Identification

Name
Ticarcillin
Accession Number
DB01607
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

An antibiotic derived from penicillin similar to carbenicillin in action.

Structure
Thumb
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
  • alpha-Carboxy-3-thienylmethylpenicillin
  • Ticarcilina
  • Ticarcillin supplement
  • Ticarcilline
  • Ticarcillinum
Product Ingredients
IngredientUNIICASInChI Key
Ticarcillin disodiumG8TVV6DSYG29457-07-6ZBBCUBMBMZNEME-QBGWIPKPSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TicarInjection, powder, for solution3 g/1IntravenousGlaxoSmithKline2006-01-262006-09-21Us
Ticar Inj Pws 1gm/vialPowder, for solution1 gIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311996-09-12Canada
Ticar Inj Pws 3gm/vialPowder, for solution3 gIntramuscular; IntravenousSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-311999-03-08Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, powder, for solutionIntravenousGlaxosmithkline Inc1990-10-222015-07-31Us
TimentinTicarcillin (3 g) + Clavulanate potassium (100 mg)Powder, for solutionIntravenousGlaxosmithkline Inc1992-12-312015-03-23Canada
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, powder, for solutionIntravenousGlaxosmithkline Inc1990-10-222015-07-31Us
TimentinTicarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL)Injection, solutionIntravenousGlaxosmithkline Inc1990-10-222014-11-20Us
TimentinTicarcillin (30 g) + Clavulanate potassium (1 g)Powder, for solutionIntravenousGlaxosmithkline Inc2005-01-282015-03-23Canada
Categories
UNII
F93UJX4SWT
CAS number
34787-01-4
Weight
Average: 384.427
Monoisotopic: 384.044977634
Chemical Formula
C15H16N2O6S2
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

Pharmacology

Indication

For the treatment of bacterial infections.

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 antibiotic properties arise from its ability to prevent cross-linking of peptidoglycan during cell wall synthesis when the bacteria tries to divide, causing death.

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
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
DrugInteraction
(R)-warfarinTicarcillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinTicarcillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinTicarcillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Ticarcillin which could result in a higher serum level.
AcenocoumarolTicarcillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Ticarcillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Ticarcillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Ticarcillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Ticarcillin.
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Ticarcillin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015545
KEGG Compound
C07139
PubChem Compound
36921
PubChem Substance
46505959
ChemSpider
33876
BindingDB
50103522
ChEBI
9587
ChEMBL
CHEMBL1449
Therapeutic Targets Database
DAP000458
PharmGKB
PA451684
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ticarcillin
ATC Codes
J01CR03 — Ticarcillin and enzyme inhibitorJ01CR50 — Combinations of penicillinsJ01CA13 — Ticarcillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
2CompletedTreatmentDiabetes Mellitus (DM) / Infection NOS1
2CompletedTreatmentInfection NOS / Pelvic Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
  • GlaxoSmithKline Inc.
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous3 g/1
Powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntramuscular; Intravenous3 g
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

Taxonomy

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
Alpha-dipeptide / Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Penam / Dicarboxylic acid or derivatives / 1,3-dicarbonyl compound / Beta-lactam / Tertiary carboxylic acid amide / Thiazolidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:9587)

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 November 02, 2018 08:47