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37091-65-9

37091-65-9 structure
37091-65-9 structure
  • Name: Azlocillin sodium salt
  • Chemical Name: azlocillin sodium
  • CAS Number: 37091-65-9
  • Molecular Formula: C20H22N5NaO6S
  • Molecular Weight: 483.473
  • Catalog: API Antibiotics Penicillin
  • Create Date: 2018-04-19 08:00:00
  • Modify Date: 2024-01-04 19:49:24
  • 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].
Name azlocillin sodium
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)
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
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.
Molecular Formula C20H22N5NaO6S
Molecular Weight 483.473
Exact Mass 483.118835
PSA 176.28000
Storage condition 2-8°C

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)
Symbol GHS08
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
HS Code 2942000000

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