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 2752
Chloride channels 4 Target ID: Chloride channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/1280136	Blocker 555	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 555
mast cell activation 5 Target ID: GO:0045576 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12396022	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Mastocytosis 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf	Primary	Approved 8583	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 8583	CROMOLYN SODIUM Approved Use Cromolyn sodium is a prophylactic agent indicated in the management of patients with bronchial asthma. Launch Date 1994
Allergic rhinitis 104 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-702_Cromolyn%20Sodium_prntlbl.pdf	Palliative	Approved 8583	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 8583	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 244 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/2000/75-271_Cromolyn%20Sodium_prntlbl.pdf	Preventing	Approved 8583	CROMOLYN SODIUM Approved Use To help prevent asthma attacks. Launch Date 1994
Allergic rhinitis 104 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b34d36ca-4df4-458c-af0f-c0d0c9a025d9	Preventing	Approved 8583	NASALCROM Approved Use To prevent and relieve nasal symptoms of hay fever and other nasal allergies Launch Date 1997
Allergic conjunctivitis 101 Sources: https://www.medicines.org.uk/emc/PIL.31398.latest.pdf	Palliative	Approved 8583	OPTREX Approved Use Optrex is used for the prevention and treatment of eye allergies.

C_max

Value	Dose	Co-administered	Analyte	Population
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
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
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) Health Status: unhealthy Age Group: 25 years (range: 5-51 years) Sex: M+F 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 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 Health Status: unhealthy Age Group: adult 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 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 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
abcr GmbH	AB540456	http://www.abcr.com/shop/en/AB540456
Acadechem	ACDC-030058	http://acadechemical.com/product/1820
Achemo Scientific Limited	AC-85374	http://www.achemo.com/search/?Keyword= 16110-51-3
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
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
BioSynth	J-009783	https://www.biosynth.com/en/products/all-products/products/J-009783.html
BLD Pharm	BD53784	http://www.bldpharm.com/products/16110-51-3.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
CSNpharm	CSN17084	https://www.csnpharm.com/products/cromolyn.html
DC Chemicals	DC20926	http://www.dcchemicals.com/product_show-DC20926.html
eNovation Chemicals	D926914	https://www.enovationchem.com/ProductDetails.asp?ProductID=D926914
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

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
Cromolyn sodium for the prevention of chronic lung disease in preterm infants.	2001	11406065
Impact of inhaled antiinflammatory therapy on hospitalization and emergency department visits for children with asthma.	2001 Apr	11335748
Cromolyn sodium suppresses eosinophilic inflammation in patients with aspirin-intolerant asthma.	2001 Aug	11527248
Asthma symptoms, morbidity, and antiinflammatory use in inner-city children.	2001 Aug	11483788
Deleterious effects of IL-9-activated mast cells and neuroprotection by antihistamine drugs in the developing mouse brain.	2001 Aug	11477207
Reasons for and costs of hospitalization for pediatric asthma: a prospective 1-year follow-up in a population-based setting.	2001 Dec	11846871
[Anti-allergy therapy in children].	2001 Mar	11386127
A retrospective study of risk factors for repeated admissions for asthma in a rural/suburban university hospital.	2001 May	11409260
[Color reactions for identification of sodium cromoglycate].	2001 May	11400557
Clinical and basic science research on allergic rhinitis and asthma from Nassau University Medical Center.	2001 May-Jun	11424878
Therapy choices beyond antihistamines. Vasomotor rhinitis.	2001 Nov	12420500
[Inhaled corticosteroid therapy in childhood asthma].	2001 Oct	11676147
Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models.	2001 Sep	11831367
Metering performance of several metered-dose inhalers with different spacers/holding chambers.	2001 Winter	11791683
Topical treatment of pyoderma gangraenosum.	2002	12399665
Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein.	2002 Apr 12	11944917
In vitro deposition of the respirable fraction of dry powder inhalations determined by laser diffractometry and inertial impaction.	2002 Aug	12227195
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
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
Assessment of the relationship between hyperalgesia and peripheral inflammation in magnesium-deficient rats.	2002 Jan 18	11860153
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
One-year trial on safety and normal linear growth with flunisolide HFA in children with asthma.	2002 Jun	12086199
(S)nifty treatment for pollen allergies.	2002 Jun	12085791
Generalized bullae in an infant.	2002 Jun	12056971
Fluticasone for the treatment of symptomatic bronchial asthma in children treated with sodium cromogylate--a prospective, randomised trial.	2002 Jun 28	12117660
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
Nebulized budesonide inhalation suspension compared with cromolyn sodium nebulizer solution for asthma in young children: results of a randomized outcomes trial.	2002 May	11986448
Airway hyperresponsiveness to adenosine induced by lipopolysaccharide in Brown Norway rats.	2002 May	11976275
Long-term management of asthma in children: effectiveness of inhaled corticosteroids compared to other medications.	2002 Nov	12518556
Inhalation and deposition of nebulized sodium cromoglycate in two different particle size distributions in children with asthma.	2002 Nov	12357479
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
[Enhancing effects of ion-pair complexes on skin permeation of cromolyn in vitro].	2002 Sep	12235858
The role of sodium cromolyn in treatment of paraquat-induced pulmonary fibrosis in rat.	2002 Sep	12220965
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

Preferred 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

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