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Cefaclor

Cefaclor structure

CAS No:
53994-73-3
Formula:
C15H14ClN3O4S
Chemical Name:
Cefaclor
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[(aminophenylacetyl)amino]-3-chloro-8-oxo-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-aminophenylacetyl]amino]-3-chloro-8-oxo-,(6R,7R)-;(6R,7R)-7-[[(2R)-2-Amino-2-phenylacetyl]amino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-(D-2-Amino-2-phenylacetamido)-3-chloro-3-cephem-4-carboxylic acid;Cefaclor;Lilly 99638;Panoral;Kefral;S 6472;Cephaclor;Ceclor;Alfacet;Distaclor;Raniclor;Ceclor MR;Losefar;142975-47-1;2222357-79-9
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefaclor, is a second-generation cephalosporin antibiotic used to treat certain infections caused by bacteria such as pneumonia and infections of the ear, lung, skin, throat, and urinary tract.Target: AntibacterialCefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary tract infections, peritonitis, and urinary tract infection

Solid

Cefaclor is a cephalosporin bearing chloro and (R)-2-amino-2-phenylacetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug and a drug allergen.|Semisynthetic, broad-spectrum antibiotic derivative of cephalexin.|Cefaclor anhydrous is a Cephalosporin Antibacterial.|Cefaclor Anhydrous is the anhydrous form of cefaclor, a beta-lactam, second-generation cephalosporin with antibacterial activity. Cefaclor binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. 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.|Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.

Cefaclor Basic Attributes

Molecular Weight：

367.81

Exact Mass：

367.81

EC Number：

258-909-5

UNII：

3Z6FS3IK0K

NSC Number：

757422

DSSTox ID：

DTXSID3022748

NCI Thesaurus Code：

C76033

ATC Code：

J - Antiinfectives for systemic use

HScode：

29349990

Characteristics

PSA：

138

XLogP3：

-1.8

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Melting Point：

327 °C

Boiling Point：

692.7°C at 760 mmHg

Flash Point：

385.2±32.9 °C

Refractive Index：

1.722

Water Solubility：

H2O: 10g/L(temperature not stated);1 M HCl: 50 mg/mL, clear to very faintly turbid, yellow

Toxicity：

TDLo orl-cld: 131 mg/kg/7D-I:MSK,SKN CMAJAX 126,1032,82

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

42/43

safety instructions：

22-36/37-45

RTECS Number：

XI0363000

Marks：

Xn,Xi

Precautionary statement(s)：

P261-P280-P342 + P311

Hazard Statements：

H317-H334

GHS Classification：

|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 80 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.

Protein Binding：

23.5%

Drug Information

Drug Indication：

For the treatment of certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections.|FDA Label

Pharmacology：

Cefaclor is a second generation cephalosporin antibiotic with a spectrum resembling first-generation cephalosporins. In vitro tests demonstrate that the bactericidal action of the cephalosporins results from inhibition of cell-wall synthesis. As indicated by _in vitro_ and _in vivo_ clinical studies, cefaclor was shown to be effective against most strains of Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, Streptococcus pyogenes (group A ß-hemolytic streptococci), as well as Gram-negative aerobes - Escherichia coli, Haemophilus influenzae (including ß-lactamase-producing ampicillin-resistant strains), Klebsiella sp, and Proteus mirabilis.

MeSH：

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

Absorption：

Well absorbed after oral administration, independent of food intake.|Approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours, the greater portion being excreted within the first 2 hours.

Metabolism/Metabolites：

No appreciable biotransformation in liver (approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours).

Biological Half-Life：

0.6-0.9 hour

Mechanism of Action：

Cefaclor, like the penicillins, is a beta-lactam antibiotic. 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. It is possible that cefaclor interferes with an autolysin inhibitor.

MeSH Entry Terms：

5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-chloro-8-oxo-, (6R-(6alpha,7beta(R*)))-

Cefaclor Use and Manufacturing

Methods of Manufacturing

It is prepared by reacting p-nitrobenzyl-7-amino-3-chloro-3-cephalosporin-4-carboxylate with ozone, dichlorosulfoxide and 2-aminophenylacetic acid.

Uses

radioopaque agent

Use Classification：

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

Computed Properties

Molecular Weight:367.8
XLogP3:-1.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:367.0393548
Monoisotopic Mass:367.0393548
Topological Polar Surface Area:138
Heavy Atom Count:24
Complexity:606
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

(6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Thionyl chloride

Price Analysis

Make your Cefaclor purchase based on the price and market insights! ECHEMI provides professional market insights with prices for you to make a better choice. Learn more on Cefaclor prices .

Drug Function and Efficacy

Antibacterial drug. It is relatively stable against the β-lactamase produced by Staphylococcus aureus, so it has a strong antibacterial effect against Gram-positive bacteria; it is unstable against the β-lactamase produced by Gram-negative bacteria, so it has a weaker effect against Gram-negative bacteria, and is ineffective against Pseudomonas aeruginosa and anaerobic bacteria.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Cefaclor Capsules
Ingredients	Main ingredient: Cefaclor
Indication	1. Furosemide, ethacrynic acid, bumetanide and other strong diuretics, carmustine, streptozocin and other antineoplastic drugs and aminoglycoside antibiotics and other nephrotoxic drugs combined with this product may increase nephrotoxicity. 2. Clavulanic acid can enhance the antibacterial activity of this product against certain Gram-negative bacteria that are resistant to this product due to the production of lactamase. 3. Oral administration of probenecid can delay the excretion of this product.
Specifications	0.25 g (calculated as C15H14ClN3O4S)
Manufacturer	Haikou Pharmaceutical Factory Co., Ltd.

Cefaclor Tablets
Ingredients	Cefaclor
Indication	1. Furosemide, ethacrynic acid, bumetanide and other strong diuretics, carmustine, streptozocin and other antineoplastic drugs and aminoglycoside antibiotics and other nephrotoxic drugs combined with this product may increase nephrotoxicity. 2. Clavulanic acid can enhance the antibacterial activity of this product against certain Gram-negative bacteria that are resistant to this product due to the production of beta-lactamase. 3. Oral administration of probenecid can delay the excretion of this product.
Specifications	0.25g
Manufacturer	ShenZhen Lijian Pharmaceutical Co., Ltd.

Cefaclor Capsules
Ingredients	The main ingredient of this product is: cefaclor.
Indication	Not yet clear.
Manufacturer	Yunnan HAOPY Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Biobetta Pharmaceuticals (Shanghai) Co., Ltd.

China
Active
Indian Lamberti Laboratories Limited Beijing Representative Office

China
Active
Rubin India Limited Shanghai Representative Office

China
Active

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