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Identification
Name Meticillin
Accession Number DB01603
Type small molecule
Groups approved
Description

One 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(2,6-Dimethoxyphenyl)penicillin
6-(2,6-Dimethoxybenzamido)penicillanic acid
Methicillinum
Methycillin
Meticilina [inn-spanish]
Meticilline [inn-french]
Meticillinum [inn-latin]
Salts Not Available
Brand names
Name Company
Dimocillin
Metacillin
Brand mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 61-32-5
Weight Average: 380.415
Monoisotopic: 380.104207072
Chemical Formula C17H20N2O6S
InChI Key InChIKey=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
Plain Text
IUPAC Name
(2S,5R,6R)-6-[(2,6-dimethoxybenzene)amido]-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)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Ethers
  • Penicillins
  • Anisoles
  • Benzoyl Derivatives
  • Benzamides
Substructures
  • Hydroxy Compounds
  • Acetates
  • Phenols and Derivatives
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Lactams
  • Benzoyl Derivatives
  • Azetidines
  • Thiazolidines
  • Phenyl Esters
  • Benzamides
Pharmacology
Indication Used 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.
Pharmacodynamics Meticillin (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 action Like 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.
Absorption Not absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hepatic (20-40%).
Route of elimination Not Available
Half life 25-60 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Apothecon inc div bristol myers squibb
Packagers Not Available
Dosage forms
Form Route Strength
Solution Parenteral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 1.22 HANSCH,C ET AL. (1995)
pKa 2.77 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 3.10e-01 g/l ALOGPS
logP 1.79 ALOGPS
logP 0.79 ChemAxon
logS -3.1 ALOGPS
pKa (strongest acidic) 2.96 ChemAxon
pKa (strongest basic) -1.8 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 105.17 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 93.4 ChemAxon
polarizability 37.27 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07177 Link_out
PubChem Compound 6087 Link_out
PubChem Substance 46508973 Link_out
ChemSpider 5862 Link_out
ChEBI 6827 Link_out
ChEMBL 6827 Link_out
Therapeutic Targets Database DAP001170 Link_out
PharmGKB PA164777034 Link_out
Wikipedia http://en.wikipedia.org/wiki/Methicillin Link_out
ATC Codes
  • J01CF03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Food Interactions Not Available
Targets

1. MecA PBP2' (penicillin binding protein 2')

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q53707 Link_out
Gene: mecA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Penicillin-binding protein 2a

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q8DNB6 Link_out
Gene: pbp2a
SNPs: SNPJam Report Link_out

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

3. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out
Gene: pbp1b Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

4. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

5. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

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

6. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on August 29, 2007 12:47 / Updated on February 08, 2013 16:20