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CAS No.: | 35607-66-0 |
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Name: | Cefoxitin |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C16H17N3O7S2 |
Molecular Weight: | 427.459 |
Synonyms: | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R,7S)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6R-cis)-;Cephoxitin; |
EINECS: | 252-641-2 |
Density: | 1.63 g/cm3 |
Melting Point: | 149 - 150oC |
Boiling Point: | 843.4 °C at 760 mmHg |
Flash Point: | 463.9 °C |
Solubility: | Predicted solubility in water is less than 0.2mg/ml |
Appearance: | White to off-white crystalline powder |
Transport Information: | UN 3077 |
PSA: | 201.80000 |
LogP: | 1.12770 |
desacetyl cephalosporin C
cefoxitin
Conditions | Yield |
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Stage #1: desacetyl cephalosporin C With N,N'-dibenzylethylenediamine diacetate In dichloromethane; water at 25℃; Stage #2: With isocyanate de chlorosulfonyle In dichloromethane at -40℃; Temperature; Further stages; | 96% |
Conditions | Yield |
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In acetone at -35 - -30℃; | 82.8% |
isocyanate de chlorosulfonyle
cefoxitin
Conditions | Yield |
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Stage #1: isocyanate de chlorosulfonyle; 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt In acetone at -50 - -45℃; for 2h; Stage #2: With water In acetone at 8 - 10℃; | 65% |
In tetrahydrofuran Cooling; | |
Stage #1: isocyanate de chlorosulfonyle; 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt In tetrahydrofuran at -50 - -45℃; for 1h; Stage #2: With water In tetrahydrofuran at 10 - 12℃; for 0.5h; Stage #3: With hydrogenchloride In water at 0 - 34℃; for 1.5h; pH=1.9 - 2.1; Solvent; Temperature; |
diphenylmethyl (6R, 7S)-7-(2'-thienyl)acetamido-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate
cefoxitin
Conditions | Yield |
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With trifluoroacetic acid In various solvent(s) 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min; | 56% |
2-thienylacetic acid chloride
cefoxitin
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
cephamycin C
cefoxitin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 5 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 4: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 6 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 4: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 5: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 6: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 5 steps 1: 1.) N-trichloroethoxycarbonylation, 2.) benzhydryl esterification 2: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 3: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 4: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
(6R)-7t-[(R)-5-benzhydryloxycarbonyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-pentanoylamino]-3-carbamoyloxymethyl-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
cefoxitin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 4 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 3: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 5 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 3: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 4: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 5: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 4 steps 1: 1.) Na2CO3, 2.) H2O / 1.) dioxane, 5 deg C, then 20 deg C, 12 h, 2.) 1 h 2: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 3: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
diphenylmethyl (6R, 7S)-7-amino-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate
cefoxitin
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
diphenylmethyl (6R,7S)-7-carboxycarbonylamino-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate
cefoxitin
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 2: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 3 steps 1: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 2: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
(6R)-7t-hydroxyoxalylamino-3-(hydroxyoxalylcarbamoyloxy-methyl)-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
cefoxitin
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 2: 1.) PhN=C=NPh, 2.) N,N-dimethylaniline / 1.) CH2Cl2, 18 h, 0 deg C, 2.) CH2Cl2 3: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme | |
Multi-step reaction with 4 steps 1: 87 percent / H2O, conc. HCl / acetone / 72 h / Ambient temperature 2: 56 percent / diphenylcarbodiimide / CH2Cl2 / 18 h / 0 °C 3: 61 percent / N,N-dimethylaniline / CH2Cl2 / 15 h / 0 °C 4: 56 percent / CF3COOH / various solvent(s) / 1.) -30 deg C, 2.) -20 deg C, 20 min, 3.) -10 deg C, 20 min View Scheme |
The Cefoxitin, with the CAS registry number 35607-66-0, has the IUPAC name of (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.
The characteristics of this chemical are as follows: (1)ACD/LogP: 0.63; (2)# of Rule of 5 Violations: 1 ; (3)#H bond acceptors: 10; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 8; (6)Polar Surface Area: 201.8; (7)Index of Refraction: 1.692; (8)Molar Refractivity: 100.47 cm3; (9)Molar Volume: 262.1 cm3; (10)Polarizability: 39.83 ×10-24 cm3; (11)Surface Tension: 86.7 dyne/cm; (12)Density: 1.63 g/cm3; (13)Flash Point: 463.9 °C; (14)Enthalpy of Vaporization: 128.44 kJ/mol; (15)Boiling Point: 843.4 °C at 760 mmHg; (16)Vapour Pressure: 3.24E-30 mmHg at 25°C; (17)Exact Mass: 427.050791; (18)MonoIsotopic Mass: 427.050791; (19)Topological Polar Surface Area: 202; (20)Heavy Atom Count: 28; (21)Complexity: 744.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
(2)Isomeric SMILES: CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
(3)InChI: InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
(4)InChIKey: WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | > 10gm/kg (10000mg/kg) | Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978. | |
mouse | LD50 | intravenous | 4970mg/kg (4970mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 26(Suppl, |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978. |
mouse | LD50 | subcutaneous | 9250mg/kg (9250mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Chemotherapy Vol. 26(Suppl, |
rat | LD50 | intravenous | 8580mg/kg (8580mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 26(Suppl, |
rat | LD50 | oral | > 10gm/kg (10000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Chemotherapy Vol. 26(Suppl1), Pg. 150, 1978. |
rat | LD50 | subcutaneous | > 10mg/kg (10mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Chemotherapy Vol. 26(Suppl, |
women | TDLo | intravenous | 75mg/kg/18H-I (75mg/kg) | BLOOD: LEUKOPENIA | Annals of Internal Medicine. Vol. 92, Pg. 874, 1980. |