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Cefadroxil

Cefadroxil structure

CAS No:
50370-12-2
Formula:
C16H17N3O5S
Chemical Name:
Cefadroxil
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-,(6R,7R)-;(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;Cefadroxil;BL-S 578;Oracefal;Bidocef;S 578;Cephadroxil;D-Cefadroxil;Ultracef;Roxil;Cefadur;Cipadur;Evacef;Neucef;Helicef;Sumacef;Cefadrox;Ibidroxil
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections.

Solid

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-).|Long-acting, broad-spectrum, water-soluble, cephalexin derivative.|Cefadroxil anhydrous is a Cephalosporin Antibacterial.|Cefadroxil Anhydrous is the anhydrous form of cefadroxil, a semisynthetic first-generation cephalosporin with antibacterial activity. Cefadroxil binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.|Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.

Cefadroxil Basic Attributes

Molecular Weight：

363.39

Exact Mass：

363.39

EC Number：

256-555-6

UNII：

Q525PA8JJB

NSC Number：

756664

DSSTox ID：

DTXSID8022749

NCI Thesaurus Code：

C79562

ATC Code：

J01DB05|J - Antiinfectives for systemic use

HScode：

2941905990

Characteristics

PSA：

158

XLogP3：

-2.1

Density：

1.6±0.1 g/cm3

Melting Point：

197 °C

Boiling Point：

789.9°C at 760 mmHg

Flash Point：

431.5±32.9 °C

Refractive Index：

1.728

Water Solubility：

3.99e-01 g/L

Collision Cross Section：

183.1 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|188.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|187.7 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|183.31 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-42/43

safety instructions：

26-36

RTECS Number：

XI0337000

Marks：

Precautionary statement(s)：

P261-P280-P305 + P351 + P338-P342 + P311

Hazard Statements：

H315-H317-H319-H334-H335

GHS Classification：

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 63 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Nausea, vomiting, diarrhoea, allergic rashes may occur

Protein Binding：

Binding rates of cefadroxil were 28.1% by U.F. method

Drug Information

Drug Indication：

For the treatment of the following infections (skin, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staphylococci and Streptococcus pyogenes|FDA Label

Pharmacology：

Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

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.

Biological Half-Life：

1.5 hours

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.

MeSH Entry Terms：

4 Hydroxycephalexin

Cefadroxil Use and Manufacturing

Uses

Antibacterial;Bacterialtranspeptidase inhibitor

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:363.4
XLogP3:-2.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:363.08889182
Monoisotopic Mass:363.08889182
Topological Polar Surface Area:158
Heavy Atom Count:25
Complexity:629
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Cephadroxil Powder CAS 50370-12-2 Cefadroxil Monohydrate

CAS No.: 50370-12-2

Grade: Pharmaceutical Grade

Content: 99%

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