ChemFOnt: Showing chemical card for Meticillin (CFc000009803)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:03 UTC

Chemfont ID

CFc000009803

Molecule Identification

Common Name

Meticillin

Definition

Meticillin is only found in individuals that have used or taken this drug. It is 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]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6beta-(2,6-Dimethoxybenzamido)penicillanic acid	ChEBI
Meticilina	ChEBI
Meticilline	ChEBI
Meticillinum	ChEBI
(2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-(2,6-Dimethoxybenzamido)penicillanate	Generator
6b-(2,6-Dimethoxybenzamido)penicillanic acid	Generator
6beta-(2,6-Dimethoxybenzamido)penicillanate	Generator
6Β-(2,6-dimethoxybenzamido)penicillanate	Generator
6Β-(2,6-dimethoxybenzamido)penicillanic acid	Generator
(2,6-Dimethoxyphenyl)penicillin	HMDB
6-(2,6-Dimethoxybenzamido)penicillanic acid	HMDB
Methicillinum	HMDB
Methycillin	HMDB
Staphcillin	HMDB
CSL Brand OF methicillin sodium	HMDB
Dimethoxyphenyl penicillin	HMDB
Penicillin, dimethoxyphenyl	HMDB
Methicillin hydrate, monosodium salt	HMDB
Methicillin monohydrate, monosodium salt	HMDB
Methicillin sodium	HMDB
Metin	HMDB
Meticillin	ChEBI

Chemical Formula

C₁₇H₂₀N₂O₆S

Average Molecular Weight

380.415

Monoisotopic Molecular Weight

380.104207072

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

Traditional Name

methicillin

CAS Registry Number

61-32-5

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O

InChI Identifier

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

InChI Key

RJQXTJLFIWVMTO-TYNCELHUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

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 acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Penam
Azepane
Acylal
Dicarboxylic acid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Carboxylic acid ester
Lactam
Acetal
Amidine
Formamidine
Carboxylic acid amidine
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Hemithioaminal
Thioether
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

penicillanic acid ester (CHEBI:51210 )
penicillin (CHEBI:51210 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015541)

Source

Exogenous

Exogenous (HMDB: HMDB0015541)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.31 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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.4 m³·mol⁻¹	ChemAxon
Polarizability	37.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon