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61-32-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:1380 http://www.chembase.cn/molecule-1380.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
51387 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.964299  H Acceptors
H Donor LogD (pH = 5.5) -1.7098374 
LogD (pH = 7.4) -2.6935103  Log P 0.78517 
Molar Refractivity 93.4028 cm3 Polarizability 36.418606 Å3
Polar Surface Area 105.17 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.79  LOG S -3.09 
Solubility (Water) 3.10e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
1.22 [HANSCH,C ET AL. (1995)] expand Show data source
RTECS
XH8930000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
IV expand Show data source
Bioavailability
Not orally absorbed expand Show data source
Excretion
renal expand Show data source
Half Life
25–60 minutes expand Show data source
Metabolism
hepatic, 20–40% expand Show data source
Grade
for microbiology expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C17H20N2O6S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB01603 external link
Item Information
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 external link
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.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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