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Ticarcillin

pharmaceutical raw materials
Ticarcillin structure

Ticarcillin 

structure
  • CAS No:

    34787-01-4

  • Formula:

    C15H16N2O6S2

  • Chemical Name:

    Ticarcillin

  • Synonyms:

    4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-2-carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-,[2S-[2α,5α,6β(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)-;(2S,5R,6R)-6-[[(2R)-2-Carboxy-2-(3-thienyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-[D-(-)-α-Carboxy-3-thienylacetamido]penicillanic acid;Ticarcillin

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ChEBI: A penicillin compound having a 6beta-[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino side-group.


Solid


Ticarcillin is a penicillin compound having a 6beta-[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino side-group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a ticarcillin(2-).|An antibiotic derived from penicillin similar to carbenicillin in action.|Ticarcillin is a Penicillin-class Antibacterial.|Ticarcillin is an extended-spectrum carboxypenicillin antibiotic and is used to treat moderate-to-severe infections due to susceptible organisms. Ticarcillin has been linked with idiosyncratic liver injury, but only rarely and as isolated case reports.|Ticarcillin is a broad-spectrum, semi-synthetic penicillin antibiotic with bactericidal activity. Similar to carbenicillin in action, ticarcillin inactivates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis.|An antibiotic derived from penicillin similar to CARBENICILLIN in action.

Ticarcillin Basic Attributes

384.43

384.43

252-213-5

F93UJX4SWT

DTXSID0023668

C889

J - Antiinfectives for systemic use

Characteristics

178

0.69

1.6±0.1 g/cm3

768.3±60.0 °C at 760 mmHg

418.4±32.9 °C

1.694

7.16e-02 g/L

2-8°C

Safety Information

NONH for all modes of transport

3

42/43

22-36/37-45

Xn

P261-P280-P342 + P311

H317-H334

|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

As with other penicillins, neurotoxic reactions may arise when very high doses of ticarcillin are administered, especially in patients with impaired renal function.

Intravenous ticarcillin therapy has been associated with mild and transient serum aminotransferase elevations that were generally self-limited and only slightly more common with ticarcillin than with comparative antibiotics. Much more commonly reported were instances of anicteric hepatic injury from carbenicillin, a similar carboxypenicillin with extend coverage against Pseudomonas. Persons receiving high doses of intravenous carbenicillin not uncommonly (15% to 30%) developed serum aminotransferase elevations without jaundice, which promptly fell to normal with discontinuation or switching to another antibiotic. Recurrence is common with retreatment using carbenicillin, but not with ticarcillin. A similar phenomenon occurs with intravenous oxacillin. Rare instances of idiosyncratic, clinically apparent cholestatic liver injury have been reported in persons receiving ticarcillin in combination with clavulanate, some of which resemble the rare idiosyncratic reactions that can occur with many penicillins and which resemble the cholestatic liver injury that occurs after amoxicillin/clavulanate.

45%

Drug Information

For the treatment of bacterial infections.

Ticarcillin is an extended-spectrum carboxypenicillin antibiotic and is used to treat moderate-to-severe infections due to susceptible organisms. Ticarcillin has been linked with idiosyncratic liver injury, but only rarely and as isolated case reports.

Antiinfective Agents

Ticarcillin is a semisynthetic antibiotic with a broad spectrum of bactericidal activity against many gram-positive and gram-negative aerobic and anaerobic bacteria. Ticarcillin is, however, susceptible to degradation by ß-lactamases, and therefore, the spectrum of activity does not normally include organisms which produce these enzymes.

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

1.1 hours

Ticarcillin's principal mechanism of action revolves around its capacity to prevent the cross-linking of peptidoglycan during bacterial cell wall synthesis. Consequently, when the offending bacteria attempt to undergo cell division, cell death occurs.

BRL 2288

Ticarcillin Use and Manufacturing

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.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:384.4
XLogP3:0.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:384.04497858
Monoisotopic Mass:384.04497858
Topological Polar Surface Area:178
Heavy Atom Count:25
Complexity:640
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Ticarcillin is a broad-spectrum bactericidal agent of the penicillin class. When combined with clavulanic acid, it becomes an antibiotic with broad-spectrum bactericidal effect and is suitable for the empirical treatment of a wide range of bacterial infectious diseases.

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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