CAS No.50-59-9,Cephaloridine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	50-59-9
Name:	Cephaloridine
Article Data:	5

Formula:	C19H17 N3 O4 S2
Molecular Weight:	415.494
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
Density:	1.3230 (rough estimate)
Melting Point:	184°C
Solubility:	>20g/L(21 oC)
Hazard Symbols:	Xn
Risk Codes:	42/43
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 NO_x and SO_x.
PSA:	146.96000
LogP:	0.01100

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

Conditions	Yield
With potassium chloride In water at 30℃; Equilibrium constant;

...Expand

: 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

Conditions	Yield
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

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

: Cephaloridine epimer

: 50-59-9
cefaloridine

Conditions

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

: 110-86-1
pyridine

: 50-59-9
cefaloridine

Conditions

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

: 39098-97-0
2-thienylacetic acid chloride

: 50-59-9
cefaloridine

Conditions

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

: 1918-77-0
Thiophene-2-acetic acid

: 50-59-9
cefaloridine

Conditions

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

: 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

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

: 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

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

: 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

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

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Chemistry

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

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.

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 NO_x and SO_x.

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 .