CAS 37091-65-9|Azlocillin sodium salt

Introduction：Basic information about CAS 37091-65-9|Azlocillin sodium salt, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Azlocillin sodium salt BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles2
8. Synonyms

Common Name	Azlocillin sodium salt
CAS Number	37091-65-9	Molecular Weight	483.473
Density	/	Boiling Point	/
Molecular Formula	C₂₀H₂₂N₅NaO₆S	Melting Point	/
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS08	Signal Word	Danger

Names

Name	azlocillin sodium
Synonym	More Synonyms

Azlocillin sodium salt BiologicalActivity

Description	Azlocillin is an acylampicillin with a broad spectrum against bacteria.Target: AntibacterialAzlocillin (12.5 μg/mL) inhibits over 75% of the isolates of Pseudomonas aeruginosa. Azlocillin (12.5 μg/mL) is also active against indole-negative and -positive Proteus spp., inhibiting 98 and 71%, respectively. Azlocillin is more active than mezlocillin, ticarcillin, and carbenicillin and as active as BLP-1654 against isolates of P. aeruginosa [1]. The acyl side chains of Azlocillin have an ureido-(urea) structurehence the name "ureidopenicillins" or, more specifically, "acylureidopenicillins." In vitro studies against P. aeruginosa demonstrates that piperacillin has activity that is twice that of azlocillin, 4 times that of mezlocillin and ticarcillin, and about 8 times that of carbenicillin. Azlocillin produces elongated bacterial forms with delayed or no lysis in morphologic studies [2].Azlocillin has MICs of 12.5 μg/mL on Pseudomonas aeruginosa. Azlocillin (3.125 μg/mL) results in a reduction in the rate of growth but no bactericidal phase on Pseudomonas aeruginosa. Azlocillin decreases an initial lag phase with increasing drug concentration. At the lower concentration of tobramycin (0.5 μg/ml), the combinations with both the high and the low concentrations of Azlocillin are more effective than the individual components on Pseudomonas aeruginosa [3]. Isolates with derepression of AmpC enzyme are one to two doubling dilutions more resistant to azlocillin than are those in which increased efflux or impermeability is inferred. Those with secondary β-lactamases are mostly (12/14 cases) susceptible to ceftazidime at 4 mg/L, but are amongst the most resistant to Azlocillin (MIC ≥128 mg/L in 10/14 cases) [4].
Related Catalog	Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection
References	[1]. Stewart, D. and G.P. Bodey, Azlocillin: in vitro studies of a new semisynthetic penicillin. Antimicrob Agents Chemother, 1977. 11(5): p. 865-70. [2]. Wright, A.J., The penicillins. Mayo Clin Proc, 1999. 74(3): p. 290-307. [3]. McFarland, M.M., E.M. Scott, and A. Li Wan Po, Time-survival studies for quantifying effects of azlocillin and tobramycin on Pseudomonas aeruginosa. Antimicrob Agents Chemother, 1994. 38(6): p. 1271-6. [4]. Livermore, D.M. and H.Y. Chen, Quality of antimicrobial susceptibility testing in the UK: a Pseudomonas aeruginosa survey revisited. J Antimicrob Chemother, 1999. 43(4): p. 517-22.

Description

Azlocillin is an acylampicillin with a broad spectrum against bacteria.Target: AntibacterialAzlocillin (12.5 μg/mL) inhibits over 75% of the isolates of Pseudomonas aeruginosa. Azlocillin (12.5 μg/mL) is also active against indole-negative and -positive Proteus spp., inhibiting 98 and 71%, respectively. Azlocillin is more active than mezlocillin, ticarcillin, and carbenicillin and as active as BLP-1654 against isolates of P. aeruginosa [1]. The acyl side chains of Azlocillin have an ureido-(urea) structurehence the name "ureidopenicillins" or, more specifically, "acylureidopenicillins." In vitro studies against P. aeruginosa demonstrates that piperacillin has activity that is twice that of azlocillin, 4 times that of mezlocillin and ticarcillin, and about 8 times that of carbenicillin. Azlocillin produces elongated bacterial forms with delayed or no lysis in morphologic studies [2].Azlocillin has MICs of 12.5 μg/mL on Pseudomonas aeruginosa. Azlocillin (3.125 μg/mL) results in a reduction in the rate of growth but no bactericidal phase on Pseudomonas aeruginosa. Azlocillin decreases an initial lag phase with increasing drug concentration. At the lower concentration of tobramycin (0.5 μg/ml), the combinations with both the high and the low concentrations of Azlocillin are more effective than the individual components on Pseudomonas aeruginosa [3]. Isolates with derepression of AmpC enzyme are one to two doubling dilutions more resistant to azlocillin than are those in which increased efflux or impermeability is inferred. Those with secondary β-lactamases are mostly (12/14 cases) susceptible to ceftazidime at 4 mg/L, but are amongst the most resistant to Azlocillin (MIC ≥128 mg/L in 10/14 cases) [4].

Related Catalog

Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection

References

[1]. Stewart, D. and G.P. Bodey, Azlocillin: in vitro studies of a new semisynthetic penicillin. Antimicrob Agents Chemother, 1977. 11(5): p. 865-70.

[2]. Wright, A.J., The penicillins. Mayo Clin Proc, 1999. 74(3): p. 290-307.

[3]. McFarland, M.M., E.M. Scott, and A. Li Wan Po, Time-survival studies for quantifying effects of azlocillin and tobramycin on Pseudomonas aeruginosa. Antimicrob Agents Chemother, 1994. 38(6): p. 1271-6.

[4]. Livermore, D.M. and H.Y. Chen, Quality of antimicrobial susceptibility testing in the UK: a Pseudomonas aeruginosa survey revisited. J Antimicrob Chemother, 1999. 43(4): p. 517-22.

Chemical & Physical Properties

Molecular Formula	C₂₀H₂₂N₅NaO₆S
Molecular Weight	483.473
Exact Mass	483.118835
PSA	176.28000
InChIKey	FUHFQQPUHNRIQM-XFAPPKAWSA-N
SMILES	CC1(C)SC2C(NC(=O)C(NC(=O)N3CCNC3=O)c3ccccc3)C(=O)N2C1C(=O)O.[Na]
Storage condition	2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XH9250000

CHEMICAL NAME :: 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)-, monosodium salt, (2S-(2-alpha,5-alpha,6-beta(S*)))-

CAS REGISTRY NUMBER :: 37091-65-9

LAST UPDATED :: 199609

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C20-H22-N5-O6-S.Na

MOLECULAR WEIGHT :: 483.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1793 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AMBIEH Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.30-V.32, 1985-1987 Volume(issue)/page/year: 32,453,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6690 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AMBIEH Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.30-V.32, 1985-1987 Volume(issue)/page/year: 32,453,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5065 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - excitement

REFERENCE :: AMBIEH Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.30-V.32, 1985-1987 Volume(issue)/page/year: 32,453,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15420 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - tremor Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AMBIEH Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.30-V.32, 1985-1987 Volume(issue)/page/year: 32,453,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 27 gm/kg/4W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: AMBIEH Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.30-V.32, 1985-1987 Volume(issue)/page/year: 32,453,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5282 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 307 (estimated) No. of Female Employees: 251 (estimated)

Safety Information

Symbol	GHS08
Signal Word	Danger
Hazard Statements	H317-H334
Precautionary Statements	P261-P280-P342 + P311
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R42/43
Safety Phrases	S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	XH9250000
HS Code	2942000000

Customs

HS Code	2942000000

Articles2

High-pressure liquid chromatographic quantitation of azlocillin.

Antimicrob. Agents Chemother. 24 , 750-753, (1983)

We describe a rapid, precise, and simple procedure for the quantitation of azlocillin in serum and in aqueous solutions by high-pressure, reverse-phase liquid chromatography. This method uses a single...

Structure-Activity Relationships of Different β-Lactam Antibiotics against a Soluble Form of Enterococcus faecium PBP5, a Type II Bacterial Transpeptidase. Andrea M. Hujer, Malgosia Kania, et. Al

J. Affect. Disord. 49 , 612-618, (2005)

Synonyms

Azlocillin sodium

Sodium (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-carboxylate

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[[(2R)-2-[[(2-oxo-1-imidazolidinyl)carbonyl]amino]-2-phenylacetyl]amino]-, sodium salt, (2S,5R,6R)- (1:1)

MFCD07793330

Azlocillin sodium salt

Sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxo-1-imidazolidinyl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Azlin

Securopen

sodium azlocillin

monosodium azlocillin

EINECS 253-347-7

Azlocillin (sodium salt)

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