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Cefazolin

HCID 33255
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
25953-19-9
Standard SMILES
Cc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)Cn4cnnn4)[C@H]3SC2)s1
InChIKey
MLYYVTUWGNIJIB-BXKDBHETSA-N
Molecular formula
C14H14N8O4S3
Average molar mass
454.5 g/mol
Monoisotopic mass
454.03001393

Overview

Cefazolin is a first-generation cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively. It has a role as an antibacterial drug. It is a cephalosporin, a member of tetrazoles, a member of thiadiazoles and a beta-lactam antibiotic allergen. It is a conjugate acid of a cefazolin(1-).

Names & identifiers

Preferred name
Cefazolin
IUPAC
(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
English name
Cefazolin
Molecular formula
C14H14N8O4S3
Molecular weight
454.51

Names & synonyms

cefazolin25953-19-9CephazolinCefazolineCephamezineCefamezinCephazolineCephazolidinCefazolinaCefazolinumElzogram(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
CEFAZOLIN ACIDCafazolin(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 acidcezCefaprim
DTXSID2022753IHS69L0Y4TJ01DB04CHEBI:474053DTXCID302753(6R,7R)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidSK&F-41558(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Database identifiers

CAS

Properties

Computed structural properties

XLogP
-0.4
Topological polar surface area
235 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
12
Rotatable bonds
7
Heavy atoms
29
Formal charge
0
Complexity
740

Experimental & physicochemical properties

Drugs · 4 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics (Cefalosporins)

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

LogP · 3 items

log Kow = -0.58

-0.58

-0.24

Color/FormNeedles from aqueous acetone
Solubility · 3 items

Mol 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, pyridine; sol in aq acetone, aq dioxane, aq ethanol; slightly sol in methanol. Practically insol in chloroform, benzene, ether.

4.87e-01 g/L

Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

Access group antibiotics

Melting Point198-200 °C (decomposes)

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 · 4 items

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 57 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 16-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30134
Other Safety InformationIMAP 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 Requirements · 1 item

The 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%)

Safety & protection

Storage Conditions · 1 item

Cefazolin 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 condition; however, such discoloration does not indicate loss of potency. /Cefazolin sodium/

Chemistry & industry

Pharmacology

ATC Code · 5 items

J01DB04

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01DB04

Protein Binding74-86%
Pharmacodynamics · 1 item

Cefazolin (also known as cefazoline or cephazolin) is a semi-synthetic first generation cephalosporin for parenteral administration. Cefazolin has broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.

Mechanism of Action · 2 items

In vitro tests demonstrate that the bactericidal action of cephalosporins results from inhibition of cell wall synthesis. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.

Bactericidal; action depends on ability to reach and bind penicillin-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/

Biological Half-Life · 2 items

The serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.

The serum half-life of cefazolin is 1.2-2.2 hr in adults with normal renal function. In one study, half-life was 6.8 hr in 1 adult with a creatinine clearance of 26 ml/min, 12 hr in 3 adults with creatinine clearances of 12-17 ml/min, and 57 hr in 3 adults with creatinine clearances less than 5 ml/min.

Metabolism/Metabolites · 2 items

Related reactions

4 records
New reaction record
HRID 1007079 reaction equation
HRID 1007079As reactantuspto-grants-2004_09
HRID 1470209 reaction equation
HRID 1470209As productuspto-grants-2015_04
HRID 1923461 reaction equation
HRID 1923461As reactantuspto-grants-2012_05
HRID 1923462 reaction equation
HRID 1923462As reactantuspto-grants-2012_05

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
25953-19-9
PubChem CID
33255
DTXSID
DTXSID2022753
ChEMBL
CHEMBL1435
ChEBI
CHEBI:474053
UNII
IHS69L0Y4T
EC Number
247-362-8
Nikkaji
J17.146H
Physical Description
Solid
Stability/Shelf Life · 4 items

Following 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 chloride; 5% or 10% dextrose; 5% dextrose and 0.2%, 0.45%, or 0.9% sodium chloride; 5% dextrose and lactated Ringer's; Ringer's; lactated Ringer's; 5% or 10% invert sugar in water; Normosol -M in D5-W; Ionosol B with 5% dextrose; Plasma-Lyte with 5% dextrose; and 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 temp; this recycling procedure must be completed within 11 days from the time of thawing. /Cefazolin sodium/

Collision Cross Section · 2 items

186.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

189.18 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
198 · 198-200 C
Density
2.01 · 2.01±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
DMSO (Slightly), Methanol (Very Slightly, Heated)
pka
2.15 · pKa 2.15 (Uncertain)
form
Solid
color
White to Off-White
Stability
Hygroscopic
Major Application
pharmaceutical (small molecule)
InChI
1S/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
InChIKey
MLYYVTUWGNIJIB-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 DataBase Reference
25953 · 25953-19-9(CAS DataBase Reference)
FDA UNII
69 L0Y4T · IHS69L0Y4T
ATC code
1 DB04 · J01DB04
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
317 · H317-H334
Precautionary statements
261 · P261-P280-P284-P304+P340-P342+P311
Hazard Codes
Xn
Risk Statements
20 · 20/21/22-36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
HS Code
2941906000 · 2941906000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 Skin · Resp. Sens. 1Skin Sens. 1
Hazardous Substances Data
25953 · 25953-19-9(Hazardous Substances Data)
Toxicity
50 · mouse,LD50,intramuscular,4gm/kg (4000mg/kg),Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
REACH Registrations
Active
Disposal Methods · 1 item

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.

Toxicology

Interactions · 5 items

Hypoprothrombinemia 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/

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.

Environmental Fate · 3 items

TERRESTRIAL 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 Concentrations · 1 item

EXPERIMENTAL 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/Mobility · 1 item

The 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 · 5 items

/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 cephalosporins; fatalities 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 Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefazolin

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Environmental Bioconcentration · 1 item

An 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/Soil · 1 item

The 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 · 5 items

/LABORATORY ANIMALS: Acute Exposure/ An antibacterial, has been tested in rabbit eyes; 25 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 Products; Cefazolin, 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; Cefazolin, 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: 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 Products; Cefazolin, 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]

Populations at Special Risk · 2 items

Patients 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 Degradation · 1 item

Cefazolin 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).

Regulatory information

FDA Requirements · 1 item

The 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/

Safety data

wgk
3
hs_code
2941906000
Toxicity
mouse,LD50,intramuscular,4gm/kg (4000mg/kg),Byoin Yakugaku. Hospital Pharmacology. Vol. 3, Pg. 220, 1978.
risk_code
20/21/22-36/37/38
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
Xn
safety_code
26-36
Storage Class
11 - Combustible Solids
Hazard statements
H317-H334
REACH Registrations
Active
Hazard Classifications
Resp. Sens. 1Skin Sens. 1
Precautionary statements
P261-P280-P284-P304+P340-P342+P311
Hazardous Substances Data
25953-19-9(Hazardous Substances Data)

Not metabolized.

Metabolism of cefazolin is very limited in most of the animal species tested and in /humans/. After parenteral administration of cefazolin nearly 100% is excreted unchanged in urine with 24 hours in /humans/, dog and horse. No major metabolites seem to occur.

FDA Pharmacological Classification · 6 items

IHS69L0Y4T

CEFAZOLIN

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefazolin is a Cephalosporin Antibacterial.

CEFAZOLIN

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion · 6 items

Not absorbed from GI tract. Must be administered parenterally. Peak serum concentrations attained 1-2 hours post intramuscular injection.

Cefazolin is present in very low concentrations in the milk of nursing mothers. Cefazolin is excreted unchanged in the urine. In the first six hours approximately 60% of the drug is excreted in the urine and this increases to 70%-80% within 24 hours.

CEFAZOLIN CROSSES INFLAMED SYNOVIAL MEMBRANES, YIELDING SYNOVIAL FLUID ANTIBIOTIC CONCN GREATER THAN THOSE IN SERUM WITHIN 2 HR OF IM DOSE... CLEARANCE OF CEFAZOLIN BY KIDNEY IS PREDOMINANTLY BY GLOMERULAR FILTRATION, & CLEARANCE RATES ARE LINEARLY RELATED TO CREATININE CLEARANCE...

CEFAZOLIN RAPIDLY PENETRATES BODY TISSUES IN RATS, & DECLINE OF TISSUE ANTIBIOTIC LEVELS AFTER DOSING IS FIRST-ORDER. VERY SMALL AMT OF DRUG CROSS BLOOD-BRAIN BARRIER & PLACENTAL TRANSFER APPEARS NEGLIGIBLE...

...DURING STUDIES OF CEFAZOLIN TRANSFERENCE IN MAN, 92-100% OF ADMIN DOSE WAS ACCOUNTED FOR BY URINARY EXCRETION...

... About 80% of cefazolin is reversibly bound to plasma protein ... is excreted in bile even when there is gallbladder disease ... concn may normally exceed that in plasma by 3 times.

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 4 items

Vet: Antibacterial ... usually quite active against many gram-positive bacteria ... moderately active against gram-negative bacteria ... relatively susceptible to beta-lactamases ... not as effective against anaerobes as ... penicillins. /First-generation cephalosporins/

Mesh Heading: anti-bacterial agents

MEDICATION

Use (kg; approx.) in Germany (2009): >10000

Methods of Manufacturing · 1 item

7-AMINOCEPHALOSPORANIC ACID IS CONVERTED TO ITS SODIUM SALT & ACETYLATED WITH 1H-TETRAZOLE-1-ACETYL CHLORIDE & ACETOXY GROUP IS THEN DISPLACED BY REACTION WITH 5-METHYL-1,3,4-THIADIAZOLE-2-THIOL IN BUFFER SOLN. ...IS ISOLATED AS CEFAZOLIN (ACID) & CONVERTED TO SODIUM SALT WITH SODIUM BICARBONATE. /CEFAZOLIN SODIUM SALT/

Formulations/Preparations · 2 items

Trade Name ... Kefzol, Zolicef /From table/

Parenteral: For injection: 500 mg (of cefazolin) Ancef, (GlaxoSmithKline), Cefazolin Sodium for Injection, (American Pharmaceutical Partners), Cefazolin Sodium for Injection, (Sandoz); 1 g (of cefazolin) Ancef, (GlaxoSmithKline), Cefazolin Sodium for Injection, (American Pharmaceutical Partners), Cefazolin Sodium for Injection, (Sandoz); 10 g (of cefazolin) pharmacy bulk package Ancef, (GlaxoSmithKline), Cefazolin Sodium for Injection, (American Pharmaceutical Partners), Cefazolin Sodium for Injection, (Sandoz); 20 g (of cefazolin) pharmacy bulk package Cefazolin Sodium for Injection, (American Pharmaceutical Partners). For injection,.for IV infusion: 1 g (of cefazolin) Ancef Piggyback, (Abbott), Cefazolin Sodium ADD-Vantage ( with 0.04% polysorbate 80), (Abbott), Cefazolin Sodium for Injection Piggyback, (American Pharmaceutical Partners), Cefazolin Sodium for Injection Piggyback, (Sandoz). /Cefazolin sodium/

General Manufacturing InformationSemi-synthetic antibiotic derived from 7-aminocephalosporanic acid, ... South African patent 6804513 corresponds to US patent 3516997 (1969, 1970 to Fujisawa).
Applications · 3 items

DescriptionCefazolin 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.

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

UsesAntibacterial (systemic).

Upstream & downstream products

Upstream raw materials

1-Phenyltetrazole-5-thiol2-Mercapto-5-methyl-1,3,4-thiadiazole1H-Tetrazole-1-acetic acid7-(5-amino-5-carboxyvaleramido)cephalosporanic acid1H-Tetrazole-1-acetyl chlorideSodium hydroxide5-Methyl-1,3-benzenediacetonitrile7-Aminocephalosporanic acidSodium bicarbonate

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
武汉鹏垒生物科技有限公司15871464247 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
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湖北威德利化学试剂有限公司17771473825 13385289472 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]
杭州鼎燕化工有限公司0571-87157530-8003 18049756717 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941 · [email protected]
湖北辰心化工有限公司17362916295 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]

Additional notes

DefinitionChEBI: A cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups.

For more Non-Human Toxicity Excerpts (Complete) data for CEFAZOLIN (6 total), please visit the HSDB record page.