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Methicillin

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Identification
Molecular formula
C17H20N2O6S
CAS number
61-32-5
IUPAC name
(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Methicillin is typically in a solid state at room temperature. It is commonly found as a crystalline powder used for laboratory and pharmaceutical applications.

Melting point (Celsius)
191.50
Melting point (Kelvin)
464.65
Boiling point (Celsius)
493.00
Boiling point (Kelvin)
766.15
General information
Molecular weight
380.43g/mol
Molar mass
380.4330g/mol
Density
1.3300g/cm3
Appearence

Methicillin typically appears as a white crystalline powder. It is usually provided in the form of its sodium salt, methicillin sodium, which is also a white crystalline substance.

Comment on solubility

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

The solubility characteristics of the compound C17H20N2O6S are influenced by its complex structure. Here are some key points to consider:

  • Polarity: The presence of polar functional groups, such as the carboxylic acid and amide linkages, generally increases solubility in polar solvents like water.
  • Hydrophobic Regions: The dimethoxybenzoyl moiety introduces hydrophobic characteristics, which can impact solubility in non-polar solvents.
  • pH Dependence: As a carboxylic acid, the solubility can change with pH. Under acidic conditions, the compound may remain protonated, increasing solubility.
  • Temperature Effects: Elevated temperatures often enhance solubility, particularly for compounds that are poorly soluble at room temperature.

Overall, the specific solubility profile of C17H20N2O6S will depend on the interaction of these factors, leading to varying solubility in different solvents and under different conditions. Understanding these nuances is critical for effective application and formulation.

Interesting facts

Interesting Facts about (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound, with a complex structure and notable features, is a fascinating example of modern medicinal chemistry. Here are several key points that highlight its significance:

  • Synthetic Origin: This compound is synthesized via a multi-step process that exemplifies the ingenuity of chemists in designing molecules with potential therapeutic effects.
  • Pharmaceutical Potential: The intricate structure suggests that it may possess biological activity, particularly in the realm of antibacterial or antiviral properties, making it a candidate for drug development.
  • Structural Complexity: The presence of a bicyclic structure and thiol groups indicates that this compound has unique stereochemistry, which can impact its biological interactions.
  • Mechanism of Action: Although specific studies are needed, the incorporation of a dimethoxybenzoyl group hints at possible interactions with enzyme systems, providing insights into its function as a potential inhibitor.
  • Analytical Techniques: The characterization of such compounds often involves techniques like NMR, mass spectrometry, and X-ray crystallography, highlighting the sophistication of modern analytical chemistry.

In summary, (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid serves as a prime example of how detailed chemical knowledge can lead to groundbreaking discoveries in pharmaceuticals. Its intriguing structure and potential applications remind us that every compound holds untold stories waiting to be explored. As the famous chemist Linus Pauling once said, "The best way to have a good idea is to have a lot of ideas."

Synonyms
methicillin
Meticillin
Methycillin
61-32-5
Metacillin
Methicillinum
Meticilina
Meticilline
Meticillinum
Dimocillin
Meticillina
Staphcillin
Meticilina [INN-Spanish]
Meticilline [INN-French]
Meticillinum [INN-Latin]
(2,6-Dimethoxyphenyl)penicillin
Meticillina [DCIT]
Meticillin [INN]
6-(2,6-Dimethoxybenzamido)penicillanic acid
CHEBI:6827
(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
BRL 1241
Methicillin [USAN]
HSDB 3121
EINECS 200-505-8
Penicillin, (2,6-dimethoxyphenyl)-
6beta-(2,6-dimethoxybenzamido)penicillanic acid
2,6-dimethoxyphenyl penicillin
Q91FH1328A
METICILLIN [HSDB]
METHICILLIN [VANDF]
METICILLIN [WHO-DD]
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
DTXSID6023284
Celbenin
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-
6-(2,3-Dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
6beta-(2,6-dimethoxybenzamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Meticilina (INN-Spanish)
Meticilline (INN-French)
Meticillinum (INN-Latin)
Methcillin
(2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3,-dimethyl-7-oxo-
Penicillin, Dimethoxyphenyl
(2S,5R,6R)-6-(2,6-DIMETHOXYBENZAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
(2S,5R,6R)-6-[(2,6-dimethoxybenzene)amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Meticillin [INN:BAN]
Dimethoxyphenyl Penicillin
UNII-Q91FH1328A
(2S,5R,6R)-6-((2,6-dimethoxybenzene)amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
Spectrum_000993
Spectrum2_001965
Spectrum3_000494
Spectrum4_000878
Spectrum5_001600
CHEMBL575
Epitope ID:139649
SCHEMBL4898
BSPBio_001987
KBioGR_001575
KBioSS_001473
DivK1c_000100
SPBio_002089
DTXCID703284
GTPL12264
KBio1_000100
KBio2_001473
KBio2_004041
KBio2_006609
KBio3_001487
NINDS_000100
BDBM50103523
AKOS030530774
DB01603
IDI1_000100
(2S,5R,6R)-6-{[(2,6-dimethoxyphenyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, [2S-(2.alpha.,5.alpha.,6.beta.)]-
DA-65418
MII
SBI-0051440.P003
HY-121544
MRSA Selective Supplement, for microbiology
CS-0082724
NS00005780
C07177
EN300-19748934
Q409262
BRD-K34388247-236-02-5
BRD-K34388247-236-08-2
BRD-K34388247-236-09-0
200-505-8