Product Name

  • Name

    Aztreonam

  • EINECS 278-839-9
  • CAS No. 78110-38-0
  • Article Data15
  • CAS DataBase
  • Density 1.83 g/cm3
  • Solubility Soluble in DMF/water (1:1) at 50 mg/ml
  • Melting Point 227 °C
  • Formula C13H17N5O8S2
  • Boiling Point
  • Molecular Weight 435.439
  • Flash Point
  • Transport Information
  • Appearance White crystalline powder
  • Safety 22-24/25-36-26
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 78110-38-0 (Aztreonam)
  • Hazard Symbols HarmfulXn
  • Synonyms 2-[[(2-amino-1,3-thiazol-4-yl)-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-azetidin-3-yl]carbamoyl]methylidene]amino]oxy-2-methyl-propanoic acid;Aztreonamum [Latin];Aztreonam [USAN:BAN:INN:JAN];Dynabiotic;Propanoic acid, 2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl-, (2S-(2alpha,3beta(Z)))-;(Z)-2-((((2-Amino-4-thiazolyl)(((2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid;Aztreonam ;azthreonam;Primbactam;Monobactam;2-[[[(Z)-1-(2-amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid;Azactam;[2S-[2alpha,3beta(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid;Aztreonam Pure;Azteronam;Aztreonam L-Arginine;
  • PSA 238.20000
  • LogP 0.81830

Synthetic route

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
80082-65-1

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

(Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester
89604-92-2

(Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester With pyridine In acetonitrile at -5℃; for 4h;
Stage #2: With nitric acid at 35℃; for 2h; pH=1; Solvent; Reagent/catalyst; Temperature;		86.9%
(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt
139714-28-6

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
80082-65-1

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: (Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In ethanol; water at -6 - -3℃; for 3h;
Stage #2: With hydrogenchloride In ethanol; water at -3 - 0℃;		81%
[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid
330944-50-8

[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With hydrogenchloride; water at 0 - 65℃; for 4.75h;72%
With water; trifluoroacetic acid at 0 - 63℃; for 1 - 21.75h;63%
With hydrogenchloride In water at 60℃; for 5h;
3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid
123539-91-3

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid In dichloromethane
2-[1-(2-Amino-thiazol-4-yl)-2-(diphenoxy-phosphoryloxy)-2-oxo-eth-(Z)-ylideneaminooxy]-2-methyl-propionic acid benzhydryl ester

2-[1-(2-Amino-thiazol-4-yl)-2-(diphenoxy-phosphoryloxy)-2-oxo-eth-(Z)-ylideneaminooxy]-2-methyl-propionic acid benzhydryl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O
2: trifluoroacetic acid, anisole / CH2Cl2
View Scheme
aztreonam

aztreonam

6,7-Dihydroxy-2,3-quinolinedicarboxylic anhydride

6,7-Dihydroxy-2,3-quinolinedicarboxylic anhydride

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide; acetonitrile
azthreonam dipotassium salt

azthreonam dipotassium salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
With hydrogenchloride In methanol; water
water
7732-18-5

water

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid
123539-91-3

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With trifluoroacetic acid In acetone-denatured alcohol; ethanol; dichloromethane; methoxybenzene
(Z)-2-Amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]-imino]-4-thiazoleacetic acid
80542-76-3

(Z)-2-Amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]-imino]-4-thiazoleacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 2 h / 30 °C
2.1: methoxybenzene / dichloromethane / 1 h / 0 - 3 °C
3.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
3.2: 10 °C / pH 1.3
View Scheme
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / acetonitrile / 3 h / 20 - 24 °C
1.2: 15 h / 20 °C
2.1: methanesulfonic acid; methoxybenzene / dichloromethane / 5 h / 0 °C
3.1: triethylamine / ethanol; water / 3 h / -6 - -3 °C
3.2: -3 - 0 °C
View Scheme
(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt
139714-26-4

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methanesulfonic acid; methoxybenzene / dichloromethane / 5 h / 0 °C
2.1: triethylamine / ethanol; water / 3 h / -6 - -3 °C
2.2: -3 - 0 °C
View Scheme
2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethylidene]amino]oxy}-2-methylpropionic acid benzhydryl ester

2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethylidene]amino]oxy}-2-methylpropionic acid benzhydryl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methoxybenzene / dichloromethane / 1 h / 0 - 3 °C
2.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
2.2: 10 °C / pH 1.3
View Scheme
2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate
477528-80-6

2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
80082-65-1

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: 2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In methanol; water at 0℃; pH=8 - 8.5;
Stage #2: With hydrogenchloride In methanol; water at 10℃; pH=1.3;		174.2 g
C16H22N4O7SSi*ClH

C16H22N4O7SSi*ClH

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / N,N-dimethyl-formamide; ethyl acetate / 0.02 h / 10 °C
1.2: 10 °C
2.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
2.2: 10 °C / pH 1.3
View Scheme
2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid

2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide / 0.25 h / 50 °C
1.2: 3 h / -5 - 5 °C
2.1: triethylamine / N,N-dimethyl-formamide; ethyl acetate / 0.02 h / 10 °C
2.2: 10 °C
3.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
3.2: 10 °C / pH 1.3
View Scheme
3-(3-amino-2-methyl-4-oxo-azetidine-1-sulfonyloxy)-2,2-dimethylpropionic acid ethyl ester methanesulfonic acid salt

3-(3-amino-2-methyl-4-oxo-azetidine-1-sulfonyloxy)-2,2-dimethylpropionic acid ethyl ester methanesulfonic acid salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

A

azthreonam
78110-38-0

azthreonam

B

3,3-dimethyltetrahydrofuran
15833-75-7

3,3-dimethyltetrahydrofuran

C

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 1.17 h / 37 °C / Enzymatic reaction
View Scheme
...Expand
4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.03 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.33 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 19 h / 37 °C / Enzymatic reaction
View Scheme
...Expand
(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid
86299-47-0

(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
C24H37N5O10S2*C2HF3O2

C24H37N5O10S2*C2HF3O2

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetic acid salt

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetic acid salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.5h; pH=4.7; Enzymatic reaction;28 %Chromat.
4-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate trifluoroacetate

4-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.03 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 1.17 h / 37 °C / Enzymatic reaction
View Scheme
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

A

azthreonam
78110-38-0

azthreonam

B

3,3-dimethyltetrahydrofuran
15833-75-7

3,3-dimethyltetrahydrofuran

C

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate In [D3]acetonitrile; water-d2 at 37℃; for 1.16667h; Mechanism; Enzymatic reaction;
...Expand
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.0333333h; pH=4.7; Enzymatic reaction;> 95 %Chromat.
ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.33 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 19 h / 37 °C / Enzymatic reaction
View Scheme
...Expand
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.333333h; pH=4.7; Enzymatic reaction;90 %Chromat.
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With sodium dihydrogenphosphate In [D3]acetonitrile; water-d2 at 37℃; for 19h; Mechanism; Enzymatic reaction;
...Expand
L-lysine
56-87-1

L-lysine

azthreonam
78110-38-0

azthreonam

aztreonam lysinate
827611-49-4

aztreonam lysinate

Conditions
ConditionsYield
In water at 0 - 5℃; Conversion of starting material;77%
In water at 0 - 5℃; Conversion of starting material;62%
In water for 0.1h; pH=4.34; Cooling with ice;56%
In water at 0 - 5℃; Conversion of starting material;
ethanol
64-17-5

ethanol

azthreonam
78110-38-0

azthreonam

aztreonam ethyl ester

aztreonam ethyl ester

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; triethylamine; diisopropyl-carbodiimide at 0 - 32℃; for 48h; Reagent/catalyst;71.6%
azthreonam
78110-38-0

azthreonam

(2S,3S)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-sulfoamino-butyric acid

(2S,3S)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-sulfoamino-butyric acid

Conditions
ConditionsYield
With citrate buffer at 35℃; Rate constant; other aqueous buffer;
With Zn2+-Tris In water at 35℃; Rate constant; other metal ions;
azthreonam
78110-38-0

azthreonam

C12H14N3O5S(1-)*Na(1+)

C12H14N3O5S(1-)*Na(1+)

Conditions
ConditionsYield
With phosphoric acid In water at 35℃; Rate constant; various pH;
azthreonam
78110-38-0

azthreonam

aztreonam

aztreonam

Conditions
ConditionsYield
With water at 59.85℃; Kinetics; Thermodynamic data; Further Variations:; Temperatures;
azthreonam
78110-38-0

azthreonam

[2S-[2α,3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, 2-[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]hydrazide, monopotassium salt

[2S-[2α,3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, 2-[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]hydrazide, monopotassium salt

Conditions
ConditionsYield
In N-methyl-acetamide

Aztreonam Chemical Properties

Molecular Structure of Aztreonam (CAS NO.78110-38-0) :

IUPAC Name: 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid
Empirical Formula: C13H17N5O8S2
Molecular Weight: 435.4328
Molar Refractivity: 95.58 cm3
Molar Volume: 236.9 cm3
Surface Tension: 84.1 dyne/cm
Index of Refraction: 1.74
Storage temp: 0-5°C
Melting Point: 227°C
Form: solid
Appearance: White to off-white crystals
Density: 1.83 g/cm3
Product Categories: Active Pharmaceutical Ingredients; Antibacterial; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals
Synonyms of   Aztreonam (CAS NO.78110-38-0) :(2s-(2-Alpha,3-beta(z)))-dinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl ; monobactam ; propanoicacid,2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azeti ; 2-[(2-amino-thiazol-4-yl)-(2-methyl-4-oxo-1-sulfo-azetidin-3-ylcarbamoyl)-methyleneaminooxy]-2-methyl-propionic acid ; 2-[[[(z)-1-(2-amino-4-thiazolyl)-2-[[(2s,3s)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid ; (2s-(2alpha,3beta(z)))-2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino)-2-oxoethylidene)amino)oxy)-2-methyl-propanoic acid

Aztreonam Toxicity Data With Reference

1.    

ivn-rat TDLo:1100 mg/kg (7-17 D preg):TER

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),203.
2.    

ipr-rat LD50:2549 mg/kg

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
3.    

scu-rat LD50:3154 mg/kg

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
4.    

ivn-rat LD50:2001 mg/kg

     KSRNAM    Kiso to Rinsho. Clinical Report. 19 (1985),468.
5.    

ipr-mus LD50:2897 mg/kg

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
6.    

scu-mus LD50:3906 mg/kg

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.
7.    

ivn-mus LD50:1963 mg/kg

     NKRZAZ    Chemotherapy (Tokyo). 33 (Suppl 1)(1985),143.

Aztreonam Safety Profile

Moderately toxic by several routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and SOx.
Hazard Codes  HarmfulXn
Risk Statements  20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements  22-24/25-36-26
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
WGK Germany: 2
RTECS: UA2451400

Aztreonam Specification

The main role of Aztreonam (CAS NO.78110-38-0) is used to treat infections which caused by sensitive gram-negative bacteria . Aztreonam (CAS NO.78110-38-0) is a toxic material, burning will produce toxic fumes of nitrogen oxides and sulfur oxides, Besides should be stored and transported in low-temperature, drying environment. separately with oxidizing agents. Fire extinguishing agents water, carbon dioxide, dry powder, foam would be used if emergency.

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