Azlocillin | CAS# 37091-66-0 | Semisynthetic Penicillin

MedKoo Cat#: 573368 | Name: Azlocillin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Azlocillin is a semisynthetic ampicillin-derived acylureido penicillin

Chemical Structure

Azlocillin

CAS#37091-66-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 573368

Name: Azlocillin

CAS#: 37091-66-0 (free acid)

Chemical Formula: C20H23N5O6S

Exact Mass: 461.1369

Molecular Weight: 461.49

Elemental Analysis: C, 52.05; H, 5.02; N, 15.18; O, 20.80; S, 6.95

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Related CAS #

37091-65-9 (sodium) 37091-66-0 (free acid)

Synonym

Azlin, Azlocillin, Azlocilline

IUPAC/Chemical Name

(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

InChi Key

JTWOMNBEOCYFNV-NFFDBFGFSA-N

InChi Code

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

SMILES Code

CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](NC(=O)N3CCNC3=O)c4ccccc4)C(=O)N2[C@H]1C(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 461.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Azlocillin. Drug Ther Bull. 1981 Aug 14;19(17):65-6. PMID: 7261905. 2: Eliopoulos GM, Moellering RC Jr. Azlocillin, mezlocillin, and piperacillin: new broad-spectrum penicillins. Ann Intern Med. 1982 Nov;97(5):755-60. doi: 10.7326/0003-4819-97-5-755. PMID: 6215872. 3: Gagaeva EV, Danilova VI. Farmakokinetika azlotsillina [Azlocillin pharmacokinetics]. Antibiot Khimioter. 1988 Feb;33(2):138-41. Russian. PMID: 3288151. 4: Drusano GL, Schimpff SC, Hewitt WL. The acylampicillins: mezlocillin, piperacillin, and azlocillin. Rev Infect Dis. 1984 Jan-Feb;6(1):13-32. doi: 10.1093/clinids/6.1.13. PMID: 6369480. 5: Pothineni VR, Potula HSK, Ambati A, Mallajosyula VVA, Sridharan B, Inayathullah M, Ahmed MS, Rajadas J. Azlocillin can be the potential drug candidate against drug-tolerant Borrelia burgdorferi sensu stricto JLB31. Sci Rep. 2020 Mar 2;10(1):3798. doi: 10.1038/s41598-020-59600-4. PMID: 32123189; PMCID: PMC7052277. 6: Xiao S, Lu J, Sun L, An S. A simple and sensitive AuNPs-based colorimetric aptasensor for specific detection of azlocillin. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Apr 15;271:120924. doi: 10.1016/j.saa.2022.120924. Epub 2022 Jan 20. PMID: 35093821. 7: Singlas E, Haegel C. Pharmacocinétique clinique de l'azlocilline [Clinical pharmacokinetics of azlocillin]. Presse Med. 1984 Mar 29;13(13):788-96. French. PMID: 6231596. 8: Azlocillin sodium (AZLIN). Med Lett Drugs Ther. 1982 Dec 24;24(625):113-4. PMID: 7144692. 9: Sanders CC. Azlocillin: a new broad spectrum penicillin. J Antimicrob Chemother. 1983 May;11 Suppl B:21-31. doi: 10.1093/jac/11.suppl_b.21. PMID: 6619029. 10: Bosso JA, Saxon BA, Herbst JJ, Matsen JM. Azlocillin pharmacokinetics in patients with cystic fibrosis. Antimicrob Agents Chemother. 1984 May;25(5):630-2. doi: 10.1128/AAC.25.5.630. PMID: 6732230; PMCID: PMC185602. 11: Fu KP, Neu HC. Azlocillin and mezlocillin: new ureido penicillins. Antimicrob Agents Chemother. 1978 Jun;13(6):930-8. doi: 10.1128/AAC.13.6.930. PMID: 677860; PMCID: PMC352365. 12: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Penicillins (4th Generation). 2020 Oct 20. PMID: 31643749. 13: Krupp A, Leuwer M, Schmidt H, Eberhardt B. Der Einfluss der kontinuierlichen arteriovenösen Hämofiltration auf die Pharmakokinetik von Azlocillin bei anurischen Patienten [The effect of continuous arteriovenous hemofiltration on the pharmacokinetics of azlocillin in anuric patients]. Anaesthesist. 1990 May;39(5):275-8. German. PMID: 2192573. 14: Wu YE, Wang T, Yang HL, Tang BH, Kong L, Li X, Gao Q, Li X, Yao BF, Shi HY, Huang X, Wang WQ, Jacqz-Aigrain E, Allegaert K, van den Anker J, Tian XY, Zhao W. Population pharmacokinetics and dosing optimization of azlocillin in neonates with early-onset sepsis: a real-world study. J Antimicrob Chemother. 2021 Feb 11;76(3):699-709. doi: 10.1093/jac/dkaa468. PMID: 33188385. 15: Bergan T. Review of the pharmacokinetics and dose dependency of azlocillin in normal subjects and patients with renal insufficiency. J Antimicrob Chemother. 1983 May;11 Suppl B:101-14. doi: 10.1093/jac/11.suppl_b.101. PMID: 6352598. 16: Whelton A, Stout RL, Delgado FA. An azlocillin dosing nomogram for renal insufficiency. J Antimicrob Chemother. 1983 May;11 Suppl B:97-9. doi: 10.1093/jac/11.suppl_b.97. PMID: 6619037. 17: Stewart D, Bodey GP. Azlocillin: in vitro studies of a new semisynthetic penicillin. Antimicrob Agents Chemother. 1977 May;11(5):865-70. doi: 10.1128/AAC.11.5.865. PMID: 18083; PMCID: PMC352088. 18: Parry MF. The tolerance and safety of azlocillin. J Antimicrob Chemother. 1983 May;11 Suppl B:223-8. doi: 10.1093/jac/11.suppl_b.223. PMID: 6619031. 19: Schacht P, Tettenborn D, Hullmann R, Bruck H. Ergebnisse der klinischen Prüfung von Azlocillin [Clinical results with azlocillin (author's transl)]. Arzneimittelforschung. 1979;29(12a):1981-5. German. PMID: 396929. 20: Alizadeh A, Salouti M, Alizadeh H, Kazemizadeh AR, Safari AA, Mahmazi S. Enhanced antibacterial effect of azlocillin in conjugation with silver nanoparticles against Pseudomonas aeruginosa. IET Nanobiotechnol. 2017 Dec;11(8):942-947. doi: 10.1049/iet-nbt.2017.0009. PMID: 29155393; PMCID: PMC8675949.