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58-71-9

Basic Information
CAS No.: 58-71-9
Name: Cephalothin
Article Data: 3
Molecular Structure:
Molecular Structure of 58-71-9 (Cephalothin)
Formula: C16H15N2NaO6S2
Molecular Weight: 418.427
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, monosodium salt,(6R-trans)-;Averon 1;Cefalothine sodium;Cemastin;Cephalothin sodium salt;Cephation;Ceporacin;Cepovenin;Coaxin;Keflin;Lilly 38253;Lospoven;Microtin;Seffin;Sodium(thienylacetamido)cephalosporanate;Sodium 3-acetoxymethyl-7b-(2-thienylacetamido)ceph-3-em-4-carboxylate;Sodium 7-(2-thienylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylate;Sodium7-[2-(2-thienyl)acetamido]cephalosporanate;Sodium cefalotin;Sodiumcephalothin;Sodium cephalotin;Synclotin;Toricelocin;
EINECS: 200-394-6
Melting Point: 240 °C
Boiling Point: 757.2 °C at 760 mmHg
Flash Point: 411.8 °C
Solubility: water: 50 mg/mL
Appearance: Crystalline
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 42/43
Safety: 22-36/37
PSA: 169.38000
LogP: -0.41360
Synthetic route
153-61-7

cephalothin

58-71-9

sodium cephalothin

Conditions
ConditionsYield
With sodium 2-ethylhexanoic acid In acetone26%
39098-97-0

2-thienylacetic acid chloride

957-68-6

7-Aminocephalosporanic acid

58-71-9

sodium cephalothin

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium 2-ethylhexanoic acid In water; acetone at 0 - 5℃; for 0.5h;
58-71-9

sodium cephalothin

100-11-8

1-bromomethyl-4-nitro-benzene

4-Nitrobenzyl 3-(acetoxymethyl)-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Conditions
ConditionsYield
In ethyl acetate; N,N-dimethyl-formamide96%
15139-21-6

5-thio-2-nitrobenzoic acid

58-71-9

sodium cephalothin

CENTA

Conditions
ConditionsYield
With sodium hydroxide In water at 65℃; for 6h; pH=7;89%

3-(2-mercapto-1-phenyl-1,3,4-triazol-5-yl)propionic acid

58-71-9

sodium cephalothin

7-(2-thienylacetamido)-3-[5-(2-carboxyethyl)-1-phenyl-1,3,4-triazol-2-yl]thiomethyl-3-cephem-4-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate In ice-water; water87.5%
56-95-1

chlorhexidine diacetate

58-71-9

sodium cephalothin

chlorhexidine dicephalothin

Conditions
ConditionsYield
In water; butan-1-ol at 20℃; for 48h;83%
58-71-9

sodium cephalothin

5935-65-9

Desacetylcephalothin

Conditions
ConditionsYield
Stage #1: sodium cephalothin With sodium hydroxide In water at -20 - -10℃; for 0.0375h;
Stage #2: With hydrogenchloride In water pH=1.5; cooling; Further stages.;
80%
58-71-9

sodium cephalothin

tin(ll) chloride

1408249-95-5, 1408250-00-9

Sn(2+)*Cl(1-)*C16H15N2O6S2(1-)

Conditions
ConditionsYield
With water at 20℃; for 6h;72%
49715-04-0

chlorosulfuric acid chloromethyl ester

58-71-9

sodium cephalothin

A

(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid chloromethyl ester

B

7-(2-thienylacetamido)cephalosporanic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20 - 25℃; for 0.5h; Title compound not separated from byproducts;A n/a
B 62%
58-71-9

sodium cephalothin

106-95-6

allyl bromide

104949-45-3

allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide51%
In water; N,N-dimethyl-formamide for 48h; Ambient temperature;48%
In water; N,N-dimethyl-formamide at 20℃; for 48h;41%
In water; N,N-dimethyl-formamide at 20℃; for 48h;41%
In water; N,N-dimethyl-formamide at 20℃; for 48h;41%
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Chemistry

Name : Cefalotin sodium
Synonyms  Cephalothin sodium; Sodium cephalothin; Synclotin; 7-(Thiophene-2-acetamido)cephalosporanic acid sodium salt; Monosodium (6R,7R)-3-acetoxymethyl-8-oxo-7-[2-(thiophen-2-yl)acetylamido]-5-thia-1-azabicyclo[4.2.0.]oct-2-ene-2-carboxylate
Molecular:Structure:   
Molecular Formula:C16H15N2NaO6S
Molecular Weight:418.41
EINECS:200-394-6
Merck:13,1994
Molecular Formula:240°C
solubility:H2O: 50 mg/mL, clear, faintly yellow
Water Solubility:158 mg/L
storage temp.:2-8°C
Appearance:Crystalline

Toxicity Data With Reference

1.    

ivn-wmn TDLo:20 mg/kg:BLD

    AIMEAS    Annals of Internal Medicine. 77 (1972),401.
2.    

ims-chd TDLo:89 mg/kg/19D-I:BLD AACHAX -,272,63

3.    

ims-man TDLo:955 mg/kg/22D-I:BLD AACHAX -,272,63

4.    

ipr-rat LD50:7000 mg/kg

    JJANAX    Japanese Journal of Antibiotics. 28 (1975),188.
5.    

scu-rat LD50:7500 mg/kg

    JIDIAQ    Journal of Infectious Diseases. 137 (1978),S51.
6.    

ipr-mus LD50:5670 mg/kg

    JJANAX    Japanese Journal of Antibiotics. 27 (1974),746.
7.    

scu-mus LD50:7500 mg/kg

    JACHDX    Journal of Antimicrobial Chemotherapy. 6 (Suppl A),(1980),79.
8.    

ivn-mus LD50:4800 mg/kg

    JJANAX    Japanese Journal of Antibiotics. 27 (1974),746.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Human systemic effects by intravenous and intramuscular routes: blood agranulocytosis and thrombocytopenia. When heated to decomposition it emits very toxic fumes of NOx, SOx, and Na2O.

Risk Statements:42/43:  May cause sensitization by inhalation and skin contact 
Safety Statements:22:  Do not breathe dust;36/37:  Wear suitable protective clothing and gloves 
Hazard Codes:Xn,Xi
WGK Germany:2