sparsentan   Click here for help

GtoPdb Ligand ID: 8448

Synonyms: DARA-a (Dual Acting Receptor Antagonist of angiotension and endothelin receptors) | BMS-346567 | compound 7 [PMID 15634011] | Filspari® | RE-021 | retrophin
Approved drug Immunopharmacology Ligand
sparsentan is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Sparsentan (RE-021) is a selective dual-acting receptor antagonist with affinity for endothelin (A type) and angiotensin II receptors (Type 1) [5-6]. Sparsentan combines the active moieties of the selective AT1 receptor antagonist irbesartan and a selective ETA receptor antagonist (see ligand 91 in [5]).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 12
Topological polar surface area 122.48
Molecular weight 592.27
XLogP 5.9
No. Lipinski's rules broken 2
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Canonical SMILES CCCCC1=NC2(C(=O)N1Cc1ccc(c(c1)COCC)c1ccccc1S(=O)(=O)Nc1noc(c1C)C)CCCC2
Isomeric SMILES CCCCC1=NC2(C(=O)N1Cc1ccc(c(c1)COCC)c1ccccc1S(=O)(=O)Nc1noc(c1C)C)CCCC2
InChI InChI=1S/C32H40N4O5S/c1-5-7-14-29-33-32(17-10-11-18-32)31(37)36(29)20-24-15-16-26(25(19-24)21-40-6-2)27-12-8-9-13-28(27)42(38,39)35-30-22(3)23(4)41-34-30/h8-9,12-13,15-16,19H,5-7,10-11,14,17-18,20-21H2,1-4H3,(H,34,35)
1. D'Agati VD, Kaskel FJ, Falk RJ. (2011)
Focal segmental glomerulosclerosis.
N Engl J Med, 365 (25): 2398-411. [PMID:22187987]
2. EMA. 
EU/3/20/2345: Orphan designation for the treatment of primary IgA nephropathy.
Accessed on 20/02/2023. Modified on 20/02/2023.,
3. Hodson EM, Sinha A, Cooper TE. (2022)
Interventions for focal segmental glomerulosclerosis in adults.
Cochrane Database Syst Rev, 2 (2): CD003233. [PMID:35224732]
4. Komers R, Diva U, Inrig JK, Loewen A, Trachtman H, Rote WE. (2020)
Study Design of the Phase 3 Sparsentan Versus Irbesartan (DUPLEX) Study in Patients With Focal Segmental Glomerulosclerosis.
Kidney Int Rep, 5 (4): 494-502. [PMID:32274453]
5. Morphy R, Rankovic Z. (2005)
Designed multiple ligands. An emerging drug discovery paradigm.
J Med Chem, 48 (21): 6523-43. [PMID:16220969]
6. Murugesan N, Gu Z, Fadnis L, Tellew JE, Baska RA, Yang Y, Beyer SM, Monshizadegan H, Dickinson KE, Valentine MT et al.. (2005)
Dual angiotensin II and endothelin A receptor antagonists: synthesis of 2'-substituted N-3-isoxazolyl biphenylsulfonamides with improved potency and pharmacokinetics.
J Med Chem, 48 (1): 171-9. [PMID:15634011]
7. Syed YY. (2023)
Sparsentan: First Approval.
Drugs, 83 (6): 563-568. [PMID:37022667]
8. Trachtman H, Nelson P, Adler S, Campbell KN, Chaudhuri A, Derebail VK, Gambaro G, Gesualdo L, Gipson DS, Hogan J et al.. (2018)
DUET: A Phase 2 Study Evaluating the Efficacy and Safety of Sparsentan in Patients with FSGS.
J Am Soc Nephrol, 29 (11): 2745-2754. [PMID:30361325]