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61-32-5

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  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- 61-32-5

    Cas No: 61-32-5

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  • 1 Kilogram

  • 10000 Metric Ton/Month

  • Shanghai Upbio Tech Co.,Ltd
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  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

    Cas No: 61-32-5

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  • 1 Kilogram

  • 1-100 Kilogram/Month

  • Afine Chemicals Limited
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61-32-5 Usage

Uses

Antibacterial.

Definition

ChEBI: A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.

Antimicrobial activity

2,6-Dimethoxyphenylpenicillin; methicillin (international non-proprietary name). The first β-lactamase-resistant semisynthetic penicillin. It was initially used widely but has been superseded by other group 3 members and is no longer commercially available. It is less active than benzylpenicillin or other group 3 penicillins. It is very stable to staphylococcal β-lactamase and is active against β-lactamaseproducing strains of Staph. aureus that do not produce a functional PBP 2a. Resistance is common among staphylococci, with the incidence geographically diverse. Most methicillin-resistant staphylococcal isolates display multiresistance. It is not acid resistant, and must therefore be administered parenterally. About 10% is metabolized, with 60–80% of the dose excreted in the urine. Toxicity is similar to that of other group 3 penicillins. Nephritis appears to be more common than with other penicillins.

Pharmacology

Like other semisynthetic penicillins, methicillin exhibits an antibacterial effect similar to that of benzylpenicillin. The main difference between methicillin and benzylpenicillin is that it is not inactivated by the enzyme penicillinase, and therefore it is effective with respect to agents producing this enzyme (staphylococci). It is used for infections caused by benzylpenicillinresistant staphylococci (septicemia, pneumonia, empyemia, osteomyelitis, abscesses, infected wounds, and others). Synonyms of this drug are cinopenil, celbenin, staphcillin, and others.

Synthesis

Methicillin, [2S-(2α,5α,6β)]-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)- 4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.3), is synthesized by acylating 6- APA with 2,6-dimethoxybenzoic acid chloride in the presence of triethylamine.

Check Digit Verification of cas no

The CAS Registry Mumber 61-32-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 61-32:
(4*6)+(3*1)+(2*3)+(1*2)=35
35 % 10 = 5
So 61-32-5 is a valid CAS Registry Number.
InChI:InChI=1/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

61-32-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name methicillin

1.2 Other means of identification

Product number -
Other names Methicillin

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:61-32-5 SDS

61-32-5Synthetic route

6-aminopenicillanic acid trimethylsilyl ester
1025-55-4

6-aminopenicillanic acid trimethylsilyl ester

2-6-dimethoxybenzoic acid
1466-76-8

2-6-dimethoxybenzoic acid

methicillin
61-32-5

methicillin

Conditions
ConditionsYield
(i) ClCO2Et, Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/; Multistep reaction;
6-Aminopenicillanic Acid
551-16-6

6-Aminopenicillanic Acid

methicillin
61-32-5

methicillin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3
2: (i) ClCO2Et, Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/
View Scheme
2-(Diethylamino)ethanol
100-37-8

2-(Diethylamino)ethanol

methicillin
61-32-5

methicillin

6-(2,6-dimethoxybenzamido)penicillinic acid 2-diethylaminoethyl ester hydrochloride
1032651-43-6

6-(2,6-dimethoxybenzamido)penicillinic acid 2-diethylaminoethyl ester hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(Diethylamino)ethanol; methicillin With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 10h;
Stage #2: With hydrogenchloride In diethyl ether; chloroform
77.5%
methanol
67-56-1

methanol

methicillin
61-32-5

methicillin

methicillin methyl ester
22668-52-6

methicillin methyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane
methicillin
61-32-5

methicillin

2-(2,6-dimethoxybenzamido)acetic acid
51579-21-6

2-(2,6-dimethoxybenzamido)acetic acid

Conditions
ConditionsYield
With water
methicillin
61-32-5

methicillin

6β-(2,6-dimethoxy-benzoylamino)-1,1-dioxo-1λ6-penicillanic acid
76350-41-9

6β-(2,6-dimethoxy-benzoylamino)-1,1-dioxo-1λ6-penicillanic acid

Conditions
ConditionsYield
With potassium permanganate; phosphoric acid

61-32-5Relevant articles and documents

Method of using deuterated calcium channel blockers

-

, (2008/06/13)

Therapeutic methods and compositions using deuterated enriched 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester and other deuterated dihydropyridine compounds are described. The deuterated compounds exhibit enhanced efficacy in blocking calcium channels over non-deuterated dihydropyridines.

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