XEVINAPANT HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H43N5O4.ClH
Molecular Weight	598.176
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@]12CC[C@H](N1C(=O)[C@H](CN(CC2)C(=O)CC(C)C)NC(=O)[C@H](C)NC)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=DBXTZCYPHKJCHF-ZZPLZQMBSA-N

InChI=1S/C32H43N5O4.ClH/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24;/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40);1H/t22-,25+,26-,27-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C32H43N5O4
Molecular Weight	561.7149
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: http://adisinsight.springer.com/drugs/800030869
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21443232

AT-406 (DEBIO-1143, SM-406), is a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of apoptosis proteins (IAPs). AT-406 inhibits cancer cell growth in various human cancer cell lines. It has good oral bioavailability in mice, rats, non-human primates, and dogs, is highly effective in induction of apoptosis in xenograft tumors, and is capable of complete inhibition of tumor growth. Debiopharm under a licence from Ascenta Therapeutics is developing AT-406 for the treatment of cancers.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Inhibitor of apoptosis protein 3 6 Target ID: CHEMBL4198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21443232	Antagonist 2778	66.4 nM [Ki]
Baculoviral IAP repeat-containing protein 2 9 Target ID: CHEMBL5462 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21443232	Antagonist 2778	1.9 nM [Ki]
Baculoviral IAP repeat-containing protein 3 9 Target ID: CHEMBL5335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21443232	Antagonist 2778	5.1 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Head and neck squamous cell carcinoma 32 Sources: http://adisinsight.springer.com/drugs/800030869	Primary	Phase II 1132	Unknown Approved Use Unknown
Ovarian cancer 157 Sources: http://adisinsight.springer.com/drugs/800030869	Primary	Phase II 1132	Unknown Approved Use Unknown
Lymphoma 58 Sources: http://adisinsight.springer.com/drugs/800030869	Primary	Phase I 428	Unknown Approved Use Unknown
Acute myelogenous leukemia 19 Sources: http://adisinsight.springer.com/drugs/800030869	Primary	Phase I 428	Unknown Approved Use Unknown
Solid tumors 145 Sources: http://adisinsight.springer.com/drugs/800030869	Primary	Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25716544 Page: p.854	unhealthy, ADULT n = 6 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/25716544 Page: p.854	Sources: https://pubmed.ncbi.nlm.nih.gov/25716544 Page: p.854

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY110883	https://www.001chemical.com/chem/search?q=DY110883
001 Chemical	DY34247	https://www.001chemical.com/chem/search?q=DY34247
1PlusChem LLC	1P008WZM	https://www.1pchem.com/search?query=1P008WZM
Angene	AGN-PC-0WACGL	http://www.angenechemical.com/productshow/AGN-PC-0WACGL.html
ApexBio Technology	A3019	https://www.apexbt.com/catalogsearch/result/?q=A3019
AstaTech	40968	http://astatechinc.com/CPSResult.php?CRNO=40968
Axon MedChem	1985	https://www.axonmedchem.com/product/1985
BLD Pharm	BD305467	http://www.bldpharm.com/search/Search.html?keyword=BD305467
BioSynth	J-501625	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501625
Cayman Chemical	19929	http://www.caymanchem.com/app/template/Product.vm/catalog/19929
ChemShuttle	101141	https://www.chemshuttle.com/catalogsearch/result/?q=101141
ChemShuttle	186419	https://www.chemshuttle.com/catalogsearch/result/?q=186419
Excenen	EX-A104	http://www.excenen.com/searchresultlist.php?id=EX-A104
Excenen	EX-A1833	http://www.excenen.com/searchresultlist.php?id=EX-A1833
KeyOrganics	AS-56453	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56453
Matrix Scientific	143800	http://www.matrixscientific.com/143800.html
MedChem Express	HY-15454	https://www.medchemexpress.com/search.html?q=HY-15454&ft=&fa=&fp=
MolPort	MolPort-023-293-541	https://www.molport.com/shop/molecule-link/MolPort-023-293-541
Molcore	MC110883	http://www.molcore.com/CatMC110883.html
Molcore	MC34247	http://www.molcore.com/CatMC34247.html
Molnova	M17137	https://www.molnova.com/en/serch-list.html?keywords=M17137
ShangHai Biochempartner	BCP000570	http://www.biochempartner.com/search_BCP000570
ShangHai Biochempartner	BCP04668	http://www.biochempartner.com/search_BCP04668
TargetMol	T3299	https://www.targetmol.com/search?keyword=T3299
TargetMol	T6763	https://www.targetmol.com/search?keyword=T6763
Toronto Research Chemicals	S564030	https://www.trc-canada.com/product-detail/?CatNum=S564030
eMolecules	44811332	https://orderbb.emolecules.com/search/#?query=44811332
eNovation Chemicals	D210848	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D210848&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-2859814510	https://mcule.com/MCULE-2859814510/
mcule	MCULE-8006490063	https://mcule.com/MCULE-8006490063/

PubMed

Title	Date	PubMed
		252160626
A potent and orally active antagonist (SM-406/AT-406) of multiple inhibitor of apoptosis proteins (IAPs) in clinical development for cancer treatment.	2011 Apr 28	21443232

Patents

Sample Use Guides

In Vivo Use Guide

5 to 900 mg AT406 (DEBIO1143) was given orally once daily on days 1-5 every 2 or 3 weeks until disease progressed or patients dropped out: DEBIO1143 was well tolerated at doses up to 900 mg and elicited pharmacodynamics effects at doses greater 80 mg.

Route of Administration: Oral

In Vitro Use Guide

AT-406 potently inhibits cell growth in the MDA-MB-231 breast and SK-OV-3 ovarian cancer cell lines with IC50 = 144 nM and 142 nM, respectively. AT-406 effectively induces cell death in a time- and dose-dependent manner, more than 50% of the MDA-MB-231 cancer cells underwent cell death upon treatment at 1 μM for 24 hours.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:44:38 GMT 2023` Edited by `admin` on `Sat Dec 16 14:44:38 GMT 2023`
Record UNII	73T1W2MF9C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XEVINAPANT HYDROCHLORIDE

Common Name

English

PYRROLO(1,2-A)(1,5)DIAZOCINE-8-CARBOXAMIDE, N-(DIPHENYLMETHYL)DECAHYDRO-5-(((2S)-2-(METHYLAMINO)-1-OXOPROPYL)AMINO)-3-(3-METHYL-1-OXOBUTYL)-6-OXO-, HYDROCHLORIDE (1:1), (5S,8S,10AR)-

Systematic Name

English

Code System Code Type Description

CAS

1071992-57-8

Created by admin on Sat Dec 16 14:44:38 GMT 2023 , Edited by admin on Sat Dec 16 14:44:38 GMT 2023

PRIMARY

PUBCHEM

25022339

Created by admin on Sat Dec 16 14:44:38 GMT 2023 , Edited by admin on Sat Dec 16 14:44:38 GMT 2023

PRIMARY

FDA UNII

73T1W2MF9C

Created by admin on Sat Dec 16 14:44:38 GMT 2023 , Edited by admin on Sat Dec 16 14:44:38 GMT 2023

PRIMARY

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ACTIVE MOIETY

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Details

SMILES

InChI

DescriptionSources: http://adisinsight.springer.com/drugs/800030869Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21443232

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Doses

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://adisinsight.springer.com/drugs/800030869
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21443232