-12-312006-06-09Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-cromolyn SterulesSolutionRespiratory (inhalation)Apotex Corporation1998-06-18Not applicableCanada flag
CrolomSolution / drops40 mg/1mLOphthalmicBauch & Lomb Incorporated1995-01-302010-02-06US flag
Cromolyn SodiumSolution / drops40 mg/1mLOphthalmicNucare Pharmaceuticals, Inc.1995-01-302019-12-31US flag
Cromolyn SodiumSolution40 mg/1mLOphthalmicPacific Pharma1999-06-112008-07-19US flag
Cromolyn SodiumSolution / drops40 mg/1mLOphthalmicTeva1998-05-262016-10-31US flag
Cromolyn SodiumSolution / drops40 mg/1mLOphthalmicProficient Rx LP1998-05-26Not applicableUS flag
Cromolyn SodiumSolution20 mg/2mLIntrabronchialTeva Pharmaceuticals USA, Inc.2000-01-18Not applicableUS flag
Cromolyn SodiumSolution / drops40 mg/1mLOphthalmicSandoz Inc1999-06-29Not applicableUS flag
Cromolyn SodiumSolution20 mg/2mLRespiratory (inhalation)Mylan Specialty2009-06-292009-06-30US flag
Cromolyn SodiumSolution20 mg/2mLOralActavis Pharma Company1999-04-022010-09-30US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Allergan Eye Itch ReliefSolutionOphthalmicAllerganNot applicableNot applicableCanada flag
Anti-allergy Eye DropsSolutionOphthalmicPendopharm Division Of Pharmascience IncNot applicableNot applicableCanada flag
Apo-cromolyn Nasal SpraySprayNasalApotex Corporation1997-07-28Not applicableCanada flag
Cromolyn Eye DropsSolutionOphthalmicPendopharm Division Of Pharmascience Inc1993-12-31Not applicableCanada flag
Cromolyn SodiumSpray, metered5.2 mg/1mLNasalCVS Health2001-07-03Not applicableUS flag
Cromolyn SodiumSpray, metered5.2 mg/1mLNasalMajor2001-07-03Not applicableUS flag
Cromolyn SodiumSpray, metered5.2 mg/1mLNasalCardinal Health2010-07-03Not applicableUS flag
Cromolyn SodiumSpray, metered5.2 mg/1mLNasalBausch & Lomb Incorporated2001-07-03Not applicableUS flag
Gen-cromolyn Nasal SprayAerosol, metered; SolutionNasalGenpharm Ulc1997-07-082001-08-03Canada flag
NasalCromSpray, metered5.2 mg/1NasalPrestige Brands Holdings, Inc.2009-10-29Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

Categories

ATC Codes
R03AK05 — Reproterol and sodium cromoglicateR03AK04 — Salbutamol and sodium cromoglicateR03BC01 — Cromoglicic acidR01AC51 — Cromoglicic acid, combinationsS01GX51 — Cromoglicic acid, combinationsR01AC01 — Cromoglicic acidS01GX01 — Cromoglicic acidD11AH03 — Cromoglicic acidA07EB01 — Cromoglicic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Chromone / Dicarboxylic acid or derivatives / Ether / Heteroaromatic compound
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid, chromones (CHEBI:59773)

Chemical Identifiers

UNII
Y0TK0FS77W
CAS number
16110-51-3
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

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]
  2. Health Canada Product Monograph: Nalcrom (sodium cromoglycate) oral capsules [Link]
Human Metabolome Database
HMDB0015138
KEGG Drug
D07753
KEGG Compound
C06928
PubChem Compound
2882
PubChem Substance
46504509
ChemSpider
2779
BindingDB
50440033
RxNav
2921
ChEBI
59773
ChEMBL
CHEMBL428880
ZINC
ZINC000001530788
Therapeutic Targets Database
DAP000819
PharmGKB
PA449138
RxList
RxList Drug Page
Wikipedia
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
4CompletedTreatmentOesophagitis, Eosinophilic1
4Unknown StatusNot AvailableDyspepsia1
3Active Not RecruitingTreatmentAlzheimer's Disease (AD)1
3Not Yet RecruitingTreatmentExercise-Induced Bronchospasm1
3Unknown StatusNot AvailableStroke, Acute1
2CompletedTreatmentEnd Stage Renal Disease (ESRD) / Pruritus1
2CompletedTreatmentPsoriasis1
2Not Yet RecruitingTreatmentPost-stroke Cognitive Impairment / Stroke, Ischemic1
2RecruitingBasic ScienceAmyotrophic Lateral Sclerosis (ALS)1
2TerminatedTreatmentUrticaria Pigmentosa1

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
  • 3M Health Care
  • Actavis Group
  • Akorn Inc.
  • Alcon Laboratories
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Automatic Liquid Packaging Inc.
  • AzurPharma Inc.
  • Bausch & Lomb Inc.
  • Cardinal Health
  • Catalent Pharma Solutions
  • CVS Pharmacy
  • Dey Pharma LP
  • Dispensing Solutions
  • Falcon Pharmaceuticals Ltd.
  • Fisons PLC
  • Ivax Pharmaceuticals
  • King Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Medisca Inc.
  • Novex Pharma
  • Pacific Pharma Lp
  • Pack Pharmaceuticals
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Rhone Poulenc Rorer Respiratory
  • Sanofi-Aventis Inc.
  • Sorter Labs
  • Teva Pharmaceutical Industries Ltd.
  • Warrick Pharmaceuticals Corp.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)1 mg
Solution / dropsOphthalmic
Solution / dropsOphthalmic10 ml
SprayNasal15 ml
Solution / dropsOphthalmic2 %
SprayNasal
Solution / dropsOphthalmic40 mg/1mL
Solution / drops; suspension / dropsOphthalmic10 mg/0.5mL
Solution / drops; suspension / dropsOphthalmic
Kit20 mg/mL
SolutionIntrasinal; Nasal20 g
SolutionConjunctival; Ophthalmic20 mg
SolutionIntrasinal; Nasal40 mg
SolutionOphthalmic
SolutionIntrabronchial20 mg/2mL
SolutionOphthalmic40 mg/1mL
SolutionOral20 mg/2mL
SolutionOral20 mg/1mL
SolutionRespiratory (inhalation)20 mg/2mL
Solution, concentrateOral20 mg/1mL
Spray, meteredNasal5.2 mg/1mL
Solution / dropsOphthalmic4 %
LiquidOral20 mg/1mL
Solution, concentrateOral100 mg/5mL
LiquidRespiratory (inhalation)
Aerosol, metered; solutionNasal
SolutionOphthalmic40 mg
InhalantRespiratory (inhalation)1 mg/1
InhalantRespiratory (inhalation)20 mg/2mL
AerosolRespiratory (inhalation)1 mg
AerosolRespiratory (inhalation)5 mg
Aerosol, meteredRespiratory (inhalation)
GasRespiratory (inhalation)1 mg
SolutionRespiratory (inhalation)20 mg
PowderRespiratory (inhalation)
PowderRespiratory (inhalation)20 MG
Solution / drops40 MG/ML
Spray20 MG/2ML
SprayNasal40 MG/ML
CapsuleOral
Spray, meteredNasal5.2 mg/1
Solution / drops; suspension / dropsOphthalmic20 MG/ML
Solution / dropsOphthalmic20 mg/ml
SolutionRespiratory (inhalation)
Liquid; sprayNasal
LiquidOphthalmic
SolutionConjunctival; Ophthalmic40 mg
CapsuleOral100 MG
SprayNasal20 MG/ML
Spray, meteredNasal
Aerosol, meteredNasal
SolutionOphthalmic1 mL
OintmentOphthalmic
Solution / dropsOphthalmic2 g/100mL
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

Targets

Kind
Protein
Organism
Humans
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 October 26, 2020 22:41

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