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

Structure Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCNC3=O)C4=CC=CC=C4)C(=O)N2[C@H]1C(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

Description
Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf | https://www.ncbi.nlm.nih.gov/pubmed/984809

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 234 Target ID: CHEMBL2354204 Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.antimicrobe.org/new/drugpopup/Azlocillin.pdf	Curative		Approved 8583	AZLIN Approved Use Treatment of Gram-positive (Streptococcus spp., Enterococcus, Listeria monocytogenes) and Gram-negative (H. influenzae, E. coli, Proteus mirabilis, Salmonella spp., Shigella spp.) infections. Launch Date 1982

C_max

Value	Dose	Co-administered	Analyte	Population
414 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:		AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
592 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
772 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
374 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2751284	5 g 3 times / day multiple, intravenous dose: 5 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.26 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3729353	4 g single, intravenous dose: 4 g route of administration: Intravenous experiment type: SINGLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3780161	4 g 4 times / day multiple, intravenous dose: 4 g route of administration: Intravenous experiment type: MULTIPLE co-administered:	AZLOCILLIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	Disc. AE: Macular rash, Pruritic rash... AEs leading to discontinuation/dose reduction: Macular rash (4 patients) Pruritic rash (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6619026

AEs

AE	Significance	Dose	Population
Macular rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6619026
Pruritic rash	4 patients Disc. AE	17 g 1 times / day multiple, intravenous\|intramuscular Dose: 17 g, 1 times / day Route: intravenous\|intramuscular Route: multiple Dose: 17 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6619026	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6619026

Sourcing

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

PubMed

Title	Date	PubMed
Molecular taxonomy, phylogeny and evolution in the family Stichopodidae (Aspidochirotida: Holothuroidea) based on COI and 16S mitochondrial DNA.	2010-09	20399872
Pleistocene climatic cycling drives intra-specific diversification in the intermediate horseshoe bat (Rhinolophus affinis) in Southern China.	2010-07	20561192
Contrasting patterns of phylogeographic relationships in sympatric sister species of ironclad beetles (Zopheridae: Phloeodes spp.) in California's Transverse Ranges.	2010-06-24	20573263
Role of the BACTEC radiometric method in the evaluation of patients with clinically probable tuberculous meningitis.	2010-04	20814497
Laboratory diagnosis of tuberculous meningitis - is there a scope for further improvement?	2010-01	21814402
In-vitro efficacy of synergistic antibiotic combinations in multidrug resistant Pseudomonas aeruginosa strains.	2010-01	20046523
Data correction pre-processing for electronically stored blood culture results: implications on microbial spectrum and empiric antibiotic therapy.	2009-06-07	19500418
Direct susceptibility testing for multi drug resistant tuberculosis: a meta-analysis.	2009-05-20	19457256
Clinical and ultrasonographic features of abdominal tuberculosis in HIV positive adults in Zambia.	2009-04-17	19374757
A critical role for CD8 T cells in a nonhuman primate model of tuberculosis.	2009-04	19381260
Detection of Extended Spectrum β-lactamase Production Among Uropathogens.	2009-01	21938241
How beta-lactam antibiotics enter bacteria: a dialogue with the porins.	2009	19434239
Dynamic root exudation of sorgoleone and its in planta mechanism of action.	2009	19357432
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008-12	19337440
Phylogeography and recolonization of the Swiss Alps by the Valais shrew (Sorex antinorii), inferred with autosomal and sex-specific markers.	2008-09	19238709
Mycobacterium ulcerans disease, Peru.	2008-03	18325248
[Bacterial meningitis and Pseudomonas aeruginosa: apropos of a case].	2007-11-01	17969281
Problematic clinical isolates of Pseudomonas aeruginosa from the university hospitals in Sofia, Bulgaria: current status of antimicrobial resistance and prevailing resistance mechanisms.	2007-07	17577062
Human oral drugs absorption is correlated to their in vitro uptake by brush border membrane vesicles.	2007-05-04	17178445
Searching for new antimalarial therapeutics amongst known drugs.	2006-06	16882315
Interaction of zwitterionic penicillins with the OmpF channel facilitates their translocation.	2006-03-01	16339889
Placental transfer of antibiotics administered to the mother: a review.	2006-02	16502764
[Enzyme immunoassay of ampicillin in milk].	2005-12-20	16358758
The Malaysian Orthopaedic Association humanitarian mission to Indonesia and Sri Lanka.	2005-07	16381273
[Azlocillin plus amikacin: an alternative therapy for sepsis caused by resistant staphylococci?].	2004-11	15729980
(-)-Epigallocatechin-3-gallate induces contraction of the rat aorta by a calcium influx-dependent mechanism.	2004-05	15083267
Characterization of the susceptibility of mycobacteria in BACTEC 12B media containing PANTA that had been supplemented with ceftazidime, and characterization of the individual components of PANTA in the presence of C18-carboxypropylbetaine.	2004-02	14744453
Natural antibiotic susceptibility of Ewingella americana strains.	2003-10	14598935
Evaluation of culture media for the recovery of Mycobacterium avium subsp. paratuberculosis from Cheddar cheese.	2003	12969490
Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains.	2002-10	12462424
[Clinical significance of microbiological monitoring of infective agents in an urological hospital in the selection of antibacterial therapy regimens].	2001-09-25	11569227
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].	2001-06	11503262
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.	2001-03-30	11290370
[Microbiology of open surgical wounds after delivery--episiotomy and cesarean section].	2001	11785348
The penicillins.	1999-03	10090000
Evaluation of the immunologic cross-reactivity of aztreonam in patients with cystic fibrosis who are allergic to penicillin and/or cephalosporin antibiotics.	1991-05-01	2068466
Sensitization to aztreonam and cross-reactivity with other beta-lactam antibiotics in high-risk patients with cystic fibrosis.	1991-01	1991925
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.	1987-10	3501698

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)).

Name

Type

Language

J01CA09

Preferred Name

English

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

(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(R)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Systematic Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-(((((2-OXO-1-IMIDAZOLIDINYL)CARBONYL)AMINO)PHENYLACETYL)AMINO)-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-

Common Name

English

NSC-758227

Code

English

AZLOCILLIN [VANDF]

Common Name

English

AZLOCILLIN [MI]

Common Name

English

azlocillin [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01CA09