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| CAS No.: | 78110-38-0 |
|---|---|
| Name: | Aztreonam |
| Molecular Structure: | |
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| 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
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| Risk Codes: | 20/21/22-36/37/38 |
| Safety: | 22-24/25-36-26 |
| PSA: | 238.20000 |
| LogP: | 0.81830 |
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- 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With methoxybenzene; trifluoroacetic acid In dichloromethane |
- 78110-38-0
azthreonam
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: H2O 2: trifluoroacetic acid, anisole / CH2Cl2 View Scheme |
| Conditions | Yield |
|---|---|
| In water; N,N-dimethyl-formamide; acetonitrile |
- 78110-38-0
azthreonam
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol; water | |
| With hydrogenchloride In methanol; water |
- 7732-18-5
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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | 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 |
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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 
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
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.