Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H18N6O8S3 |
| Molecular Weight | 542.566 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H](C(=O)N[C@H]1[C@H]2SCC(CSC3=NN=NN3CS(O)(=O)=O)=C(N2C1=O)C(O)=O)C4=CC=CC=C4
InChI
InChIKey=DYAIAHUQIPBDIP-AXAPSJFSSA-N
InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1
| Molecular Formula | C18H18N6O8S3 |
| Molecular Weight | 542.566 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Cefonicid is a semi-synthetic broad-spectrum cephalosporin antibiotic resistant to beta-lactamases. Similarly to other cephalosporins, cefonicid exerts its antibacterial activity through the inhibition of the bacterial cell-wall synthesis. Its in vitro and in vivo activity against a wide range of Gram-positive and Gram-negative microorganisms is documented.
CNS Activity
Originator
Sources: http://www.google.ch/patents/US4048311
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/cefonicid.html
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6376452 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MONOCID Approved UseTreatment of serious bacterial infections caused by microorganisms susceptible to
cefonicid.
Studies on specimens obtained prior to therapy should be used to determine the
susceptibility of the causative organisms to cefonicid. Therapy with cefonicid may be
initiated pending results of the studies; however, treatment should be adjusted
according to study findings.
CEFONICID TEVA is indicated in the treatment of the infections of the lower
respiratory tract, urinary tract, skin and skin structure, bone and joints. In the
treatment of the above-mentioned infections, the product is particularly used in weak
and/or immuno-depressed patients.
Surgical Prophylaxis:
The administration of a single 1 g dose of CEFONICID TEVA before
surgery may reduce the incidence of post-operative infections, caused by
susceptible microorganisms, in patients undergoing surgical procedures
classified as contaminated or potentially contaminated, or in patients in whom
infection at the operative site would present a serious risk; providing
protection during all the surgery period and for about 24 hours following
administration.
Supplementary doses of CEFONICID TEVA may be administered for two additional
days to patients undergoing prosthetic arthroplasty.
In cesarean section, the intra-operative administration of CEFONICID TEVA (after
the umbilical cord has been clamped) reduces the incidence of post-operative sepsis. Launch Date1984 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
213 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2917594 |
50 mg/kg bw single, intramuscular dose: 50 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
127 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8340557 |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.11 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2917594 |
50 mg/kg bw single, intramuscular dose: 50 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
1644 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8340557 |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2917594 |
50 mg/kg bw single, intramuscular dose: 50 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
|
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8340557 |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFONICID serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g single, intramuscular |
unhealthy, 19 - 88 years Health Status: unhealthy Age Group: 19 - 88 years Sex: M+F Sources: |
|
1 g single, intravenous |
unhealthy, 19 - 88 years Health Status: unhealthy Age Group: 19 - 88 years Sex: M+F Sources: |
|
50 mg/kg single, intramuscular Dose: 50 mg/kg Route: intramuscular Route: single Dose: 50 mg/kg Sources: |
unhealthy, 36 -142 months Health Status: unhealthy Age Group: 36 -142 months Sex: M+F Sources: |
|
2 g 2 times / day single, intravenous Highest studied dose Dose: 2 g, 2 times / day Route: intravenous Route: single Dose: 2 g, 2 times / day Sources: |
unhealthy, 59.9 ± 10.74 years Health Status: unhealthy Age Group: 59.9 ± 10.74 years Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of a rabbit osteoporosis model induced by ovariectomy and glucocorticoid. | 2010-06 |
|
| Characteristics of microorganisms cultured from infected wounds post-hysterectomy. | 2008-12 |
|
| Empiric treatment with once-daily cefonicid and gentamicin for febrile non-neutropenic pediatric cancer patients with indwelling central venous catheters. | 2008-07 |
|
| Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter. | 2008-06-17 |
|
| Immobilization of the acylase from Escherichia coli on glyoxyl-agarose gives efficient catalyst for the synthesis of cephalosporins. | 2008-01 |
|
| Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst. | 2007-12 |
|
| Severe anaphylaxis to royal jelly attributed to cefonicid. | 2007 |
|
| Solid-state chemistry and particle engineering with supercritical fluids in pharmaceutics. | 2006-03 |
|
| Immediate allergic reactions to cephalosporins: evaluation of cross-reactivity with a panel of penicillins and cephalosporins. | 2006-02 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Is prophylactic antimicrobial treatment necessary after hypospadias repair? | 2004-06 |
|
| Analysis of genetic relationships and antimicrobial susceptibility of Escherichia coli isolated from Clethrionomys glareolus. | 2003-12 |
|
| Determination of cefonicid in human urine by adsorptive square-wave stripping voltammetry. | 2003-04-10 |
|
| Impact of drug policy on the use of parenteral cephalosporins in Italy. | 2002-10 |
|
| Eosinophilic hepatitis associated with cefonicid therapy. | 2001-12 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001-11 |
|
| Ertapenem: a new carbapenem. | 2001-06 |
|
| The hematologic effects of cefonicid and cefazedone in the dog: a potential model of cephalosporin hematotoxicity in man. | 1987-08 |
Patents
Sample Use Guides
The usual adult dosage is 1 g CEFONICID administered once every 24 hours, intravenously or by deep intramuscular injection. Daily doses higher
than 1 g are rarely necessary. However, in exceptional cases, doses up to 2 g given once daily have been well tolerated. In case of administration of 2 g I.M. once daily, half the dose should be administered in different large muscle masses.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3752979
The MIC50 and MIC90 for the 60 strains of viridans group streptococci isolated from blood of patients with bacteremia and infective endocarditis were 4 and 32 micrograms/ml for cefonicid.
| Substance Class |
Chemical
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