Identification
- Summary
Cefotiam is a cephalosporin antibiotic used to treat a variety of bacterial infections.
- Generic Name
- Cefotiam
- DrugBank Accession Number
- DB00229
- Background
One of the cephalosporins that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cefotiam (DB00229)
- Weight
- Average: 525.628
Monoisotopic: 525.103512339 - Chemical Formula
- C18H23N9O4S3
- Synonyms
- (6R,7R)-7-[2-(2-Amino-thiazol-4-yl)-acetylamino]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefotiam
- Cefotiamum
- CTM
Pharmacology
- Indication
For treatment of severe infections caused by susceptible bacteria.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Cefotiam is a third generation beta-lactam cephalosporin antibiotic that works by inhibiting bacterial cell wall biosynthesis. It is a broad spectrum antibiotic that is effective against Gram positive and Gram negative bacteria.
- Mechanism of action
The bactericidal activity of cefotiam results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Target Actions Organism APenicillin-binding protein 1A inducerClostridium perfringens (strain 13 / Type A) - Absorption
Rapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.
- Volume of distribution
Not Available
- Protein binding
40%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Approximately 1 hour.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
- 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 Integrate drug-drug
interactions in your softwareAbacavir Cefotiam 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 Cefotiam. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefotiam. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefotiam is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefotiam is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefotiam is combined with Acenocoumarol. Acetaminophen Cefotiam may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide The excretion of Cefotiam can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Cefotiam can be decreased when combined with Acetylsalicylic acid. Aclidinium Cefotiam may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefotiam hydrochloride H7V12WDZ93 66309-69-1 SVSFIELZISOJDT-XRZFDKQNSA-N - International/Other Brands
- Ceradon / Pansporin (Takeda Pharmaceutical)
Categories
- ATC Codes
- J01DC07 — Cefotiam
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephacetrile
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Second-Generation Cephalosporins
- Sulfur Compounds
- Thiazines
- Chemical TaxonomyProvided by Classyfire
- 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 / 2,4-disubstituted thiazoles / Alkylarylthioethers / 1,3-thiazines / 2-amino-1,3-thiazoles / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Azetidines show 13 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alkylarylthioether / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, semisynthetic derivative (CHEBI:355510)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 91W6Z2N718
- CAS number
- 61622-34-2
- InChI Key
- QYQDKDWGWDOFFU-IUODEOHRSA-N
- InChI
- InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
- IUPAC Name
- (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-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=NN3CCN(C)C)=C(N1C(=O)[C@H]2NC(=O)CC1=CSC(N)=N1)C(O)=O
References
- General References
- Muller R, Bottger C, Wichmann G: Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. Arzneimittelforschung. 2003;53(2):126-32. [Article]
- Kolben M, Mandoki E, Ulm K, Freitag K: Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. Eur J Clin Microbiol Infect Dis. 2001 Jan;20(1):40-2. [Article]
- Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. [Article]
- External Links
- Human Metabolome Database
- HMDB0014374
- KEGG Drug
- D07648
- PubChem Compound
- 43708
- PubChem Substance
- 46506679
- ChemSpider
- 39831
- BindingDB
- 50485561
- 2188
- ChEBI
- 355510
- ChEMBL
- CHEMBL1296
- ZINC
- ZINC000003830445
- Therapeutic Targets Database
- DAP001177
- PharmGKB
- PA164749298
- Wikipedia
- Cefotiam
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Unknown Status Prevention Cirrhosis of the Liver / Gastric Varices 2
Pharmacoeconomics
- Manufacturers
- Takeda chemical industries ltd
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution 1 g Injection, powder, for solution - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble Not Available logP -2.1 Not Available - Predicted Properties
Property Value Source Water Solubility 1.29 mg/mL ALOGPS logP -0.33 ALOGPS logP -3.1 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 2.6 Chemaxon pKa (Strongest Basic) 8.34 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 172.46 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 142.34 m3·mol-1 Chemaxon Polarizability 49.87 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 + 0.5528 Blood Brain Barrier - 0.9865 Caco-2 permeable - 0.6981 P-glycoprotein substrate Substrate 0.9008 P-glycoprotein inhibitor I Non-inhibitor 0.7087 P-glycoprotein inhibitor II Non-inhibitor 0.92 Renal organic cation transporter Non-inhibitor 0.8475 CYP450 2C9 substrate Non-substrate 0.8441 CYP450 2D6 substrate Non-substrate 0.8071 CYP450 3A4 substrate Substrate 0.568 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8496 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7105 Ames test Non AMES toxic 0.6519 Carcinogenicity Non-carcinogens 0.9074 Biodegradation Not ready biodegradable 0.7808 Rat acute toxicity 2.4511 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.891 hERG inhibition (predictor II) Non-inhibitor 0.806
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
Targets
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- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inducer
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Matsuda K, Nakamura K, Adachi Y, Inoue M, Kawakami M: Autolysis of methicillin-resistant Staphylococcus aureus is involved in synergism between imipenem and cefotiam. Antimicrob Agents Chemother. 1995 Dec;39(12):2631-4. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate activity towards rat OAT1 was suggested in vitro studies using Xenopus laevis.
- 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
- Uwai Y, Saito H, Inui K: Rat renal organic anion transporter rOAT1 mediates transport of urinary-excreted cephalosporins, but not of biliary-excreted cefoperazone. Drug Metab Pharmacokinet. 2002;17(2):125-9. [Article]
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor activity was demonstrated in vitro using human OAT3 expressed on HEK293 cells.
- 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
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 07, 2023 13:20