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HCID 33255Erstellt: 3. November 2026

Cefazolin

cefazoline · CEFAZOLIN ACID · cephazolin · Cafazolin · cephazoline · (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid · cez · Cefaprim

https://huagongshe.com/de/chemical/33255

Molekülstruktur von Cefazolin

Identifikatoren & physikalische Daten

CAS No.25953-19-9
SummenformelC14H14N8O4S3
Durchschnittliche Molmasse454,5 g/mol
Monoisotopische Masse454,03001393 g/mol
SMILESCc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)Cn4cnnn4)[C@H]3SC2)s1
InChIKeyMLYYVTUWGNIJIB-BXKDBHETSA-N
PubChem CID33255
ChEMBLCHEMBL1435
ChEBICHEBI:474053
EC No.247-362-8
DTXSIDDTXSID2022753
Lokaler NameCefazolin

Chemische & physikalische Eigenschaften

XLogP-0,4
Polarare Oberfläche (TPSA)235
H-Brücken-Donoren2
H-Brücken-Akzeptoren12
Frei drehbare Bindungen7
Schwere Atome29
Formalladung0
Komplexität740
ArzneimittelPharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Cefalosporins)Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland
LogP (Verteilungskoeffizient)log Kow = -0.58-0.24
Color/FormNeedles from aqueous acetone
LöslichkeitMol wt 476.50. White to yellowish-white, odorless crystalline powder with a bitter, salty taste. Crystallizes in alpha, beta, and gamma forms (Kariyone). Easily sol in water, slightly sol in methanol, ethanol. Practically insol in benzene, acetone, chloroform /Sodium salt/Easily sol in DMF, pyridinesol in aq acetone, aq dioxane, aq ethanolslightly sol in methanol. Practically insol in chloroform, benzene, ether.4.87e-01 g/LDMSO (Slightly), Methanol (Very Slightly, Heated)
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsCephalosporinsAccess group antibiotics
Schmelzpunkt198-200 °C (decomposes)198-200 C
Physical DescriptionSolid
Stability/Shelf LifeFollowing reconstitution with sterile water for injection, bacteriostatic water for injection, or 0.9% sodium chloride injection, soln containing approx 225 or 330 mg of cefazolin per ml have a pH of approx 4.5-6 and are stable for 24 hr @ room temp or 96 hr @ 5 °C. Rapid hydrolysis of the drug occurs when pH exceeds 8.5, and precipitation of the insoluble free acid may occur when pH is below 4.5.Soln containing 2.25-4.5 mg of cefazolin per ml are stable for 24 hr @ room temp or 96 hr @ 5 °C in the following infusion fluids: 0.9% sodium chloride5% or 10% dextrose5% dextrose and 0.2%, 0.45%, or 0.9% sodium chloride5% dextrose and lactated Ringer'slactated Ringer's5% or 10% invert sugar in waterNormosol -M in D5-WIonosol B with 5% dextrosePlasma-Lyte with 5% dextroseand 5% sodium carbonate. The manufacturers of Ancef and Kefzol state that these cefazolin sodium soln are stable for 10 days when refrigerated.Soln containing approx 225 or 330 mg of cefazolin per ml may be frozen in their original containers immediately after reconstitution with sterile water for injection, bacteriostatic water for injection, or 0.9% sodium chloride injection and are stable for 12 wk when stored at -20 °C. If the soln are warmed to facilitate thawing, care should be taken to avoid heating after thawing has been completed. Once thawed, solutions should not be refrozen.Commercially available frozen cefazolin sodium injections are stable for 24 mo when stored @ -20 °C. ... Thawed soln of the commercially available frozen injections are stable for 48 hr @ room temp (25 °C) or 10 days when refrigerated at 5 °C. If the commercially available frozen cefazolin sodium injections are refrigerated immediately after removal from the freezer, the injections are stable for a total of 12 days (ie, 10 days @ 5 °C followed by 48 hr @ room temp). Soln that have been thawed and stored @ room temp for up to 24 hr may then be refrigerated @ 5 °C for up to 3 days and stored for an additional 24 hr @ room tempthis recycling procedure must be completed within 11 days from the time of thawing. /Cefazolin sodium/
Collision Cross Section186.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]189.18 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Dichte2.01±0.1 g/cm3(Predicted)
LagerbedingungenHygroscopic, -20°C Freezer, Under inert atmosphere
pKa (Säurekonstante)pKa 2.15 (Uncertain)
AggregatzustandSolid
FarbeWhite to Off-White
StabilitätHygroscopic
Hauptanwendungenpharmaceutical (small molecule)
InChI1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
InChIKeyMLYYVTUWGNIJIB-BXKDBHETSA-N
SMILES[s]1c(nnc1C)SCC2=C(N3[C@H](SC2)[C@@H](C3=O)NC(=O)C[n]4nnnc4)C(=O)O
CAS Datenbank25953-19-9(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungDangerH317 (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 57 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenStatus: Active Update: 16-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30134
Weitere SicherheitsinformationenIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-, (6R-trans)-: Environment tier I assessment
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl cefazolin sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Cefazolin sodium/
Hazard Classes and CategoriesSkin Sens. 1 (100%)
LagerbedingungenCefazolin sodium and soln of the drug should be protected from light. Cefazolin sodium sterile powder should be stored @ a temp less than 40 °C, preferable between 15-30 °C. Cefazolin sodium powder tends to darken, depending on storage conditionhowever, such discoloration does not indicate loss of potency. /Cefazolin sodium/
EntsorgungsverfahrenSRP: 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.
WechselwirkungenHypoprothrombinemia induced by large doses of salicylates and/or cephalosporins, and the gastrointestinal ulcerative or hemorrhagic potential of nonsteroidal anti-inflammatory drugs (NSAIDs), salicylates, or sulfinpyrazone may increase the risk of hemorrhage. /Cephalosporins/

Anwendungen & Verwendung

Beschreibung

Cefazolin has the natural acetyl side chain at C-3 replaced by a thio-linked thiadiazole ring. Although this group is an activating leaving group, the moiety is not subject to the inactivating host hydrolysis reaction that characterizes cephapirin. At C-7, it possesses a tetrazoylmethylene unit. Cefazolin is less irritating on injection than its cohort in this generation of drugs and has a longer half-life than cephapirin. Its dosing should be reduced in the presence of renal impairment. It is comparatively unstable and should be protected from heat and light.

Verwenden

Cefazolin is an antibacterial compound derived from 7-amino-cephalosporanic acid.

Probenecid decreases renal tubular secretion of those cephalosporins excreted by this mechanism, resulting in increased and prolonged cephalosporin serum concentrations, prolonged elimination half-life, and increased risk of toxicity
probenecid has no effect on the excretion of cefoperazone, ceftazidime, or ceftriaxone
however, other cephalosporins and probenecid might be used concurrently in the treatment of infections, such as sexually transmitted diseases (STDs) or other infections, in which high and/or prolonged antibiotic serum and tissue concentrations are required. /Cephalosporins/
Concomitant admin of oral probenecid competitively inhibits tubular secretion resulting in higher and more prolonged serum concn of most cephalosporins. /Cephalosporins/
Concurrent use of nephrotoxic agents such as aminoglycosides, colistin, polymyxin B, or vancomycin may increase the risk of nephrotoxicity with some cephalosporins ... . /Cephalosporins/
For more Interactions (Complete) data for CEFAZOLIN (6 total), please visit the HSDB record page.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.58(2) and a regression derived equation(3), indicates that cefazolin is expected to have very high mobility in soil(SRC). An estimated pKa of 3.6 (caboxylic acid)(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(4), indicates that this compound will exist primarily as an anion in the environment and anions generally have higher mobility in soil than their neutral counterparts(5). Volatilization of cefazolin from moist soil surfaces is not expected to be an important fate process(SRC) because anions do not volatilize. Cefazolin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-18 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2006).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.58(2) and a regression-derived equation(3), indicates that cefazolin is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 3.6 (caboxylic acid)(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(4), indicates that this compound will exist primarily as an anion in the environment. Volatilization from water surfaces is not expected(SRC) because anions do not volatilize. According to a classification scheme(5), an estimated BCF of 0.2(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cefazolin, which has an estimated vapor pressure of 1.5X10-18 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cefazolin may be removed from the air by wet or dry deposition(SRC). Cefazolin absorbs light at wavelengths >290 nm (UV max = 272 nm with a possible shoulder above 290 nm)(3) and therefore may be susceptible to direct photolysis by sunlight(4).
Milk ConcentrationsEXPERIMENTAL MILK: In depletion studies carried out in lactating cows it was shown that after the recommended treatment with the commercial formulation intended for lactating cows (two treatments of all four quarters at two successive milkings), residues in composite milk samples were below 50 ug/L at the 7th milking and below 25 ug/L at the 8th milking after the last treatment.
Soil Adsorption/MobilityThe Koc of cefazolin is estimated as 12(SRC), using a log Kow of -0.58(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cefazolin is expected to have very high mobility in soil. An estimated pKa of 3.6(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(4), indicates that this compound will exist primarily as an anion in the environment and anions generally have higher mobility in soils than their neutral counterparts(5).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Anaphylaxis presents clinically as the acute onset of peripheral vascular collapse and shock. This may begin minutes after contact with the precipitating allergen. It is the most feared and serious of the allergic reactions and carries with it a significant risk of death. Skin and mucosal lesions, including urticaria and angioedema, may immediately precede the onset of anaphylaxis. Nausea, vomiting, diarrhea, and bronchospasm may occur as part of the acute reaction to the drug. These end-organ responses are initiated by the release of histamine, serotonin, bradykinin and other vasoactive substances released by the basophils and mast cells. ... Penicillins, cephalosporins, and sulfonamides are the antimicrobials most often associated with anaphylactic reactions. /Penicillins and cephalosporins//SIGNS AND SYMPTOMS/ Rarely, Clostridium difficile-associated diarrhea and colitis (also known as antibiotic-associated pseudomembranous colitis) has occurred during or following discontinuance of cephalosporins, including following single doses of certain cephalosporinsfatalities have been reported rarely. /Cephalosporins//SIGNS AND SYMPTOMS/ 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 ... Serious bleeding related either to ... thrombocytopenia, and/or platelet dysfunction has been reported with several beta-lactam antibiotics. This appears to be a particular problem with certain patients (elderly, poorly nourished, or those with renal insufficiency) who are receiving moxalactam. /Cephalosporins//SIGNS AND SYMPTOMS/ Hypersensitivity reactions have been reported to occur in approx 5% or less of patients receiving a cephalosporin. These reactions include urticaria, pruritus, rash (maculopapular, erythematous, or morbilliform), fever and chills, reactions resembling serum sickness, eosinophilia, joint pain or inflammation, edema, erythema, genital and anal pruritus, angioedema, shock, hypotension, vasodilatation, Stevens-Johnson syndrome, erythema multiforme, toxic epidermal necrolysis, and exfoliative dermatitis. Anaphylaxis, including a few fatalities, has occurred rarely. /Cephalosporins/For more Human Toxicity Excerpts (Complete) data for CEFAZOLIN (10 total), please visit the HSDB record page.
Artificial Pollution SourcesCefazolin's production and use as an actibacterial drug for both humans and animals(1-3) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)cefazolinDILI PositiveIntravenousDOI:10.1016/j.drudis.2019.09.022
Environmental BioconcentrationAn estimated BCF of 0.2 was calculated for cefazolin(SRC), using a log Kow of -0.58(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilThe estimated pKa of cefazolin is 3.6 (carboxylic acid), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(1). Based on this pKa value, cefazolin is expected to exist primarily as an anion in the environment(SRC). Volatilization of cefazolin from moist soil or water surfaces is not expected to be an important fate process(SRC) because anions do not volatilize. Cefazolin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.5X10-18 mm Hg(SRC), determined from a fragment constant method(2).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ An antibacterial, has been tested in rabbit eyes25 mg subconjunctivally or 2.25 mg injected into the vitreous humor appeared to be non-toxic by ophthalmoscopy, ERG, and histology. /Cefazolin sodium/[Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 196]/LABORATORY ANIMALS: Acute Exposure/ In a guinea pig maximization test cefazolin did not cause sensitization.[European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal ProductsCefazolin, Summary Report. EMEA/MRL/0126/96-Final (July 1996). Available from, as of July 21, 2006: http://www.ema.europa.eu/ema/index.jsp?curl=pages/document_library/landing/document_library_search.jsp&murl=menus/document_library/document_library.jsp&mid]/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Repeated-dose toxicity studies of up to six months duration were carried out in rats and dogs in most cases using subcutaneous administration. Apart from local toxicity at the injection site most effects occurred in the intestinal tract resulting in diarrhea and enlargement of the cecum. In a 90 day subcutaneous study in rat 250 mg/kg bw only caused reaction at the injection site and cecal enlargement (2/20 animals). In a 3 and 6 month subcutaneous study in dogs, 250 mg/kg and 125 mg/kg, respectively, were without effect. An oral 90 day study was performed in rats. Diarrhea and abdominal swelling was observed together with cecal enlargement. The NOEL in this study was 20 mg/kg bw.[European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The effect of cefazolin on reproduction was investigated in segment I, II and III studies in rats, mice and rabbits. Cefazolin administered subcutaneously did not affect male or female fertility, or the post natal development of the offspring in rats. Cefazolin was not teratogenic in mice and rabbits after subcutaneous dosing. Oral administration of cefazolin to pregnant rats caused maternal toxicity (diarrhea and cecal enlargement) and reduction in litter size and fetal weight, but showed no specific effects on the fetuses. The NOEL for dams (and fetuses) was 10 mg/kg bw.[European Medicines Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal ProductsFor more Non-Human Toxicity Excerpts (Complete) data for CEFAZOLIN (6 total), please visit the HSDB record page.
Populations at Special RiskPatients who are allergic to one class of agents may manifest cross-reactivity when a member of the other class is admin. Immunological studies have demonstrated cross-reactivity in as many as 20% of patients who are allergic to penicillin, but clinical studies indicate a much lower frequency (about 1%) ... /Cephalosporins and penicillins/Serious bleeding related either to ... thrombocytopenia, and/or platelet dysfunction has been reported with several beta-lactam antibiotics. This appears to be a particular problem with certain patients (elderly, poorly nourished, or those with renal insufficiency) who are receiving moxalactam. /Cephalosporins/
Environmental Abiotic DegradationCefazolin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Cefazolin absorbs light at wavelengths >290 nm (UV max = 272 nm with a possible shoulder above 290 nm)(2) and therefore may be susceptible to direct photolysis by sunlight(1).
Wassergefährdungsklasse (WGK)3
Zollcode2941906000
R-Sätze (R)20/21/22-36/37/38
Toxizitätmouse,LD50,intramuscular,4gm/kg (4000mg/kg),Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
GefahrensymboleXn
Sicherheitshinweise (S)26-36
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten25953-19-9(Hazardous Substances Data)
GefahrenklasseResp. Sens. 1Skin Sens. 1