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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H16N4O6S
Molecular Weight 416.408
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINACILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=NC4=CC=CC=C4N=C3C(O)=O)C(O)=O

InChI

InChIKey=GPMSLJIYNWBYEL-TYNCELHUSA-N
InChI=1S/C18H16N4O6S/c1-18(2)12(17(27)28)22-14(24)11(15(22)29-18)21-13(23)9-10(16(25)26)20-8-6-4-3-5-7(8)19-9/h3-6,11-12,15H,1-2H3,(H,21,23)(H,25,26)(H,27,28)/t11-,12+,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H16N4O6S
Molecular Weight 416.408
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Quinacillin is semisynthetic penicillase-resistant penicillin patented by Boots Pure Drug Co. Ltd. For the treatment of bacterial infection. Quinacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis. In clinical trials Staph. aureus was eradicated from all but two patients during treatment but recurred in 4 after withdrawal. The antibiotic was especially useful in the treatment of staphylococcal respiratory infections, as it has little effect on the normal bacterial flora of the chest.

Approval Year

PubMed

PubMed

TitleDatePubMed
Reversible inhibition of penicillinase by quinacillin: evaluation of mechanisms involving two conformational states of the enzyme.
1978 Jun 14
Patents

Sample Use Guides

0.5g x 2/day for 5 days
Route of Administration: Intramuscular
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:36:55 UTC 2023
Edited
by admin
on Fri Dec 15 16:36:55 UTC 2023
Record UNII
83NB50X92M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINACILLIN
INN   MI  
INN  
Official Name English
quinacillin [INN]
Common Name English
QUINACILLIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
Code System Code Type Description
MESH
C011097
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
PUBCHEM
92894
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID401043140
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
EVMPD
SUB10198MIG
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
WIKIPEDIA
Quinacillin
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
SMS_ID
100000081105
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
INN
1680
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
MERCK INDEX
m9429
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY Merck Index
FDA UNII
83NB50X92M
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
CAS
1596-63-0
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
216-481-7
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104733
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
NCI_THESAURUS
C80593
Created by admin on Fri Dec 15 16:36:55 UTC 2023 , Edited by admin on Fri Dec 15 16:36:55 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY