SB-705498

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H16BrF3N4O
Molecular Weight	429.234
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)C1=CN=C(C=C1)N2CC[C@H](C2)NC(=O)NC3=CC=CC=C3Br

InChI

InChIKey=JYILLRHXRVTRSH-GFCCVEGCSA-N

InChI=1S/C17H16BrF3N4O/c18-13-3-1-2-4-14(13)24-16(26)23-12-7-8-25(10-12)15-6-5-11(9-22-15)17(19,20)21/h1-6,9,12H,7-8,10H2,(H2,23,24,26)/t12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H16BrF3N4O
Molecular Weight	429.234
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17392405 | https://www.ncbi.nlm.nih.gov/pubmed/16580202

SB-705498 is a selective vanilloid receptor-1 (VR1/TRPV1) antagonist developed by GlaxoSmithKline. The drug was tested in phase II of clinical trials for the treatment of pain (dental, rectal, in migraine) and rhinitis/cough. The development of the drug has been terminated by unknown reason (SB-705498 is no longer in GSK pipeline).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17392405	Antagonist 2778		3.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Non allergic rhinitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23735181	Curative	Phase II 1132	Unknown Approved Use Unknown
Rectal pain 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00461682	Primary	Phase II 1132	Unknown Approved Use Unknown
Toothache 15 Sources: https://clinicaltrials.gov/ct2/show/NCT00281684	Primary	Phase II 1132	Unknown Approved Use Unknown
Acute migraine 7 Sources: https://clinicaltrials.gov/ct2/show/NCT00269022	Palliative	Phase II 1132	Unknown Approved Use Unknown
Chronic cough 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24666696	Palliative	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
196.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23909699	12 mg 2 times / day multiple, nasal dose: 12 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.18 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17659837	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
86.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23909699	12 mg single, nasal dose: 12 mg route of administration: Nasal experiment type: SINGLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3416.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23909699	12 mg 2 times / day multiple, nasal dose: 12 mg route of administration: Nasal experiment type: MULTIPLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
42.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17659837	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
903.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23909699	12 mg single, nasal dose: 12 mg route of administration: Nasal experiment type: SINGLE co-administered:	SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
54.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17659837	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		SB-705498 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY103520	https://www.001chemical.com/chem/search?q=DY103520
1PlusChem LLC	1P00DAS0	https://www.1pchem.com/search?query=1P00DAS0
AChemBlock	G-6731	http://www.achemblock.com/catalogsearch/result/?q=G-6731
AK Scientific	Y0365	https://aksci.com/item_detail.php?cat=Y0365
Aceschem	ACF020013	https://www.aceschem.com/catalog/search.do?q=ACF020013
Angene	AGN-PC-0S6YWL	http://www.angenechemical.com/productshow/AGN-PC-0S6YWL.html
ApexBio Technology	A8519	https://www.apexbt.com/catalogsearch/result/?q=A8519
AstaTech	41210	http://astatechinc.com/CPSResult.php?CRNO=41210
BLD Pharm	BD300171	http://www.bldpharm.com/search/Search.html?keyword=BD300171
Capot Chemical	34119	https://www.capotchem.com/search.do?q=34119
Cayman Chemical	17313	http://www.caymanchem.com/app/template/Product.vm/catalog/17313
Chem Scene	CS-0757	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0757
ChemShuttle	104915	https://www.chemshuttle.com/catalogsearch/result/?q=104915
Hairui	HR33163	http://www.hairuichem.com/en/product/search.do?q=HR33163
KeyOrganics	AS-56093	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56093
Matrix Scientific	122170	http://www.matrixscientific.com/122170.html
MedChem Express	HY-10633	https://www.medchemexpress.com/search.html?q=HY-10633&ft=&fa=&fp=
MolPort	MolPort-027-720-959	https://www.molport.com/shop/molecule-link/MolPort-027-720-959
Molcore	MC103520	http://www.molcore.com/CatMC103520.html
Molnova	M14693	https://www.molnova.com/en/serch-list.html?keywords=M14693
MuseChem	I003768	https://www.musechem.com/product/I003768.html
ShangHai Biochempartner	BCP000529	http://www.biochempartner.com/search_BCP000529
ShangHai Biochempartner	BCP22698	http://www.biochempartner.com/search_BCP22698
Synthonix	10193	https://synthonix.com/catalogsearch/result/?q=10193
TargetMol	T6660	https://www.targetmol.com/search?keyword=T6660
eMolecules	195316748	https://orderbb.emolecules.com/search/#?query=195316748
eMolecules	300797708	https://orderbb.emolecules.com/search/#?query=300797708
eMolecules	44786224	https://orderbb.emolecules.com/search/#?query=44786224
eNovation Chemicals	D493886	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D493886&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4767189465	https://mcule.com/MCULE-4767189465/
mcule	MCULE-6474794441	https://mcule.com/MCULE-6474794441/

PubMed

Title	Date	PubMed
Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development.	2006 Jun 15	16580202
Characterization of SB-705498, a potent and selective vanilloid receptor-1 (VR1/TRPV1) antagonist that inhibits the capsaicin-, acid-, and heat-mediated activation of the receptor.	2007 Jun	17392405

Patents

Sample Use Guides

In Vivo Use Guide

Non Allergic Rhinitis: 12mg intra-nasal SB-705498 once daily. Chronic Cough: take 400 or 600mg orally.

Route of Administration: Other

In Vitro Use Guide

The pharmacological activity of SB-705498 was characterized on HEK293 cells expressing the human TRPV1, using fluorometric calcium imaging. The cells were treated with different concentrations (10(-5)-10(-10) M) of the drug for 1 min or with 1uM for 30 min. The IC50 for the inhibition of 20 nM capsaicin-induced responses was estimated as 46 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:55:49 UTC 2023` Edited by `admin` on `Sat Dec 16 02:55:49 UTC 2023`
Record UNII	T74V9O0Y2W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SB-705498

Common Name

English

UREA, N-(2-BROMOPHENYL)-N'-((3R)-1-(5-(TRIFLUOROMETHYL)-2-PYRIDINYL)-3-PYRROLIDINYL)-

Systematic Name

English

GSK705498

Code

English

Code System Code Type Description

FDA UNII

T74V9O0Y2W