QUINACILLIN DISODIUM

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 Search

SMILES

[Na+].[Na+].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=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	22.98976928
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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5941626 | https://www.ncbi.nlm.nih.gov/pubmed/6200139 | https://www.ncbi.nlm.nih.gov/pubmed/308803

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
Reversible inhibition of penicillinase by quinacillin: evaluation of mechanisms involving two conformational states of the enzyme.	1978-06-14	308803

Patents

Sample Use Guides

In Vivo Use Guide

0.5g x 2/day for 5 days

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:41:02 GMT 2025` Edited by `admin` on `Mon Mar 31 23:41:02 GMT 2025`
Record UNII	K8064V0P9V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUINACILLIN DISODIUM

Common Name

English

RD-13962

Preferred 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

Code System Code Type Description

PUBCHEM

71463610