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Cephaloridine
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Name

Cephaloridine

 EINECS N/A
CAS No. 50-59-9 Density 1.3230 (rough estimate)
PSA 146.96000 LogP 0.01100
Solubility >20g/L(21 oC) Melting Point 184°C
Formula C19H17 N3 O4 S2 Boiling Point N/A
Molecular Weight 415.494 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Experimental poison by intracerebral route. Moderately toxic to humans by intravenous route. Moderately toxic experimentally by ingestion, subcutaneous, intraperitoneal, and intravenous routes. Human systemic effects by intravenous route: nausea or vomiting and fatty liver degeneration. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and SOx. Risk Codes 42/43
Molecular Structure Molecular Structure of 50-59-9 (Cephaloridine) Hazard Symbols Xn
Synonyms

Pyridinium,1-[[(6R,7R)-2-carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-,inner salt (9CI); Pyridinium,1-[[2-carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-,hydroxide, inner salt, (6R-trans)-; Pyridinium,1-[[2-carboxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-,hydroxide, inner salt (8CI); 7-[a-(2-Thienyl)acetamido]-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acidbetaine; Aliporina; Ampligram; Cefaloridin; Cefaloridine; Ceflorin;Cepaloridin; Cepalorin; Ceph 87/4; Cephaloridin; Cephaloridine; Cephlodine;Ceporan; Ceporin; Ceporine; Cer; Cilifor; Deflorin; Faredina; Floridin;Glaxoridin; Intrasporin; Keflodin; Keflordin; Kefspor; Lilly 40602; Lloncefal;Loridine; Pyridinium,1-[[2-carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-,inner salt, (6R-trans)-; Sch 11527; Sefacin

Article Data 5

Cephaloridine Synthetic route

110-86-1

pyridine

5-Methylene-2-[propylcarbamoyl-(2-thiophen-2-yl-acetylamino)-methyl]-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid

A

107-10-8

propylamine

B

50-59-9

cefaloridine

Conditions
ConditionsYield
With potassium chloride In water at 30℃; Equilibrium constant;
85904-88-7

2,2,2-trichloroethyl (6R,7R)-N-<7-(thien-2-ylacetamido)ceph-3-em-3-ylmethyl>pyridinium chloride 4-carboxylate

50-59-9

cefaloridine

Conditions
ConditionsYield
With Deacidite FF ion-exchange resin; zinc(II) chloride; zinc 1.) formic acid, 22 deg C, 2 h; Multistep reaction;

Δ2-cephaloridine

50-59-9

cefaloridine

Conditions
ConditionsYield
With water-d2 at 37℃; Kinetics; Isomerization; pD = 10.5;

Cephaloridine epimer

50-59-9

cefaloridine

Conditions
ConditionsYield
With water-d2 at 37℃; Kinetics; Isomerization; pD = 10.5;
110-86-1

pyridine

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67.3 percent / 1.5 h / 20 °C
2: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
3: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme
39098-97-0

2-thienylacetic acid chloride

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min
2: 67.3 percent / 1.5 h / 20 °C
3: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme
1918-77-0

Thiophene-2-acetic acid

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C
2: 67.3 percent / 1.5 h / 20 °C
3: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme
85904-87-6

2,2,2-trichloroethyl (1S,6R,7R)-3-chloromethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 67.3 percent / 1.5 h / 20 °C
2: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
3: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme
33492-94-3

2,2,2-trichloroethyl (1S,6R,7R)-N-<7-(thien-2-ylacetamido)ceph-3-em-3-ylmethyl>pyridinium chloride 4-carboxylate 1-oxide

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
2: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme
85904-84-3

2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-chloromethylceph-3-em-4-carboxylate 1-oxide

50-59-9

cefaloridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C
2: 67.3 percent / 1.5 h / 20 °C
3: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C
4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h
View Scheme

Cephaloridine Chemical Properties

Molecular Formula: C19H17N3O4S2
Molar mass: 415.486 g/mol
EINECS: 200-052-6
Structure of Cephaloridine (50-59-9):
    
XLogP3-AA: 1.9
H-Bond Donor: 1
H-Bond Acceptor: 4
Systematic Name: (6R,7R)-8-oxo-3-(Pyridin-1-ium-1-ylmethyl)-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
SMILES: O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)C[n+]4ccccc4)C([O-])=O 
InChI: InChI=1/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1 
InChIKey: CZTQZXZIADLWOZ-CRAIPNDOBC 
Std. InChI: InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1 
Std. InChIKey: CZTQZXZIADLWOZ-CRAIPNDOSA-N

Cephaloridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intramuscular > 200mg/kg (200mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
dog LD intravenous > 1gm/kg (1000mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
dog LD50 subcutaneous > 200mg/kg (200mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
guinea pig LD50 subcutaneous 550mg/kg (550mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
man LDLo intravenous 1137mg/kg/4D (1137mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING
LIVER: FATTY LIVER DEGERATION		 JAMA, Journal of the American Medical Association. Vol. 200, Pg. 724, 1967.
monkey LD50 intramuscular > 200mg/kg (200mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
mouse LD50 intracrebral 10mg/kg (10mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES
BEHAVIORAL: EXCITEMENT		 Chemotherapy Vol. 26, Pg. 196, 1980.
 
mouse LD50 intramuscular 7gm/kg (7000mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
mouse LD50 intraperitoneal 5355mg/kg (5355mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
BEHAVIORAL: TREMOR
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Japanese Journal of Antibiotics. Vol. 29, Pg. 735, 1976.
mouse LD50 intravenous 2200mg/kg (2200mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
mouse LD50 oral > 20gm/kg (20000mg/kg)   Japanese Journal of Antibiotics. Vol. 29, Pg. 735, 1976.
mouse LD50 subcutaneous 7745mg/kg (7745mg/kg)   Drugs in Japan Vol. -, Pg. 557, 1990.
rabbit LD50 intramuscular > 200mg/kg (200mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
rat LD50 intraperitoneal 3170mg/kg (3170mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 1065mg/kg (1065mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
BEHAVIORAL: STRAUB TAIL		 Japanese Journal of Antibiotics. Vol. 29, Pg. 735, 1976.
rat LD50 oral 2500mg/kg (2500mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.
rat LD50 parenteral 2500ug/kg (2.5mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 863, 1965.
rat LD50 subcutaneous 2500mg/kg (2500mg/kg)   Toxicology and Applied Pharmacology. Vol. 8, Pg. 398, 1966.

Cephaloridine Safety Profile

Experimental poison by intracerebral route. Moderately toxic to humans by intravenous route. Moderately toxic experimentally by ingestion, subcutaneous, intraperitoneal, and intravenous routes. Human systemic effects by intravenous route: nausea or vomiting and fatty liver degeneration. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Cephaloridine Specification

 Cephaloridine (50-59-9) also can be called Cefaloridine ; N-[7-(2'-Thienylacetamidoceph-3-ylmethyl)]pyridinium-2-carboxylate ; (6R,7R)-8-Oxo-3-(1-pyridiniumylmethyl)-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate ; (6R-trans)-1-[[2-Carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium Hydroxide Inner Salt ; Pyridinium, 1-[[(6R,7R)-2-carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt ; and ; Cephaloridin .

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