U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

CC1(C)S[C@@H]2[C@H](NC(=O)C3=NC4=C(C=CC=C4)N=C3C(O)=O)C(=O)N2[C@H]1C(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
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.
1978-06-14
Patents

Sample Use Guides

0.5g x 2/day for 5 days
Route of Administration: Intramuscular
Name Type Language
QUINACILLIN [MI]
Preferred Name English
QUINACILLIN
INN   MI  
INN  
Official Name English
quinacillin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
Code System Code Type Description
MESH
C011097
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PRIMARY
PUBCHEM
92894
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PRIMARY
EPA CompTox
DTXSID401043140
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PRIMARY
EVMPD
SUB10198MIG
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
PRIMARY
WIKIPEDIA
Quinacillin
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SMS_ID
100000081105
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INN
1680
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MERCK INDEX
m9429
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
PRIMARY Merck Index
FDA UNII
83NB50X92M
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CAS
1596-63-0
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ECHA (EC/EINECS)
216-481-7
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
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ChEMBL
CHEMBL2104733
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
PRIMARY
NCI_THESAURUS
C80593
Created by admin on Mon Mar 31 18:32:39 GMT 2025 , Edited by admin on Mon Mar 31 18:32:39 GMT 2025
PRIMARY