| Identification | More | [Name]
Ticarcillin | [CAS]
34787-01-4 | [Synonyms]
(2s,5r,6r)-6-[[(2r)-2-carboxy-2-thiophen-3-yl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
TICARCILLIN
Ticcarcillin acid
Temocillin Disodium
TRIARCILLIN
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2a,5a,6b(S*)]]-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-carboxy-3-thienylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-(9CI)
6-[D-(-)-a-Carboxy-3-thienylacetamido]penicillanic acid
(2S,5R,6R)-6-[[(2R)-2-carboxy-2-thiophen-3-yl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | [EINECS(EC#)]
252-213-5 | [Molecular Formula]
C15H16N2O6S2 | [MDL Number]
MFCD00864998 | [Molecular Weight]
384.43 | [MOL File]
34787-01-4.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
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| Hazard Information | Back Directory | [Description]
Temocillin disodium is a broad-spectrum, β-lactamase resistant, injectable penicillin.
High serum levels and a five hour half-life allow once or twice-daily dosing. | [Originator]
Beecham (United Kingdom) | [Uses]
Ticarcillin (SB) is a significant penicillin antibiotic that incorporates the thiophene ring system. | [Uses]
Ticarcillin is a carboxypenicillin belonging to the beta-lactam class of antibiotics. Ticarcillin is an injectable antibiotic used in the treatment of infections caused by gram-negative bacteria, part
icularly Pseudomonas aeruginosa. | [Uses]
Ticarcillin is a carboxypenicillin belonging to the beta-lactam class of antibiotics. Ticarcillin is an injectable antibiotic used in the treatment of infections caused by gram-negative bacteria, particularly Pseudomonas aeruginosa. | [Definition]
ChEBI: A penicillin compound having a 6beta-[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino side-group. | [Brand name]
TEMOPEN | [Antimicrobial activity]
Because it is hydrolyzed less rapidly than ampicillin, non-β-
lactamase-producing strains of N. gonorrhoeae, ampicillin-susceptible
H. influenzae and some Enterobacteriaceae are susceptible.
Most aerobic and anaerobic Gram-positive bacteria are susceptible,
with the exception of E. faecalis and β-lactamase-producing
Staph. aureus. Anaerobic Gram-negative bacteria including B. fragilis
are usually susceptible. Bactericidal synergy with aminoglycosides
is demonstrable against Ps. aeruginosa and enterobacteria. | [Acquired resistance]
Ticarcillin is generally cross-resistant with carbenicillin.
It is somewhat stable to hydrolysis by AmpC-mediated β-lactamases of Gram-negative bacilli, but can be hydrolyzed
by most other chromosomally and plasmid-mediated enzymes
unless protected by a β-lactamase inhibitor. | [Pharmacokinetics]
Oral absorption: Negligible
Cmax 1 g intramuscular: 35 mg/L after 1 h
Plasma half-life: 1.3 h
Volume of distribution: 0.21 L/kg
Plasma protein binding: 50–60%
Absorption and distribution
It is not orally absorbed. On parenteral co-administration
with gentamicin, the plasma concentration of ticarcillin is
unaffected, but the concentration of gentamicin is lowered. It
enters the serous fluids, providing concentrations up to 60%
of those of the plasma. It does not cross the normal meninges
but levels of up to 50% of those of the plasma can be found
in meningitis.
Metabolism and excretion
Up to 15% is excreted as penicilloic acid, a higher percentage
than for carbenicillin (up to 5%). Some is excreted in
the bile, producing levels 2–3 times those in the plasma, but
the main route of excretion is through the kidneys (80%),
principally as unchanged drug, appearing in the urine in the
first 6 h. It is more rapidly eliminated in children with cystic
fibrosis. | [Clinical Use]
Serious infection, including septicemia, respiratory tract infections,
genitourinary tract infections and skin and soft-tissue infections caused
by susceptible bacteria | [Side effects]
As with all penicillins, hypersensitivity reactions may occur,
but are less frequent and severe than those associated with
benzylpenicillin. Rashes and eosinophilia occur; reversible
abnormalities of liver function can develop. Since large doses
of the drug have to be used, convulsions can occur, as with
other penicillins, and being a disodium salt, electrolyte disturbances
can result from the sodium load and from loss of
potassium. | [Synthesis]
Ticarcillin, [2S-(2|á,5|á,6|?)]-3,3-dimethyl-7-oxo-6-[2-carboxy-2-(3-thienyl)
acetamido]-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.34), is synthesized by direct acylation of 6-APA in the presence of sodium hydroxide, but with
3-thienylmalonic acid chloride (32.1.1.33), which gives ticarcillin.
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| Company Name: |
LGM Pharma
|
| Tel: |
1-(800)-881-8210 |
| Website: |
www.lgmpharma.com |
| Company Name: |
BOC Sciences
|
| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
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