AZLOCILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H23N5O6S
Molecular Weight	461.492
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N3CCNC3=O)C4=CC=CC=C4)C(O)=O

InChI

InChIKey=JTWOMNBEOCYFNV-NFFDBFGFSA-N

InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H23N5O6S
Molecular Weight	461.492
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Azlocillin is a semisynthetic penicillin with broad spectrum of anti-bacterial action. The drug is effective against gram-negative and gram-positive infections and acts by inhibition of penicillin-binding protein (PBP)-dependent bacterial cell wall synthesis. Azlocillin was marketed in the USA under the name Azlin (sodium salt), however, its approval was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234	Curative		Approved 8,429	AZLIN

C_max

Value	Dose	Co-administered	Analyte	Population
414 μg/mL	4 g 4 times / day multiple, intravenous		AZLOCILLIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
374 μg × h/mL	4 g single, intravenous	AZLOCILLIN plasma	Homo sapiens
592 μg × h/mL	4 g 4 times / day multiple, intravenous	AZLOCILLIN plasma	Homo sapiens
772 μg × h/mL	5 g 3 times / day multiple, intravenous	AZLOCILLIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.26 h	4 g single, intravenous	AZLOCILLIN plasma	Homo sapiens
1.29 h	4 g 4 times / day multiple, intravenous	AZLOCILLIN plasma	Homo sapiens
1.46 h	5 g 3 times / day multiple, intravenous	AZLOCILLIN plasma	Homo sapiens
1.1 h	4 g 4 times / day multiple, intravenous	AZLOCILLIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
17 g 1 times / day multiple, intravenous\|intramuscular	unhealthy n = 21	Disc. AE: Macular rash, Pruritic rash...

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AEs

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AE	Significance	Dose	Population
Macular rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular	unhealthy n = 21
Pruritic rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular	unhealthy n = 21

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2956	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2956
ChemicalBook	CB6511850	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6511850
MolPort	MolPort-023-314-370	https://www.molport.com/shop/molecule-link/MolPort-023-314-370
ZINC	ZINC000003830261	http://zinc15.docking.org/substances/ZINC000003830261

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PubMed

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Title	Date	PubMed
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987 Oct	3501698
Evaluation of the immunologic cross-reactivity of aztreonam in patients with cystic fibrosis who are allergic to penicillin and/or cephalosporin antibiotics.	1991 May-Jun	2068466
The Malaysian Orthopaedic Association humanitarian mission to Indonesia and Sri Lanka.	2005 Jul	16381273
[Enzyme immunoassay of ampicillin in milk].	2005 Nov-Dec	16358758
Placental transfer of antibiotics administered to the mother: a review.	2006 Feb	16502764

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Patents

Sample Use Guides

In Vivo Use Guide

Gram-negative infections: 2 to 5 grams every 8 hours IV. Serious infections: 225 to 300 mg/kg/day IV in 4 to 6 divided doses (usual IV doses 3g q4h or 4g q6h) (up to 18 g/day).

Route of Administration: Intravenous

In Vitro Use Guide

In vitro activity of Azlocillin against different bacterial strains was determined. MIC50 values were 2 ugml (Enterococcus), 8 ug/ml (E. coli), 16 ug/ml (Enterobacter spp.), 64 ug/ml (Klebsiella spp.), 4 ug/ml (P. mirabilis), 16 ug/ml (P. aeruginosa, gentamicin susceptible)).

Substance Class	Chemical
Record UNII	HUM6H389W0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZLOCILLIN

Official Name

English

AZLOCILLIN [USAN]

Common Name

English

Azlocillin [WHO-DD]

Common Name

English

AZLOCILLIN [MART.]

Common Name

English

(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(((2R)-2-(((2-OXOIMIDAZOLIDIN-1-YL)CARBONYL)AMINO)-2-PHENYLACETYL)AMINO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID

Systematic Name

English

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