- Cefotaxime
- Cefotaxime sodium
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Cas Database |
| Name |
Cefotaxime |
EINECS | 264-299-1 |
| CAS No. | 63527-52-6 | Density | 1.8 g/cm3 |
| PSA | 227.05000 | LogP | 0.28750 |
| Solubility | soluble in water | Melting Point |
N/A |
| Formula | C16H17N5O7S2 | Boiling Point | N/A |
| Molecular Weight | 455.472 | Flash Point | N/A |
| Transport Information | N/A | Appearance | white power |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Zeefotax;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[(acetyloxy)methyl]-7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-,[6R-[6a,7b(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-,(6R,7R)- (9CI);Cefabol;Cefotaxime acid;Ceftax;Claforan;Omnatax;Taxim; |
Article Data | 47 |
Cefotaxime Synthetic route
- 80756-85-0
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
- 957-68-6
7-Aminocephalosporanic acid
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| With TEA In dichloromethane at 20℃; for 1h; Substitution; | 95% |
| With triethylamine In dichloromethane at 20℃; for 1h; | 95% |
| Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In methanol at 0 - 5℃; Stage #2: With hydrogenchloride In methanol; water at 0 - 5℃; for 1h; pH=2.3 - 2.5; | |
| Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In 1,2-dimethoxyethane at -5 - 0℃; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water for 1h; pH=2.6 - 2.8; Product distribution / selectivity; |
- 957-68-6
7-Aminocephalosporanic acid
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 20℃; for 1h; Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In dichloromethane at 20℃; for 8h; Stage #3: With sodium hydroxide In dichloromethane; water at 15 - 20℃; pH=7.5 - 7.8; | 94.4% |
| Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In DMF (N,N-dimethyl-formamide) at 20 - 25℃; Stage #2: diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate In DMF (N,N-dimethyl-formamide) at 20℃; for 18h; | 93.5% |
| Conditions | Yield |
|---|---|
| With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at -5 - 0℃; for 1h; Temperature; | 93.1% |
- 957-68-6
7-Aminocephalosporanic acid
- 207725-19-7
(2-Amino-thiazol-4-yl)-[(Z)-methoxyimino]-acetic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| With N,O-bis-dimethylsilyl acetamide In acetonitrile at 0 - 5℃; for 1.5h; | 75.4% |
- 17356-08-0
thiourea
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| Stage #1: 7-[4-bromo-2(Z)-methoxyimino-3-oxobutyramido]-cephalosporanic acid; thiourea With sodium acetate In dichloromethane; water for 2.5 - 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2.8; | 40.3% |
- 957-68-6
7-Aminocephalosporanic acid
- 64485-90-1
2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H; Multistep reaction; |
- 65243-53-0
pyvaloyloxymethyl 7β-<2-(2-aminothiazol-4-yl)-(Z)-methoxyiminoacetamido>-3-acetoxymethyl-3-cephem-4-carboxylate
A
- 63527-52-6
cefotaxime
B
- 126747-48-6
(2R,6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid
| Conditions | Yield |
|---|---|
| With water In N,N-dimethyl-formamide at 37℃; Rate constant; phosphate buffer, var. pH; |
- 64485-88-7
ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: Et3N / dimethylformamide / 3 h 2: aq. NaOH / dioxane / 0.5 h / Heating 3: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme |
- 65872-39-1
(Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: ethanol; H2O / 1 h / 20 °C 2: Et3N / dimethylformamide / 3 h 3: aq. NaOH / dioxane / 0.5 h / Heating 4: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme |
- 64485-89-8
ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate
- 63527-52-6
cefotaxime
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aq. NaOH / dioxane / 0.5 h / Heating 2: (i) DCC, CH2Cl2, (ii) /BRN= 622638/, Et3N, (iii) aq. HCO2H View Scheme |
Cefotaxime Specification
The Cefotaxime with CAS registry number of 63527-52-6 is also known as Cefotaximum. The IUPAC name is (6R,7R)-3-(Acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Its EINECS registry number is 264-299-1. In addition, the formula is C16H17N5O7S2 and the molecular weight is 455.47. This chemical is a white power.
Physical properties about Cefotaxime are: (1)ACD/LogP: 1.20; (2)# of Rule of 5 Violations: 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 12; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 8; (10)Index of Refraction: 1.778; (11)Molar Refractivity: 105.95 cm3; (12)Molar Volume: 252.8 cm3; (13)Surface Tension: 81.2 dyne/cm; (14)Density: 1.8 g/cm3.
Preparation of Cefotaxime: it is prepared by reaction of cephalosporin C. Firstly, cefotaxime is crystallizated after cracking, silicon esterification, condensation and hydrolysis. Secondly, add sodium acetate to get sodium. Product is obtained after bleaching, sterile filtration and crystallization.
Uses of Cefotaxime: it is used as antibacterial drugs and is a semi-synthetic oxime-type cephalosporins. It is used for infections of the respiratory tract, skin, bones, joints, urogenital system, meningitis, and septicemia. This chemical is used to produce 7b-(2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid sodium salt. The reaction occurs with reagent aq. NaHCO3 and solvent ethanol. The yield is about 95.4%.
You can still convert the following datas into molecular structure:
1. SMILES: O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=NOC)c3nc(sc3)N)COC(=O)C)C(=O)O
2. InChI: InChI=1/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/t10-,14-/m1/s1
3. InChIKey: GPRBEKHLDVQUJE-QMTHXVAHBP
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