7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid
cefixime
Conditions | Yield |
---|---|
Stage #1: 7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid With sodium hydroxide; water at 0 - 5℃; for 0.0833333h; Stage #2: With hydrogenchloride In water at 34 - 36℃; pH=2.3; Product distribution / selectivity; | |
With sodium hydrogencarbonate; sodium hydroxide In water at 0 - 15℃; for 0.25h; | 162 g |
2-(2-aminothiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]acetic acid
cefixime
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,4-diaza-bicyclo[2.2.2]octane; tributyl-amine / dichloromethane / -5 - 20 °C / 7125.71 Torr 2: sodium hydroxide; sodium hydrogensulfite / tetrahydrofuran; water / 6 h / 5 - 10 °C 3: sodium hydroxide; sodium hydrogencarbonate / water / 0.25 h / 0 - 15 °C View Scheme |
cefixime
Conditions | Yield |
---|---|
at 10℃; for 5h; Temperature; | 4.7 g |
salicylaldehyde
cefixime
8-(2-carboxymethoxyimino-2-{2-[(2-hydroxybenzylidene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: salicylaldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux; Stage #2: With acetic acid In methanol pH=7; | 85% |
furfural
cefixime
8-(2-carboxymethoxyimino-2-{2-[(furan-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: furfural; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux; Stage #2: With acetic acid In methanol pH=7; | 80% |
2-pyrrole aldehyde
cefixime
8-(2-carboxymethoxyimino-2-{2-[(1H-pyrrol-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-pyrrole aldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux; Stage #2: With acetic acid In methanol pH=7; | 78% |
thiophene-2-carbaldehyde
cefixime
8-(2-carboxymethoxyimino-2-{2-[(thiophen-2-ylmethylene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: thiophene-2-carbaldehyde; cefixime With potassium hydroxide In methanol for 0.5h; pH=7 - 8; Reflux; Stage #2: With acetic acid In methanol pH=7; | 78% |
cefixime
benzenesulfonyl chloride
Conditions | Yield |
---|---|
With sodium carbonate In water at 20℃; pH=6 - 8; | 75.8% |
cefixime
p-acetylaminobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With sodium carbonate In water at 20℃; pH=6 - 8; | 69.8% |
cefixime
Conditions | Yield |
---|---|
With sodium hydroxide In water for 4h; Ambient temperature; pH 12; | 15% |
In water at 25℃; Rate constant; Mechanism; pH 9; |
cefixime
Conditions | Yield |
---|---|
With sodium hydroxide In water at 50℃; for 0.25h; pH 11.5; | 4% |
In water at 25℃; Rate constant; Mechanism; pH 9; |
cefixime
Conditions | Yield |
---|---|
With sodium hydroxide In water at 37℃; for 168h; | 3.1% |
cefixime
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide 1.) water, 50 deg C, 30 min, 2.) room temperature, 15 min; Yield given. Multistep reaction; |
cefixime
Conditions | Yield |
---|---|
In water at 25℃; Rate constant; Mechanism; pH 1; | |
With hydrogenchloride; sodium hydroxide In water at 50℃; for 48h; Yield given; |
cefixime
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide 1.) water, 50 deg C, 40 min, 2.) room temperature, 30 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In methanol; water |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at -5 - 0℃; for 3h; |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at -5 - 0℃; for 3h; |
Conditions | Yield |
---|---|
In methanol; water at 100℃; for 0.75h; Heating; |
cefixime
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; thionyl chloride / 4 h / 65 °C / Cooling with ice 2: triethylamine / dichloromethane / 3 h / 40 °C / Cooling with ice View Scheme |
cefixime
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; thionyl chloride / 4 h / 65 °C / Cooling with ice 2: triethylamine / dichloromethane / 3 h / 40 °C / Cooling with ice 3: lithium hydroxide / acetonitrile; water / 2.25 h / -10 °C View Scheme |
methanol
cefixime
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine at 65℃; for 4h; Cooling with ice; | 8.27 g |
The Cefixime, with the CAS registry number 79350-37-1, has the IUPAC name of (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethyloxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Being a kind of white or light yellow crystalline powder with no odour, it is easily soluble in ethanol or dimethylsulfoxide, slightly soluble in acetone while insoluble in hexane, acetic acid or water. And its product categories are including Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds.
The physical properties of this chemical are as follows: (1)ACD/LogP: 1.00; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3.61; (4)ACD/LogD (pH 7.4): -3.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 184.48; (13)Index of Refraction: 1.811; (14)Molar Refractivity: 105.6 cm3; (15)Molar Volume: 244.4 cm3; (16)Polarizability: 41.86×10-24 cm3; (17)Surface Tension: 89.9 dyne/cm; (18)Density: 1.85 g/cm3; (19)Exact Mass: 453.041289; (20)MonoIsotopic Mass: 453.041289; (21)Topological Polar Surface Area: 238; (22)Heavy Atom Count: 30; (23)Complexity: 861.
As to its usage, it is widely applied in many ways. It could be used in the third generation oral cephalosporins broad-spectrum antibiotic, with good antibacterial action to the streptococcus, Gram-negative bacteria, colibacillus, pneumobacillus, and proteus mirabilis. It could also be used to treat pharyngitis, gonorrhes and tonsilitis.
When you are dealing with this chemical, you should be much more cautious. For being a kind of harmful chemical, it may cause damage to health and may cause sensitisation by inhalation and skin contact. Therefore, you should wear suitable protective clothing and gloves and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Then do not breathe dust.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
(2)Isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
(3)InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
(4)InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | > 3200mg/kg (3200mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
dog | LD50 | oral | > 600mg/kg (600mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
mouse | LD50 | intravenous | 4420mg/kg (4420mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
mouse | LD50 | subcutaneous | > 10gm/kg (10000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
rat | LD50 | intravenous | 6990mg/kg (6990mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
rat | LD50 | oral | > 10gm/kg (10000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
rat | LD50 | subcutaneous | > 10gm/kg (10000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986. |
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