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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H15N2O6S2.Na.H2O
Molecular Weight 424.424
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TICARCILLIN MONOSODIUM

SMILES

O.[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](C([O-])=O)C3=CSC=C3)C(O)=O

InChI

InChIKey=BVGLWBKHBMAPKY-QBGWIPKPSA-M
InChI=1S/C15H16N2O6S2.Na.H2O/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);;1H2/q;+1;/p-1/t7-,8-,9+,12-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H16N2O6S2
Molecular Weight 384.427
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Ticarcillin (also known as Ticar) is a semisynthetic antibiotic with a broad spectrum of bactericidal activity against many gram-positive and gram-negative aerobic and anaerobic bacteria. Ticarcillin is not absorbed orally; therefore, it must be given intravenously or intramuscularly. 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. Usage of ticar was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TICAR

Approved Use

Unknown

Launch Date

2.16345608E11
Curative
TICAR

Approved Use

Unknown

Launch Date

2.16345608E11
Curative
TICAR

Approved Use

Unknown

Launch Date

2.16345608E11
Curative
TICAR

Approved Use

Unknown

Launch Date

2.16345608E11
Curative
TICAR

Approved Use

Unknown

Launch Date

2.16345608E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
324 μg/mL
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
431.5 mg/L
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
621.8 mg/L
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
576.2 mg/L
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
485 μg × h/mL
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
538 mg × h/L
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
890 mg × h/L
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
747 mg × h/L
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
339 μg × h/mL
50 mg/kg bw single, intravenous
dose: 50 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
76 min
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TICARCILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.1 h
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80.7 min
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
84.7 min
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANIC ACID
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
74.8 min
5 g single, intravenous
dose: 5 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TICARCILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1 h
50 mg/kg bw single, intravenous
dose: 50 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
3 g single, intravenous
dose: 3 g
route of administration: Intravenous
experiment type: SINGLE
co-administered: CLAVULANATE POTASSIUM
TICARCILLIN serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 g 4 times / day multiple, intravenous
Recommended
Dose: 3 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 4 times / day
Co-administed with::
ciavuianate potassium iv(200 mg/kg/day)
Sources: Page: p.90
unhealthy, 19-91
n = 37
Health Status: unhealthy
Condition: Urinary tract infections
Age Group: 19-91
Sex: M+F
Population Size: 37
Sources: Page: p.90
Disc. AE: Rash, Nausea...
Other AEs: Elevated liver enzymes, Eosinophilia...
AEs leading to
discontinuation/dose reduction:
Rash (grade 1, 2.7%)
Nausea (grade 2, 2.7%)
Other AEs:
Elevated liver enzymes
Eosinophilia
Sources: Page: p.90
80 mg/kg single, intravenous
Highest studied dose
Dose: 80 mg/kg
Route: intravenous
Route: single
Dose: 80 mg/kg
Sources: Page: p.360
healthy, 22-26
n = 8
Health Status: healthy
Age Group: 22-26
Sex: M+F
Population Size: 8
Sources: Page: p.360
3 g 5 times / day multiple, intravenous
Overdose
Dose: 3 g, 5 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 5 times / day
Co-administed with::
ciavuianate potassium iv(>100 mg)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Other AEs: Convulsions...
3 g 5 times / day multiple, intravenous
Recommended
Dose: 3 g, 5 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 5 times / day
Co-administed with::
ciavuianate potassium iv(100 mg)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Other AEs: Hypersensitivity reaction, Diarrhea, Clostridium difficile...
Other AEs:
Hypersensitivity reaction (grade 3-5)
Diarrhea, Clostridium difficile
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Elevated liver enzymes
3 g 4 times / day multiple, intravenous
Recommended
Dose: 3 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 4 times / day
Co-administed with::
ciavuianate potassium iv(200 mg/kg/day)
Sources: Page: p.90
unhealthy, 19-91
n = 37
Health Status: unhealthy
Condition: Urinary tract infections
Age Group: 19-91
Sex: M+F
Population Size: 37
Sources: Page: p.90
Eosinophilia
3 g 4 times / day multiple, intravenous
Recommended
Dose: 3 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 4 times / day
Co-administed with::
ciavuianate potassium iv(200 mg/kg/day)
Sources: Page: p.90
unhealthy, 19-91
n = 37
Health Status: unhealthy
Condition: Urinary tract infections
Age Group: 19-91
Sex: M+F
Population Size: 37
Sources: Page: p.90
Rash grade 1, 2.7%
Disc. AE
3 g 4 times / day multiple, intravenous
Recommended
Dose: 3 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 4 times / day
Co-administed with::
ciavuianate potassium iv(200 mg/kg/day)
Sources: Page: p.90
unhealthy, 19-91
n = 37
Health Status: unhealthy
Condition: Urinary tract infections
Age Group: 19-91
Sex: M+F
Population Size: 37
Sources: Page: p.90
Nausea grade 2, 2.7%
Disc. AE
3 g 4 times / day multiple, intravenous
Recommended
Dose: 3 g, 4 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 4 times / day
Co-administed with::
ciavuianate potassium iv(200 mg/kg/day)
Sources: Page: p.90
unhealthy, 19-91
n = 37
Health Status: unhealthy
Condition: Urinary tract infections
Age Group: 19-91
Sex: M+F
Population Size: 37
Sources: Page: p.90
Convulsions
3 g 5 times / day multiple, intravenous
Overdose
Dose: 3 g, 5 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 5 times / day
Co-administed with::
ciavuianate potassium iv(>100 mg)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Diarrhea, Clostridium difficile
3 g 5 times / day multiple, intravenous
Recommended
Dose: 3 g, 5 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 5 times / day
Co-administed with::
ciavuianate potassium iv(100 mg)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Hypersensitivity reaction grade 3-5
3 g 5 times / day multiple, intravenous
Recommended
Dose: 3 g, 5 times / day
Route: intravenous
Route: multiple
Dose: 3 g, 5 times / day
Co-administed with::
ciavuianate potassium iv(100 mg)
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Bacterial infections
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
[Identification and susceptibility to antimicrobial agents of strictly anaerobic bacteria isolated from hospitalized patients].
2002
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Efficiency of procedures for induction and cultivation of Pseudomonas syringae pv. pisi L-form.
2003
Evaluation of ticarcillin/clavulanic acid versus ceftriaxone plus amikacin for fever and neutropenia in pediatric patients with leukemia and lymphoma.
2003 Apr
Natural antimicrobial susceptibilities of strains of 'unusual' Serratia species: S. ficaria, S. fonticola, S. odorifera, S. plymuthica and S. rubidaea.
2003 Apr
Application of MEKC for determination of ticarcillin and clavulanic acid in Timentin intravenous preparation.
2003 Apr 24
Early antibiotic selection and efficient rooting and acclimatization improve the production of transgenic plum plants (Prunus domestica L.).
2003 Aug
Antimicrobial susceptibility and synergistic activity of meropenem against Gram-negative non-fermentative bacteria isolated from cystic fibrosis patients.
2003 Dec
Late bacterial keratitis after implantation of intrastromal corneal ring segments.
2003 Feb
Agrobacterium radiobacter bacteremia in pediatric patients: case report and review.
2003 Feb
Antimicrobial susceptibility profile of molecular typed cystic fibrosis Stenotrophomonas maltophilia isolates and differences with noncystic fibrosis isolates.
2003 Feb
Dead bugs don't mutate: susceptibility issues in the emergence of bacterial resistance.
2003 Jan
[Phenotypes of beta-lactam resistance in the genus Aeromonas].
2003 Jul
Natural antibiotic susceptibility of strains of Serratia marcescens and the S. liquefaciens complex: S. liquefaciens sensu stricto, S. proteamaculans and S. grimesii.
2003 Jul
[Community-acquired Pseudomonas aeruginosa bacteremic pneumonia in a "healthy" subject].
2003 Jul 12
Ticarcillin-clavulanic acid plus amikacin versus ceftazidime plus amikacin in the empirical treatment of fever in acute leukemia: a prospective randomized trial.
2003 Jun
Cefepime versus ticarcillin and clavulanate potassium and aztreonam for febrile neutropenia therapy in high-dose chemotherapy patients.
2003 Jun
Beta-lactamase production in Prevotella and in vitro susceptibilities to selected beta-lactam antibiotics [corrected].
2003 Mar
Retrospective analysis of antibiotic susceptibility patterns of respiratory isolates of Pseudomonas aeruginosa in a Turkish University Hospital.
2003 Mar 7
Sequence analysis and biochemical characterisation of chromosomal CAV-1 (Aeromonas caviae), the parental cephalosporinase of plasmid-mediated AmpC 'FOX' cluster.
2003 May 16
Natural antibiotic susceptibility of Ewingella americana strains.
2003 Oct
Natural antimicrobial susceptibilities and biochemical profiles of Yersinia enterocolitica-like strains: Y. frederiksenii, Y. intermedia, Y. kristensenii and Y. rohdei.
2003 Sep 22
Simultaneous determination of ticarcillin and clavulanate in rabbit serum and tissue cage fluid by liquid chromatography.
2003 Sep 5
Beta-lactamase characterization in Escherichia coli isolates with diminished susceptibility or resistance to extended-spectrum cephalosporins recovered from sick animals in Spain.
2003 Summer
[Antibiotic susceptibility and occurrence of ESBL in Pseudomonas aeruginosa strains isolated from different clinical specimens].
2004
[Mechanisms of resistance in Enterobacteriaceae towards beta-lactamase antibiotics].
2004
Detection of ticarcillin-clavulonic acid susceptibility with microdilution method in Citrobacter, Hafnia, Proteus and some gram negative bacteria.
2004
An epidemiological analysis of Stenotrophomonas maltophilia strains in a university hospital.
2004 Apr
Comparative activity of beta-lactam agents (carbapenem excepted) against Pseudomonas aeruginosa strains with CARB or OXA beta-lactamases.
2004 Apr
A laboratory evaluation of antibiotic therapy for ciprofloxacin-resistant Pseudomonas aeruginosa.
2004 Aug
Detection and assay of beta-lactamases in clinical and non-clinical strains of Yersinia enterocolitica biovar 1A.
2004 Aug
The value of a CT-guided fine needle aspirate in infants with lung abscess.
2004 Aug
Antibiotic susceptibility patterns among respiratory isolates of Gram-negative bacilli in a Turkish university hospital.
2004 Aug 22
[Pseudomonas aeruginosa: a multicentric study of antibiotic resistance (1999-2000)].
2004 Dec
[Infectious cellulitis and Shewanella alga septicemia in an immunocompetent patient].
2004 Dec
Impact of a formulary switch from ticarcillin-clavulanate to piperacillin-tazobactam on colonization with vancomycin-resistant enterococci.
2004 Dec
Pharmacodynamic study of beta-lactams alone and in combination with beta-lactamase inhibitors against Pseudomonas aeruginosa possessing an inducible beta-lactamase.
2004 Feb
Detection of an IS21 insertion sequence in the mexR gene of Pseudomonas aeruginosa increasing beta-lactam resistance.
2004 Jan 15
[A 4-year study of Pseudomonas aeruginosa susceptibility to antibiotics (1998-2001) in northern Lebanon].
2004 Jul
Antibiotic resistance rates and phenotypes among isolates of Enterobacteriaceae in French extra-hospital practice.
2004 Mar
Clinical efficacy, tolerability, and cost savings associated with the use of open-label metronidazole plus ceftriaxone once daily compared with ticarcillin/clavulanate every 6 hours as empiric treatment for diabetic lower-extremity infections in older males.
2004 Sep
CTX-M beta-lactamase-producing Escherichia coli in long-term care facilities, France.
2004 Sep
Resistance to beta-lactam antibiotics in Aeromonas hydrophila isolated from rainbow trout (Oncorhynchus mykiss).
2004 Sep
Antimicrobial resistance of selected Salmonella isolates from food animals and food in Alberta.
2005 Feb
Effect of bovine lactoferrin on the MICs of ampicillin/sulbactam (UNASYN), amoxicillin/clavulanic acid (Augmentin), ticarcillin clavulanate (Timentin), and piperacillin-tazobactam (ZOSYN), against clinical and environmental isolates of motile Aeromonas.
2005 Jan
Antimicrobial susceptibility of bifidobacteria.
2005 Jan
Natural antimicrobial susceptibility patterns and biochemical identification of Escherichia albertii and Hafnia alvei strains.
2005 Mar
Inquilinus limosus in patients with cystic fibrosis, Germany.
2005 Mar
Antimicrobial use and Pseudomonas aeruginosa susceptibility profile in a cystic fibrosis centre.
2005 Mar
Acinetobacter baumanii folliculitis in a patient with AIDS.
2005 May
Patents

Sample Use Guides

In Vivo Use Guide
Bacterial septicemia: 200 to 300 mg/kg/day by I.V. infusion in divided doses every 4 or 6 hours. Respiratory tract infections: (The usual dose is 3 grams given every 4 hours [18 grams/day] or 4 grams given every 6 hours [16 grams/day] depending on weight and the severity of the infection.) Urinary tract infections: Complicated: 150 to 200 mg/kg/day by I.V. infusion in divided doses every 4 or 6 hours. (Usual recommended dosage for average [70 kg] adults: 3 grams q.i.d.) Uncomplicated: 1 gram I.M. or direct I.V. every 6 hours.
Route of Administration: Other
In Vitro Use Guide
A total of 632 clinical bacterial isolates were tested for susceptibility to twofold dilutions of ticarcillin alone and in combination with 1, 2, and 4 micrograms of clavulanic acid (CA) (Timentin) per ml by a reference microdilution method. With the addition of CA, ticarcillin MICs were reduced eightfold or greater with 54 of 59 (92%) strains of the family Enterobacteriaceae with ticarcillin MICs of greater than or equal to 64 micrograms/ml. Ticarcillin MICs for beta-lactamase-producing Haemophilus influenzae, Neisseria gonorrhoeae, and most Staphylococcus aureus were reduced to less than or equal to 0.5 micrograms/ml when CA was added.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:41:32 UTC 2023
Edited
by admin
on Fri Dec 15 18:41:32 UTC 2023
Record UNII
34GZ64SH49
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TICARCILLIN MONOSODIUM
USP  
Common Name English
TICARCILLIN MONOSODIUM [USP MONOGRAPH]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)(HEPTANE-2-CARBOXYLIC ACID, 6-((CARBOXY-3-THIENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO, MONOSODIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-, MONOHYDRATE
Common Name English
(R)-N-((2S,5R,6R)-2-CARBOXY-3,4-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-6-YL)-3-THIOPHENEMALONAMIC ACID MONOHYDRATE MONOSODIUM SALT
Common Name English
TICARCILLIN MONOSODIUM MONOHYDRATE [USP-RS]
Common Name English
TICARCILLIN MONOSODIUM MONOHYDRATE
Common Name English
Code System Code Type Description
PUBCHEM
23725050
Created by admin on Fri Dec 15 18:41:32 UTC 2023 , Edited by admin on Fri Dec 15 18:41:32 UTC 2023
PRIMARY
ChEMBL
CHEMBL1449
Created by admin on Fri Dec 15 18:41:32 UTC 2023 , Edited by admin on Fri Dec 15 18:41:32 UTC 2023
PRIMARY
RS_ITEM_NUM
1667304
Created by admin on Fri Dec 15 18:41:32 UTC 2023 , Edited by admin on Fri Dec 15 18:41:32 UTC 2023
PRIMARY
FDA UNII
34GZ64SH49
Created by admin on Fri Dec 15 18:41:32 UTC 2023 , Edited by admin on Fri Dec 15 18:41:32 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY