methicillin

CAS No.
61-32-5
Chemical Name:
methicillin
Synonyms
Metin;C07177;BRL-1241;Metacillin;Dimocillin;Methcilline;methicillin;Dimethoxyphenyl Penicillin;MRSA Selective Supplement;2,6-Dimethoxyphenylpenicillin
CBNumber:
CB3889080
Molecular Formula:
C17H20N2O6S
Molecular Weight:
380.42
MDL Number:
MFCD00242880
MOL File:
61-32-5.mol
Last updated:2023-05-04 15:10:44

methicillin Properties

Boiling point 640.0±55.0 °C(Predicted)
Density 1.44±0.1 g/cm3(Predicted)
pka pKa 2.77± 0.04(H2O,t = 25,c=0.0097) (Uncertain)
FDA UNII Q91FH1328A

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  XH2379000

methicillin price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 51387 MRSA Selective Supplement for microbiology 61-32-5 5vials $168 2024-03-01 Buy
Product number Packaging Price Buy
51387 5vials $168 Buy

methicillin Chemical Properties,Uses,Production

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.

brand name

Staphcillin (Apothecon).

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 It was initially used widely but has been superseded by other group 3 members and is no longer commercially available.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-(2|á,5|á,6|?)]-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.

Synthesis_61-32-5

551-16-6
61-32-5
Synthesis of methicillin from 6-Aminopenicillanic acid

methicillin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 13)Suppliers
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TargetMol Chemicals Inc.
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ZHEJIANG JIUZHOU CHEM CO., LTD
+86-0576225566889 +86-13454675544 admin@jiuzhou-chem.com;jamie@jiuzhou-chem.com;alice@jiuzhou-chem.com China 20000 58
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Guangzhou Isun Pharmaceutical Co., Ltd 020-39119399 18927568969 isunpharm@qq.com China 4428 55
Chizhou Kailong Import and Export Trade Co., Ltd. xg01_gj@163.com China 9503 50
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51471 80
Alta Scientific Co., Ltd. 022-6537-8550 15522853686 sales@altasci.com.cn China 4515 55
Shanghai Han-Xiang Chemical Co., Ltd. 15971444841 amber@biochempartner.com China 3063 58
BOC Sciences -- info@bocsci.com USA 0 65

Related articles

methicillin Methcilline 2,6-Dimethoxyphenyl-penicillin, Methicillin Selective Supplement, Methicillin, Staphcillin MRSA Selective Supplement (2S,5R,6R)-6-(2,6-Dimethoxybenzoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylic acid 2,6-Dimethoxyphenylpenicillin BRL-1241 Dimocillin Metacillin C07177 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(2,6-diMethoxybenzoyl)aMino]-3,3-diMethyl-7-oxo-, (2S,5R,6R)- Dimethoxyphenyl Penicillin Metin 61-32-5