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Identification
NameCefotiam
Accession NumberDB00229  (APRD00855)
TypeSmall Molecule
GroupsApproved
Description

One of the cephalosporins that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms. [PubChem]

Structure
Thumb
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CeradonNot Available
PansporinTakeda Pharmaceutical
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefotiam hydrochloride
Thumb
  • InChI Key: SVSFIELZISOJDT-XRZFDKQNSA-N
  • Monoisotopic Mass: 561.080190078
  • Average Mass: 562.089
DBSALT000796
Categories
UNII91W6Z2N718
CAS number61622-34-2
WeightAverage: 525.628
Monoisotopic: 525.103512339
Chemical FormulaC18H23N9O4S3
InChI KeyInChIKey=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)[[email protected]]2NC(=O)CC1=CSC(N)=N1)C(O)=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • 2,4-disubstituted 1,3-thiazole
  • Primary aromatic amine
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiazole
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of severe infections caused by susceptible bacteria.
PharmacodynamicsCefotiam is a third generation beta-lactam cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotiam works by inhibiting bacterial cell wall biosynthesis.
Mechanism of actionThe bactericidal activity of cefotiam results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Related Articles
AbsorptionRapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.
Volume of distributionNot Available
Protein binding40%
MetabolismNot Available
Route of eliminationNot Available
Half lifeApproximately 1 hour.
ClearanceNot Available
ToxicityAdverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5528
Blood Brain Barrier-0.9865
Caco-2 permeable-0.6981
P-glycoprotein substrateSubstrate0.9008
P-glycoprotein inhibitor INon-inhibitor0.7087
P-glycoprotein inhibitor IINon-inhibitor0.92
Renal organic cation transporterNon-inhibitor0.8475
CYP450 2C9 substrateNon-substrate0.8441
CYP450 2D6 substrateNon-substrate0.8071
CYP450 3A4 substrateSubstrate0.568
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8496
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7105
Ames testNon AMES toxic0.6519
CarcinogenicityNon-carcinogens0.9074
BiodegradationNot ready biodegradable0.7808
Rat acute toxicity2.4511 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.891
hERG inhibition (predictor II)Non-inhibitor0.806
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Takeda chemical industries ltd
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP-2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.29 mg/mLALOGPS
logP-0.33ALOGPS
logP-3.1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area172.46 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity142.34 m3·mol-1ChemAxon
Polarizability49.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. 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. [PubMed:12642969 ]
  2. 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. [PubMed:11245321 ]
  3. Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. [PubMed:8829507 ]
External Links
ATC CodesJ01DC07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolCefotiam may increase the anticoagulant activities of Acenocoumarol.
ProbenecidThe serum concentration of Cefotiam can be increased when it is combined with Probenecid.
WarfarinCefotiam may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:8592992 ]

Transporters

Kind
Protein
Organism
Human
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. 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. [PubMed:15618660 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08