Ticarcillin

Identification

Name
Ticarcillin
Accession Number
DB01607
Description

An antibiotic derived from penicillin similar to carbenicillin in action.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 384.427
Monoisotopic: 384.044977634
Chemical Formula
C15H16N2O6S2
Synonyms
  • (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
  • Ticarcilina
  • Ticarcillin
  • Ticarcilline
  • Ticarcillinum
  • α-carboxy-3-thienylmethylpenicillin

Pharmacology

Indication

For the treatment of bacterial infections.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

TargetActionsOrganism
APenicillin binding protein 2a
inhibitor
Staphylococcus aureus
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

45%

Metabolism
Not Available
Route of elimination
Not Available
Half-life

1.1 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

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

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Ticarcillin which could result in a higher serum level.
AcenocoumarolTicarcillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Ticarcillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Ticarcillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Ticarcillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Ticarcillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Ticarcillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Ticarcillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Ticarcillin.
Cyproterone acetateThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Ticarcillin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Product Ingredients
IngredientUNIICASInChI Key
Ticarcillin disodiumG8TVV6DSYG29457-07-6ZBBCUBMBMZNEME-QBGWIPKPSA-L
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TicarInjection, powder, for solution3 g/1IntravenousGlaxoSmithKline2006-01-262006-09-21US flag
Ticar Inj Pws 1gm/vialPowder, for solutionIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311996-09-12Canada flag
Ticar Inj Pws 3gm/vialPowder, for solutionIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311999-03-08Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, powder, for solutionIntravenousGlaxosmithkline Inc1990-10-222015-07-31US flag
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, solutionIntravenousGlaxosmithkline Inc1990-10-222014-11-20US flag
TimentinTicarcillin (30 g) + Clavulanate potassium (1 g)Powder, for solutionIntravenousGlaxosmithkline Inc2005-01-282015-03-23Canada flag
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, powder, for solutionIntravenousGlaxosmithkline Inc1990-10-222015-07-31US flag
TimentinTicarcillin (3 g) + Clavulanate potassium (100 mg)Powder, for solutionIntravenousGlaxosmithkline Inc1992-12-312015-03-23Canada flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA13 — Ticarcillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-alpha amino acids and derivatives / 1,3-dicarbonyl compounds / Dicarboxylic acids and derivatives / Thiophenes / Thiazolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines
show 8 more
Substituents
1,3-dicarbonyl compound / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:9587)

Chemical Identifiers

UNII
F93UJX4SWT
CAS number
34787-01-4
InChI Key
OHKOGUYZJXTSFX-KZFFXBSXSA-N
InChI
InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1
IUPAC Name
(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
SMILES
[H][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](C(O)=O)C1=CSC=C1)C(O)=O

References

General References
  1. FDA Approved Drug Products: TIMENTIN (sterile ticarcillin disodium and clavulanate potassium) for Intravenous Administration [Link]
Human Metabolome Database
HMDB0015545
KEGG Compound
C07139
PubChem Compound
36921
PubChem Substance
46505959
ChemSpider
33876
BindingDB
50103522
RxNav
10591
ChEBI
9587
ChEMBL
CHEMBL1449
ZINC
ZINC000003831540
Therapeutic Targets Database
DAP000458
PharmGKB
PA451684
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ticarcillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentDiabetes / Infection1
2CompletedTreatmentInfection / Pelvic Infections1
1CompletedTreatmentSystemic Infections1
1WithdrawnNot AvailableSepsis1
0RecruitingTreatmentOsteomyelitis1
Not AvailableActive Not RecruitingTreatmentAppendicitis1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
  • GlaxoSmithKline Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntravenous3 g/1
Powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
Injection, solutionIntravenous
Powder, for solutionIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0716 mg/mLALOGPS
logP0.99ALOGPS
logP0.6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area124.01 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.93 m3·mol-1ChemAxon
Polarizability36.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9432
Blood Brain Barrier-0.9921
Caco-2 permeable-0.7652
P-glycoprotein substrateSubstrate0.5239
P-glycoprotein inhibitor INon-inhibitor0.9303
P-glycoprotein inhibitor IINon-inhibitor0.9878
Renal organic cation transporterNon-inhibitor0.9685
CYP450 2C9 substrateNon-substrate0.7871
CYP450 2D6 substrateNon-substrate0.857
CYP450 3A4 substrateNon-substrate0.5961
CYP450 1A2 substrateNon-inhibitor0.8764
CYP450 2C9 inhibitorNon-inhibitor0.9219
CYP450 2D6 inhibitorNon-inhibitor0.9317
CYP450 2C19 inhibitorNon-inhibitor0.9171
CYP450 3A4 inhibitorNon-inhibitor0.9318
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9875
Ames testNon AMES toxic0.8681
CarcinogenicityNon-carcinogens0.6121
BiodegradationNot ready biodegradable0.9573
Rat acute toxicity1.4591 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9997
hERG inhibition (predictor II)Non-inhibitor0.9124
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
mecA
Uniprot ID
C1KC03
Uniprot Name
Penicillin binding protein 2a
Molecular Weight
54918.915 Da
References
  1. Chambers HF, Sachdeva M, Kennedy S: Binding affinity for penicillin-binding protein 2a correlates with in vivo activity of beta-lactam antibiotics against methicillin-resistant Staphylococcus aureus. J Infect Dis. 1990 Sep;162(3):705-10. [PubMed:2387996]

Drug created on August 29, 2007 12:51 / Updated on June 13, 2020 10:24

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