Basic information
- CAS
50-59-9- Standard SMILES
O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12- InChIKey
CZTQZXZIADLWOZ-CRAIPNDOSA-N- Molecular formula
- C19H17N3O4S2
- Average molar mass
- 415.5 g/mol
- Monoisotopic mass
- 415.06604838
Overview
Cefaloridine is a cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C. It has a role as an antibacterial drug. It is a cephalosporin, a semisynthetic derivative and a beta-lactam antibiotic allergen.
Names & identifiers
- Preferred name
- Cephaloridine
- IUPAC
- (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- Cephaloridine
- Molecular formula
- C19H17N3O4S2
- Molecular weight
- 415.48
Names & synonyms
cephaloridinecefaloridine50-59-9CephaloridinCephaloridinumCefaloridinCefalorizinCepaloridinCephalomycineLoridineCefaloridinaCeflorin
Show more names
SefacinCeporanKeflodinKeflordinSch 11527Cephaloridine IICephaloridine USP/EP/BP
CepalorinKefloridinCeporinCefaloridinumGlaxoridinAmpligramCeporineDeflorin
Database identifiers
- CAS
50-59-9- PubChem CID
- 5773
- DTXSID
DTXSID9022782- ChEMBL
CHEMBL316157- ChEBI
CHEBI:3537- UNII
- LVZ1VC61HB
- EC Number
- 200-052-6
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 147 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 687
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
pHAQ SOLN ARE SLIGHTLY ACID (PH 4.5-5)
LogPLogP = -1.70 at pH = 2
Color/Form
CRYSTALS
WHITE TO OFF-WHITE, CRYSTALLINE POWDER
Solubility
SOL IN WATER
PRACTICALLY INSOL IN MOST ORG SOLVENTS
In water, >2.0X10+4 at 21 °C
Flash PointNo data
Optical RotationSPECIFIC OPTICAL ROTATION: +47.7 °FOR D (SODIUM) LINE (WATER, 1.25%)
Stability/Shelf LifeAQ SOLN (20% WT/VOL) ARE STABLE FOR 4 WK @ 4 °C IN DARK
Other Experimental Properties
EXPOSURE TO SUNLIGHT CAUSES DISCOLORATION
Aqueous solutions (20% w/v) are stable for four weeks at 4 °C in the dark.
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
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationChemical: Pyridinium, 1-[[(6R,7R)-2-carboxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, inner salt
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 ReportsWHO; Environmental Health Criteria 119: Principles and Methods for the Assessment of Nephrotoxicity Associated with Exposure to Chemicals (1991)
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
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of Action
CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOSPORINS/
Cephaloglycin and cephaloridine are acutely toxic to the proximal renal tubule, in part because of their cellular uptake by a contraluminal anionic secretory carrier and in part through their intracellular attack on the mitochondrial transport and oxidation of tricarboxylic acid (TCA) cycle anionic substrates. Preliminary studies with cephaloglycin have provided evidence of a role of fatty acid (FA) metabolism in its nephrotoxicity, and work with cephaloridine has shown it to be a potent inhibitor of renal tubular cell and mitochondrial carnitine (Carn) transport.
Biological Half-Life
.../CEPHALORIDINE/ PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED... WHILE ITS T/2 (60 TO 90 MIN)...ONLY SMALL AMT ARE DETECTABLE AFTER 8 HR.
/IN RATS/ RATIOS OF BONE TO SERUM CONCN AVG...1:7 FOR CEPHALORIDINE...DURING 0.25-4 HR AFTER /ORAL OR SC/ DOSING. DESPITE DIFFERENCES IN CONCN, T/2 IN BONE & SERUM WERE SIMILAR.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Renal.
.../CEPHALORIDINE/ POORLY ABSORBED FROM GI TRACT. PEAK PLASMA CONCN ARE REACHED ABOUT 30 MIN AFTER DRUG IS INJECTED; 10 TO 20% OF PLASMA CEPHALORIDINE IS BOUND TO PROTEIN.
IM INJECTIONS OF 0.5 & 1 G YIELD PEAK PLASMA CONCN OF 15 & 30 UG/ML, RESPECTIVELY. APPROX 75% OF GIVEN DOSE IS EXCRETED IN URINE, MAINLY BY GLOMERULAR FILTRATION. CEPHALORIDINE ACCUM IN BLOOD OF PATIENTS WITH DECR RENAL FUNCTION, & IN AZOTEMIC PATIENTS PLASMA CONCN ARE VERY HIGH...
PLACENTAL DRUG TRANSFER- CEPHALORIDINE: TIME TO APPEAR IN FETUS 30 MIN; TIME TO FETAL/MATERNAL CONCN EQUIL 5 HR. /FROM TABLE/
.../CEPHALORIDINE/ READILY PENETRATE NORMAL EYE FOLLOWING SYSTEMIC OR SUBCONJUNCTIVAL ADMIN...
Related reactions
1 records
Compound notes
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