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
Structure for Ticarcillin (DB01607)
- 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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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism APenicillin binding protein 2a inhibitorStaphylococcus 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcemetacin Acemetacin may decrease the excretion rate of Ticarcillin which could result in a higher serum level. Acenocoumarol Ticarcillin may increase the anticoagulant activities of Acenocoumarol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Ticarcillin. Articaine The risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Articaine. Atracurium The therapeutic efficacy of Atracurium can be increased when used in combination with Ticarcillin. Atracurium besylate The therapeutic efficacy of Atracurium besylate can be increased when used in combination with Ticarcillin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ticarcillin. Benzocaine The risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Ticarcillin is combined with Bupivacaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ticarcillin disodium G8TVV6DSYG 29457-07-6 ZBBCUBMBMZNEME-QBGWIPKPSA-L - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ticar Injection, powder, for solution 3 g/1 Intravenous GlaxoSmithKline 2006-01-26 2006-09-21 US 
Ticar Inj Pws 1gm/vial Powder, for solution 1 g / vial Intramuscular; Intravenous Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1992-12-31 1996-09-12 Canada 
Ticar Inj Pws 3gm/vial Powder, for solution 3 g / vial Intramuscular; Intravenous Smithkline Beecham Pharma Division Of Smithkline Beecham Inc 1992-12-31 1999-03-08 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Timentin Ticarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL) Injection, solution Intravenous Glaxosmithkline Inc 1990-10-22 2014-11-20 US Timentin Ticarcillin disodium (30 g / vial) + Clavulanate potassium (1 g / vial) Powder, for solution Intravenous Glaxosmithkline Inc 2005-01-28 2015-03-23 Canada Timentin Ticarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL) Injection, powder, for solution Intravenous Glaxosmithkline Inc 1990-10-22 2015-07-31 US Timentin Ticarcillin disodium (3 g / vial) + Clavulanate potassium (100 mg / vial) Powder, for solution Intravenous Glaxosmithkline Inc 1992-12-31 2015-03-23 Canada Timentin Ticarcillin disodium (30 mg/1mL) + Clavulanate potassium (1 mg/1mL) Injection, powder, for solution Intravenous Glaxosmithkline Inc 1990-10-22 2015-07-31 US
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- 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
- FDA Approved Drug Products: TIMENTIN (sterile ticarcillin disodium and clavulanate potassium) for Intravenous Administration [Link]
- External Links
- Human Metabolome Database
- HMDB0015545
- KEGG Compound
- C07139
- PubChem Compound
- 36921
- PubChem Substance
- 46505959
- ChemSpider
- 33876
- BindingDB
- 50103522
- 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
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Cystic Fibrosis (CF) 1 2 Completed Treatment Diabetes / Infection 1 2 Completed Treatment Infection / Pelvic Infections 1 2, 3 Completed Treatment Acute Exacerbation of Chronic Obstructive Pulmonary Disease 1 1 Completed Treatment Systemic Infection 1 1 Withdrawn Not Available Sepsis 1 0 Terminated Treatment Osteomyelitis 1 Not Available Completed Treatment Appendicitis 1 Not Available Completed Treatment Chronic Bronchitis / Cystic Fibrosis (CF) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Baxter International Inc.
- GlaxoSmithKline Inc.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous 3 g/1 Powder, for solution Intramuscular; Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 3 g / vial Injection, powder, for solution Intravenous Injection, solution Intravenous Powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0716 mg/mL ALOGPS logP 0.99 ALOGPS logP 0.6 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 3.09 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 124.01 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 87.93 m3·mol-1 Chemaxon Polarizability 36.14 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9432 Blood Brain Barrier - 0.9921 Caco-2 permeable - 0.7652 P-glycoprotein substrate Substrate 0.5239 P-glycoprotein inhibitor I Non-inhibitor 0.9303 P-glycoprotein inhibitor II Non-inhibitor 0.9878 Renal organic cation transporter Non-inhibitor 0.9685 CYP450 2C9 substrate Non-substrate 0.7871 CYP450 2D6 substrate Non-substrate 0.857 CYP450 3A4 substrate Non-substrate 0.5961 CYP450 1A2 substrate Non-inhibitor 0.8764 CYP450 2C9 inhibitor Non-inhibitor 0.9219 CYP450 2D6 inhibitor Non-inhibitor 0.9317 CYP450 2C19 inhibitor Non-inhibitor 0.9171 CYP450 3A4 inhibitor Non-inhibitor 0.9318 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9875 Ames test Non AMES toxic 0.8681 Carcinogenicity Non-carcinogens 0.6121 Biodegradation Not ready biodegradable 0.9573 Rat acute toxicity 1.4591 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9997 hERG inhibition (predictor II) Non-inhibitor 0.9124
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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 March 03, 2023 17:50