CROMOLYN SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H14O11.2Na
Molecular Weight	512.3302
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].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=VLARUOGDXDTHEH-UHFFFAOYSA-L

InChI=1S/C23H16O11.2Na/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);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C23H14O11
Molecular Weight	466.3507
Charge	-2
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://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 9 Target ID: CHEMBL1293267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22218743 \| https://www.ncbi.nlm.nih.gov/pubmed/3110245	Agonist 2637
Target ID: Chloride channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/1280136	Blocker 530	19.0 µM [IC50]
calcium ion import 6 Target ID: GO:0070509 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18887slr020_intal_lbl.pdf	Blocker 530

Conditions

Condition	Modality	Highest Phase	Product
Mastocytosis 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/090954s000lbl.pdf	Primary	Approved 8307	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 7.6731843E11
Bronchial asthma 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18887slr020_intal_lbl.pdf	Preventing	Approved 8307	CROMOLYN SODIUM Approved Use Cromolyn sodium is a prophylactic agent indicated in the management of patients with bronchial asthma. Launch Date 7.6723198E11
Allergic rhinitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/2001/75-702_Cromolyn%20Sodium_prntlbl.pdf	Palliative	Approved 8307	CROMOLYN SODIUM Approved Use Cromolyn sodium is used to prevent and relieve nasal symptoms of hay fever and other nasal allergies. Launch Date 7.6723198E11
Vernal keratoconjunctivitis 4 Sources: http://www.rxlist.com/crolom-drug.htm	Primary	Approved 8307	CROMOLYN SODIUM Approved Use Cromolyn sodium ophthalmic solution is indicated in the treatment of vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis. Launch Date 7.6723198E11

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 252

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 252	substrate 3264 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
[A sniffing child].	2001	12092406
[Changes in biochemical inflammation markers in evaluation of the effectiveness of basic chemotherapy in bronchial asthma].	2001	11417175
Cromolyn sodium for the prevention of chronic lung disease in preterm infants.	2001	11406065
Comparative functional characterization of mouse bone marrow-derived mast cells and peritoneal mast cells in response to non-immunological stimuli.	2001 Apr	11491575
Pyrazolopyrimidines: synthesis, effect on histamine release from rat peritoneal mast cells and cytotoxic activity.	2001 Apr	11461757
Antibacterial activity of apical surface fluid from the human airway cell line Calu-3: pharmacologic alteration by corticosteroids and beta(2)-agonists.	2001 Aug	11509329
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
[Inhalation therapy].	2001 Dec	11937990
Sodium cromoglycate in the management of chronic or recurrent enterocolitis in patients with Hirschsprung's disease.	2001 Jul	11431770
[Exercise-induced asthma. The spray belongs in the "athletic shoe"].	2001 Jul 19	11499151
Antihistamines and serum adhesion molecule levels.	2001 Jun	11505807
The efficacy and safety of asthma medications during pregnancy.	2001 Jun	11453610
Asthma in the hospitalized obstetrical patient.	2001 Jun	11413902
Time to consign cromoglycate to history?	2001 Jun	11403037
The necessity for dual food intake to provoke food-dependent exercise-induced anaphylaxis (FEIAn): a case report of FEIAn with simultaneous intake of wheat and umeboshi.	2001 Jun	11398092
Disodium cromoglycate inhibits production of immunoglobulin E.	2001 May	11417850
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
[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
Sodium cromoglycate attenuates pulmonary inflammation without influencing bronchial responsiveness in healthy subjects exposed to organic dust.	2001 Sep	11591185
Inhaled sodium cromoglycate in the management of asthma: should it be consigned to history?	2001 Sep	11591181
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
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
Efficacy and safety of inhaled steroid and cromone treatment in school-age children: a randomized pragmatic pilot study.	2002 Feb	12000495
Medical management of Cronkhite-Canada syndrome.	2002 Feb	11846261
Assessment of the relationship between hyperalgesia and peripheral inflammation in magnesium-deficient rats.	2002 Jan 18	11860153
Water dynamics in channel hydrates investigated using H/D exchange.	2002 Jul 25	12100853
Efficacy and patient satisfaction with cromolyn sodium nasal solution in the treatment of seasonal allergic rhinitis: a placebo-controlled study.	2002 Jun	12117084
Improved strategies and new treatment options for allergic rhinitis.	2002 Jun	12090644
Allergic rhinitis remains an important disease.	2002 Jun	12090642
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
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
The effect of disodium cromoglycate, budesonide, and cyclosporin A on interleukin-4, interleukin-5, and interleukin-13 secretions in Der p I-stimulated T cells from house dust mite-sensitive atopic and nonatopic individuals.	2002 Mar-Apr	12001789
Perinatal immunomodulation.	2002 May	12389669
Management of allergic and nonallergic rhinitis.	2002 May	12173440
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
[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

Oral: Two ampules four times daily, taken one-half hour before meals and at bedtime. Topical: The dose is 1 or 2 drops in each eye 4 to 6 times a day at regular intervals. One drop contains approximately 1.6 mg cromolyn sodium. Respiratory: The usual starting dosage is the contents of one vial (20 mg of sodium cromolyn) administrated by nebulization four times a day at regular intervals. Nasal: Spray once in each nostril in the morning, at noon, at dinner and at bedtime. Begin use 1-2 weeks before nasal allergens exposition.

Route of Administration: Other

In Vitro Use Guide

Sodium cromoglycate was shown to inhibit in dose-related fashion the chemotaxis of eosinophils to zymosan activated serum with an IC50 of approximately 0.2 uM and the chemotaxis of neutrophils to platelet-activating factor with an IC50 of approximately 20 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:46:44 UTC 2022` Edited by `admin` on `Fri Dec 16 16:46:44 UTC 2022`
Record UNII	Q2WXR1I0PK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CROMOLYN SODIUM

Official Name

English

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

Systematic Name

English

SODIUM CROMOGLICATE [JAN]

Common Name

English

NASALCROM

Brand Name

English

DISODIUM CROMOLYN

Official Name

English

NSC-109500

Code

English

INTAL

Brand Name

English

GASTROCROM

Brand Name

English

CROMOLYN SODIUM [USP MONOGRAPH]

Common Name

English

CROLOM

Brand Name

English

OPTICROM

Brand Name

English

CROMOLYN SODIUM [VANDF]

Common Name

English

SODIUM CROMOGLICATE [EP MONOGRAPH]

Common Name

English

NATRII CROMOGLICAS [WHO-IP LATIN]

Common Name

English

FPL.670

Code

English

CROMOLYN SODIUM [USP-RS]

Common Name

English

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

Common Name

English

SODIUM CROMOGLYCATE

Common Name

English

CROMOLYN SODIUM [ORANGE BOOK]

Common Name

English

CROMOGLICATE SODIUM

Common Name

English

FPL-670

Code

English

SODIUM CROMOGLICATE [WHO-IP]

Common Name

English

DISODIUM CROMOLYN [INCI]

Common Name

English

CROMOLYN SODIUM [USAN]

Common Name

English

CROMOPTIC

Brand Name

English

SODIUM CROMOGLICATE [MART.]

Common Name

English

SODIUM CROMOGLICATE

Common Name

English

CROMOLYN DISODIUM SALT [MI]

Common Name

English

Cromoglicate sodium [WHO-DD]

Common Name

English

SODIUM CROMOLYN

Common Name

English

ASTILYN

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QR03AK05