CEFONICID

US Previously Marketed

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

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=NN3CS(O)(=O)=O)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C4=CC=CC=C4)C(O)=O

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

HIDE SMILES / InChI

Description
Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/3767.pdf | https://www.ncbi.nlm.nih.gov/pubmed/3530703

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6376452	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/3767.pdf	Curative		Approved 8429	MONOCID Approved Use Treatment 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 Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
1 g single, intramuscular Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/6395280	unhealthy, 19 - 88 years n = 57 Health Status: unhealthy Age Group: 19 - 88 years Sex: M+F Population Size: 57 Sources: https://pubmed.ncbi.nlm.nih.gov/6395280	Sources: https://pubmed.ncbi.nlm.nih.gov/6395280
1 g single, intravenous Dose: 1 g Route: intravenous Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/6395280	unhealthy, 19 - 88 years n = 57 Health Status: unhealthy Age Group: 19 - 88 years Sex: M+F Population Size: 57 Sources: https://pubmed.ncbi.nlm.nih.gov/6395280	Sources: https://pubmed.ncbi.nlm.nih.gov/6395280
50 mg/kg single, intramuscular Dose: 50 mg/kg Route: intramuscular Route: single Dose: 50 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/2917594	unhealthy, 36 -142 months n = 17 Health Status: unhealthy Condition: respiratory infection \| urinary tract infection Age Group: 36 -142 months Sex: M+F Population Size: 17 Sources: https://pubmed.ncbi.nlm.nih.gov/2917594	Sources: https://pubmed.ncbi.nlm.nih.gov/2917594
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: https://pubmed.ncbi.nlm.nih.gov/8215267	unhealthy, 59.9 ± 10.74 years n = 30 Health Status: unhealthy Condition: Spontaneous bacterial peritonitis Age Group: 59.9 ± 10.74 years Sex: M+F Population Size: 30 Sources: https://pubmed.ncbi.nlm.nih.gov/8215267	Sources: https://pubmed.ncbi.nlm.nih.gov/8215267

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3491	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3491
ChemicalBook	CB5283109	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5283109
ZINC	ZINC000003830428	http://zinc15.docking.org/substances/ZINC000003830428

PubMed

Title	Date	PubMed
The hematologic effects of cefonicid and cefazedone in the dog: a potential model of cephalosporin hematotoxicity in man.	1987 Aug	3629586
Eosinophilic hepatitis associated with cefonicid therapy.	2001 Dec	11793641
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Impact of drug policy on the use of parenteral cephalosporins in Italy.	2002 Oct	12426958
Analysis of genetic relationships and antimicrobial susceptibility of Escherichia coli isolated from Clethrionomys glareolus.	2003 Dec	14747972
Is prophylactic antimicrobial treatment necessary after hypospadias repair?	2004 Jun	15118434
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Severe anaphylaxis to royal jelly attributed to cefonicid.	2007	17694707
Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst.	2007 Dec	17879093
Characteristics of microorganisms cultured from infected wounds post-hysterectomy.	2008 Dec	18775598
Immobilization of the acylase from Escherichia coli on glyoxyl-agarose gives efficient catalyst for the synthesis of cephalosporins.	2008 Jan	22578861
Empiric treatment with once-daily cefonicid and gentamicin for febrile non-neutropenic pediatric cancer patients with indwelling central venous catheters.	2008 Jul	18797200
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.	2008 Jun 17	18452908

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

CEFONICID

Official Name

English

CEFONICID [VANDF]

Common Name

English

Cefonicid [WHO-DD]

Common Name

English

MONOCEF

Brand Name

English

cefonicid [INN]

Common Name

English

CEFONICIDE

Common Name

English

CEFONICID [MI]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2R)-2-HYDROXY-2-PHENYLACETYL)AMINO)-8-OXO-3-(((1-(SULFOMETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-, (6R,7R)-

Common Name

English

(6R,7R)-7-(((2R)-2-HYDROXY-2-PHENYLACETYL)AMINO)-8-OXO-3-(((1-(SULFOMETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

J01DC06