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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
Structure of GS-9411

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)

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H26ClN7O4
Molecular Weight 451.907
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Record UNII
81U49K9009
Record Status Validated (UNII)
Record Version