Cephaloridine supplier | CasNO.50-59-9

Name
Cephaloridine
EINECS
CAS No. 50-59-9
Article Data5
CAS DataBase
Density 1.3230 (rough estimate)
Solubility >20g/L(21 oC)
Melting Point 184°C
Formula C19H17 N3 O4 S2
Boiling Point
Molecular Weight 415.494
Flash Point
Transport Information
Appearance
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.
Risk Codes 42/43
Molecular Structure
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
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

: 33465-56-4
2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-formamidoceph-3-em-4-carboxylate 1-oxide

: 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
Multi-step reaction with 5 steps 1: 46.2 percent / conc. hydrochloric acid / tetrahydrofuran / 30 h / 6 °C 2: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 3: 67.3 percent / 1.5 h / 20 °C 4: 72.6 percent / phosphorus trichloride / CH2Cl2; dimethylformamide / 1.5 h / 21 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h View Scheme

: 50-59-9
cefaloridine

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

Conditions

Conditions	Yield
With nitric acid In water	46.7%

: 503-17-3
dimethylacetylene

: 50-59-9
cefaloridine

A: 107-00-6
but-1-yne

B: 590-19-2
2,3-dimethylbutene

Conditions

Conditions	Yield
at 280℃;

...Expand

: 598-25-4
Dimethylallene

: 50-59-9
cefaloridine

A: 598-23-2
3-methyl-but-1-yne

B: 78-79-5
isoprene

Conditions

Conditions	Yield
at 215 - 334℃;

...Expand

: 558-37-2
tert-butylethylene

: 50-59-9
cefaloridine

: 563-79-1
2,3-Dimethyl-2-butene

Conditions

Conditions	Yield
at 160 - 170℃;

: 690-08-4
(E)-4,4-dimethyl-2-pentene

: 50-59-9
cefaloridine

: 10574-37-5
2,3-dimethylpent-2-ene

Conditions

Conditions	Yield
at 150 - 270℃;

: 590-19-2
2,3-dimethylbutene

: 50-59-9
cefaloridine

A: 107-00-6
but-1-yne

B: 106-99-0
buta-1,3-diene

Conditions

Conditions	Yield
at 330℃;

...Expand

: 26981-77-1
t-butylallene

: 50-59-9
cefaloridine

: 1000-87-9
2,4-dimethyl-2,3-pentadiene

Conditions

Conditions	Yield
at 230 - 235℃;

: 50-59-9
cefaloridine

: 75-07-0
acetaldehyde

A: 64-19-7
acetic acid

B: 141-78-6
ethyl acetate

Conditions

Conditions	Yield
at 250 - 400℃;

...Expand

: 50-59-9
cefaloridine

: 141-78-6
ethyl acetate

A: 64-17-5
ethanol

B: 75-07-0
acetaldehyde

C: 64-19-7
acetic acid

Conditions

Conditions	Yield
at 300 - 400℃;

...Expand

: 50-59-9
cefaloridine

: 122-66-7
diphenyl hydrazine

: 71-43-2
benzene

A: 62-53-3
aniline

B: 1227476-15-4
Azobenzene

...Expand

: 107-10-8
propylamine

: 50-59-9
cefaloridine

A: 110-86-1
pyridine

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

Conditions

Conditions	Yield
With potassium chloride In water at 30℃; Rate constant; Equilibrium constant; effects of sodium hydroxide;

...Expand

: 107-10-8
propylamine

: 50-59-9
cefaloridine

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

Conditions

Conditions	Yield
With potassium chloride In water at 30℃;

: 677-71-4
hexafluoroacetone hydrate

: 50-59-9
cefaloridine

A: C22H19F6N3O6S2

B: C22H19F6N3O6S2

Conditions

Conditions	Yield
In water at 30℃; Rate constant; Mechanism; pH 5.5-12.5, I = 1.0 M (KCl);

...Expand

: 75-89-8
2,2,2-trifluoroethanol

: 50-59-9
cefaloridine

A: C21H20F3N3O5S2

B: C21H20F3N3O5S2

Conditions

Conditions	Yield
In water at 30℃; Rate constant; Mechanism; pH 10.5-13.5, I = 1.0 M (KCl);

...Expand

: 920-66-1
1,1,1,3',3',3'-hexafluoro-propanol

: 50-59-9
cefaloridine

A: C22H19F6N3O5S2

B: C22H19F6N3O5S2

Conditions

Conditions	Yield
In water at 30℃; Rate constant; Mechanism; pH 8.35-12.5, I = 1.0 M (KCl);

...Expand

: 50-59-9
cefaloridine

A: 110-86-1
pyridine

B: 151338-10-2
(2R)-2-<(R)-carboxylato<(thien-2-yl)acetylamino>methyl>-5,6-dihydro-5-methylidene-1,3-thiazine-4-carboxylate

C: Δ2-cephaloridine

D: Cephaloridine epimer

Conditions

Conditions	Yield
at 37℃; for 1h; Product distribution; Rate constant; Mechanism; carbonate-buffer solution, pH 10.5;
With water-d2 at 37℃; Kinetics; Isomerization; hydrolysis; pD = 10.5;

...Expand

: 50-59-9
cefaloridine

: C19H19N3O5S2

Conditions

Conditions	Yield
copper(II) ion In water at 30℃; Rate constant; Mechanism; further metal-ions, pH;
With hydrogenchloride In water at 30℃; Rate constant; hydrolysis;
With potassium chloride; 2-hydroxyethanethiol In water at 30℃; pH=10.10; Kinetics;
With potassium chloride; hydroxide In water at 30℃; Kinetics;

: 50-59-9
cefaloridine

diamylene: diamylene

: 563-45-1
3-Methyl-1-butene

Conditions

Conditions	Yield
at 150 - 160℃;

: 50-59-9
cefaloridine

: 115-11-7
isobutene

tetraisobutylene: tetraisobutylene

Conditions

Conditions	Yield
Nachweis von 2,4,4,6,6,8,8-Heptamethyl-non-1-en in dem erhaltenen Produkt;

: 50-59-9
cefaloridine

: 115-11-7
isobutene

A: 107-39-1
2,4,4-trimethyl-1-pentene

B: 2437-52-7
3-tert-Butyl-2,4,4-trimethyl-pent-2-ene

C tetraisobutylene: tetraisobutylene

D pentaisobutylene: pentaisobutylene

Conditions

Conditions	Yield
at 300℃; weitere Produkte: Hexaisobutylen, Heptaisobutylen;

...Expand

: 50-59-9
cefaloridine

diamylene: diamylene

: 513-35-9
2-methyl-but-2-ene

Conditions

Conditions	Yield
at 150 - 160℃;

: 530-48-3
1,1-Diphenylethylene

: 50-59-9
cefaloridine

A: 19244-53-2
1,1,3,3-tetraphenyl-1-butene

B 1.1.3.3-tetraphenyl-cyclobutane(?): 1.1.3.3-tetraphenyl-cyclobutane(?)

...Expand

: 50-59-9
cefaloridine

diamylene: diamylene

: 922-61-2
3-methyl-2-pentene

Conditions

Conditions	Yield
at 150 - 160℃;

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 NO_x and SO_x.

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 .

Product Name

Cephaloridine

Synthetic route

Cephaloridine Chemical Properties

Cephaloridine Toxicity Data With Reference

Cephaloridine Safety Profile

Cephaloridine Specification

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