Basic information
- CAS
34787-01-4- Standard SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](C(=O)O)c3ccsc3)C(=O)N2[C@H]1C(=O)O- InChIKey
OHKOGUYZJXTSFX-KZFFXBSXSA-N- Molecular formula
- C15H16N2O6S2
- Average molar mass
- 384.4 g/mol
- Monoisotopic mass
- 384.04497858
Overview
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-).
Names & identifiers
- Preferred name
- Ticarcillin
- IUPAC
- (2S,5R,6R)-6-[[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- Ticarcillin
- Molecular formula
- C15H16N2O6S2
- Molecular weight
- 384.43
Names & synonyms
TICARCILLIN34787-01-4TicarcilinaTicarcillineTicarcillinumCHEBI:9587F93UJX4SWTalpha-carboxy-3-thienylmethylpenicillin4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-DTXSID0023668BRL2288(2S,5R,6R)-6-[[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Show more names
Temocillin DisodiumicarcillinTRIARCILLINTicarcillin acidTiccarcillin acidTicarcillin USP/EP/BPTicarcillin free baseTicarcillin Impurity 11Ticarcillin See T437901
(2S,5R,6R)-6-[(2R)-2-carboxy-2-(thiophen-3-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(2S,5R,6R)-6-{[(2R)-2-carboxy-2-thiophen-3-ylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidTarcil(2S,5R,6R)-6-(((2R)-2-carboxy-2-thiophen-3-ylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid(2S,5R,6R)-6-((2R)-2-carboxy-2-(thiophen-3-yl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidDisodium, TicarcillinRefChem:389326DTXCID503668
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 178 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 640
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Solubility7.16e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Penicillins
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 768.3 · 768.3±60.0 °C(Predicted)
- Density
- 1.62 · 1.62±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 2.89 · pKa 2.89±0.05(H2O t=25.0 I=0.15 (KCl)) (Uncertain);3.28±0.04 (Uncertain)
- CAS DataBase Reference
- 34787 · 34787-01-4(CAS DataBase Reference)
- FDA UNII
- 93 UJX4SWT · F93UJX4SWT
- ATC code
- 1 CA13 · J01CA13
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Toxicology
Hepatotoxicity
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.
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding45%
Pharmacodynamics
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.
Mechanism of Action
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.
Biological Half-Life1.1 hours
FDA Pharmacological Classification
F93UJX4SWT
TICARCILLIN
Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial
Chemical Structure [CS] - Penicillins
Ticarcillin is a Penicillin-class Antibacterial.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
UsesUse (kg) in USA (2002): 14700
Applications
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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