Ceforanide is administered parenterally. It has a longer elimination half-life than any currently available cephalosporin. Its activity is very similar to that of cefamandole, another second-generation cephalosporin antibiotic, except that ceforanide is less active against most gram-positive organisms. Many coliforms, including Escherichia coli, Klebsiella, Enterobacter, and Proteus, are susceptible to ceforanide, as are most strains of Salmonella, Shigella, Hemophilus, Citrobacter and Arizona species.

Structure

Similar Structures

Synonyms

(6R,7R)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-[O-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1H-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acid
7β-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1H-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acid
Ceforanide
Ceforanido
Ceforanidum

External IDs

BL-S786

International/Other Brands

Precef

Categories

UNII

8M1YF8951V

CAS number

60925-61-3

Weight

Average: 519.554
Monoisotopic: 519.099472819

Chemical Formula

C₂₀H₂₁N₇O₆S₂

InChI Key

SLAYUXIURFNXPG-CRAIPNDOSA-N

InChI

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

IUPAC Name

(6R,7R)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(CSC3=NN=NN3CC(O)=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1CN)C(O)=O

Pharmacology

Indication

For the treatment of infections caused by susceptible organisms.

Pharmacodynamics

Ceforanide is a semisynthetic second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins.

Mechanism of action

The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

Target	Actions	Organism
APenicillin-binding protein 2	inhibitor	Bacteroides fragilis

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Rapidly absorbed following intramuscular injection.

Volume of distribution

Not Available

Protein binding

80.6%

Metabolism

The major drug elimination route was urinary excretion with 85% of the dose being excreted unchanged in the urine within 12 hr, and no metabolites with antibiotic activity were observed in urine.

Route of elimination

Not Available

Half life

2.6 to 2.98 hours

Clearance

Not Available

Toxicity

Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
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(R)-warfarin	The risk or severity of bleeding can be increased when Ceforanide is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of bleeding can be increased when Ceforanide is combined with (S)-Warfarin.
4-hydroxycoumarin	The risk or severity of bleeding can be increased when Ceforanide is combined with 4-hydroxycoumarin.
Abacavir	Ceforanide may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Ceforanide.
Acarbose	Ceforanide may decrease the excretion rate of Acarbose which could result in a higher serum level.
Aceclofenac	Ceforanide may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
Acemetacin	The risk or severity of nephrotoxicity can be increased when Ceforanide is combined with Acemetacin.
Acenocoumarol	The risk or severity of bleeding can be increased when Ceforanide is combined with Acenocoumarol.
Acetaminophen	Ceforanide may decrease the excretion rate of Acetaminophen which could result in a higher serum level.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

Evidence Level

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

General References

Crowle AJ, Sbarbaro JA, May MH: Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages. Tubercle. 1988 Mar;69(1):15-25. [PubMed:3140456]
Campoli-Richards DM, Lackner TE, Monk JP: Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy. Drugs. 1987 Oct;34(4):411-37. [PubMed:3315624]
Cone LA, Barton SM, Woodard DR: Treatment of scleroma with ceforanide. Arch Otolaryngol Head Neck Surg. 1987 Apr;113(4):374-6. [PubMed:3814386]
Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. [PubMed:6762529]

External Links

Human Metabolome Database: HMDB0015059
KEGG Drug: D00259
KEGG Compound: C06884
PubChem Compound: 43507
PubChem Substance: 46504532
ChemSpider: 39656
ChEBI: 3495
ChEMBL: CHEMBL1201046
Therapeutic Targets Database: DAP001175
PharmGKB: PA164746057
Wikipedia: Ceforanide

ATC Codes

J01DC11 — Ceforanide

Clinical Trials

Clinical Trials: Not Available

Pharmacoeconomics

Manufacturers

Apothecon inc div bristol myers squibb
Bristol laboratories inc div bristol myers co

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	-3.7	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.197 mg/mL	ALOGPS
logP	-1.4	ALOGPS
logP	-3.2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	193.63 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	139.87 m³·mol^-1	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.5918
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.7463
P-glycoprotein substrate	Substrate	0.7962
P-glycoprotein inhibitor I	Non-inhibitor	0.8318
P-glycoprotein inhibitor II	Non-inhibitor	0.9607
Renal organic cation transporter	Non-inhibitor	0.7981
CYP450 2C9 substrate	Non-substrate	0.8253
CYP450 2D6 substrate	Non-substrate	0.8124
CYP450 3A4 substrate	Non-substrate	0.5421
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8308
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.577
Ames test	Non AMES toxic	0.6325
Carcinogenicity	Non-carcinogens	0.8446
Biodegradation	Not ready biodegradable	0.8569
Rat acute toxicity	2.3203 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9112
hERG inhibition (predictor II)	Non-inhibitor	0.7227

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Lactams
Sub Class: Beta lactams
Direct Parent: Cephalosporins
Alternative Parents: N-acyl-alpha amino acids and derivatives / Phenylacetamides / Benzylamines / Phenylmethylamines / Alkylarylthioethers / Aralkylamines / 1,3-thiazines / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Tetrazoles
show 14 more
Substituents: Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenylacetamide / Phenylmethylamine / Aryl thioether / Benzylamine / Alkylarylthioether / Aralkylamine / Meta-thiazine
show 32 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: cephalosporin (CHEBI:3495)

Targets

Details1. Penicillin-binding protein 2

Kind: Protein
Organism: Bacteroides fragilis
Pharmacological action: Yes
Actions: Inhibitor

General Function: Penicillin binding
Specific Function: Not Available
Gene Name: pbpA
Uniprot ID: Q70KI2
Uniprot Name: Penicillin-binding protein 2
Molecular Weight: 69434.305 Da

References

Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. [PubMed:6762529]
Yotsuji A, Mitsuyama J, Hori R, Yasuda T, Saikawa I, Inoue M, Mitsuhashi S: Mechanism of action of cephalosporins and resistance caused by decreased affinity for penicillin-binding proteins in Bacteroides fragilis. Antimicrob Agents Chemother. 1988 Dec;32(12):1848-53. [PubMed:3266730]

Drug created on June 13, 2005 07:24 / Updated on May 09, 2019 00:01

Ceforanide

Identification

Structure for Ceforanide (DB00923)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References