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Ticarcillin

HCID 36921
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

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
Summenformel
C15H16N2O6S2
Durchschnittliche Molmasse
384,4 g/mol
Monoisotopische Masse
384,04497858

Überblick

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-).

Namen und Bezeichner

Bevorzugter 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
Lokaler Name
Ticarcillin
Englischer Name
Ticarcillin
Summenformel
C15H16N2O6S2
Molmasse
384.43

Namen und Synonyme

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
Weitere Namen anzeigen
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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,8
Polarare Oberfläche (TPSA)
178 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
5
Schwere Atome
25
Formalladung
0
Komplexität
640

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

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

Physikochemische Eigenschaften

Siedepunkt
768.3 · 768.3±60.0 °C(Predicted)
Dichte
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 Datenbank
34787 · 34787-01-4(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding45%
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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 · 5 Einträge

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.

Verwendung und Herstellung

UsesUse (kg) in USA (2002): 14700

Anwendungen

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.

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Datenbank-Bezeichner

CAS
34787-01-4
PubChem CID
36921
DTXSID
DTXSID0023668
ChEMBL
CHEMBL1449
ChEBI
CHEBI:9587
UNII
F93UJX4SWT
EC Number
252-213-5
Nikkaji
J17.850K
Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Ticarcillin

DILI Negative

Intramuscular; Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
risk_code
42/43
hazard_code
Xn
safety_code
22-36/37-45
Beschreibung

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Ergänzende Hinweise

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