DEBIO-1452

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H21N3O3
Molecular Weight	375.4204
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CN(CC1=C(C)C2=C(O1)C=CC=C2)C(=O)\C=C\C3=CC4=C(NC(=O)CC4)N=C3

InChI

InChIKey=QXTWSUQCXCWEHF-JXMROGBWSA-N

InChI=1S/C22H21N3O3/c1-14-17-5-3-4-6-18(17)28-19(14)13-25(2)21(27)10-7-15-11-16-8-9-20(26)24-22(16)23-12-15/h3-7,10-12H,8-9,13H2,1-2H3,(H,23,24,26)/b10-7+

HIDE SMILES / InChI

Molecular Formula	C22H21N3O3
Molecular Weight	375.4204
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

AFN-1252 (now known as Debio-1452) is an antibiotic drug which is in phase II of clinical trials for the treatment of Staphylococcal skin and skin structure infections. The drug was effective in vitro against all isolates of S.aureus and its effect was explained by inhibition of enoyl-acyl carrier protein Reductase (FabI).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial enoyl-[acyl-carrier-protein] reductase 8	Inhibitor 8,297		9.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Staphylococcal skin and skin structure infections 5	Curative		Phase II 1,132	Unknown

C_max

Value	Dose	Analyte	Population
1413 ng/mL	100 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
1323 ng/mL	100 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
1753 ng/mL	200 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
2008 ng/mL	200 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
2707 ng/mL	300 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
2842 ng/mL	400 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
2807 ng/mL	300 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
2900 ng/mL	400 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
23931 ng × h/mL	100 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
27025 ng × h/mL	100 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
30755 ng × h/mL	200 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
41918 ng × h/mL	200 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
53322 ng × h/mL	300 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
53887 ng × h/mL	400 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
61215 ng × h/mL	300 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
65276 ng × h/mL	400 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
8.57 h	100 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
9.12 h	100 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
9.72 h	200 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
8.81 h	200 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
9.42 h	300 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
7.74 h	400 mg 1 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
10.31 h	300 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens
8.95 h	400 mg 2 times / day multiple, oral	AFN-1252 plasma	Homo sapiens

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ECVU	https://www.1pchem.com/search?query=1P00ECVU
AstaTech	C75910	http://astatechinc.com/CPSResult.php?CRNO=C75910
BLD Pharm	BD284776	http://www.bldpharm.com/search/Search.html?keyword=BD284776
Chem Scene	CS-4313	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4313
KeyOrganics	AS-56008	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56008

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

200 mg of AFN-1252 should be given by mouth twice daily.

Route of Administration: Oral

In Vitro Use Guide

AFN-1252 was very active against S.aureu. All S.aureus isolates were inhibited by the drug, with MICs of 0.12 ug/ml and MIC50 and MIC90 values of 0.004 ug/ml and 0.008 ug/ml, respectively.

Substance Class	Chemical
Record UNII	T3O718IKKM
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

DEBIO-1452

Code

English

DEBIO1452

Code

English

API-1252

Code

English

AFN-1252

Code

English

2-PROPENAMIDE, N-METHYL-N-((3-METHYL-2-BENZOFURANYL)METHYL)-3-(5,6,7,8-TETRAHYDRO-7-OXO-1,8-NAPHTHYRIDIN-3-YL)-, (2E)-

Systematic Name

English

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Code System

Code

Type

Description

DRUG BANK

DB12658

PRIMARY

EPA CompTox

DTXSID10211069

PRIMARY

FDA UNII

T3O718IKKM

PRIMARY

CAS

620175-39-5

PRIMARY

PUBCHEM

10407120

PRIMARY

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Related Record

Type

Details


					VDH5PP94F0

DEBIO-1452 TOSYLATE

SALT/SOLVATE -> PARENT

Amount:


					D3R3P8KG3A

ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADPH) FABI (STAPHYLOCOCCUS AUREUS (STRAIN NCTC 8325))

TARGET -> INHIBITOR

Amount:


					O478WX4004

STAPHYLOCOCCUS AUREUS

TARGET -> INHIBITOR

Qualification:

MIC

Amount:

0.005 microgram/mL [0.002 to 0.12] (average)


					O478WX4004

STAPHYLOCOCCUS AUREUS

TARGET -> INHIBITOR

Qualification:

MIC95

Amount:

0.015 microgram/mL (average)


					004HXS4MNN

DEBIO-1452 TOSYLATE MONOHYDRATE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					DMM8663H2R

AFABICIN

PRODRUG -> METABOLITE ACTIVE

Amount:

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Related Record

Type

Details


					T3O718IKKM

DEBIO-1452

ACTIVE MOIETY

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2