Jump to section
IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Cefamandole
- Accession Number
- DB01326
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Description
Cefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. It is generally formulated as a formate estercefamandole nafate. It is no longer marketed in the United States.
- Structure
Structure for Cefamandole (DB01326)
- Synonyms
- (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid
- (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefadole
- Cefamandol
- Céfamandole
- Cefamandole
- Cefamandolum
- Cephadole
- Cephamandole
- L-Cefamandole
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataMandol Add-vantage Inj 1gm/vial Powder, for solution Intravenous Eli Lilly & Co. Ltd. 1989-12-31 1998-08-04 Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Second-Generation Cephalosporins
- Sulfur Compounds
- Thiazines
- UNII
- 5CKP8C2LLI
- CAS number
- 34444-01-4
- Weight
- Average: 462.503
Monoisotopic: 462.078009096 - Chemical Formula
- C18H18N6O5S2
- InChI Key
- OLVCFLKTBJRLHI-AXAPSJFSSA-N
- InChI
- InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C1=CC=CC=C1)C(O)=O
Pharmacology
- Indication
For the treatment of serious infections caused by susceptible strains of microorganisms.
- Pharmacodynamics
The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.
- Mechanism of action
Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 2 inhibitorBacteroides fragilis - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
75%
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.
- Clearance
- Not Available
- Toxicity
Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data(R)-warfarin The risk or severity of bleeding can be increased when Cefamandole is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Cefamandole is combined with (S)-Warfarin. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Cefamandole is combined with 4-hydroxycoumarin. Abacavir Cefamandole 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 Cefamandole. Acarbose Cefamandole may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac Cefamandole 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 Cefamandole is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefamandole is combined with Acenocoumarol. Acetaminophen Cefamandole may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- Synthesis Reference
Ta Sen Chou, Gary D. Zintgraff, "Process for preparing pure cefamandole from alkali metal and ammonium salts thereof." U.S. Patent US4115644, issued June, 1977.
US4115644- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015421
- KEGG Drug
- D02344
- KEGG Compound
- C06879
- PubChem Compound
- 456255
- PubChem Substance
- 46508882
- ChemSpider
- 401748
- BindingDB
- 50350468
- RxNav
- 2178
- ChEBI
- 3480
- ChEMBL
- CHEMBL1146
- ZINC
- ZINC000003830394
- Therapeutic Targets Database
- DAP000448
- PharmGKB
- PA448837
- PDBe Ligand
- SMX
- RxList
- RxList Drug Page
- Wikipedia
- Cefamandole
- ATC Codes
- J01DC03 — Cefamandole
- PDB Entries
- 3ny4
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Recruiting Treatment Osteomyelitis 1 Not Available Not Yet Recruiting Not Available Community Acquired Pneumonia (CAP) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 182-184 Greene, J.M. and Indelicato, J.M.; US. Patent 3,928,592; December 23,1975; assigned to Eli Lilly & Co. logP 0.50 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.581 mg/mL ALOGPS logP -0.05 ALOGPS logP 0.027 ChemAxon logS -2.9 ALOGPS pKa (Strongest Acidic) 3.32 ChemAxon pKa (Strongest Basic) -1.7 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 150.54 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 126.65 m3·mol-1 ChemAxon Polarizability 42.45 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.8573 Blood Brain Barrier - 0.9918 Caco-2 permeable - 0.795 P-glycoprotein substrate Substrate 0.769 P-glycoprotein inhibitor I Non-inhibitor 0.8401 P-glycoprotein inhibitor II Non-inhibitor 0.8066 Renal organic cation transporter Non-inhibitor 0.8467 CYP450 2C9 substrate Non-substrate 0.7367 CYP450 2D6 substrate Non-substrate 0.822 CYP450 3A4 substrate Substrate 0.5185 CYP450 1A2 substrate Non-inhibitor 0.8336 CYP450 2C9 inhibitor Non-inhibitor 0.7509 CYP450 2D6 inhibitor Non-inhibitor 0.8653 CYP450 2C19 inhibitor Non-inhibitor 0.7454 CYP450 3A4 inhibitor Non-inhibitor 0.7111 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5818 Ames test Non AMES toxic 0.7075 Carcinogenicity Non-carcinogens 0.9222 Biodegradation Not ready biodegradable 0.8565 Rat acute toxicity 2.2075 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9594 hERG inhibition (predictor II) Non-inhibitor 0.5988
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 / Alkylarylthioethers / 1,3-thiazines / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Secondary carboxylic acid amides / Secondary alcohols show 12 more
- Substituents
- Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenylacetamide / Aryl thioether / Alkylarylthioether / Benzenoid / Meta-thiazine / Monocyclic benzene moiety / Heteroaromatic compound show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, semisynthetic derivative (CHEBI:3480)
Targets
- 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
- 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]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
- Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [PubMed:12650826]
Drug created on June 30, 2007 11:22 / Updated on April 02, 2020 01:58
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
![]({"Clinical-1.jpg":"/assets/ads/Clinical-1-0efffcd68b99e28deae3611717239df1f86dcd50500066e39a7c19d08f91988b.jpg","Drug-Search-2.jpg":"/assets/ads/Drug-Search-2-2f3603461a3ccebb5cf2387e5b24146852d1952a198725dfb72abd325bf1d4a9.jpg","DDI-2.jpg":"/assets/ads/DDI-2-0b012e4822a96439344683dad971ca9f896e601daf48ee0d8932e45e6a3036a2.jpg","CS-Molecular-Health-1.jpg":"/assets/ads/CS-Molecular-Health-1-a30b86c438f5468a993dfa1b02728b4c9b8c406771ab717321f242913f105eae.jpg","Covid.jpg":"/assets/ads/Covid-b36ff36fa999f6e848e56a47b413deb0d6327c37ec1860a961e18153c8841d1c.jpg","Drug-Dev-2.jpg":"/assets/ads/Drug-Dev-2-126f59819adfcc111994629f2e55bdec8802bd17f9268e5ed4931222d586f88f.jpg","Drug-Search-3.jpg":"/assets/ads/Drug-Search-3-b939cf2cc5f6c8d114a532430ca265ecec02ddf02a50c9302912da5e477097a7.jpg","PM-3.jpg":"/assets/ads/PM-3-f1ca930890153399424501785b8c386b545ed612b7c88b6513e11d90b920e110.jpg"})
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates