Cephalothin Group

Identification

Name
Cephalothin Group
Accession Number
DB03450  (EXPT00891)
Type
Small Molecule
Groups
Experimental
Description

Cephalothin group is a solid. This compound belongs to the 1,3-thiazines. These are organic compounds containing 1,3-thiazine, a six-member ring with a nitrogen and a sulfur atom in ring positions 1 and 3 respectively, as well as two double bonds. This substance is known to target beta-lactamase Toho-1 and D-alanyl-D-alanine carboxypeptidase.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 398.454
Monoisotopic: 398.060627698
Chemical Formula
C16H18N2O6S2
InChI Key
UUWFGEKEQSCSMB-IAQYHMDHSA-N
InChI
InChI=1S/C16H18N2O6S2/c1-24-13(21)5-9-8-26-15(18-14(9)16(22)23)11(7-19)17-12(20)6-10-3-2-4-25-10/h2-4,7,11,15,18H,5-6,8H2,1H3,(H,17,20)(H,22,23)/t11-,15-/m1/s1
IUPAC Name
(2R)-5-(2-methoxy-2-oxoethyl)-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
SMILES
[H][C@@](NC(=O)CC1=CC=CS1)(C=O)[C@]1([H])NC(C(O)=O)=C(CC(=O)OC)CS1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-lactamase Toho-1Not AvailableEscherichia coli
UD-alanyl-D-alanine carboxypeptidaseNot AvailableStreptomyces sp. (strain R61)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenCephalothin Group may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cephalothin Group.
AcyclovirCephalothin Group may decrease the excretion rate of Acyclovir which could result in a higher serum level.
Adefovir DipivoxilThe risk or severity of nephrotoxicity can be increased when Cephalothin Group is combined with Adefovir Dipivoxil.
Alendronic acidThe risk or severity of nephrotoxicity and hypocalcemia can be increased when Cephalothin Group is combined with Alendronic acid.
AlmotriptanCephalothin Group may decrease the excretion rate of Almotriptan which could result in a higher serum level.
AlprazolamCephalothin Group may decrease the excretion rate of Alprazolam which could result in a higher serum level.
AmantadineCephalothin Group may decrease the excretion rate of Amantadine which could result in a higher serum level.
AmikacinThe risk or severity of nephrotoxicity can be increased when Amikacin is combined with Cephalothin Group.
AmitriptylineCephalothin Group may decrease the excretion rate of Amitriptyline which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
46936680
PubChem Substance
46506959
ChemSpider
25058774
HET
CEP
PDB Entries
1ceg / 1iyp / 4ivk / 4r0q

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0279 mg/mLALOGPS
logP0.77ALOGPS
logP0.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.8 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.06 m3·mol-1ChemAxon
Polarizability38.44 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8735
Blood Brain Barrier-0.9708
Caco-2 permeable-0.709
P-glycoprotein substrateSubstrate0.8021
P-glycoprotein inhibitor INon-inhibitor0.8027
P-glycoprotein inhibitor IINon-inhibitor0.9967
Renal organic cation transporterNon-inhibitor0.9072
CYP450 2C9 substrateNon-substrate0.7925
CYP450 2D6 substrateNon-substrate0.82
CYP450 3A4 substrateNon-substrate0.5219
CYP450 1A2 substrateNon-inhibitor0.7082
CYP450 2C9 inhibitorNon-inhibitor0.7293
CYP450 2D6 inhibitorNon-inhibitor0.9083
CYP450 2C19 inhibitorNon-inhibitor0.7272
CYP450 3A4 inhibitorNon-inhibitor0.9435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7551
Ames testNon AMES toxic0.7803
CarcinogenicityNon-carcinogens0.9595
BiodegradationNot ready biodegradable0.8304
Rat acute toxicity2.3451 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.9282
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
1,3-thiazines / Dicarboxylic acids and derivatives / Thiophenes / Methyl esters / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Thiohemiaminal derivatives / Azacyclic compounds / Carboxylic acids
show 7 more
Substituents
Alpha-amino acid or derivatives / Meta-thiazine / Dicarboxylic acid or derivatives / Thiophene / Methyl ester / Heteroaromatic compound / Carboxamide group / Carboxylic acid ester / Secondary carboxylic acid amide / Amino acid
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
Has strong cefotaxime-hydrolyzing activity.
Gene Name
bla
Uniprot ID
Q47066
Uniprot Name
Beta-lactamase Toho-1
Molecular Weight
31446.6 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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Streptomyces sp. (strain R61)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e....
Gene Name
Not Available
Uniprot ID
P15555
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
42916.725 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:35