Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H26ClN7O4.CH4O3S |
Molecular Weight | 548.013 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.NC1=NC(N)=C(Cl)N=C1C(=O)NC(=N)NCCCCC2=CC=C(OCC(O)CO)C=C2
InChI
InChIKey=ZYOATBKPEFZNGP-UHFFFAOYSA-N
InChI=1S/C19H26ClN7O4.CH4O3S/c20-15-17(22)26-16(21)14(25-15)18(30)27-19(23)24-8-2-1-3-11-4-6-13(7-5-11)31-10-12(29)9-28;1-5(2,3)4/h4-7,12,28-29H,1-3,8-10H2,(H4,21,22,26)(H3,23,24,27,30);1H3,(H,2,3,4)
Compound 552-02 is a potent, selective inhibitor of epithelial sodium channels that is effective in enhancing mucociliary clearance and is well tolerated when administered as a single dose by inhalation aerosol in normal healthy adult volunteers. Parion Sciences was developing 552 02 for the treatment of xerostomia, cystic fibrosis, chronic bronchitis, chronic obstructive pulmonary disease, radiation injuries. Compound 552-02 was specifically designed for aerosol delivery to the pulmonary system as a more selective, potent, long-acting ENaC blocker to promote an expansion in ASL volume, with or without hypertonic saline. Compound 552-02 was selected from a series of novel ENaC blockers to
produce a selective block on airway epithelial sodium channels, with a potency up to 2 orders of magnitude greater than
amiloride. 552-02 blocked the majority (95%) of Isc, with a calculated IC50 value of 7 nM. Drug development was discontinued.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacological properties of N-(3,5-diamino-6-chloropyrazine-2-carbonyl)-N'-4-[4-(2,3-dihydroxypropoxy)phenyl]butyl-guanidine methanesulfonate (552-02), a novel epithelial sodium channel blocker with potential clinical efficacy for cystic fibrosis lung disease. | 2008 Apr |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00852839
Dry Mouth Associated With Sjogren's Syndrome, Xerostomia: The oromucosal formulation of 552-02 contains 552-02 (25 ug/mL), surfactant, flavoring agents, a humectant, and preservatives.
Route of Administration:
Irrigation
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18218832
552-02 blocked sodium-dependent Isc using primary canine and human bronchial epithelial cells with IC50 value of 7.54 and 6.40 nM, resp.
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81U49K9009
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11548455
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587879-54-7
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ACTIVE MOIETY
SUBSTANCE RECORD