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CAS No.: | 78110-38-0 |
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Name: | Aztreonam |
Article Data: | 15 |
Molecular Structure: | |
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: | Xn |
Risk Codes: | 20/21/22-36/37/38 |
Safety: | 22-24/25-36-26 |
PSA: | 238.20000 |
LogP: | 0.81830 |
(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
azthreonam
Conditions | Yield |
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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
(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
azthreonam
Conditions | Yield |
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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
azthreonam
Conditions | Yield |
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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
azthreonam
Conditions | Yield |
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With methoxybenzene; trifluoroacetic acid In dichloromethane |
azthreonam
Conditions | Yield |
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Multi-step reaction with 2 steps 1: H2O 2: trifluoroacetic acid, anisole / CH2Cl2 View Scheme |
Conditions | Yield |
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In water; N,N-dimethyl-formamide; acetonitrile |
azthreonam
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water | |
With hydrogenchloride In methanol; water |
water
3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid
azthreonam
Conditions | Yield |
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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
azthreonam
Conditions | Yield |
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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
azthreonam
Conditions | Yield |
---|---|
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 |
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
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. |
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 Xn
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
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.