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Cefoxitin sodium
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Name

Cefoxitin sodium

 EINECS 251-574-6
CAS No. 33564-30-6 Density N/A
PSA 204.63000 LogP -0.20700
Solubility Soluble in water or methanol Melting Point >160°C
Formula C16H16N3NaO7S2 Boiling Point 843.4 °C at 760 mmHg
Molecular Weight 449.441 Flash Point 463.9 °C
Transport Information UN 3077 Appearance White powder
Safety 22-26-36/37-36/37/39 Risk Codes 36/37/38-42/43
Molecular Structure Molecular Structure of 33564-30-6 (Cefoxitin sodium) Hazard Symbols HarmfulXn, IrritantXi
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]-,monosodium salt, (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]-,monosodium salt, (6R-cis)-;Betacef;Cefaxilin sodium;Cefoxitin sodium salt;Cenomycin;Farmoxin;MK 306;Mefoxin;Mefoxithin;Mefoxitin;Merxin;Monosodium cefoxitin;Serviflox;Sodium cefoxitin;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,sodium salt (1:1), (6R,7S)-;

Article Data 4

Cefoxitin sodium Synthetic route

35607-66-0

cefoxitin

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
With sodium lactate In acetone at 30℃; for 0.166667h; Reagent/catalyst;95%
With sodium lactate In isopropyl alcohol; acetone at 10℃; Temperature;

7-α-methoxy-7-[(2-thienyl)acetamido]-4-cephalosporanic acid cyclohexylamine

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol; water / pH 10
1.2: 25 °C
2.1: tetrahydrofuran / Cooling
3.1: sodium lactate / acetone / 0.17 h / 30 °C
View Scheme
153-61-7

cephalothin

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: methanesulfonic acid; N-Bromosuccinimide / dichloromethane; methanol / 2 h / -20 °C
1.2: 2 h / 0 °C / pH 6.5
2.1: sodium hydroxide / methanol; water / pH 10
2.2: 25 °C
3.1: tetrahydrofuran / Cooling
4.1: sodium lactate / acetone / 0.17 h / 30 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane; tetrahydrofuran / 1.75 h / -60 °C
1.2: 0.75 h
2.1: sodium hydroxide; water / methanol / 3 h / -30 °C
3.1: tetrahydrofuran / 0.75 h / -40 - -37 °C
3.2: 2 h / 10 - 12 °C
View Scheme
1189-71-5

isocyanate de chlorosulfonyle

C15H16N2O6S2

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Stage #1: isocyanate de chlorosulfonyle; C15H16N2O6S2 In tetrahydrofuran at -40 - -37℃; for 0.75h;
Stage #2: With sodium lactate In methanol; acetone at 10 - 12℃; for 2h; Temperature;
39098-97-0

2-thienylacetic acid chloride

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate; tetrabutylammomium bromide / dichloromethane; water / -5 - 0 °C
2.1: dichloromethane; tetrahydrofuran / 1.75 h / -60 °C
2.2: 0.75 h
3.1: sodium hydroxide; water / methanol / 3 h / -30 °C
4.1: tetrahydrofuran / 0.75 h / -40 - -37 °C
4.2: 2 h / 10 - 12 °C
View Scheme
58-71-9

sodium cephalothin

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid; N-chloro-succinimide / dichloromethane; methanol / 3 h / -65 °C
1.2: 5 h
2.1: N,N'-dibenzylethylenediamine diacetate / methanol; water / -25 °C
2.2: -40 °C
3.1: sodium lactate / acetone; isopropyl alcohol / 10 °C
View Scheme
957-68-6

7-Aminocephalosporanic acid

33564-30-6

cefoxitin sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate; tetrabutylammomium bromide / dichloromethane; water / -5 - 0 °C
2.1: dichloromethane; tetrahydrofuran / 1.75 h / -60 °C
2.2: 0.75 h
3.1: sodium hydroxide; water / methanol / 3 h / -30 °C
4.1: tetrahydrofuran / 0.75 h / -40 - -37 °C
4.2: 2 h / 10 - 12 °C
View Scheme
33564-30-6

cefoxitin sodium

silver nitrate

C32H32Ag2N6O14S4

Conditions
ConditionsYield
In methanol for 1h; Reflux;75%

rhodium(III) chloride hydrate

7732-18-5

water

33564-30-6

cefoxitin sodium

C16H20Cl2N3O9RuS2

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 3h; Reflux;75%
33564-30-6

cefoxitin sodium

C16H16N3O7S2(1-)*Na(1+)*0.2H2O

Conditions
ConditionsYield
With water; pyrographite at 25℃; for 0.5h; Temperature;48.72 g

Cefoxitin sodium Chemical Properties

Molecular Structure of Cefoxitin sodium (CAS NO.33564-30-6):

IUPAC Name: Sodium(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-carboxylate
Molecular Weight: 449.43391 [g/mol]
Molecular Formula: C16H16N3NaO7S2
H-Bond Donor: 2
H-Bond Acceptor: 7 
EINECS: 251-574-6
Product Categories: API; Intermediates & Fine Chemicals; Pharmaceuticals; Alphabetic; C; CA - CGForensic and Veterinary Standards; Chemical Structure; Drugs & Metabolites; Neat Compounds Drugs of Abuse; Others 
Flash Point: 463.9 °C
Enthalpy of Vaporization: 128.44 kJ/mol
Boiling Point: 843.4 °C at 760 mmHg
Vapour Pressure: 3.24E-30 mmHg at 25 °C
Appearance: White to almost white powder
storage temp.: 2-8 °C
Classification Code: Antibacterial; Antibiotics; Drug / Therapeutic Agent; Human Data
SMILES: [Na+].O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)Cc3sccc3)COC(=O)N)C([O-])=O
InChI: InChI=1/C16H17N3O7S2.Na/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);/q;+1/p-1/t14-,16+;/m1./s1
InChIKey: GNWUOVJNSFPWDD-QPEAJTHOBU

Cefoxitin sodium Uses

 Cefoxitin sodium (CAS NO.33564-30-6) is an antibacterial.

Cefoxitin sodium Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 10000mg/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 410, 1982.
man TDLo intravenous 100mg/kg/2D-I (100mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Southern Medical Journal. Vol. 80, Pg. 274, 1987.
man TDLo intravenous 229mg/kg/4D-I (229mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: APLASTIC ANEMIA		 Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 816, 1983.
mouse LD50 intravenous 4970mg/kg (4970mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 291, 1980.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.
mouse LD50 subcutaneous 9250mg/kg (9250mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.
rat LD50 intravenous 8580mg/kg (8580mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 oral > 10gm/kg (10000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 22, Pg. 123, 1980.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 629, 1980.

Cefoxitin sodium Safety Profile

Mildly toxic by ingestion subcutaneous, and intravenous routes. Human systemic effects: aplastic anemia, interstitial nephritis, normocytic anemia. When heated to decomposition it emits toxic fumes of SOx, NOx, and Na2O.
Safety Information of Cefoxitin sodium (CAS NO.33564-30-6):
Hazard Codes: HarmfulXn,IrritantXi
RIDADR: 3077
WGK Germany: 3
HazardClass: 9 
RTECS: XI0330500
Risk Statements: 36/37/38-42/43 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 22-26-36/37-36/37/39
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.

Cefoxitin sodium Specification

 Cefoxitin sodium (CAS NO.33564-30-6), its Synonyms are 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)-, sodium salt, (6R-cis)- ; Betacef ; Cefoxil ; Cefoxitin ; Cefoxitin and dextrose in duplex container ; Mefoxin ; Mefoxin in dextrose 5% in plastic container ; Mefoxin in plastic container ; Mefoxin in sodium chloride 0.9% in plastic container ; Mefoxitin ; Merxin ; Monosodium cefoxitin ; Sodium (6R,7S)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate carbamate (ester) .

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