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Cephaloglycin

Cephaloglycin structure

Cephaloglycin 

structure
  • CAS No:

    3577-01-3

  • Formula:

    C18H19N3O6S

  • Chemical Name:

    Cephaloglycin

  • Synonyms:

    5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-,acetate (ester),D-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[(aminophenylacetyl)amino]-8-oxo-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[[(2R)-aminophenylacetyl]amino]-8-oxo-,(6R,7R)-;(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cephaloglycin;Cephaloglycine;D-(-)-Cephaloglycin;7-(2-D-α-Aminophenylacetamido)cephalosporanic acid;D-Cephaloglycine;Kefglycin;Cefaloglycin;Kafocin;Lilly 39435;Cefaloglycine;15686-39-2;26790-39-6

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ChEBI: A cephalosporin antibiotic containing at the 7beta-position of the cephem skeleton an (R)-amino(phenyl)acetamido group.


Solid


Cefaloglycin is a cephalosporin antibiotic containing at the 7beta-position of the cephem skeleton an (R)-amino(phenyl)acetamido group. It has a role as an antimicrobial agent. It is a cephalosporin and a beta-lactam antibiotic allergen.|A cephalorsporin antibiotic that is no longer commonly used.|Cephaloglycin Anhydrous is the anhydrous form of cephaloglycin, a semisynthetic first-generation cephalosporin with antibacterial activity. Cephaloglycin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.|A cephalorsporin antibiotic.

Cephaloglycin Basic Attributes

405.425

405.42

222-696-7

HD2D469W6U

DTXSID4022781

C76593

Characteristics

164

-0.3

Solid

1.52 g/cm3

237 °C (decomp)

761.8ºC at 760mmHg

414.5ºC

1.678

10.5g/L(25 ºC)

2-8°C

Peritoneal-rat LD50: 1300 mg/kg; peritoneal-mouse LD50: 1030 mg/kg

Thermal decomposition of toxic nitrogen oxide and sulfur oxide gases

MP: 223-250 °C, DECOMP; MAX ABSORPTION (2% DIMETHYLFORMAMIDE): 258 NM (E= 166, 1%, 1 CM) /DIHYDRATE/|ISOELECTRIC POINT & PH OF MAX STABILITY: 4.5 /DIHYDRATE/|CRYSTALLINE POWDER /DIHYDRATE/|WHITE TO OFF-WHITE, CRYSTALLINE POWDER /DIHYDRATE/

Safety Information

42/43

36

Xn

Warehouse ventilated, low temperature and dry

P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501

H317

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.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

WANG RIH, GARTHWAITE; DRUG THER 6: 103-106, 111-113 (1976). A COMPARISON OF SPECTRUM & THERAPEUTIC USAGES & DOSAGE OF THE CEPHALOSPORIN DERIV IS PRESENTED ALONG WITH METABOLISM AND TOXICITY.

|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

moderately toxic

Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.

CONCURRENT ADMIN OF CEPHALEXIN & PROBENECID RESULTS IN HIGHER & PROLONGED SERUM ANTIBIOTIC LEVELS. ... OTHER CEPHALOSPORIN ANALOGS WHOSE SERUM LEVELS ARE ENHANCED BY PROBENCID ARE...CEPHALOGLYCIN...

Drug Information

For treatment of severe infections caused by susceptible bacteria.

Cephalosporins|...BECAUSE CEPHALOGLYCIN IS CONCENTRATED IN URINE, IT MAY BE EFFECTIVE IN TREATMENT OF URINARY TRACT INFECTIONS... /DIHYDRATE/|MOST OF CEPHALOGLYCIN...IS EXCRETED IN URINE AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE. URINARY CONCN OF METABOLITE AVG 350 UG/ML OVER 8-HR PERIOD FOLLOWING ADMIN OF 500 MG OF CEPHALOGLYCIN; THIS IS SUFFICIENT TO INHIBIT MOST STRAINS OF E COLI, MIRABILIS, & KLEBSIELLA-ENTEROBACTER (AEROBACTER) GROUP.|ITS IN VITRO SPECTRUM IS SIMILAR TO THAT OF OTHER CEPHALOSPORINS...& INCL MANY PATHOGENS THAT INFECT URINARY TRACT (EG, ESCHERICHIA COLI, CERTAIN SPECIES OF KLEBSIELLA, STAPHYLOCOCCUS AUREUS). /DIHYDRATE/|For more Therapeutic Uses (Complete) data for CEPHALOGLYCIN (7 total), please visit the HSDB record page.

...CEPHALOGLYCIN IS NOT DRUG OF CHOICE FOR TREATING URINARY TRACT INFECTIONS... IS NOT EVEN A CEPHALOSPORIN OF 1ST CHOICE FOR SEVERE URINARY TRACT INFECTIONS. AVAILABILITY OF...CEPHALOSPORINS...EXCRETED BY KIDNEY...ACHIEVING HIGHER BACTERICIDAL CONCN IN URINE THAN CEPHALOGLYCIN...RENDERED CEPHALOGLYCIN OBSOLETE. /DIHYDRATE/|CEPHALOGLYCIN IS INEFFECTIVE AGAINST PSEUDOMONAS, & MOST SPECIES OF ENTEROCOCCI, ENTEROBACTER, & INDOLE-POSITIVE PROTENS. BECAUSE OF LIMITED ABSORPTION, SERUM LEVELS OF DRUG ADEQUATE TO TREAT SYSTEMIC INFECTIONS CANNOT BE ATTAINED CLINICALLY. /DIHYDRATE/|SUPRAINFECTIONS, USUALLY DUE TO GRAM-NEGATIVE BACTERIA, MAY OCCUR WHEN THESE ANTIBIOTICS ARE EMPLOYED. /CEPHALOSPORINS/|Hypersensitivity reactions to the cephalosporins are the most common side effects...the reactions appear to be identical to those caused by the penicillins. /Cephalosporins/|For more Drug Warnings (Complete) data for CEPHALOGLYCIN (12 total), please visit the HSDB record page.

Cephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Well absorbed following oral administration.|MOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED IN URINE AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE. URINARY CONCN OF METABOLITE AVG 350 UG/ML OVER 8-HR PERIOD FOLLOWING ADMIN OF 500 MG OF CEPHALOGLYCIN...|CEPHALOGLYCIN IS NOT DESTROYED IN GASTRIC ACID, BUT IT GRADUALLY DECOMP IN NEUTRAL & ALKALINE SECRETIONS OF INTESTINES. ONLY 1/4 TO 1/3 IS ABSORBED. /DIHYDRATE/|...CEPHALOSPORINS ARE UNPREDICTABLE IN MANNER IN WHICH THEY CROSS BLOOD-BRAIN BARRIER & THEY PENETRATE POORLY INTO CEREBROSPINAL FLUID... /CEPHALOSPORINS/

MOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED...AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE.

THIS ANTIBIOTIC IS PARTIALLY ABSORBED FROM GI TRACT... PLASMA CONCN REACH PEAK OF ONLY 2-6 UG/ML @ ABOUT 2 HR FOLLOWING SINGLE DOSE OF 0.5 G; DRUG IS NO LONGER DETECTABLE IN PLASMA 8 HR AFTER THIS DOSE. HALF-LIFE...IS ABOUT 4 HR.|PLASMA LEVELS AFTER ORAL ADMIN VARY WIDELY AMONG PT. PEAK LEVEL OF AT LEAST 0.6 UG/ML IS USUALLY ACHIEVED WITH ORAL DOSE OF 500 MG, & IT MAY REACH 6 UG/ML IN FAIR PROP OF CASES. FOOD IN STOMACH INTERFERES WITH ABSORPTION. HALF-LIFE IN PLASMA...ABOUT 3-5 HR, BUT WHEN...SEVERE RENAL IMPAIRMENT...MAY BE 9-20 HR. /DIHYDRATE/

The bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).|CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOTHIN & ITS CONGENERS/|/PENICILLINS & CEPHALOSPORINS/...HAVE SIMILAR MECHANISM OF ANTIBACTERIAL ACTION; BOTH INTERFERE WITH TERMINAL STEP IN BACTERIAL CELL WALL SYNTH BY INACTIVATING TRANSPEPTIDASE, THEREFORE PREVENTING CROSS-LINKAGE OF PEPTIDOGLYCAN CHAINS. /PENICILLINS & CEPHALOSPORINS/

Cefaloglycin

Cephaloglycin Use and Manufacturing

Methods of Manufacturing

Antibiotic substance produced along with penicillin N by a Cepahlosporium sp. cultivated from sea water near a sewage outlet on the coast of Sardinia.|7-AMINOCEPHALOSPORANIC ACID, PREPD FROM NATURAL ANTIBIOTIC CEPHALOSPORIN C BY EITHER PROTONCATALYZED OR ENZYMATIC HYDROLYSIS, IS ACYLATED WITH 2-PHENYLGLYCINE IN APPROPRIATE DEHYDRATING ENVIRONMENT. /DIHYDRATE/

Uses

Antibacterial.

CEPHALOGLYCIN, NF (KAFOCIN), IS AVAILABLE AS DIHYDRATE IN CAPSULES CONTAINING 250 MG.|Kafocin /Dihydrate/

COLORIMETRIC ESTIMATION OF CEPHALEXIN, CEPHALOGLYCIN, AND RELATED COMPOUNDS.|RAPID & SENSITIVE FLUOROMETRIC ANALYSIS FOR CEPHALOSPORINS WHICH IS APPLICABLE TO PENICILLIN. CEPHALOGLYCIN STUDIED. ANTIBIOTICS REACTED WITH 0.1 N NAOH @ 100 DEG TO PRODUCE STABLE FLUORESCENT PRODUCTS. CONCN AS LOW AS 0.01 UG/ML WERE DETECTABLE.

FLUOROMETRIC ASSA FOR CEPHALOGLYCIN IN PLASMA INVOLVING ADDN OF FORMALDEHYDE WHICH CATALYZES FORMATION OF FLUORESCENT DERIV ON HYDROLYSIS IS PRESENTED.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:405.4
XLogP3:-3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:7
Exact Mass:405.09945651
Monoisotopic Mass:405.09945651
Topological Polar Surface Area:164
Heavy Atom Count:28
Complexity:718
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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