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Identification
NameMeticillin
Accession NumberDB01603
TypeSmall Molecule
GroupsApproved
DescriptionOne of the penicillins which is resistant to penicillinase but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection. [PubChem]
Structure
Thumb
Synonyms
(2,6-Dimethoxyphenyl)penicillin
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-(2,6-Dimethoxybenzamido)penicillanic acid
6beta-(2,6-Dimethoxybenzamido)penicillanic acid
Methicillin
Methicillinum
Methycillin
Meticilina
Meticillin
Meticilline
Meticillinum
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
DimocillinNot Available
MetacillinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methicillin sodium
ThumbNot applicableDBSALT001467
Categories
UNIIQ91FH1328A
CAS number61-32-5
WeightAverage: 380.415
Monoisotopic: 380.104207072
Chemical FormulaC17H20N2O6S
InChI KeyInChIKey=RJQXTJLFIWVMTO-TYNCELHUSA-N
InChI
InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
IUPAC Name
(2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[[email protected]]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Salicylamide
  • Alpha-amino acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed to treat infections caused by susceptible Gram-positive bacteria, particularly beta-lactamase-producing organisms such as Staphylococcus aureus that would otherwise be resistant to most penicillins.
PharmacodynamicsMeticillin (INN, BAN) or methicillin (USAN) is a narrow spectrum beta-lactam antibiotic of the penicillin class. It is no longer clinically used. Its role in therapy has been largely replaced by flucloxacillin and dicloxacillin, however the term methicillin-resistant Staphylococcus aureus (MRSA) continues to be used to describe Staphylococcus aureus strains resistant to all penicillins.
Mechanism of actionLike other beta-lactam antibiotics, meticillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.
Related Articles
AbsorptionNot absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic (20-40%).

Route of eliminationNot Available
Half life25-60 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Gram-positive Bacteria
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Staphylococcus aureus
  • Staphylococcus epidermidis
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9304
Blood Brain Barrier-0.9958
Caco-2 permeable-0.6628
P-glycoprotein substrateSubstrate0.5813
P-glycoprotein inhibitor INon-inhibitor0.9099
P-glycoprotein inhibitor IINon-inhibitor0.9535
Renal organic cation transporterNon-inhibitor0.9476
CYP450 2C9 substrateNon-substrate0.7962
CYP450 2D6 substrateNon-substrate0.8715
CYP450 3A4 substrateNon-substrate0.5144
CYP450 1A2 substrateNon-inhibitor0.8626
CYP450 2C9 inhibitorNon-inhibitor0.8793
CYP450 2D6 inhibitorNon-inhibitor0.921
CYP450 2C19 inhibitorNon-inhibitor0.8738
CYP450 3A4 inhibitorNon-inhibitor0.7747
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.95
Ames testNon AMES toxic0.8607
CarcinogenicityNon-carcinogens0.6826
BiodegradationNot ready biodegradable0.9376
Rat acute toxicity1.8893 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.8358
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP1.22HANSCH,C ET AL. (1995)
pKa2.77SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.31 mg/mLALOGPS
logP1.79ALOGPS
logP0.79ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.17 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.4 m3·mol-1ChemAxon
Polarizability37.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01CF03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolMeticillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Meticillin.
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Meticillin.
DicoumarolMeticillin may increase the anticoagulant activities of Dicoumarol.
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Meticillin.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Meticillin.
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Meticillin.
Ethyl biscoumacetateMeticillin may increase the anticoagulant activities of Ethyl biscoumacetate.
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Meticillin.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Meticillin.
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Meticillin.
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Meticillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Meticillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Meticillin.
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Meticillin.
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Meticillin resulting in a loss in efficacy.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Meticillin.
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Meticillin.
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Meticillin.
PhenindioneMeticillin may increase the anticoagulant activities of Phenindione.
PhenprocoumonMeticillin may increase the anticoagulant activities of Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Meticillin.
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Meticillin.
ProbenecidThe serum concentration of Meticillin can be increased when it is combined with Probenecid.
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Meticillin.
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Meticillin.
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Meticillin.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Meticillin.
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Meticillin.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Meticillin.
WarfarinMeticillin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
mecA
Uniprot ID:
Q53707
Molecular Weight:
76265.485 Da
References
  1. Gardete S, de Lencastre H, Tomasz A: A link in transcription between the native pbpB and the acquired mecA gene in a strain of Staphylococcus aureus. Microbiology. 2006 Sep;152(Pt 9):2549-58. [PubMed:16946250 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp2a
Uniprot ID:
Q8DNB6
Molecular Weight:
80797.94 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp1b
Uniprot ID:
Q7CRA4
Molecular Weight:
89479.92 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M6
Molecular Weight:
73872.305 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not Available
Gene Name:
pbp3
Uniprot ID:
Q75Y35
Molecular Weight:
45209.84 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Cell wall formation.
Gene Name:
pbpA
Uniprot ID:
Q8DR59
Molecular Weight:
79700.9 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421 ]
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Drug created on August 29, 2007 12:47 / Updated on August 17, 2016 12:23