Cephradine

CEPHRADINE · CEPHRADINE COMPACTED · Anspor · CEFRADIN · cephradin · velosef · Megacef · Cefradine CRS

https://huagongshe.com/de/chemical/38103

Identifikatoren & physikalische Daten

CAS No.	38821-53-3
Summenformel	C16H19N3O4S
Durchschnittliche Molmasse	349,4 g/mol
Monoisotopische Masse	349,10962709 g/mol
SMILES	CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1
InChIKey	RDLPVSKMFDYCOR-UEKVPHQBSA-N
PubChem CID	38103
ChEMBL	CHEMBL1604
ChEBI	CHEBI:3547
EC No.	254-137-8
DTXSID	DTXSID4022785

Chemische & physikalische Eigenschaften

XLogP	0,4
Polarare Oberfläche (TPSA)	138
H-Brücken-Donoren	3
H-Brücken-Akzeptoren	6
Frei drehbare Bindungen	4
Schwere Atome	24
Formalladung	0
Komplexität	697
Arzneimittel	Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics
LogP (Verteilungskoeffizient)	LogP = -1.50
Color/Form	WHITE, CRYSTALLINE POWDERPOLYMORPHIC
Löslichkeit	SPARINGLY SOL IN WATERVERY SLIGHTLY SOL ALCPRACTICALLY INSOL IN CHLOROFORM & ETHER7.78e-01 g/L1 M NH4OH: soluble50mg/mLSoluble in water
Flammpunkt	No Data>110°(230°F)
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsCephalosporinsFDA approved drugs -> Active ingredient
Schmelzpunkt	140 °C140-142 C
Physical Description	Solid
Stability/Shelf Life	ACID STABLE
Dissociation Constants	PKA1 ABOUT 2.6, PKA2 ABOUT 7.3
Collision Cross Section	177.93 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental Properties	MP 140-142 °C (DECOMP)PK1 = 2.63, PK2 = 7.57 /CEPHRADINE MONOHYDRATE/SMALL, COLORLESS CRYSTALS /CEPHRADINE MONOHYDRATE/Soluble in propylene glycol, slightly soluble in acetone, ethanol. Insoluble in ether, chloroform, benzene, hexane /Cephradine monohydrate/
Siedepunkt	898℃
Dichte	1.2794 (rough estimate)
Brechungsindex	1.6320 (estimate)
Lagerbedingungen	Keep in dark place,Inert atmosphere,2-8°C
pKa (Säurekonstante)	2.63, 7.27(at 25℃)
Aggregatzustand	powder
Farbe	White
Stabilität	Light Sensitive
CAS Datenbank	38821-53-3(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Weitere Sicherheitsinformationen	IMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(amino-1,4-cyclohexadien-1-ylacetyl)amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment
FDA-Anforderungen	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 amended21 U.S.C. 321-392).
Hazard Classes and Categories	Skin Irrit. 2 (100%)
Entsorgungsverfahren	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.
Wechselwirkungen	...PARAMETERS OF RENAL FUNCTION...SHOULD BE MONITORED...WHEN...CEPHALOSPORIN & POLYPEPTIDE ANTIBIOTICS ARE USED CONCURRENTLY. /CEPHALOSPORINS/URINARY EXCRETION OF...WEAK ACIDS...CAN BE AFFECTED BY THESE URICOSURIC AGENTS. THUS...CEPHALOSPORINS...MAY BE AFFECTED BY CONCURRENT USE OF PROBENECID OR SULFINPYRAZONE. /CEPHALOSPORINS/CONCURRENT AS WELL AS INDIVIDUAL USE OF GENTAMICIN & CEPHALOTHIN MAY INCR NEPHROTOXICITY & ACUTE RENAL FAILURE. ... NEITHER IT NOR OTHER CEPHALOSPORINS USED PARENTERALLY SUCH AS CEPHRADINE, SHOULD BE USED WITH GENTAMICIN UNLESS LIFE-THREATENING CONDITION EXISTS.Acetaldehyde, at concentrations occurring in vivo was found to avidly react in vitro with several clinically relevant drugs. The greatest reactivity was observed for the hydrazine and hydrazide-containing drugs, hydralazine and isoniazid, respectively. Substantial reactivity was also evidenced for the amine-containing penicillins cyclacillin and ampicillin and for the cephalosporins cephalexin, cephradroxyl and cephradine. However, the virtual lack of reactivity of the amine-containing penicillanic and cephalosporanic acids reveals a major role of the acyl groups of these antibiotics in their reactivity towards acetaldehyde. The presence of moieties which increase the electron density of the amine group appears to favor the molecule reactivity. Amongst several phenylethylallines tested, dopamine and noradrenaline were the most active in forming adducts with acetaldehyde. It is suggested that in vitro binding of acetaldehyde to the above-mentioned drugs could lead in vivo to decreased drug bioavailability, and conceivably the adducts formed may mediate some of the side effects associated with simultaneous drug and alcohol ingestion.

Anwendungen & Verwendung

Beschreibung

Cefradine is an orally bioavailable β-lactam cephalosporin antibiotic. It is active against S. pyogenes, E. coli, K. pneumoniae, and E. cloacae (MICs = 0.04, 9.4, 9.4, and 6.3 μg/ml, respectively). Cefradine is also active against clinical isolates of S. aureus (MICs = 0.8-6 μg/ml) and S. pyogenes (MICs = 0.1-0.4 μg/ml), as well as H. influenzae, E. coli, and K. pneumoniae (MICs = 6.2-12.5 μg/ml). It increases survival in mouse models of systemic lethal infection by S. pyogenes, E. coli, K. pneumoniae, or E. cloacae (ED50s = 5, 37, 122, and 50 mg/kg, respectively), as well as by penicillin-susceptible or -resistant strains of S. aureus (ED50s = 18 and 91 mg/kg, respectively). Formulations containing cefradine have previously been used in the treatment of respiratory and urinary tract infections, skin infections, and otitis media.

Verwenden

Cephalosporin antibacterial.