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Basic Information
CAS No.: 78110-38-0
Name: Aztreonam
Article Data: 15
Molecular Structure:
Molecular Structure of 78110-38-0 (Aztreonam)
Formula: C13H17N5O8S2
Molecular Weight: 435.439
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;
EINECS: 278-839-9
Density: 1.83 g/cm3
Melting Point: 227 °C
Solubility: Soluble in DMF/water (1:1) at 50 mg/ml
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 22-24/25-36-26
PSA: 238.20000
LogP: 0.81830
Synthetic route
80082-65-1

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

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

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%
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

80082-65-1

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

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%
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

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;
123539-91-3

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

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

78110-38-0

azthreonam

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

aztreonam

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

78110-38-0

azthreonam

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide; acetonitrile

azthreonam dipotassium salt

78110-38-0

azthreonam

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
With hydrogenchloride In methanol; water
123539-91-3

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

78110-38-0

azthreonam

Conditions
ConditionsYield
With trifluoroacetic acid In acetone-denatured alcohol; ethanol; dichloromethane; methoxybenzene
80542-76-3

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

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
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

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
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    Chemical Name: Aztreonam Other name: Aztreonam sterile Molecular Formula: C13H17N5O8S2 Formula Weight: 435.43 CAS No.: 78110-38-0;80951-91-3;149496-40-2 EINECS号: 278-839-9 Appearance:white to off-white crystals Assay: 92.0% ~105.

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Chemistry

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

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.

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

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.