CEFORANIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H21N7O6S2
Molecular Weight	519.554
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=NN3CC(O)=O)=C(N1C(=O)[C@H]2NC(=O)CC4=C(CN)C=CC=C4)C(O)=O

InChI

InChIKey=SLAYUXIURFNXPG-CRAIPNDOSA-N

InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H21N7O6S2
Molecular Weight	519.554
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6762529
Curator's Comment: description was created based on several sources, including: http://www.druginfosys.com/drug.aspx?drugcode=845 | http://erx.gr/p/z/?type=pl&bcode=2801821902010 | http://www.medindia.net/doctors/drug_information/cefoperazone_sodium_injection.htm

Ceforanide is a new cephalosporin with a longer elimination half-life than any currently available cephalosporin. Its activity is very similar to that of cefamandole, a second-generation cephalosporin, except that ceforanide is less active against most gram-positive organisms. The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Ceforanide is primarily indicated in conditions like bone and joint infection, endocarditis, respiratory tract infections, skin infections, surgical infections, urinary tract infection. Rash and pruritus, and nausea, vomiting and other mild gastrointestinal side effects were noted in a few of the subjects but were mild and transient.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.druglib.com/activeingredient/ceforanide/	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Bone and joint infections 27 Sources: http://www.druginfosys.com/drug.aspx?drugcode=845	Curative	Approved 8429	RADACEF Approved Use Ceforanide is primarily indicated in conditions like Bone and joint infection, Endocarditis, Respiratory tract infections, Skin infections, Surgical infections, Urinary tract infection.
Endocarditis 16 Sources: http://www.druginfosys.com/drug.aspx?drugcode=845	Curative	Approved 8429	RADACEF Approved Use Ceforanide is primarily indicated in conditions like Bone and joint infection, Endocarditis, Respiratory tract infections, Skin infections, Surgical infections, Urinary tract infection.
Respiratory tract infections 85 Sources: http://www.druginfosys.com/drug.aspx?drugcode=845	Curative	Approved 8429	RADACEF Approved Use Ceforanide is primarily indicated in conditions like Bone and joint infection, Endocarditis, Respiratory tract infections, Skin infections, Surgical infections, Urinary tract infection.
Skin infections 59 Sources: http://www.druginfosys.com/drug.aspx?drugcode=845	Curative	Approved 8429	RADACEF Approved Use Ceforanide is primarily indicated in conditions like Bone and joint infection, Endocarditis, Respiratory tract infections, Skin infections, Surgical infections, Urinary tract infection.
Urinary tract infections 205 Sources: http://www.druginfosys.com/drug.aspx?drugcode=845	Curative	Approved 8429	RADACEF Approved Use Ceforanide is primarily indicated in conditions like Bone and joint infection, Endocarditis, Respiratory tract infections, Skin infections, Surgical infections, Urinary tract infection.
Sepsis 71 Sources: http://erx.gr/p/z/?type=pl&bcode=2801821902010	Curative	Approved 8429	RADACEF Approved Use Ceforanide is indicated for the treatment of Bacteremia

C_max

Value	Dose	Analyte	Population
39 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
21 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intramuscular dose: 250 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
71 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
38 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intramuscular dose: 500 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intramuscular dose: 1000 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
135 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1.28 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
120 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intramuscular dose: 250 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
227 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
241 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intramuscular dose: 500 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
393 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intramuscular dose: 1000 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
398 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	250 mg single, intramuscular dose: 250 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.89 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	500 mg single, intramuscular dose: 500 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intramuscular dose: 1000 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7073268	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	CEFORANIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 mg/kg 3 times / day steady, intramuscular Highest studied dose Dose: 15 mg/kg, 3 times / day Route: intramuscular Route: steady Dose: 15 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6634466	unhealthy, 1 month - 17 years n = 1 Health Status: unhealthy Condition: childhood infections Age Group: 1 month - 17 years Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6634466	Sources: https://pubmed.ncbi.nlm.nih.gov/6634466
4 g 2 times / day multiple, intravenous Highest studied dose Dose: 4 g, 2 times / day Route: intravenous Route: multiple Dose: 4 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/526003	healthy, 21 - 35 years n = 7 Health Status: healthy Age Group: 21 - 35 years Sex: M Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/526003	Disc. AE: Localized rash... AEs leading to discontinuation/dose reduction: Localized rash (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/526003
4 g single, intravenous Highest studied dose Dose: 4 g Route: intravenous Route: single Dose: 4 g Sources: https://pubmed.ncbi.nlm.nih.gov/526003	healthy, 21 - 35 years n = 7 Health Status: healthy Age Group: 21 - 35 years Sex: M Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/526003	Sources: https://pubmed.ncbi.nlm.nih.gov/526003

AEs

AE	Significance	Dose	Population
Localized rash	1 patient Disc. AE	4 g 2 times / day multiple, intravenous Highest studied dose Dose: 4 g, 2 times / day Route: intravenous Route: multiple Dose: 4 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/526003	healthy, 21 - 35 years n = 7 Health Status: healthy Age Group: 21 - 35 years Sex: M Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/526003

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3495	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3495
ChemicalBook	CB2501637	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2501637
MolPort	MolPort-006-167-662	https://www.molport.com/shop/molecule-link/MolPort-006-167-662
ZINC	ZINC000003830434	http://zinc15.docking.org/substances/ZINC000003830434
eMolecules	32452414	https://www.emolecules.com/cgi-bin/more?vid=32452414

PubMed

Title	Date	PubMed
Ceforanide: antibacterial activity, pharmacology, and clinical efficacy.	1982 Nov-Dec	6762529
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.	1985 Jan	3920957
Treatment of scleroma with ceforanide.	1987 Apr	3814386
Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy.	1987 Oct	3315624
Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages.	1988 Mar	3140456
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.	1988 Sep	3143305
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.	1995 Apr	7624446
The pharmacokinetics of the interstitial space in humans.	2003 Jul 30	12890292
Primary lymphocutaneous nocardiosis in an immunocompetent patient.	2004 Nov 15	15544704
Chemoprophylactic and bactericidal efficacy of 80 mg gentamicin in a single and once-daily dosing.	2005 Sep	15605270
Prophylactic antibiotics for burns patients: systematic review and meta-analysis.	2010 Feb 15	20156911

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 2-4 g/day in 2 divided doses, up to 12 g/day for severe infections.

Route of Administration: Other

In Vitro Use Guide

Ceforanide at 4 ug/ml, inhibited 62 strains and, at 8 ug/ml, all 63 strains of S. aureus. Furthermore, Ceforanide inhibited all strains of S. pneumoniae at 0.25 ug/ml, all strains of S. pyogenes at 0.5 ug/ml, and all strains of S. viridans at 4 ug/ml.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:15:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:34 GMT 2023`
Record UNII	8M1YF8951V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFORANIDE

Official Name

English

7-(O-(AMINOMETHYL)PHENYLACETAMIDO)-3-(((1-(CARBOXYMETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-3-CEPHEM-4-CARBOXYLIC ACID

Common Name

English

CEFORANIDE [USP-RS]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-(AMINOMETHYL)PHENYL)ACETYL)AMINO)-3-(((1-(CARBOXYMETHYL)-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, (6R-TRANS)-

Common Name

English

ceforanide [INN]

Common Name

English

CEFORANIDE [USAN]

Common Name

English

(6R,7R)-7-[2-(α-Amino-O-tolyl)acetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Common Name

English

NSC-760049

Code

English

CEFORANIDE [ORANGE BOOK]

Common Name

English

Ceforanide [WHO-DD]

Common Name

English

CEFORANIDE [MI]

Common Name

English

BL-S786

Code

English

PRECEF

Brand Name

English

CEFORANIDE [USP IMPURITY]

Common Name

English

CEFORANIDE [MART.]

Common Name

English

CEFORANIDE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01DC11