Cephalothin (CED0003134)

Record Information
Version1.0
Creation Date2016-05-22 03:38:43 UTC
Update Date2026-08-19 15:28:24 UTC
Accession NumberCHEM016623
Identification
Common NameCephalothin
ClassSmall Molecule
Description
Cephalothin is an organic compound with the chemical formula C16H16N2O6S2 and an average molecular weight of 396.44 g/mol. Cephalothin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. The compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically within the categories of antibiotics and beta-lactam antibacterials. Recorded exposure routes for this substance include oral, intravenous, intramuscular, and inhalation. In terms of biological activity, cephalothin acts on seven recorded protein targets. It serves as an inhibitor or potentiator of penicillin-binding protein 1A (pbpA), penicillin-binding protein 1b (pbp1b), D-alanyl-D-alanine carboxypeptidase, and beta-lactamase (ampC), as well as three other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acidChEBI
7-(2'-Thienylacetamido)cephalosporanic acidChEBI
7-(2-Thienylacetamido)cephalosporanic acidChEBI
7-(Thiophene-2-acetamido)cephalosporinChEBI
CefalothinChEBI
CefalotinaChEBI
CefalotineChEBI
CefalotinumChEBI
CephalothinChEBI
CephalotinChEBI
CETChEBI
Cefalotina fabraKegg
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylateGenerator
7-(2'-Thienylacetamido)cephalosporanateGenerator
7-(2-Thienylacetamido)cephalosporanateGenerator
CephalothinumHMDB
CLSHMDB
CeftinaHMDB
Cephalothin monosodium saltHMDB
Cephalothin, sodiumHMDB
Lilly brand OF cephalothin sodiumHMDB
Sodium cephalothinHMDB
Spaly brand OF cephalothin sodiumHMDB
Cefalotina normonHMDB
Cefalotina sodica spalyHMDB
KeflinHMDB
Monosodium salt, cephalothinHMDB
Galen brand OF cephalothin sodiumHMDB
Normon brand OF cephalothin sodiumHMDB
Salt, cephalothin monosodiumHMDB
SeffinHMDB
Chemical FormulaC16H16N2O6S2
Average Molecular Mass396.438 g/mol
Monoisotopic Mass396.045 g/mol
CAS Registry Number153-61-7
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecephalothin
SMILES[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CS1)C(O)=O
InChI IdentifierInChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
InChI KeyXIURVHNZVLADCM-IUODEOHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporin 3'-esters
Alternative Parents
Substituents
  • Cephalosporin 3'-ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Thiophene
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP0.63ALOGPS
logP0.016ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.01 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.79 m³·mol⁻¹ChemAxon
Polarizability37.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0005-9233000000-c08aaf4337c171abf2daNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0005-9112200000-c01dd68b0d32151deaf5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-3497000000-39a3be7aed177d83e29cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06di-3592000000-2698fe462f117a84d906Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9450000000-e6bd7e836bf0464a7e99Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2924000000-f38cb8a2317e06bae695Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05is-6972000000-229017165a4e6bbe3d04Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9320000000-99d96c92501fa08d35a3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000b-0009000000-18bd1b9850bf3f0bc0deNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-2966000000-8c53c8dfe4afef2539ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-8983000000-bb2bc75f48bda3159248Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0019000000-2e169e448b42641dbb9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06r2-5659000000-26ef58de43fbebf7d124Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0537-9110000000-871abeea509049c819edNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5721.0Log mg/kg[3200:10000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Cefalotin Drug Metabolism Action Pathway
Cefalotin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.0778492
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.0778492
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.0778492
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)0.311397
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)4.9045
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.155698
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.155698
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)10.0426
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)0.233548
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)71.8548
Click to view 3D structureSolute carrier family 15 member 2Q63424Rattus norvegicusPredicted (SEA)1.86838
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)253.711
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)90.3051
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)133.745
Tyrosine-protein phosphatase non-receptor type 7 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 7P35236HumansPredicted (SEA)194.623
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.233548
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)147.446
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)1100.48
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)1365.24
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)696.673
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)533.656
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)403.726
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)413.846
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)682.348
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)2040.58
Concentrations
Not Available
External Links
DrugBank IDDB00456
HMDB IDHMDB0014599
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCLS
Wikipedia LinkCephalothin
Chemspider ID5802
ChEBI ID124991
PubChem Compound ID6024
Kegg Compound IDC07761
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=13963283
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23472927
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23680238
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6176550