Cefadroxil
Basic information
- CAS
50370-12-2- Standard SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N- Molecular formula
- C16H17N3O5S
- Average molar mass
- 363.4 g/mol
- Monoisotopic mass
- 363.08889182
Overview
Cefadroxil is a cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug. It is a conjugate acid of a cefadroxil(1-).
Names & identifiers
- Preferred name
- Cefadroxil
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- CEFADROXIL
- Molecular formula
- C16H17N3O5S
- Molecular weight
- 363.39
Names & synonyms
cefadroxil50370-12-2CephadroxilCefadroxil anhydrousCefadroxiloCefadroxilumD-CefadroxilDuricefUltracefAnhydrous cefadroxilCefadropsDuracef
Show more names
cdx(6R,7R)-7-[[(R)-Amino(p-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidRoxilEvacefNeucefNSC438
DTXSID8022749BL-S578S-578(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidQ525PA8JJBCHEBI:3479S 578NSC-756664
Database identifiers
- CAS
50370-12-2、66592-87-8- PubChem CID
- 47965
- DTXSID
DTXSID8022749- ChEMBL
CHEMBL1644- ChEBI
CHEBI:3479
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 158 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 629
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics (Cefalosporins)
LogP-0.4
Solubility3.99e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Melting Point197 °C
Physical DescriptionSolid
Collision Cross Section
182.13 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
183.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
187.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
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
Danger
H315 (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 65 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCefadroxil anhydrous: 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.
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-, [6R-[6.alpha.,7.beta.(R*)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
cefadroxil
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Chemistry & industry
Pharmacology
ATC Code
J01DB05
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingBinding rates of cefadroxil were 28.1% by U.F. method
PharmacodynamicsCefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
Mechanism of Action
Like all beta-lactam antibiotics, cefadroxil binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefadroxil interferes with an autolysin inhibitor.
Biological Half-Life1.5 hours
FDA Pharmacological Classification
Q525PA8JJB
CEFADROXIL ANHYDROUS
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefadroxil anhydrous is a Cephalosporin Antibacterial.
CEFADROXIL
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
Over 90% of the drug is excreted unchanged in the urine within 24 hours. Cefadroxil was detected in the placenta and breast milk.
Cellular LocationsMembrane
Related reactions
17 records
Compound notes
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