CROMOLYN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H16O11
Molecular Weight	468.3665
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O)COC3=CC=CC4=C3C(=O)C=C(O4)C(O)=O

InChI

InChIKey=IMZMKUWMOSJXDT-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2000/75-271_Cromolyn%20Sodium_prntlbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18887slr020_intal_lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf |http://www.rxlist.com/crolom-drug.htm | https://www.ncbi.nlm.nih.gov/pubmed/8809432

Cromolyn is a mast cell stabilizer. In vitro and in vivo animal studies have shown that cromolyn sodium inhibits the degranulation of sensitized mast cells, which occurs after exposure to specific antigens. Cromolyn sodium acts by inhibiting the release of histamine and SRS-A (slow-reacting substance of anaphylaxis) from the mast cell. Cromolyn is indicated in the management of patients with mastocytosis, prophylaxis (long-term control) of bronchial asthma, prevention of exercise-induced bronchospasm, prevention and treatment of seasonal and perennial allergic rhinitis The most frequently reported adverse reactions attributed to cromolyn sodium treatment were: throat irritation or dryness, bad taste, cough, wheeze, nausea.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
G-protein coupled receptor 35 11 Target ID: CHEMBL1293267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22218743 \| https://www.ncbi.nlm.nih.gov/pubmed/3110245	Agonist 2678
Chloride channels 4 Target ID: Chloride channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/1280136	Blocker 537	19.0 µM [IC50]
calcium ion import 8 Target ID: GO:0070509 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18887slr020_intal_lbl.pdf	Blocker 537
mast cell activation 6 Target ID: GO:0045576 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12396022	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Mastocytosis 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf	Primary	Approved 8429	CROMOLYN SODIUM Approved Use GASTROCROM is indicated in the management of patients with mastocytosis. Use of this product has been associated with improvement in diarrhea, flushing, headaches, vomiting, urticaria, abdominal pain, nausea, and itching in some patients. Launch Date 1994
Bronchial asthma 50 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18887slr020_intal_lbl.pdf	Preventing	Approved 8429	CROMOLYN SODIUM Approved Use Cromolyn sodium is a prophylactic agent indicated in the management of patients with bronchial asthma. Launch Date 1994
Allergic rhinitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-702_Cromolyn%20Sodium_prntlbl.pdf	Palliative	Approved 8429	CROMOLYN SODIUM Approved Use Cromolyn sodium is used to prevent and relieve nasal symptoms of hay fever and other nasal allergies. Launch Date 1994
Vernal keratoconjunctivitis 6 Sources: http://www.rxlist.com/crolom-drug.htm	Primary	Approved 8429	CROMOLYN SODIUM Approved Use Cromolyn sodium ophthalmic solution is indicated in the treatment of vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis. Launch Date 1994
Asthma 241 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2000/75-271_Cromolyn%20Sodium_prntlbl.pdf	Preventing	Approved 8429	CROMOLYN SODIUM Approved Use To help prevent asthma attacks. Launch Date 1994
Allergic rhinitis 100 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b34d36ca-4df4-458c-af0f-c0d0c9a025d9	Preventing	Approved 8429	NASALCROM Approved Use To prevent and relieve nasal symptoms of hay fever and other nasal allergies Launch Date 1997
Allergic conjunctivitis 100 Sources: https://www.medicines.org.uk/emc/PIL.31398.latest.pdf	Palliative	Approved 8429	OPTREX Approved Use Optrex is used for the prevention and treatment of eye allergies.

C_max

Value	Dose	Co-administered	Analyte	Population
0.24 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	17.1 mg single, respiratory dose: 17.1 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN cerebrospinal fluid	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.34 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	34.2 mg single, respiratory dose: 34.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN cerebrospinal fluid	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
46.69 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	17.1 mg single, respiratory dose: 17.1 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
96.75 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	34.2 mg single, respiratory dose: 34.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
156 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32944204/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
236 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32944204/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
338 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32944204/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
526 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32944204/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:		CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	17.1 mg single, respiratory dose: 17.1 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28856569/	34.2 mg single, respiratory dose: 34.2 mg route of administration: Respiratory experiment type: SINGLE co-administered: IBUPROFEN	IBUPROFEN	CROMOLYN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
62.4 mg 1 times / day multiple, intranasal Dose: 62.4 mg, 1 times / day Route: intranasal Route: multiple Dose: 62.4 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/402406	unhealthy, 25 years (range: 5-51 years) n = 45 Health Status: unhealthy Age Group: 25 years (range: 5-51 years) Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/402406	Sources: https://pubmed.ncbi.nlm.nih.gov/402406
200 mg 4 times / day multiple, oral Recommended Dose: 200 mg, 4 times / day Route: oral Route: multiple Dose: 200 mg, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: mastocytosis Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf
2 % multiple, ophthalmic Dose: 2 % Route: ophthalmic Route: multiple Dose: 2 % Sources: https://pubmed.ncbi.nlm.nih.gov/22118312	unhealthy, adult n = 37 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: adult Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/22118312	Sources: https://pubmed.ncbi.nlm.nih.gov/22118312

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://pdf.hres.ca/dpd_pm/00015714.PDF#page=2 Page: 2.0	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1127	http://www.3bsc.com/index/pro_info.php?id=54843
AHH Chemical co.,ltd	MT-00052	http://www.ahhchemical.com/product/MT-00052.html
AK Scientific, Inc. (AKSCI)	O542	http://www.aksci.com/item_detail.php?cat=O542
Acadechem	ACDC-030058	http://acadechemical.com/product/1820
Achemo Scientific Limited	AC-85374	http://www.achemo.com/search/?Keyword= 16110-51-3
Ambeed	A839184	https://www.ambeed.com/products/16110-51-3.html
Ambinter	Amb20243267	http://www.ambinter.com/reference/20243267
Angene	AGN-PC-07Y4GQ	http://www.angenechemical.com/productshow/AGN-PC-07Y4GQ.html
Anward	ANW-71958	http://www.anward.com/pro_result/58409
Aurora Fine Chemicals LLC	A13.110.125	http://online.aurorafinechemicals.com/info?ID=A13.110.125
BLD Pharm	BD53784	http://www.bldpharm.com/products/16110-51-3.html
BioSynth	J-009783	https://www.biosynth.com/en/products/all-products/products/J-009783.html
CSNpharm	CSN17084	https://www.csnpharm.com/products/cromolyn.html
ChemMol	30102492	http://www.chemmol.com/chemmol/30102492.html
ChemMol	44002046	http://www.chemmol.com/chemmol/44002046.html
Chemspace	CSSS00020617570	https://chem-space.com/CSSS00020617570
Clearsynth	CS-L-00099	https://www.clearsynth.com/en/CSL00099.html
DC Chemicals	DC20926	http://www.dcchemicals.com/product_show-DC20926.html
Finetech	FT-0601561	http://www.finetechnology-ind.com/prod/detail/pub/16110-51-3.html
Matrix Scientific	97021	https://www.matrixscientific.com/097021.html
MolPort	MolPort-005-934-024	https://www.molport.com/shop/molecule-link/MolPort-005-934-024
Smolecule	S591882	https://www.smolecule.com/products/s591882
THE BioTek	bt-315145	https://www.thebiotek.com/product/others/bt-315145
abcr GmbH	AB540456	http://www.abcr.com/shop/en/AB540456
eNovation Chemicals	D926914	https://www.enovationchem.com/ProductDetails.asp?ProductID=D926914

PubMed

Title	Date	PubMed
Pro-drugs for the oral delivery of disodium cromoglycate.	1988 Jan	3132335
[Effects of orally available prodrug of cromoglycic acid on collagen-induced arthritis mice].	1999 Oct	10629873
[A sniffing child].	2001	12092406
Cromolyn sodium suppresses eosinophilic inflammation in patients with aspirin-intolerant asthma.	2001 Aug	11527248
Adenosine-mediated mast cell degranulation in adenosine deaminase-deficient mice.	2001 Aug	11454903
Reasons for and costs of hospitalization for pediatric asthma: a prospective 1-year follow-up in a population-based setting.	2001 Dec	11846871
Determination of sodium cromoglycate in human plasma by liquid chromatography-mass spectrometry in the turbo ion spray mode.	2001 Dec 25	11767311
Inhaled sodium cromoglycate.	2001 Jul	11450654
A novel pharmacologic action of glucocorticosteroids on leukotriene C4 catabolism.	2001 Jul	11447392
The efficacy and safety of asthma medications during pregnancy.	2001 Jun	11453610
[Preventive monotherapy with montelukast versus DNCG in children with mild asthma. Results of and exploratory pilot study].	2001 May	11449608
Therapy choices beyond antihistamines. Vasomotor rhinitis.	2001 Nov	12420500
Effect of specific immunotherapy versus loratadine on serum adhesion molecules.	2001 Oct	11763722
Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models.	2001 Sep	11831367
[Sodium cromoglycate in the treatment of food hypersensitivity in children under 3 years of age].	2001 Sep	11761817
Metering performance of several metered-dose inhalers with different spacers/holding chambers.	2001 Winter	11791683
Use of intranasal cromolyn sodium for allergic rhinitis.	2002 Apr	11936930
Inhaled sodium cromoglycate in children with asthma.	2002 Aug	12149542
Cause and effect relationship between myocardial mast cell number and matrix metalloproteinase activity.	2002 Aug	12124196
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].	2002 Aug 5	12162793
Efficacy and safety of inhaled steroid and cromone treatment in school-age children: a randomized pragmatic pilot study.	2002 Feb	12000495
Using case management to increase antiinflammatory medication use among a managed care population with asthma.	2002 Feb	11883740
Medical management of Cronkhite-Canada syndrome.	2002 Feb	11846261
From khellin to sodium cromoglycate--a tribute to the work of Dr. R. E. C. Altounyan (1922-1987).	2002 Jan	11836935
Effects of topical anti-inflammatory and antiallergic eyedrops on prostaglandin E2-induced aqueous flare elevation in pigmented rabbits.	2002 Jul	12096966
Water dynamics in channel hydrates investigated using H/D exchange.	2002 Jul 25	12100853
Single dose of ketotifen fumarate .025% vs 2 weeks of cromolyn sodium 4% for allergic conjunctivitis.	2002 Jul-Aug	12431044
The combination of nebulized sodium cromoglycate and salbutamol in the treatment of moderate-to-severe asthma in children.	2002 Jun	12144644
Efficacy and patient satisfaction with cromolyn sodium nasal solution in the treatment of seasonal allergic rhinitis: a placebo-controlled study.	2002 Jun	12117084
Allergic rhinitis remains an important disease.	2002 Jun	12090642
(S)nifty treatment for pollen allergies.	2002 Jun	12085791
Balancing safety and efficacy in the treatment of pediatric asthma.	2002 Jun	12063513
Generalized bullae in an infant.	2002 Jun	12056971
Management of suspected acute viral upper respiratory tract infection in children with intranasal sodium cromoglicate: a randomised controlled trial.	2002 Jun 22	12090980
[Exercise-induced asthma. Not a reason to be benched].	2002 Jun 27	12154481
Fluticasone for the treatment of symptomatic bronchial asthma in children treated with sodium cromogylate--a prospective, randomised trial.	2002 Jun 28	12117660
Effects of budesonide inhalation suspension on hypothalamic-pituitary-adrenal-axis function in infants and young children with persistent asthma.	2002 Mar	11926625
Inhaled sodium cromoglycate in children with asthma.	2002 Mar	11867840
Perinatal immunomodulation.	2002 May	12389669
Management of allergic and nonallergic rhinitis.	2002 May	12173440
Effect of interventions during acute respiratory syncytial virus bronchiolitis on subsequent long term respiratory morbidity.	2002 May	12150194
Ischaemic preconditioning and mast cell histamine release: microdialysis of isolated rat hearts.	2002 May	12123626
Floating a metered-dose inhaler is not an accurate measure of remaining medicine.	2002 May	12027080
Relative lung and systemic bioavailability of sodium cromoglycate inhaled products using urinary drug excretion post inhalation.	2002 May	12015790
Nebulized budesonide inhalation suspension compared with cromolyn sodium nebulizer solution for asthma in young children: results of a randomized outcomes trial.	2002 May	11986448
Long-term management of asthma in children: effectiveness of inhaled corticosteroids compared to other medications.	2002 Nov	12518556
A comparison of the efficacy and tolerability of olopatadine hydrochloride 0.1% ophthalmic solution and cromolyn sodium 2% ophthalmic solution in seasonal allergic conjunctivitis.	2002 Oct	12462286
Sodium cromoglycate and doxantrazole are oxygen radical scavengers.	2002 Oct	12412677
Mast cells as a target of rheumatoid arthritis treatment.	2002 Sep	12396022
Mast cells mediate the microvascular inflammatory response to systemic hypoxia.	2003 Jan	12391033

Patents

Sample Use Guides

In Vivo Use Guide

Two metered inhalations four times daily at regular intervals (asthma).

Route of Administration: Respiratory

In Vitro Use Guide

Cromoglycate (the active component of cromoglicate lisetil) significantly inhibits histamine release from lung and tonsillar mast cells at 1000 uM.

Name

Type

Language

CROMOLYN

Common Name

English

Cromoglicic acid [WHO-DD]

Common Name

English

4H-1-BENZOPYRAN-2-CARBOXYLIC ACID, 5,5'-((2-HYDROXY-1,3-PROPANEDIYL)BIS(OXY))BIS(4-OXO-)

Common Name

English

CROMO-COMOD

Brand Name

English

CROMOGLICATE

Common Name

English

CROMOGLYCIC ACID

Common Name

English

5,5'-((2-HYDROXYTRIMETHYLENE)DIOXY)BIS(4-OXO-4H-1-BENZOPYRAN-2-CARBOXYLATE)

Systematic Name

English

CROMOGLICIC ACID

Official Name

English

CROMOLYN [HSDB]

Common Name

English

R03BC01

Code

English

cromoglicic acid [INN]

Common Name

English

CROMOGLYCATE

Common Name

English

CROMOLYN [VANDF]

Common Name

English

CROMOLYN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R01AC01