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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 of XEVINAPANT HYDROCHLORIDE

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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: 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: Page: p.854
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

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
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
  • Download
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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