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Conditions | Yield |
---|---|
With potassium chloride In water at 30℃; Equilibrium constant; |
2,2,2-trichloroethyl (6R,7R)-N-<7-(thien-2-ylacetamido)ceph-3-em-3-ylmethyl>pyridinium chloride 4-carboxylate
cefaloridine
Conditions | Yield |
---|---|
With Deacidite FF ion-exchange resin; zinc(II) chloride; zinc 1.) formic acid, 22 deg C, 2 h; Multistep reaction; |
cefaloridine
Conditions | Yield |
---|---|
With water-d2 at 37℃; Kinetics; Isomerization; pD = 10.5; |
cefaloridine
Conditions | Yield |
---|---|
With water-d2 at 37℃; Kinetics; Isomerization; pD = 10.5; |
Conditions | Yield |
---|---|
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 |
2-thienylacetic acid chloride
cefaloridine
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
2,2,2-trichloroethyl (1S,6R,7R)-3-chloromethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide
cefaloridine
Conditions | Yield |
---|---|
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 |
2,2,2-trichloroethyl (1S,6R,7R)-N-<7-(thien-2-ylacetamido)ceph-3-em-3-ylmethyl>pyridinium chloride 4-carboxylate 1-oxide
cefaloridine
Conditions | Yield |
---|---|
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 |
2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-chloromethylceph-3-em-4-carboxylate 1-oxide
cefaloridine
Conditions | Yield |
---|---|
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 |
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
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. |
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 (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 .