Cefotetan - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Carriers (1)

Targets (1)Carriers (1)Biointeractions (1)

Identification

Name

Cefotetan

Accession Number

DB01330

Type

Small Molecule

Groups

Approved

Description

A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms. [PubChem]

Structure

MOL SDF PDB SMILES InChI

Synonyms

(6R,7S)-7-(4-(Carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5- yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid

Cefotetanum

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Cefotetan disodium	0GXP746VXB	74356-00-6	ZQQALMSFFARWPK-GLHLDKNHSA-L	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cefotan	Injection, powder, for solution	2 g/20mL	Intramuscular; Intravenous	Teligent Pharma, Inc.	2015-10-01	Not applicable	US
Cefotan	Injection, powder, for solution	1 g/10mL	Intramuscular; Intravenous	Teligent Pharma, Inc.	2015-10-01	Not applicable	US
Cefotan Inj 2gm/vial	Powder, for solution	2 g	Intramuscular; Intravenous	Ayerst Laboratories	1990-12-31	1996-09-10	Canada
Cefotan Injection - 1g	Powder, for solution	1 g	Intramuscular; Intravenous	Wyeth Ltd.	1994-12-31	2006-08-04	Canada
Cefotan Injection - 2 G	Powder, for solution	2 g	Intramuscular; Intravenous	Wyeth Ltd.	1994-12-31	2006-08-04	Canada
Cefotetan and Dextrose	Injection, solution	1 g/50mL	Intravenous	B. Braun Medical Inc.	2010-08-20	Not applicable	US
Cefotetan and Dextrose	Injection, solution	2 g/50mL	Intravenous	B. Braun Medical Inc.	2010-08-20	Not applicable	US

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cefotetan	Injection, powder, for solution	10 g/1	Intravenous	Fresenius Kabi	2009-12-03	Not applicable	US
Cefotetan	Injection, powder, for solution	1 g/10mL	Intramuscular; Intravenous	Fresenius Kabi	2009-11-18	Not applicable	US
Cefotetan	Injection, powder, for solution	2 g/20mL	Intramuscular; Intravenous	Fresenius Kabi	2009-11-18	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Cefotan	Not Available
Yamatetan	Not Available

Brand mixtures

Not Available

Categories

UNII

48SPP0PA9Q

CAS number

69712-56-7

Weight

Average: 575.619
Monoisotopic: 575.002143315

Chemical Formula

C₁₇H₁₇N₇O₈S₄

InChI Key

SRZNHPXWXCNNDU-IXOPCIAXSA-N

InChI

InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1

IUPAC Name

(6R,7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-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][[email protected]]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[[email protected]]2(NC(=O)C1SC(S1)=C(C(N)=O)C(O)=O)OC)C(O)=O

Pharmacology

Indication

For prophylaxis and treatment of bacterial infections.

Structured Indications

Pharmacodynamics

Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

Mechanism of action

The bactericidal action of cefotetan results from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Penicillin-binding protein 3	Protein	yes	inhibitor	Streptococcus pneumoniae	Q75Y35	details

Absorption

Not Available

Volume of distribution

10.4 L [elderly patients (greater than 65 years) with normal renal function]
10.3 L [healthy volunteers (aged 25 to 28 years)]

Protein binding

Cefotetan is 88% plasma protein bound.

Metabolism

Route of elimination

No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.

Half life

In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged

Clearance

1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]
1.8 +/- 0.3 L/h [healthy volunteers (aged 25 to 28 years)]

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Acenocoumarol	Cefotetan may increase the anticoagulant activities of Acenocoumarol.	Approved
BCG vaccine	The therapeutic efficacy of Bcg can be decreased when used in combination with Cefotetan.	Investigational
Carbocisteine	The risk or severity of adverse effects can be increased when Cefotetan is combined with Carbocisteine.	Approved
Dicoumarol	Cefotetan may increase the anticoagulant activities of Dicoumarol.	Approved
Ethanol	The risk or severity of adverse effects can be increased when Cefotetan is combined with Ethanol.	Approved
Ethyl biscoumacetate	Cefotetan may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Fluindione	Cefotetan may increase the anticoagulant activities of Fluindione.	Investigational
Phenindione	Cefotetan may increase the anticoagulant activities of Phenindione.	Approved
Phenprocoumon	Cefotetan may increase the anticoagulant activities of Phenprocoumon.	Approved
Picosulfuric acid	The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefotetan.	Approved
Probenecid	The serum concentration of Cefotetan can be increased when it is combined with Probenecid.	Approved
Warfarin	Cefotetan may increase the anticoagulant activities of Warfarin.	Approved

Food Interactions

Avoid alcohol as it can cause a disulfiram effect.

References

Synthesis Reference

Maurizio Zenoni, "Process for obtaining compounds usable in the production of Cefotetan, and new compounds obtained thereby." U.S. Patent US20020169327, issued November 14, 2002.

US20020169327

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15425
KEGG Drug	D00260
KEGG Compound	C06886
PubChem Compound	53025
PubChem Substance	46506572
ChemSpider	47904
BindingDB	80643
ChEBI	3499
ChEMBL	CHEMBL474579
Therapeutic Targets Database	DAP000451
PharmGKB	PA164784033
Drug Product Database	1225
RxList	http://www.rxlist.com/cgi/generic/cefotet.htm
Drugs.com	http://www.drugs.com/cdi/cefotetan.html
Wikipedia	Cefotetan

ATC Codes

J01DC05 — Cefotetan

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (275 KB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Treatment	Osteomyelitis	1
2	Completed	Treatment	Surgery, Colorectal	1
3	Completed	Prevention	Surgery, Colorectal	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Injection, powder, for solution	Intramuscular; Intravenous	1 g/10mL
Injection, powder, for solution	Intramuscular; Intravenous	2 g/20mL
Powder, for solution	Intramuscular; Intravenous	2 g
Powder, for solution	Intramuscular; Intravenous	1 g
Injection, powder, for solution	Intravenous	10 g/1
Injection, solution	Intravenous	1 g/50mL
Injection, solution	Intravenous	2 g/50mL

Prices

Unit description	Cost	Unit
Cefotetan 2 gm vial	27.31USD	vial
Cefotetan-dextr 2 g duplex bag	25.14USD	each
Cefotetan-dextr 1 g duplex bag	17.58USD	each
Cefotetan 1 gm vial	13.66USD	vial

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.521 mg/mL	ALOGPS
logP	-0.65	ALOGPS
logP	-0.38	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	219.93 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	153.55 m³·mol^-1	ChemAxon
Polarizability	51.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	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	-	0.9451
Blood Brain Barrier	-	0.9903
Caco-2 permeable	-	0.799
P-glycoprotein substrate	Substrate	0.7418
P-glycoprotein inhibitor I	Non-inhibitor	0.8992
P-glycoprotein inhibitor II	Non-inhibitor	0.7207
Renal organic cation transporter	Non-inhibitor	0.9032
CYP450 2C9 substrate	Non-substrate	0.8489
CYP450 2D6 substrate	Non-substrate	0.8219
CYP450 3A4 substrate	Non-substrate	0.5
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8308
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6374
Ames test	Non AMES toxic	0.7712
Carcinogenicity	Non-carcinogens	0.9274
Biodegradation	Not ready biodegradable	0.9081
Rat acute toxicity	1.7915 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9933
hERG inhibition (predictor II)	Non-inhibitor	0.7103

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as cephamycins. These are compounds containing a the cephalosporin (oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid) nucleus, with an alkyloxy group attached to the C6 carbon atom.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Lactams

Direct Parent

Cephamycins

Alternative Parents

N-acyl-alpha amino acids and derivatives / Alkylarylthioethers / Vinylogous thioesters / 1,3-thiazines / Dicarboxylic acids and derivatives / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Secondary carboxylic acid amides

Substituents

Cephamycin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Aryl thioether / Alkylarylthioether / Meta-thiazine / Dicarboxylic acid or derivatives / Vinylogous thioester / Azole / Heteroaromatic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3499 )

Targets

Details

1. Penicillin-binding protein 3

Kind: Protein
Organism: Streptococcus pneumoniae
Pharmacological action: yes
Actions: inhibitor

General Function:: Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:: Not Available
Gene Name:: pbp3
Uniprot ID:: Q75Y35
Uniprot Name:: Penicillin-binding protein 3
Molecular Weight:: 45209.84 Da

References

Nolan RD, Jude DA: The interactions of [14C]cefotetan with penicillin binding proteins of a wide variety of Gram-positive and gram-negative species. J Antimicrob Chemother. 1983 Jan;11 Suppl:169-77. [PubMed:6573313 ]

Carriers

Details

1. Serum albumin

Kind: Protein
Organism: Human
Pharmacological action: no

General Function:: Toxic substance binding
Specific Function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:: ALB
Uniprot ID:: P02768
Uniprot Name:: Serum albumin
Molecular Weight:: 69365.94 Da

References

Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [PubMed:2311445 ]
Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510 ]

Drug created on June 30, 2007 11:52 / Updated on September 01, 2017 10:38

Structure for DB01330 (Cefotetan)

Targets

References

Carriers

References