Ticarcillin

Identification

Summary

Ticarcillin is a beta lactam antibiotic used to treat a variety of infections in the body.

Generic Name
Ticarcillin
DrugBank Accession Number
DB01607
Background

An antibiotic derived from penicillin similar to carbenicillin in action.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatInfectionCombination Product in combination with: Clavulanic acid (DB00766)••••••••••••
Contraindications & Blackbox Warnings
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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
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Toxicity

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

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.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Ambroxol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Ticarcillin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Articaine.
Food Interactions
Not Available

Products

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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 solution1 g / vialIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311996-09-12Canada flag
Ticar Inj Pws 3gm/vialPowder, for solution3 g / vialIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311999-03-08Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TimentinTicarcillin disodium (30 g / vial) + Clavulanate potassium (1 g / vial)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 disodium (3 g / vial) + Clavulanate potassium (100 mg / vial)Powder, for solutionIntravenousGlaxosmithkline Inc1992-12-312015-03-23Canada flag
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

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)
Affected organisms
  • Enteric bacteria and other eubacteria

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][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](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
4Unknown StatusTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentDiabetes / Infection1
2CompletedTreatmentInfection / Pelvic Infections1
2, 3CompletedTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
1CompletedTreatmentSystemic Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
  • GlaxoSmithKline Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntravenous3 g/1
Powder, for solutionIntramuscular; Intravenous1 g / vial
Powder, for solutionIntramuscular; Intravenous3 g / vial
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-MSsplash10-0006-9546000000-6f3ebd66c2d3c7a7045c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bvi-0941000000-378c099316dd34b6e198
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0091000000-a3cd9c3f437759b9bc5d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0910000000-f8284de48236d73cce3e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9671000000-2075f331e98e7ad80ee1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-2900000000-b5c7d70f99a4f8404d60
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9224000000-22e99e4d67046ded46ef
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.3903576
predicted
DarkChem Lite v0.1.0
[M-H]-186.0795576
predicted
DarkChem Lite v0.1.0
[M-H]-180.33586
predicted
DeepCCS 1.0 (2019)
[M+H]+185.5913576
predicted
DarkChem Lite v0.1.0
[M+H]+184.7422576
predicted
DarkChem Lite v0.1.0
[M+H]+182.73143
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.3360576
predicted
DarkChem Lite v0.1.0
[M+Na]+185.8479576
predicted
DarkChem Lite v0.1.0
[M+Na]+188.64397
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at August 29, 2007 18:51 / Updated at December 02, 2023 07:02