Sivelestat

Sivelestat
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV
ATC code	None;
Legal status
Legal status	US: Not approved; In general: ℞ (Prescription only);
Identifiers
	IUPAC name N-{2-[({4-[(2,2-dimethylpropanoyl)oxy]phenyl}sulfonyl)amino]benzoyl}glycine;
CAS Number	127373-66-4 ;
PubChem CID	107706;
IUPHAR/BPS	6441;
ChemSpider	96875 ;
UNII	DWI62G0P59;
KEGG	D03788 ;
ChEMBL	ChEMBL76688 ;
CompTox Dashboard (EPA)	DTXSID9048304 ;
Chemical and physical data
Formula	C20H22N2O7S
Molar mass	434.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)C(=O)OC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=C2C(=O)NCC(=O)O;
	InChI InChI=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) ; Key:BTGNGJJLZOIYID-UHFFFAOYSA-N ;
	(what is this?) (verify)

Sivelestat (INN, research name ONO 5046, marketed as Elaspol) is an inhibitor of human neutrophil elastase.^[1]

It is used in the treatment of acute respiratory failure^[2] and preliminary studies show it may also improve neuropathic pain.^[3]

Synthesis

Sivelestat is synthesised as follows:^[4]

^ Kawabata K, Suzuki M, Sugitani M, Imaki K, Toda M, Miyamoto T (June 1991). "ONO-5046, a novel inhibitor of human neutrophil elastase". Biochemical and Biophysical Research Communications. 177 (2): 814–820. Bibcode:1991BBRC..177..814K. doi:10.1016/0006-291X(91)91862-7. PMID 2049103.
^ Imokawa S, Mori K, Harada M, Sagisaka S, Sano T, Uchiyama H, et al. (June 2008). "[Acute respiratory failure due to pneumocystis pneumonia successfully treated with combined use of sivelestat sodium hydrate]". Nihon Kokyuki Gakkai Zasshi = The Journal of the Japanese Respiratory Society (in Japanese). 46 (6): 461–465. PMID 18592991.
^ Weyer AD, Stucky CL (May 2015). "Repurposing a leukocyte elastase inhibitor for neuropathic pain". Nature Medicine. 21 (5): 429–430. doi:10.1038/nm.3861. PMID 25951529. S2CID 10240018.
^ US 5017610, Imaki K, Arai Y, Okegawa T, "Derivatives of p-substituted phenyl ester of pivalic acid", issued 21 May 1991, assigned to Ono Pharmaceutical Co Ltd

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	IV
ATC code	None
Legal status
Legal status	US: Not approved In general: ℞ (Prescription only)
Identifiers
IUPAC name N-{2-[({4-[(2,2-dimethylpropanoyl)oxy]phenyl}sulfonyl)amino]benzoyl}glycine
CAS Number	127373-66-4^N
PubChem CID	107706
IUPHAR/BPS	6441
ChemSpider	96875^Y
UNII	DWI62G0P59
KEGG	D03788^Y
ChEMBL	ChEMBL76688^Y
CompTox Dashboard (EPA)	DTXSID9048304
Chemical and physical data
Formula	C₂₀H₂₂N₂O₇S
Molar mass	434.46 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)(C)C(=O)OC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=C2C(=O)NCC(=O)O
InChI InChI=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)^Y Key:BTGNGJJLZOIYID-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)