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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H14N4O6S.2Na
Molecular Weight 460.371
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINACILLIN DISODIUM

SMILES

[Na+].[Na+].[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=WFAXHOKRRRZBNN-HWROMZCQSA-L
InChI=1S/C18H16N4O6S.2Na/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);;/q;2*+1/p-2/t11-,12+,15-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H14N4O6S
Molecular Weight 414.392
Charge -2
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 Sat Dec 16 11:11:03 GMT 2023
Edited
by admin
on Sat Dec 16 11:11:03 GMT 2023
Record UNII
K8064V0P9V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINACILLIN DISODIUM
Common Name English
DISODIUM QUINACILLIN
Common Name English
(2S,5R,6R)-6-(((3-CARBOXY-2-QUINOXALINYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, DISODIUM SALT
Systematic Name English
QUINACILLIN SODIUM
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-CARBOXY-2-QUINOXALINYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, DISODIUM SALT, (2S,5R,6R)-
Systematic Name English
QUINACILLIN DISODIUM SALT [MI]
Common Name English
RD-13962
Code English
Code System Code Type Description
PUBCHEM
71463610
Created by admin on Sat Dec 16 11:11:03 GMT 2023 , Edited by admin on Sat Dec 16 11:11:03 GMT 2023
PRIMARY
MERCK INDEX
m9429
Created by admin on Sat Dec 16 11:11:03 GMT 2023 , Edited by admin on Sat Dec 16 11:11:03 GMT 2023
PRIMARY Merck Index
CAS
985-32-0
Created by admin on Sat Dec 16 11:11:03 GMT 2023 , Edited by admin on Sat Dec 16 11:11:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID40913246
Created by admin on Sat Dec 16 11:11:03 GMT 2023 , Edited by admin on Sat Dec 16 11:11:03 GMT 2023
PRIMARY
FDA UNII
K8064V0P9V
Created by admin on Sat Dec 16 11:11:03 GMT 2023 , Edited by admin on Sat Dec 16 11:11:03 GMT 2023
PRIMARY