sivelestat

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464392270

| IUPAC_name = N-{2-[({4-[(2,2-dimethylpropanoyl)oxy]phenyl}sulfonyl)amino]benzoyl}glycine

| image = Sivelestat.svg

| tradename =

| Drugs.com = {{drugs.com|international|sivelestat}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Not approved

| legal_status = Rx-only

| routes_of_administration = IV

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 6441

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 127373-66-4

| ATC_prefix = None

| ATC_suffix =

| ATC_supplemental =

| PubChem = 107706

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = DWI62G0P59

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03788

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 96875

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 76688

| chemical_formula =

| C=20 | H=22 | N=2 | O=7 | S=1

| smiles = CC(C)(C)C(=O)OC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=C2C(=O)NCC(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H22N2O7S/c1-20(2,3)19(26)29-13-8-10-14(11-9-13)30(27,28)22-16-7-5-4-6-15(16)18(25)21-12-17(23)24/h4-11,22H,12H2,1-3H3,(H,21,25)(H,23,24)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BTGNGJJLZOIYID-UHFFFAOYSA-N

}}

Sivelestat (INN, research name ONO 5046, marketed as Elaspol) is an inhibitor of human neutrophil elastase.{{cite journal | vauthors = Kawabata K, Suzuki M, Sugitani M, Imaki K, Toda M, Miyamoto T | title = ONO-5046, a novel inhibitor of human neutrophil elastase | journal = Biochemical and Biophysical Research Communications | volume = 177 | issue = 2 | pages = 814–820 | date = June 1991 | pmid = 2049103 | doi = 10.1016/0006-291X(91)91862-7 }}

It is used in the treatment of acute respiratory failure{{cite journal | vauthors = Imokawa S, Mori K, Harada M, Sagisaka S, Sano T, Uchiyama H, Yasuda K, Ukita T, Fujisawa T, Suda T, Chida K | display-authors = 6 | title = [Acute respiratory failure due to pneumocystis pneumonia successfully treated with combined use of sivelestat sodium hydrate] | language = Japanese | journal = Nihon Kokyuki Gakkai Zasshi = the Journal of the Japanese Respiratory Society | volume = 46 | issue = 6 | pages = 461–465 | date = June 2008 | pmid = 18592991 | name-list-style = vanc }} and preliminary studies show it may also improve neuropathic pain.{{cite journal | vauthors = Weyer AD, Stucky CL | title = Repurposing a leukocyte elastase inhibitor for neuropathic pain | journal = Nature Medicine | volume = 21 | issue = 5 | pages = 429–430 | date = May 2015 | pmid = 25951529 | doi = 10.1038/nm.3861 | s2cid = 10240018 }}

Synthesis

Sivelestat is synthesised as follows:{{cite patent | country = US | number = 5017610 | title = Derivatives of p-substituted phenyl ester of pivalic acid | inventor = Imaki K, Arai Y, Okegawa T | assign1 = Ono Pharmaceutical Co Ltd | url = https://patents.google.com/patent/US5017610 | gdate = 21 May 1991 }}

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References