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Identification
NameCromoglicic acid
Accession NumberDB01003  (APRD00336)
TypeSmall Molecule
GroupsApproved
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
Thumb
Synonyms
SynonymLanguageCode
5-[3-(2-Carboxy-4-oxo-4H-5-chromenyloxy)-2-hydroxypropoxy]-4-oxo-4H-2-chromenecarboxylic acidNot AvailableNot Available
Acide CromogliciqueFrenchINN
Acido CromoglicicoSpanishINN
Acidum CromoglicicumLatinINN
CromoglicateNot AvailableNot Available
Cromoglicic AcidNot AvailableINN
CromoglycateNot AvailableFormer BAN
CromolynNot AvailableUSAN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gastrocromsolution, concentrate20 mg/mLoralJazz Pharmaceuticals Commercial Corp.1996-11-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AaraneSanofi
AllergocromUrsapharm
ColimuneSanofi
CrolomCrolom
Cromo-ComodUrsapharm
CromopticBausch & Lomb
GastrofrenalMarvecs Pharma Services
IntalSanofi
LomudalSanofi
LomusolSanofi
NalcromSanofi
OpticromAllergan
OpticronCooper
RynacromSanofi
VividrinBausch & Lomb
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Sodium cromoglicate
ThumbNot applicableDBSALT000985
Categories
CAS number16110-51-3
WeightAverage: 468.3665
Monoisotopic: 468.069261354
Chemical FormulaC23H16O11
InChI KeyIMZMKUWMOSJXDT-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chromones. These are compounds containing a benzopyran-4-one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentChromones
Alternative Parents
Substituents
  • Chromone
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Vinylogous ester
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the management of patients with bronchial asthma. Also used in the treatment of vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.
PharmacodynamicsCromoglicate 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 actionCromoglicate 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.
Absorption1%
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life1.3 hours
ClearanceNot Available
ToxicitySymptoms of overdose include cough, nasal congestion, nausea, sneezing and wheezing.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.8521
CYP450 2D6 substrateNon-inhibitor0.8726
CYP450 2C19 substrateNon-inhibitor0.7856
CYP450 3A4 substrateNon-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
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, concentrateoral20 mg/mL
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point241 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 Reference
  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
External Links
ATC CodesR03BC01S01GX01A07EB01D11AH03R01AC01
AHFS Codes
  • 48:10.32
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (58.3 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Calcium-activated potassium channel subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Calcium-activated potassium channel subunit alpha-1 Q12791 Details

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
  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

2. Protein S100-P

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Protein S100-P P25815 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12