21593-23-7CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CSc3ccncc3)[C@H]2SC1UQLLWWBDSUHNEB-CZUORRHYSA-NCephapirin is a cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. It is used (as its sodium salt) as an antibiotic, being effective against gram-negative and gram-positive organisms. It has a role as an antibacterial drug. It is a conjugate acid of a cephapirin(1-).
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
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SOL IN WATER /CEPHAPIRIN SODIUM/
VERY SOL IN DIL HYDROCHLORIC & GLACIAL ACETIC ACID; INSOL IN CHLOROFORM, ETHER, TOLUENE /CEPHAPIRIN SODIUM/
1.51e-01 g/L
STABLE DRY STATE FOR 18 MO @ ROOM TEMP /CEPHAPIRIN SODIUM/
Solutions containing cephapirin sodium 50 to 600 mg/ml in water for injection are stable for 12 hr at 25 °C or 10 days at 4 °C. /Cephapirin sodium/
If frozen immediately after reconstitution with sterile water for injection, bacteriostatic water for injection, 0.9% sodium chloride injection, or 5% dextrose injection, solutions retain their potency for up to 60 days at -15 °C (5 °F). After thawing at room temperature, solutions retain their potency for 12 hours at room temperature or for 10 days if refrigerated at 4 °C (39 °F).
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Danger
H317 (14.6%): 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 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
REACH registered substance: Cefapirin (EC: 244-466-5)
Cephapirin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QG - Genito urinary system and sex hormones
Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.
The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
... VERY RESISTANT TO ACTION OF PENICILLINASE, FOR WHICH IT IS BOTH COMPETITIVE & NONCOMPETITIVE INHIBITOR ... IT DOES NOT SUPPRESS BREAKDOWN OF PENICILLIN G BY STAPHYLOCOCCAL PENICILLINASE. CEPHALOSPORIN C & ITS SEMISYNTHETIC CONGENERS INDUCE SYNTH OF PENICILLINASE BY B CEREUS & STAPH AUREUS. /CEPHALOSPORIN C/
... ENZYME ACTING SPECIFICALLY ON CEPHALOSPORIN C TO DESTROY ITS ANTIBACTERIAL ACTIVITY. THIS SUBSTANCE, CEPHALOSPORINASE IS ALSO BETA-LACTAMASE. MOST PREPN OF ENZYME ALSO EXHIBIT PENICILLINASE ACTIVITY, & SOME MICROORGANISMS PRODUCE ONE BETA-LACTAMASE THAT ACTS ON BOTH PENICILLIN & CEPHALOSPORINS. /CEPHALOSPORIN C/
Bactericidal; action depends on ability to reach and bind pencillin-binding proteins located in bacterial cytoplasmic membranes; cephalosporins inhibit bacterial septum and cell wall synthesis, probably by acylation of membrane-bound transpeptidase enzymes. This prevents cross-linkage of peptidoglycan chains, which is necessary for bacterial cell wall strength and rigidity. Also, cell division and growth are inhibited, and lysis and elongation of susceptible bacteria frequently occur. Rapidly dividing bacteria are those most susceptible to the action of cephalosporins. /Cephalosporins/
EIGHT HEALTHY ADULTS RECEIVED 1 G, IV AND IM. BIOLOGICAL HALF-LIFE OF CEPHAPIRIN WAS 43 MIN. ABSORPTION HALF-LIFE OF CEPHAPIRIN FROM IM ADMIN WAS 1.25 HR.
IV SODIUM CEPHAPIRIN SHOWED BIEXPONENTIAL DISPOSITION CHARACTERISTICS IN SERUM & SUBCHONDRAL BONE, REACHING DISTRIBUTION EQUIL WITHIN 20 MIN. RAPIDLY ELIMINATED, WITH BETA HALF-LIFE OF ABOUT 0.3 HR & BODY CLEARANCE OF 400 ML/MIN.
불러오는 중…
21593-23-7DTXSID9022784CHEMBL1599CHEBI:554446173.05 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
183.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
Beige Solid
PROBENECID & SULFINPYRAZONE COMPETE WITH URIC ACID @ RENAL TUBULE TRANSPORT SITES. URINARY EXCRETION OF OTHER WEAK ACIDS ALSO CAN BE AFFECTED BY THESE URICOSURIC AGENTS. ... CEPHALOSPORINS ... MAY BE AFFECTED BY CONCURRENT USE OF PROBENECID OR SULFINPYRAZONE. /CEPHALOSPORINS/
The admixture of beta-lactam antibacterials (penicillins and cephalosporins) and aminoglycosides may result in substantial mutual inactivation. If they are administered concurrently, they should be administered in separate sites. Do not mix them in the same intravenous bag or bottle. /Cephalosporins/
... ADVERSE REACTIONS ... INCL LOCAL PAIN, INDURATION, STERILE ABSCESS, OR TISSUE SLOUGH AFTER IM INJECTION ... . /IV INFUSION/ IS CONSIDERABLY LESS IRRITATING THAN CEPHALOTHIN TO BLOOD VESSELS ... . REACTIONS ... DURING TREATMENT ARE TRANSIENT ELEVATIONS OF SERUM TRANSAMINASES & ALKALINE PHOSPHATASE, HALLUCINATIONS, NYSTAGMUS ... .
A positive Coombs' reaction appears frequently in patients who receive large doses of a cephalosporin. Hemolysis is not usually associated with this phenomenon, although it has been reported. Cephalosporins have produced rare instances of bone-marrow depression, characterized by granulocytopenia. The cephalosporins have /also/ been implicated as potentially nephrotoxic agents. /Cephalosporins/
TRANSIENT NEUTROPENIA HAS BEEN OBSERVED BETWEEN 10TH & 20TH DAYS OF THERAPY. /SEMISYNTHETIC CEPHALOSPORINS/
... MILD HYPERSENSITIVITY, MANIFESTED MOST FREQUENTLY AS ... LEUKOPENIA, ... TRANSIENT INCR IN SGOT, SGPT, ... BILIRUBIN, & BUN LEVELS. ... FALSE-POSITIVE REACTIONS FOR URINE GLUCOSE MAY BE OBSERVED ... OVERGROWTH OF NONSUSCEPTIBLE ORGANISMS CAN OCCUR AFTER PROLONGED USE.
For more Human Toxicity Excerpts (Complete) data for CEPHAPIRIN (12 total), please visit the HSDB record page.
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cephapirin
DILI Negative
DOI:10.1016/j.drudis.2019.09.022
First-generation cephalosporins /including cephapirin/ have the highest degree of activity against most gram-positive bacteria, including beta-lactamase producing Staphylococcus aureus and most streptococci; exceptions include methicillin resistant staphylococci, and penicillin resistant Streptococcus pneumonia. No cephalosporin is effective against Enterococcus faecalis infections. Gram-negative bacteria coverage is generally limited to Escherichia coli, Klebsiella species, and Proteus mirabilis. /Cephalosporins/
These medications sould not be used when the following medical problem exists: Previous allergic reaction (anaphylaxis) to penicillins, penicillin derivatives penicillamine, or cephalosporins; Gastrointestinal disease, history of, especially ulcerative colitis, regional enteritis, or antibiotic-associated colitis (cephalosporins may cause pseudomembranous colitis); Hepatic function impairment (cefoperazone is primarily excreted in bile; may also cause elevated SGOT, SGPT, and alkaline phosphatase; it is recommended that patients with both severe liver disease and significant renal disease receive a reduced dosage of cefoperazone. /Cephalosporins/
Serum half-life is 0.6 hr /From table/
Major metabolite detected is desacetylcephapirin.
MAJOR METABOLITE OF CEPHAPIRIN IS DEACETYLCEPHAPIRIN, WHICH IS ABOUT ONE HALF OF ANTIMICROBIAL ACTIVITY OF PARENT CMPD; 20% OF ANTIBIOTIC ACTIVITY IN PLASMA IS DUE TO DEACETYLATED CMPD.
Cephapirin is partially metabolized in the plasma, liver and kidneys to diacetyl cephapirin, which has about 50% of the antibacterial activity of the parent cmpd. ... Up to 20% of the antibiotic activity in serum is due to the desacetyl metabolite.
... PENETRATION OF CEPHALOSPORINS INTO /CEREBROSPINAL FLUID/ IS POOR. /CEPHALOSPORINS/
CLOSE TO 50% OF CEPHAPIRIN IS BOUND TO PLASMA PROTEIN. HALF-LIFE ... IN NORMAL INDIVIDUALS IS ABOUT 40 MIN & IS DEPENDENT ON RENAL FUNCTION. SIGNIFICANT AMT ... PRESENT IN BLOOD IS REMOVED BY HEMODIALYSIS. ... EXCRETED MAINLY BY KIDNEY; ONLY 1% PRESENT IN BILE.
... /CEPHAPIRIN/ NOT ABSORBED FROM GI TRACT. IM INJECTION OF 0.5 G OF CEPHAPIRIN PRODUCES MAX PLASMA CONCN OF ABOUT 10 UG/ML @ 45 MIN; 1 G ABOUT 16 UG/ML. PLASMA CONCN ... EFFECTIVE AGAINST MANY SENSITIVE MICROORGANISMS ARE STILL DETECTABLE 6 HR AFTER SINGLE IM DOSE OF 1 G.
ABOUT 30% OF IM DOSE OF CEPHAPIRIN IS EXCRETED IN URINE IN EACH OF 1ST 2 HR PERIODS AFTER INJECTION.
For more Absorption, Distribution and Excretion (Complete) data for CEPHAPIRIN (8 total), please visit the HSDB record page.
7-AMINOCEPHALOSPORANIC ACID, PREPD FROM NATURAL ANTIBIOTIC CEPHALOSPORIN C ... IS ACYLATED ... IN APPROPRIATE DEHYDROCHLORINATING ENVIRONMENT, & RESULTING CEPHAPIRIN (ACID) IS CONVERTED INTO ITS SODIUM SALT BY INTERACTION WITH SODIUM 2-ETHYLHEXANOATE IN SUITABLE ORG SOLVENT. /CEPHARIRIN SODIUM/
용도An antimicrobial agent.