Basic information
- CAS
16673-34-0- Standard SMILES
COc1ccc(Cl)cc1C(=O)NCCc1ccc(S(N)(=O)=O)cc1- InChIKey
KVWWTCSJLGHLRM-UHFFFAOYSA-N- Molecular formula
- C16H17ClN2O4S
- Average molar mass
- 368.8 g/mol
- Monoisotopic mass
- 368.0597557
Overview
an anti-inflammatory agent; structure in first source
Names & identifiers
- Preferred name
- 5-chloro-2-methoxy-N-(2-(4-sulfamoylphenyl)ethyl)benzamide
- IUPAC
- 5-chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide
- English name
- 4-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfamide
- Molecular formula
- C16H17ClN2O4S
- Molecular weight
- 368.84
Names & synonyms
5-Chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide5-chloro-2-methoxy-N-(2-(4-sulfamoylphenyl)ethyl)benzamideRefChem:82472616673-34-05-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamideNLRP3 Inflammasome Inhibitor INLRP3-IN-2Glibenclamide Impurity A4-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzene SulfonamideDTXSID10576604-[2-(5-Chloro-2-methoxybenzamido)ethyl]phenylsulfonamideMFCD00193756
Show more names
NLRP3iEinecs 240-722-516673-34-0 NLRP3iGlyburide USP RC AGlibenclamide Impurity 7Glibenclamide EP Impurity AGlyburide Related CoMpound A
8TF6P2NUB5CHEMBL3188223N-(2-(4-sulfamoyl)phenyl)ethyl-5-chloro-2-methoxybenzamide4-[2-(5-Chloro-2-methoxybenzamido) ethyl] benzenesulfonamide4-(2-(5-CHLORO-2-METHOXYBENZAMIDO)ETHYL)PHENYLSULFONAMIDEBenzamide, N-(2-(4-(aminosulfonyl)phenyl)ethyl)-5-chloro-2-methoxy-4-[2-(2-Methoxy-5-chlorobenzene-1-carboxamido)ethyl]benzenesulfonamideGlyburide USP RC A;Glibenclamide EP Impurity A
Database identifiers
- CAS
16673-34-0- PubChem CID
- 85542
- DTXSID
DTXSID1057660- ChEMBL
CHEMBL3188223- UNII
- 8TF6P2NUB5
- EC Number
- 240-722-5
- Nikkaji
- J318.290H
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 515
Physicochemical properties
- Melting point
- 209 · 209-214 °C
- Density
- 1.356 · 1.356±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO (up to 45 mg/ml).
- pka
- 10.14 · 10.14±0.10(Predicted)
- form
- Solid
- color
- White
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
- InChI
- InChI=1S/C16H17ClN2O4S/c1-23-15-7-4-12(17)10-14(15)16(20)19-9-8-11-2-5-13(6-3-11)24(18,21)22/h2-7,10H,8-9H2,1H3,(H,19,20)(H2,18,21,22)
- InChIKey
- KVWWTCSJLGHLRM-UHFFFAOYSA-N
- SMILES
- C(NCCC1=CC=C(S(N)(=O)=O)C=C1)(=O)C1=CC(Cl)=CC=C1OC
- CAS DataBase Reference
- 16673 · 16673-34-0(CAS DataBase Reference)
- FDA UNII
- 8 TF6P2NUB5 · 8TF6P2NUB5
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Hazard Codes
- T
- Risk Statements
- 23 · 23-24-25
- Safety Statements
- 24 · 24/25
- WGK Germany
- 1 · 1
- HS Code
- 2935909550 · 2935909550
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 62.5% (5 of 8) of all reports.
Warning
H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 09-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11547
Hazard Classes and CategoriesAcute Tox. 4 (25%)
Safety data
- wgk
- 1
- hs_code
- 2935909550
- risk_code
- 23-24-25
- hazard_code
- T
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- REACH Registrations
- Active
Chemistry & industry
Applications
DescriptionNLRP3i (16673-34-0) is an NLRP3 inflammasome inhibitor which likely acts via interfering with the formation of the NLRP3 inflammasome complex and which exhibits promisingin vivoprotective activities in mouse acute myocardial infarction models. It blocks ASC aggregation, blocks the release of IL-1β and the activation of caspase-1 in macrophages expressing constitutively active NLRP3 but does not directly inhibit caspase-1.1,2Limits infarct size after myocardial ischemia-reperfusion as well as leukocyte infiltration in a peritonitis model in mice.2
UsesAn impurity arising in the synthesis of Glyburide (G598350).
General Description5-Chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide is an organic building block. It has been reported as an intermediate in the synthesis of glyburide. Synthesis of 5-chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide has been reported.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
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济南百隆化学有限公司[email protected] · [email protected]
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Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
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Standardpharm Co. Ltd.86-714-3992388 · [email protected]
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Related reactions
2 records
Compound notes
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