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132-92-3

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  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, sodium salt (1:1),(2S,5R,6R)-

    Cas No: 132-92-3

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  • 1 Gram

  • 10000 Metric Ton/Month

  • Shanghai Upbio Tech Co.,Ltd
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132-92-3 Usage

Description

Methicillin is a semisynthetic penicillin antibiotic that can inhibit bacterial cell wall synthesis. It can be used to study methicillin-resistance in S. aureus.

Uses

Different sources of media describe the Uses of 132-92-3 differently. You can refer to the following data:
1. Targets primarily the cell wall of Gram-positive organisms especially Staphylococcus aureus. Methicillin is used to study bacterium susceptibility, and to inhibit cell-wall synthesis. PBP's are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Methicillin Sodium Salt is inactivated by gastric acid so it is given to cells by other means in which gastric acid is not present in vitro.
2. Semi-synthetic antibiotic related to Penicillin. Antimicrobial.
3. antibacterial

Brand name

Staphcillin (Apothecon).

Clinical Use

During 1960, methicillin sodium, 2,6-dimethoxyphenylpenicillinsodium (Staphcillin), the second penicillin produced asa result of the research that developed synthetic analogs, wasintroduced for medicinal use. Methicillin sodium is particularly resistant to inactivationby the penicillinase found in staphylococci and somewhatmore resistant than penicillin G to penicillinase fromBacillus cereus.

in vitro

similar to other β-lactam antibiotics, meticillin acts via inhibiting the synthesis of bacterial cell walls. meticillin can block the cross-linkage between the linear peptidoglycan polymer chains by binding to and competitively inhibiting the transpeptidase enzyme or penicillin-binding proteins [1].

in vivo

in a previous animal study, the treatment with methicillin or gentamicin or both was started 3 days after infection to a experimental mouse model of foreign body infection. results found that the treatment showed a significant effect, demonstrated as reduction of bacteria on the foreign body, for all three regimens with a reduction of up to 2 log units, but there was no synergism. however, the actual efficacy of the treatment was poor, though the local methicillin concentrations was greater than the mic for at least 72 h [2].

references

[1] https://en. wikipedia.org/wiki/meticillin[2] espersen f, frimodt-m ller n, corneliussen l, riber u, rosdahl vt, skinh j p. effect of treatment with methicillin and gentamicin in a new experimental mouse model of foreign body infection. antimicrob agents chemother. 1994 sep;38(9):2047-53.

Check Digit Verification of cas no

The CAS Registry Mumber 132-92-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 132-92:
(5*1)+(4*3)+(3*2)+(2*9)+(1*2)=43
43 % 10 = 3
So 132-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H20N2O6S.Na.H2O/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);;1H2/q;+1;/p-1/t11-,12+,15-;;/m1../s1

132-92-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name methicillin sodium

1.2 Other means of identification

Product number -
Other names (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:132-92-3 SDS

132-92-3Synthetic route

Chloromethyl pivalate
18997-19-8

Chloromethyl pivalate

methicillin sodium
132-92-3

methicillin sodium

methicillin t. butylcarbonyloxymethyl ester
104430-18-4

methicillin t. butylcarbonyloxymethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 6h; Ambient temperature;56%
methicillin sodium
132-92-3

methicillin sodium

(4S)-2t-[(2,6-dimethoxy-benzoylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid
57414-10-5

(4S)-2t-[(2,6-dimethoxy-benzoylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid

Conditions
ConditionsYield
(i) aq. NaOH, (ii) aq. EtOH; Multistep reaction;
methicillin sodium
132-92-3

methicillin sodium

(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid
106215-27-4

(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid

Conditions
ConditionsYield
With hydrogen cation; 4-methyl-2-pentanone for 168h; Ambient temperature;
methicillin sodium
132-92-3

methicillin sodium

N-[2-(2,6-dimethoxy-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-D-penicillamine
3568-15-8

N-[2-(2,6-dimethoxy-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-D-penicillamine

Conditions
ConditionsYield
(i) aq. HgCl2, (ii) aq. H2S; Multistep reaction;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

methicillin sodium
132-92-3

methicillin sodium

chloromethyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
34582-70-2

chloromethyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water for 0.5h; below 30 deg C;4.24 g
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogen sulfate In dichloromethane; water
methicillin sodium
132-92-3

methicillin sodium

<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
122648-61-7

<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C
2: 3 g / dimethylformamide / 144 h / Ambient temperature
View Scheme
methicillin sodium
132-92-3

methicillin sodium

<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
122648-68-4

<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C
2: 3 g / dimethylformamide / 144 h / Ambient temperature
3: 1.6 g / nitromethane / 168 h / 20 - 25 °C
4: 0.25 g / Na2S2O4, NaHCO3 / ethyl acetate; H2O / 1.17 h / 0 - 5 °C
View Scheme
methicillin sodium
132-92-3

methicillin sodium

<2S-(2α,5α,6β)>-3-<<<<<3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>hept-2-yl>carbonyl>oxy>methoxy>carbonyl>-1-methylpyridinium iodide

<2S-(2α,5α,6β)>-3-<<<<<3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>hept-2-yl>carbonyl>oxy>methoxy>carbonyl>-1-methylpyridinium iodide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C
2: 3 g / dimethylformamide / 144 h / Ambient temperature
3: 1.6 g / nitromethane / 168 h / 20 - 25 °C
View Scheme
methicillin sodium
132-92-3

methicillin sodium

(2R,4S)-2-[(R)-(2,6-Dimethoxy-benzoylamino)-hydroxycarbamoyl-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
104430-22-0

(2R,4S)-2-[(R)-(2,6-Dimethoxy-benzoylamino)-hydroxycarbamoyl-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56 percent / dimethylformamide / 6 h / Ambient temperature
2: 100 percent / hydroxylaminehydrochloride, NaOH / methanol / 1.) -30 deg C to 20 deg C for 1h, 2.) room temperature, 1h
View Scheme
methicillin sodium
132-92-3

methicillin sodium

(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid dimethyl ester
106095-84-5

(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: MeCOiBu, H+ / 168 h / Ambient temperature
2: diethyl ether; methanol
View Scheme

132-92-3Upstream product

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