SC-236

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H11ClF3N3O2S
Molecular Weight	401.791
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NS(=O)(=O)C1=CC=C(C=C1)N2N=C(C=C2C3=CC=C(Cl)C=C3)C(F)(F)F

InChI

InChIKey=NSQNZEUFHPTJME-UHFFFAOYSA-N

InChI=1S/C16H11ClF3N3O2S/c17-11-3-1-10(2-4-11)14-9-15(16(18,19)20)22-23(14)12-5-7-13(8-6-12)26(21,24)25/h1-9H,(H2,21,24,25)

HIDE SMILES / InChI

Molecular Formula	C16H11ClF3N3O2S
Molecular Weight	401.791
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135032 | https://www.ncbi.nlm.nih.gov/pubmed/11772429

SC 236 is a selective COX-2 inhibitor with anti-cancer and anti-inflammatory properties. SC 236 exhibited an unacceptably long plasma half-life and this limited its development.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 2 48 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8663121	Inhibitor 8297		0.005 µM [IC50]
Transcription factor AP-1 1 Target ID: P05412 Gene ID: 3725.0 Gene Symbol: JUN Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14699495	Inhibitor 8297		25.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Cerebral edema 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11772429	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12684433	Primary	Preclinical	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17822719	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 specific inhibitors.	1996 Jun 28	8663121
Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).	1997 Apr 25	9135032
A cyclooxygenase-2 (COX-2) inhibitor compared with dexamethasone in a survival study of rats with intracerebral 9L gliosarcomas.	2002 Jan	11772429
Cyclooxygenase-2 inhibitor (SC-236) suppresses activator protein-1 through c-Jun NH2-terminal kinase.	2004 Jan	14699495

Sample Use Guides

In Vivo Use Guide

SC 236 was given at a dose 3 mg/kg p.o. daily (preclinical study).

Route of Administration: Oral

In Vitro Use Guide

Gastric cancer cells were exposed to SC 236 at concentrations of 6.25, 12.5, 25 and 50 uM. SC 236 inhibited anchorage-independent cell growth in a concentration-dependent manner in all of the 3 gastric cancer cell lines tested. However, the inhibitory effect was most profound in AGS cells with IC50 at about 20-25 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:30:53 GMT 2023` Edited by `admin` on `Sat Dec 16 14:30:53 GMT 2023`
Record UNII	9HGW1H8S2M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SC-236

Code

English

BENZENESULFONAMIDE, 4-(5-(4-CHLOROPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL)-

Systematic Name

English

4-(5-(4-CHLOROPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL)BENZENESULFONAMIDE

Systematic Name

English

Code System Code Type Description

DRUG BANK

DB14059