Cephaloglycin
Basic information
- CAS
3577-01-3- Standard SMILES
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)[C@H]2SC1- InChIKey
FUBBGQLTSCSAON-PBFPGSCMSA-N- Molecular formula
- C18H19N3O6S
- Average molar mass
- 405.4 g/mol
- Monoisotopic mass
- 405.09945651
Overview
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.
Names & identifiers
- Preferred name
- Cephaloglycin
- IUPAC
- (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- cefaloglycin
- Molecular formula
- C18H19N3O6S
- Molecular weight
- 405.42
Names & synonyms
CefaloglycinCEPHALOGLYCINCephaloglycineKafocin3577-01-3Cephaloglycin anhydrousD-CephaloglycineCephaoglycin acidCefaloglycineKefglycinCefaloglicinaCefaloglycinum
Show more names
Lilly-39435Cephaloglycin(anhydrous)FUBBGQLTSCSAON-PBFPGSCMSA-N(6R,7R)-7-[(R)-2-Amino-2-phenylacetylamino]-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
D-(-)-CephaloglycinLilly 39435Cefaloglycin dihydrate7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acidKefocin7-(2-D-alpha-Aminophenylacetamido)cephalosporanic acid(6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHD2D469W6U
Database identifiers
- CAS
3577-01-3- PubChem CID
- 19150
- DTXSID
DTXSID4022781- ChEMBL
CHEMBL1200971- ChEBI
CHEBI:34613
Properties
Computed structural properties
- XLogP
- -3
- Topological polar surface area
- 164 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 718
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP-0.3
Solubility
SLIGHTLY SOL IN WATER; PRACTICALLY INSOL IN MOST ORGANIC SOLVENTS /DIHYDRATE/
1.48e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
DecompositionWhen heated to decomposition it emits toxic fumes of sulfoxides and nitroxides.
Melting Point237 °C
Physical DescriptionSolid
Other Experimental Properties
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 & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[(aminophenylacetyl)amino]-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
FDA Requirements
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).
Special ReportsWANG 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.
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety & protection
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.
Chemistry & industry
Pharmacology
PharmacodynamicsCephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.
Mechanism of Action
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/
Biological Half-Life
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/
Metabolism/MetabolitesMOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED...AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
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/
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
6 records
Compound notes
Loading…