EMAPUNIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H23N5O2
Molecular Weight	401.461
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC1=CC=CC=C1)C(=O)CN2C(=O)N(C)C3=CN=C(N=C23)C4=CC=CC=C4

InChI

InChIKey=NBMBIEOUVBHEBM-UHFFFAOYSA-N

InChI=1S/C23H23N5O2/c1-3-27(15-17-10-6-4-7-11-17)20(29)16-28-22-19(26(2)23(28)30)14-24-21(25-22)18-12-8-5-9-13-18/h4-14H,3,15-16H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C23H23N5O2
Molecular Weight	401.461
Charge	0
Count

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

Description
Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/XBD173.pdf
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800013611 https://en.wikipedia.org/wiki/Emapunil

Emapunil acts as a selective agonist at the peripheral benzodiazepine receptor (TSPO). At the cellular level, the selective TSPO ligand XBD173 potentiated the amplitude and duration of GABA-mediated inhibitory postsynaptic currents in mouse medial prefrontal cortical neurons, which was prevented by finasteride. In animal and human trials, XBD173 produced rapid anxiolytic and anti-panic effects probably via newly synthesized neurosteroids, without producing sedation or withdrawal symptoms, and may represent a promising target for the development of fast-acting anxiolytics with a more favourable side-effect profile than benzodiazepines.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Translocator protein 13 Target ID: CHEMBL5742 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15249420	Agonist 2678		0.297 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Panic disorder 22 Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/XBD173.pdf	Primary	Phase I 428	Unknown Approved Use Unknown
Generalized anxiety disorder 32 Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/XBD173.pdf	Primary	Phase II 1132	Unknown Approved Use Unknown
Post-traumatic stress disorder 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23624119	Primary	Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
90 mg 1 times / day multiple, oral Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects and initiatives/Medicines Chest/XBD173.pdf	healthy n = 14 Health Status: healthy Sex: M Food Status: UNKNOWN Population Size: 14 Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects and initiatives/Medicines Chest/XBD173.pdf	Sources: https://www.ecnp.eu/~/media/Files/ecnp/Projects and initiatives/Medicines Chest/XBD173.pdf

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY442976	https://www.001chemical.com/chem/search?q=DY442976
1PlusChem LLC	1P00BERW	https://www.1pchem.com/search?query=1P00BERW
AChemBlock	M22573	http://www.achemblock.com/catalogsearch/result/?q=M22573
AK Scientific	SYN5155	https://aksci.com/item_detail.php?cat=SYN5155
AOBIOUS INC	AOB3568	http://aobious.com/aobious/search?search_query=AOB3568
Aceschem	ACS019819	https://www.aceschem.com/catalog/search.do?q=ACS019819
Alfa Chemistry	ACM226954047	http://www.alfa-chemistry.com/search.aspx?q=ACM226954047
AstaTech	40751	http://astatechinc.com/CPSResult.php?CRNO=40751
BLD Pharm	BD630568	http://www.bldpharm.com/search/Search.html?keyword=BD630568
BOC Sciences	226954-04-7	http://www.bocsci.com/description.asp?cas=226954-04-7
Capot Chemical	33947	https://www.capotchem.com/search.do?q=33947
Cayman Chemical	18522	http://www.caymanchem.com/app/template/Product.vm/catalog/18522
Chem Scene	CS-3470	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3470
ChemShuttle	156585	https://www.chemshuttle.com/catalogsearch/result/?q=156585
Debye Scientific	DA-43175	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-43175
Excenen	EX-A1040	http://www.excenen.com/searchresultlist.php?id=EX-A1040
Hairui	HR32972	http://www.hairuichem.com/en/product/search.do?q=HR32972
KeyOrganics	AS-16517	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16517
MedChem Express	HY-15527	https://www.medchemexpress.com/search.html?q=HY-15527&ft=&fa=&fp=
MolPort	MolPort-005-943-292	https://www.molport.com/shop/molecule-link/MolPort-005-943-292
Molcore	MC442976	http://www.molcore.com/CatMC442976.html
Molnova	M17446	https://www.molnova.com/en/serch-list.html?keywords=M17446
MuseChem	I002736	https://www.musechem.com/product/I002736.html
PI Chemicals	PI-39465	http://www.pipharm.com/catalog_products/PI-39465.html
Ryan Scientific	HTH-01-015	https://ryansci.com/products?q=HTH-01-015&list_q=&search_type=exact
ShangHai Biochempartner	BCP001517	http://www.biochempartner.com/search_BCP001517
ShangHai Biochempartner	BCP14398	http://www.biochempartner.com/search_BCP14398
TargetMol	T2371	https://www.targetmol.com/search?keyword=T2371
Tocris	5281	https://www.tocris.com/search.php?Type=QuickSearch&Value=5281
Toronto Research Chemicals	E520615	https://www.trc-canada.com/product-detail/?CatNum=E520615
eMolecules	50282785	https://orderbb.emolecules.com/search/#?query=50282785
eNovation Chemicals	D481242	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D481242&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-6286432956	https://mcule.com/MCULE-6286432956/

PubMed

Title	Date	PubMed
Synthesis and structure-activity relationship studies in translocator protein ligands based on a pyrazolo[3,4-b]quinoline scaffold.	2011 Oct 27	21916402
Synthesis and evaluation of novel carbon-11 labeled oxopurine analogues for positron emission tomography imaging of translocator protein (18 kDa) in peripheral organs.	2011 Sep 8	21790126

Patents

Sample Use Guides

In Vivo Use Guide

10, 30, or 90 mg/day

Route of Administration: Oral

In Vitro Use Guide

50uM XBD173 treatment of murine and human microglial cells promoted the formation of filopodia and increased their phagocytic capacity to ingest latex beads or photoreceptor debris. Finally, treatment with XBD173 (20 uM)reversed the amoeboid alerted phenotype of microglial cells in explanted organotypic mouse retinal cultures after challenge with LPS.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:40 UTC 2023` Edited by `admin` on `Fri Dec 15 16:20:40 UTC 2023`
Record UNII	OG837L732J
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EMAPUNIL

Official Name

English

N-BENZYL-N-ETHYL-2-(7-METHYL-8-OXO-2-PHENYL-7,8-DIHYDRO-9H-PURIN-9-YL)ACETAMIDE

Systematic Name

English

XBD173

Code

English

AC-5216

Code

English

XBD-173

Code

English

emapunil [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197