DEBIO-1452 TOSYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H21N3O3.C7H8O3S
Molecular Weight	547.622
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.CN(CC2=C(C)C3=C(O2)C=CC=C3)C(=O)\C=C\C4=CC5=C(NC(=O)CC5)N=C4

InChI

InChIKey=NHTYVWVPSCBFQW-HCUGZAAXSA-N

InChI=1S/C22H21N3O3.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h3-7,10-12H,8-9,13H2,1-2H3,(H,23,24,26);2-5H,1H3,(H,8,9,10)/b10-7+;

HIDE SMILES / InChI

Molecular Formula	C22H21N3O3
Molecular Weight	375.4204
Charge	0
Count

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

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17220418 | https://www.ncbi.nlm.nih.gov/pubmed/26711777

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 Target ID: CHEMBL2364678 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17220418	Inhibitor 8297		9.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Staphylococcal skin and skin structure infections 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26711777	Curative		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1413 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1323 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1753 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2008 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2707 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2842 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2807 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2900 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
23931 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
27025 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
30755 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
41918 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
53322 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
53887 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
61215 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
65276 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
8.57 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 1 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.81 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.74 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.95 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26357940/	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	AFN-1252 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

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
Lab Network	LN01342382	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342382
MedChem Express	HY-16911	https://www.medchemexpress.com/search.html?q=HY-16911&ft=&fa=&fp=
MolPort	MolPort-045-018-009	https://www.molport.com/shop/molecule-link/MolPort-045-018-009
MolPort	MolPort-046-417-166	https://www.molport.com/shop/molecule-link/MolPort-046-417-166
MolPort	MolPort-046-702-167	https://www.molport.com/shop/molecule-link/MolPort-046-702-167
Molnova	M15347	https://www.molnova.com/en/serch-list.html?keywords=M15347
MuseChem	I004343	https://www.musechem.com/product/I004343.html
ShangHai Biochempartner	BCP19135	http://www.biochempartner.com/search_BCP19135
TargetMol	T4105	https://www.targetmol.com/search?keyword=T4105
Toronto Research Chemicals	A425005	https://www.trc-canada.com/product-detail/?CatNum=A425005
eMolecules	168776457	https://orderbb.emolecules.com/search/#?query=168776457
eMolecules	303196440	https://orderbb.emolecules.com/search/#?query=303196440
eMolecules	72973061	https://orderbb.emolecules.com/search/#?query=72973061
eMolecules	76738501	https://orderbb.emolecules.com/search/#?query=76738501
eNovation Chemicals	D503711	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D503711&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7005022615	https://mcule.com/MCULE-7005022615/
mcule	MCULE-9665475361	https://mcule.com/MCULE-9665475361/

PubMed

Title	Date	PubMed
In vitro activity of API-1252, a novel FabI inhibitor, against clinical isolates of Staphylococcus aureus and Staphylococcus epidermidis.	2007 Apr	17220418
AFN-1252, a FabI inhibitor, demonstrates a Staphylococcus-specific spectrum of activity.	2009 Aug	19487444
Pharmacokinetics, pharmacodynamics and efficacy of novel FabI inhibitor AFN-1252 against MSSA and MRSA in the murine thigh infection model.	2013 Feb	23433441

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 Created by `admin` on `Sat Dec 16 02:55:44 UTC 2023` Edited by `admin` on `Sat Dec 16 02:55:44 UTC 2023`
Record UNII	VDH5PP94F0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEBIO-1452 TOSYLATE

Common Name

English

AFN-1252 TOSYLATE

Common Name

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)-, 4-METHYLBENZENESULFONATE (1:1)

Systematic Name

English

API-1252 TOSYLATE

Code

English

Code System Code Type Description

PUBCHEM

24880177

Created by admin on Sat Dec 16 02:55:44 UTC 2023 , Edited by admin on Sat Dec 16 02:55:44 UTC 2023

PRIMARY

EPA CompTox

DTXSID90146744

Created by admin on Sat Dec 16 02:55:44 UTC 2023 , Edited by admin on Sat Dec 16 02:55:44 UTC 2023

PRIMARY

FDA UNII

VDH5PP94F0

Created by admin on Sat Dec 16 02:55:44 UTC 2023 , Edited by admin on Sat Dec 16 02:55:44 UTC 2023

PRIMARY

CAS

1047981-31-6

Created by admin on Sat Dec 16 02:55:44 UTC 2023 , Edited by admin on Sat Dec 16 02:55:44 UTC 2023

PRIMARY

Related Record Type Details


					004HXS4MNN

DEBIO-1452 TOSYLATE MONOHYDRATE

SOLVATE->ANHYDROUS


					T3O718IKKM

DEBIO-1452

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					T3O718IKKM

DEBIO-1452

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17220418 | https://www.ncbi.nlm.nih.gov/pubmed/26711777

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17220418 | https://www.ncbi.nlm.nih.gov/pubmed/26711777

C_max

T_1/2