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Home > Encyclopedia > Oxacillin

Oxacillin

pharmaceutical raw materials
Oxacillin structure

Oxacillin 

structure
  • CAS No:

    66-79-5

  • Formula:

    C19H19N3O5S

  • Chemical Name:

    Oxacillin

  • Synonyms:

    4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamido)-7-oxo-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-,[2S-(2α,5α,6β)]-;(2S,5R,6R)-3,3-Dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-(5-Methyl-3-phenyl-4-isoxazolyl)aminopenicillanic acid;5-Methyl-3-phenyl-4-isoxazolylpenicillin;MPi-PC;MPI-penicillin;Penicillin,(5-methyl-3-phenyl-4-isoxazolyl)-;Prostaphlyn;5-Methyl-3-phenyl-4-isooxazolylpenicillin;Oxazocillin;Oxacillin;Oxazocilline;1258378-00-5

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ChEBI: A penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6.


Solid


Oxacillin is a penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6beta. It has a role as an antibacterial agent and an antibacterial drug. It is a conjugate acid of an oxacillin(1-).|An antibiotic similar to [flucloxacillin] used in resistant staphylococci infections.|Oxacillin is a Penicillin-class Antibacterial.|Oxacillin is a parenteral, second generation penicillin antibiotic that is used to treat moderate-to-severe, penicillinase-resistant staphylococcal infections. Oxacillin has been linked to rare instances of clinically apparent, idiosyncratic liver injury, but it more commonly causes transient elevations in serum aminotransferases without jaundice.|Oxacillin is a semisynthetic penicillinase-resistant and acid-stable penicillin with an antimicrobial activity. Oxacillin binds to penicillin-binding proteins in the bacterial cell wall, thereby blocking the synthesis of peptidoglycan, a critical component of the bacterial cell wall. This leads to inhibition of cell growth and causes cell lysis.|An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.

Oxacillin Basic Attributes

401.44

401.44

200-635-5

UH95VD7V76

DTXSID8023397

C62063

J - Antiinfectives for systemic use

Characteristics

138

2.4

Solid

1.49±0.1 g/cm3(Predicted)

188 °C

8.62e-02 g/L

2.72None

2.72

191.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|195.4 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|198.25 Ų [M-H]-

Safety Information

P261, P264, P271, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P337+P313, P342+P311, P362, P403+P233, P405, P501

H315

|Danger|H315 (40%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Oxacillin has been linked to two forms of hepatotoxicity, first an acute and transient elevation in serum aminotransferase levels occurring with high doses of intravenous therapy; and second, a more prolonged, usually cholestatic, idiosyncratic liver injury that is similar to the hepatotoxicity of other second-generation penicillins such as dicloxacillin, flucloxacillin, and nafcillin.|Three forms of liver injury have been attributed to the penicillinase-resistant and other penicillins. The first is a transient and usually asymptomatic elevation in serum aminotransferase levels that occurs with high dose intravenous therapy with oxacillin (Case 1, Oxacillin) and rarely with standard penicillins (Case 1, Penicillin G). This reaction has not been described with nafcillin or dicloxacillin and patients can be safety switched to these or other forms of penicillin in the face of oxacillin injury. This form of penicillin-induced liver injury occurs only with high dose therapy that is likely due to direct hepatotoxicity.

94.2 +/- 2.1% (binds to serum protein, mainly albumin)

Drug Information

Used in the treatment of resistant staphylococci infections.

Oxacillin is a parenteral, second generation penicillin antibiotic that is used to treat moderate-to-severe, penicillinase-resistant staphylococcal infections. Oxacillin has been linked to rare instances of clinically apparent, idiosyncratic liver injury, but it more commonly causes transient elevations in serum aminotransferases without jaundice.

Penicillin (Penicillinase-Resistant)

Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Oxacillin Sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.

20 to 30 minutes

By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Oxacillin interferes with an autolysin inhibitor.

Methylphenylisoxazolyl Penicillin

Oxacillin Use and Manufacturing

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:401.4
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:401.10454189
Monoisotopic Mass:401.10454189
Topological Polar Surface Area:138
Heavy Atom Count:28
Complexity:681
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is an acid-resistant and penicillinase-resistant penicillin. It has good antibacterial activity against penicillinase-producing Staphylococci, but its antibacterial activity against various streptococci and non-penicillinase-producing Staphylococci is inferior to penicillin G. It exerts its bactericidal effect by inhibiting bacterial cell wall synthesis.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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