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Ceftiofur hydrochloride(CAS No. 103980-44-5)

Ceftiofur hydrochloride C19H18ClN5O7S3 (cas 103980-44-5) Molecular Structure

103980-44-5 Structure

Identification and Related Records

【Name】
Ceftiofur hydrochloride
【CAS Registry number】
103980-44-5
【Synonyms】
Ceftiofur Hydrochloride [USAN]
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo, monohydrochloride, (6R,7R)
(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-methyloxime), 2-furoate (ester), monohydrochloride
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo-, monohydrochloride, (6R-(6alpha,7beta(Z)))-
【Molecular Formula】
C19H18ClN5O7S3 (Products with the same molecular formula)
【Molecular Weight】
560.03
【Inchi】
InChI=1/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1
【Canonical SMILES】
CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)O
【Isomers smiles】
CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=
CO4)C(=O)O
【MOL File】
103980-44-5.mol

Chemical and Physical Properties

【Appearance】
off-white solid
【Boiling Point】
814.1 °C at 760 mmHg
【Vapour】
5.14E-28mmHg at 25°C
【Flash Point】
446.1 °C
【Solubilities】
In water, 23 mg/L at 25 deg C (est)
【Computed Properties】
Molecular Weight:523.56258 [g/mol]
Molecular Formula:C19H17N5O7S3
XLogP3:0.2
H-Bond Donor:3
H-Bond Acceptor:11
Rotatable Bond Count:9
Tautomer Count:14
Exact Mass:523.02901
MonoIsotopic Mass:523.02901
Topological Polar Surface Area:256
Heavy Atom Count:34
Formal Charge:0
Complexity:945
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:6
Feature 3D Donor Count:2
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:4
Effective Rotor Count:10.6
Conformer Sampling RMSD:1
CID Conformer Count:127

Safety and Handling

【Formulations/Preparations】
Veterinary-labeled product(s): 50 mg per mL (Rx) (Naxcel). /Ceftiofur sodium for injection/
Veterinary-labeled product(s): 50 mg per mL (Rx) (Excenel RTU). /Ceftiofur hydrochloride injection/
【Exposure Standards and Regulations】
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Ceftiofur crystalline free acid, ceftiofur hydrochloride and ceftiofur sodium are included on this list. /Ceftiofur crystalline free acid; Ceftiofur hydrochloride; Ceftiofur sodium/
【Specification】

?Ceftiofur Hydrochloride , its cas register number is 103980-44-5. It also can be called Ceftiofur Hydrochloride [USAN] ; (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-methyloxime), 2-furoate (ester), monohydrochloride ; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo-, monohydrochloride, (6R-(6alpha,7beta(Z)))- ;? 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo, monohydrochloride, (6R,7R) .It is a off-white solid.

【Octanol/Water Partition Coefficient】
log Kow = 1.6 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... B. Labeeuw, A. Salhi, European patent 36812; ... US patent 4464367 (1981, 1984 both to Sanofi).
【Usage】

An antibacterial

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
【Therapeutic Uses】
MEDICATION (VET): Ceftiofur is used in the treatment of respiratory infections in cattle and pigs.
THERAP CAT (VET): Antibacterial
MEDICATION (VET): Ceftiofur is an injectable cephalosporin approved for respiratory disease in horses and cattle and for treatment of canine bacterial urinary tract infections caused by E coli and Proteus.
MEDICATION (VET): Dogs: ... Ceftiofur sodium for injection are indicated in the treatment of urinary tract infections caused by susceptible organisms, including E. coli, P. mirabilis, and S. aureus. /Ceftiofur sodium/
MEDICATION (VET): Sheep: Ceftiofur sodium for injection is indicated in the treatment of respiratory tract infections caused by susceptible M. haemolytica and P. multocida. /Ceftiofur sodium/
MEDICATION (VET): Pigs: Ceftiofur hydrochloride injection and ceftiofur sodium for injection are indicated in the treatment of respiratory tract infections caused by susceptible organisms, including Actinobacillus pleuropneumoniae, P. multocida, Salmonella choleraesuis, and Streptococcus suis type 2.
MEDICATION (VET): Horses: Ceftiofur sodium for injection is indicated in the treatment of respiratory tract infections caused by susceptible organisms, including Streptococcus zooepidemicus. /Ceftiofur sodium/
MEDICATION (VET): Goats: Ceftiofur sodium for injection is indicated in the treatment of caprine respiratory disease caused by susceptible organisms, including M. haemolytica and P. multocida. /Ceftiofur sodium/
MEDICATION (VET): Cattle: Ceftiofur sodium for injection and ceftiofur hydrochloride injection are indicated in the treatment of respiratory tract infections, including bovine respiratory disease complex (shipping fever), caused by susceptible organisms, including Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus. /Ceftiofur sodium; Ceftiofur hydrochloride/
MEDICATION (VET): Cattle: Ceftiofur sodium for injection and ceftiofur hydrochloride injection are indicated in the treatment of bovine interdigital necrobacillosis associated with F. necrophorum and B. melaninogenicus. /Ceftiofur sodium; Ceftiofur hydrochloride/
MEDICATION (VET): Cattle: Ceftiofur hydrochloride injection is indicated in the treatment of acute metritis (up to 14 days postpartum), caused by susceptible organisms. /Ceftiofur hydrochloride/
MEDICATION (VET): Chicks and turkey poults, day old: Ceftiofur sodium for injection is indicated in the treatment of infections (colibacillosis) caused by susceptible E. coli. /Ceftiofur sodium/
Ceftiofur ... has been called a "new-generation" cephalosporin. It has broader gram-positive activity, including good activity against Streptococci, and less activity against Pseudomonas than other third-generation cephalosporins. It is active against beta-lactamase-producing strains as well as anaerobes, such as Fusobacterium necrophorum and Bacteroides melaninogenicus. Ceftiofur is rapidly metabolized to desfuroylceftiofur in vivo and S. aureus is four- to eightfold less sensitive to desfuroylceftiofur than to the parent ceftiofur. Proteus mirabilis has a widely variable susceptibility to some metabo lites of ceftiofur.
【Biomedical Effects and Toxicity】
A study of 4 male and 4 female Sprague-Dawley rats treated intramuscularly with (14)C-ceftiofur (2 mg/kg bw) revealed that 55% of the administered dose was excreted in the urine and about 30% in the GI tract and feces. The major urinary metabolite was desfuroylceftiofur (DFC). The metabolism of ceftiofur was similar in calves administered (14)C-ceftiofur (2 mg/kg bw) via the i.m. route. Unmetabolized ceftiofur was also present in the urine (4.4-21% of total radioactivity).
A group of Sprague-Dawley rats (7/sex) received single oral doses of (14)C-ceftiofur (200 mg/kg bw) in a comparative study with calves. Approximately 55% of the total dose was recovered in the urine and the rest was present in the feces and GI tract. Plasma concentration at 6 hr was 1 mg/kg and trace amounts of ceftiofur were present in all tissues (i.e. liver, muscle and fat). The highest residue levels (0.7 mg/kg) were present in kidney.
A study of lactating cows treated with (14)C-ceftiofur (2.3 mg/kg bw/day for 5 days) revealed that 32-38% of the radioactivity was present in the milk as free metabolites. The major metabolite was desfuroylceftiofur cysteine disulfide representing 7-9% of the total radioactivity. No parent compound was detected in the milk.
A study of im administration of (14)C-ceftiofur in a bull revealed that 55% of the administered dose was excreted in the urine and approximately 30% in the GI tract and feces. The initial metabolite in both urine and plasma was desfuroylceftiofur. HPLC analysis of radioactive metabolites was similar to the results found in the rat studies. A number of metabolites were produced, the major metabolite (87% of total urinary metabolites) being desfuroylceftiofur acetamide conjugates. No parent compound was observed in the urine.
Six Friesian calves (3/sex) were treated with ceftiofur according to different protocols including one single im and iv injection at 1 mg/kg bw, and 5 im injections at 1 mg/kg bw at 24 hr intervals. Time to maximal plasma concentration following im. administration was 0.75 hr ....
... Four calves (sex and breed unspecified) /were/ administered ceftiofur intramuscularly daily for 4 days at 2 dose levels (2.2 or 4.4 mg/kg bw/day). ... Peak serum concentration of 8.8 and 17.3 mg/mL were obtained at 2 hr after doses of 2.2 and 4.4 mg/kg bw/day, respectively.
A study of 4- to 5-month old Yorkshire-Hampshire pigs (6/sex) treated with 3 daily im injections of (14)C-ceftiofur (5.2 mg/kg bw) produced similar results to those observed in rats and cattle. The peak plasma levels of radioactivity (15.4 mg/kg) occurred at 2 hr after the last dose, declining to 7.0 mg/kg 12 hr after the last dose. Tissue levels in various tissues 12 hr after the last dose were as follows: lung, 2.9 mg/kg; muscle, 0.8 mg/kg; kidney, 4.5 mg/kg; GI tract 2.1, and its contents, 5.7 mg/kg; mesentery glands, 1.9 mg/kg; turbinate, 2.7 mg/kg; tonsil, 1.7 mg/kg; brain, 0.1 mg/kg. Radioactivity in urine and feces accounted for 62% and 11% of the dose, respectively.
Cephalosporins are distributed into milk; however, when administered systemically at accepted doses, therapeutic concentrations are not reached in milk. When ceftiofur is administered systemically at recommended dosages, distribution is too low to produce residues greater than established regulatory tolerances.
Dairy cows were given intramuscular injections of 2.2 mg/kg bw/day of ceftiofur on 5 consecutive day.s Milk samples were taken at 2 hour intervals for up to 14 hours after the las dose. Residues in milk were determined using the proposed routine analytical method. The highest residues were found in sample taken 10 hours after the last dose (71 ug/kg) and depleted to approximately 40 ug/kg at 12 hours after the last dose.
Lactating cows were given intramuscular dose of 2.3 mg (14)C-ceftiofur/kg bw/day of 5 consecutive days, urine, feces and milk residue elimination accounted for 63, 36 and 0.15% fo the dose administered, respectively.
In veal calves, intramuscular dose of 1 mg/kg bw/day ceftiofur on 5 days resulted in a plasma Cmax of 4.34 ug/ml, Tmax of 2.4 hours, AUC(0-24 hr) of 42 ug/ml/hr, a half life of elimination of 10 hours and a mean residence time of 13 hours.
Pigs were given intramuscular injections of 3 mg ceftiofur/kg/bw/day for 3 days. The pigs were slaughtered (6 animals/time point) 12 hours and 5 days after the last dose. Mean tissue residue concentrations were 590 and less than 100 up/kg in liver, 1190 and less than 100 ug/kg in kidney, 250 and less than 30 ug/kg in muscle, 400 and less than 100 ug/kg in skin+fat and 1320 and 40 ug/kg in injection site muscle, respectively.
Twenty-four pigs were given intramuscular injections of 3 mg/kg bw/day of ceftiofur on 3 consecutive days. The pigs were slaughtered 12 hours or 2 days after the last dose. ... Mean residue concentrations were 1510 and less than 200 ug/kg in liver, 2170 and less than 200 ug/kg in injection site muscle, respectively.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,700(SRC), determined from a structure estimation method(2), indicates that ceftiofur is expected to have slight mobility in soil(SRC). An estimated pKa of 3.7 (carboxylic acid)(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(3), indicates that this compound will exist primarily as an anion in the environment and anions generally have higher mobility in soils than their neutral counterparts(4). Volatilization of ceftiofur from moist soil surfaces is not expected to be an important fate process(SRC) since anions do not volatilize. Ceftiofur is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6X10-20 mm Hg(SRC), determined from a fragment constant method(6). Half-lives reported for the aerobic biodegradation of cefiofur sodium in clay loam at pH 5, sand at pH 7, and silty clay loam at pH 9 were 22.2, 49, and 41.1 days, respectively(7-9).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,700(SRC), determined from a structure estimation method(2), indicates that ceftiofur is expected to adsorb to suspended solids and sediment(SRC). However, an estimated pKa of 3.7 (carboxylic acid)(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(3), indicates that this compound will exist primarily as an anion in the environment, and anions do not adsorb to sediment as strongly as their neutral counterparts(4). Volatilization from water surfaces is not expected because anions do not volatilize. According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.6(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Half-lives reported for the aqueous hydrolysis of ceftiofur sodium were 22.2 days at pH 5, 49 days at pH 7, and 41.1 days at pH 9(8,9). Half-lives reported for the aerobic biodegradation of ceftiofur sodium in clay loam at pH 5, sand at pH 7, and silty clay loam at pH 9 were 22.2, 49, and 41.1 days, respectively(8-10).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ceftiofur, which has an estimated vapor pressure of 6X10-20 mm Hg(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ceftiofur may be removed from the air by wet or dry deposition(SRC). Ceftiofur contains chromophores that absorb at wavelengths >290 nm indicating that this substance may be susceptible to direct photolysis by sunlight(3); however photodegradation of ceftiofur sodium has been reported to be minimal(4).

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