(2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 1380
• Molecular Formular: C17H20N2O6S
• Molecular Mass: 380.4155
• Monoisotopic Mass: 380.10420737
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)c1c(OC)cccc1OC
• Canonical SMILES: COc1cccc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)OC
• 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
• InChIKey: RJQXTJLFIWVMTO-TYNCELHUSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: methicillin; (2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Dimocillin; Metacillin
• Synonyms: 2,6-Dimethoxyphenyl-penicillin; Methicillin Selective Supplement; Methicillin; Staphcillin; MRSA Selective Supplement; (2,6-Dimethoxyphenyl)penicillin; 6-(2,6-Dimethoxybenzamido)penicillanic acid; Meticilina [inn-spanish]; Meticilline [inn-french]; Meticillinum [inn-latin]; Methicillinum; Methycillin; Meticillin; Meticillin; 2,6-二甲氧基苯基青霉素; 新青霉素 I; 甲氧西林; 甲氧西林选择性添加剂; MRSA 选择性添加剂

Database IDs

• CAS Number: 61-32-5
• EC Number: 200-505-8
• MDL Number: MFCD00242880
• PubChem SID: 160964840; 46508973
• PubChem CID: 6087
• ATC CODE: QJ51CF03; J01CF03
• CHEMBL: 575
• Chemspider ID: 5862
• DrugBank ID: DB01603
• Unique Ingredient Identifier: Q91FH1328A
• Wikipedia Title: Meticillin

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.964299
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.7098374
• LogD (pH = 7.4): -2.6935103
• Log P: 0.78517
• Molar Refractivity: 93.4028 cm^3
• Polarizability: 36.418606 Å^3
• Polar Surface Area: 105.17 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.79
• LOG S: -3.09
• Solubility (Water): 3.10e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.22 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: XH8930000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: IV
• Bioavailability: Not orally absorbed
• Excretion: renal
• Half Life: 25–60 minutes
• Metabolism: hepatic, 20–40%

Product Information

• Grade: for microbiology
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C17H20N2O6S

DETAILS

DrugBank - DB01603

• Drug 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]
• 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.
• Pharmacology: 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.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic (20-40%).
• Absorption: Not absorbed following oral administration.
• Half Life: 25-60 minutes
• External Links: Wikipedia

Sigma Aldrich - 51387

Components
(per vial, sufficient for 500 ml medium) Methicillin 2 mg
General description
An antimicrobial supplement recommended for the selective isolation of Methicillin Resistant Staphylococcus aureus (MRSA) from clinical specimens.