WCK-1152

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26FN3O4
Molecular Weight	403.4472
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N3CC[C@H](N)C(C)(C)C3)C4CC4

InChI

InChIKey=PMBHAWNZPPNADR-HNNXBMFYSA-N

InChI=1S/C21H26FN3O4/c1-21(2)10-24(7-6-15(21)23)17-14(22)8-12-16(19(17)29-3)25(11-4-5-11)9-13(18(12)26)20(27)28/h8-9,11,15H,4-7,10,23H2,1-3H3,(H,27,28)/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H26FN3O4
Molecular Weight	403.4472
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:29:52 UTC 2023` Edited by `admin` on `Sat Dec 16 11:29:52 UTC 2023`
Record UNII	WT7488BZD3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

WCK-1152

Code

English

7-((4S)-4-AMINO-3,3-DIMETHYL-1-PIPERIDYL)-1-CYCLOPROPYL-6-FLUORO-8-METHOXY-4-OXO-QUINOLINE-3-CARBOXYLIC ACID

Systematic Name

English

WCK-1152A

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 7-((4S)-4-AMINO-3,3-DIMETHYL-1-PIPERIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-

Systematic Name

English

WCK1152

Code

English

Code System Code Type Description

FDA UNII

WT7488BZD3

Created by admin on Sat Dec 16 11:29:52 UTC 2023 , Edited by admin on Sat Dec 16 11:29:52 UTC 2023

PRIMARY

CAS

473839-20-2

Created by admin on Sat Dec 16 11:29:52 UTC 2023 , Edited by admin on Sat Dec 16 11:29:52 UTC 2023

PRIMARY

PUBCHEM

11619057

Created by admin on Sat Dec 16 11:29:52 UTC 2023 , Edited by admin on Sat Dec 16 11:29:52 UTC 2023

PRIMARY

Related Record Type Details


					49WMW4VH6D

7-((4R)-4-AMINO-3,3-DIMETHYL-1-PIPERIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID

ENANTIOMER -> ENANTIOMER

Amount:


					XSU9YAX3AA

WCK-1152 HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:

Related Record Type Details


					WT7488BZD3

WCK-1152

ACTIVE MOIETY

Comments:

Class: Antibacterial, Fluoroquinolone; Mechanism of Action: DNA topoisomerase inhibitor, Membrane protein inhibitor; Highest Development Phase: Phase I Respiratory tract infections; Most Recent Events: 01 Nov 2006 Phase-I clinical trials in Respiratory tract infections in India (PO), 01 Nov 2006 Phase-I clinical trials in Respiratory tract infections in India (IV)


					WT7488BZD3

WCK-1152

ACTIVE MOIETY

Comments:

Since the introduction of the fluoroquinolones, ciprofloxacin and ofloxacin over 10 years ago, there has been a small but significant increase in the number of resistant clinical isolates of species previously susceptible to these agents. More recent fluoroquinolones have better activity against Gram-positive species while retaining activity against Gram-negative species. The comparative in vitro activity of the novel fluoroquinolone WCK 1152A was determined against a range of clinical isolates.(open web address to view data table)


					WT7488BZD3

WCK-1152

ACTIVE MOIETY

Comments:

MIC50/MIC90 values (mg/L) of WCK 771, WCK 1152 and WCK 1153 for quinolone-susceptible S. pneumoniae (n = 119; 54 penicillin G-susceptible, 53 penicillin G-intermediate, and 12 penicillin G-resistant strains) were 0.25/0.5, 0.03/0.06 and 0.016/0.03, respectively. MIC50/MIC90 values (mg/L) for quinolone-resistant pneumococci (n = 40) increased to 4/16, 0.25/1 and 0.125/0.5, respectively. Against S. pyogenes, WCK 771, WCK 1152 and WCK 1153 were also highly active with MIC50/MIC90 values (mg/L) of 0.25/0.25, 0.03/0.06 and 0.03/0.03, respectively. CONCLUSIONS: Overall, WCK 771 was highly active against quinolone-susceptible, but not against quinolone-resistant S. pneumoniae, whereas WCK 1152 and WCK 1153 were more potent and were able to overcome quinolone resistance in both S. pneumoniae and S. pyogenes.