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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+].CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](C([O-])=O)C3=CSC=C3)C(=O)N2[C@H]1C(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 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
[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
[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
[A 4-year study of Pseudomonas aeruginosa susceptibility to antibiotics (1998-2001) in northern Lebanon].
2004 Jul
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: intravenous; intramuscular
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 Mon Oct 21 20:02:06 UTC 2019
Edited
by admin
on Mon Oct 21 20:02:06 UTC 2019
Record UNII
34GZ64SH49
Record Status Validated (UNII)
Record Version
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Name Type Language
TICARCILLIN MONOSODIUM
USP  
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
Common Name English
TICARCILLIN MONOSODIUM [USP]
Common Name English
Code System Code Type Description
PUBCHEM
76964899
Created by admin on Mon Oct 21 20:02:06 UTC 2019 , Edited by admin on Mon Oct 21 20:02:06 UTC 2019
PRIMARY
ChEMBL
CHEMBL1449
Created by admin on Mon Oct 21 20:02:06 UTC 2019 , Edited by admin on Mon Oct 21 20:02:06 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY