TICARCILLIN CRESYL SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H21N2O6S2.Na
Molecular Weight	496.532
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].CC1=CC=C(OC(=O)[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C([O-])=O)C4=CSC=C4)C=C1

InChI

InChIKey=JNUHVWONFHNMHH-UVKKPQQBSA-M

InChI=1S/C22H22N2O6S2.Na/c1-11-4-6-13(7-5-11)30-21(29)14(12-8-9-31-10-12)17(25)23-15-18(26)24-16(20(27)28)22(2,3)32-19(15)24;/h4-10,14-16,19H,1-3H3,(H,23,25)(H,27,28);/q;+1/p-1/t14-,15-,16+,19-;/m1./s1

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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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Sepsis 74	Curative	Approved 8,583	TICAR
Skin and soft tissue infections 33	Curative	Approved 8,583	TICAR
Acute and chronic respiratory tract infections 6	Curative	Approved 8,583	TICAR
Intra-abdominal infections 50	Curative	Approved 8,583	TICAR
Infections of the female pelvis and genital tract 6	Curative	Approved 8,583	TICAR

C_max

Value	Dose	Co-administered	Analyte	Population
576.2 mg/L	5 g single, intravenous		TICARCILLIN serum	Homo sapiens
621.8 mg/L	5 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
431.5 mg/L	3 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
324 μg/mL	3 g single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
747 mg × h/L	5 g single, intravenous		TICARCILLIN serum	Homo sapiens
890 mg × h/L	5 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
538 mg × h/L	3 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
485 μg × h/mL	3 g single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens
339 μg × h/mL	50 mg/kg bw single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
74.8 min	5 g single, intravenous		TICARCILLIN serum	Homo sapiens
84.7 min	5 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
80.7 min	3 g single, intravenous	CLAVULANIC ACID	TICARCILLIN serum	Homo sapiens
76 min	5 g single, intravenous		TICARCILLIN plasma	Homo sapiens
1.1 h	3 g single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens
1 h	50 mg/kg bw single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
55%	3 g single, intravenous	CLAVULANATE POTASSIUM	TICARCILLIN serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3 g 4 times / day multiple, intravenous Recommended	unhealthy, 19-91	Disc. AE: Rash, Nausea... Other AEs: Elevated liver enzymes, Eosinophilia...
80 mg/kg single, intravenous Highest studied dose	healthy, 22-26
3 g 5 times / day multiple, intravenous Overdose	unhealthy	Other AEs: Convulsions...
3 g 5 times / day multiple, intravenous Recommended	unhealthy	Other AEs: Hypersensitivity reaction, Diarrhea, Clostridium difficile...

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AEs

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AE	Significance	Dose	Population
Elevated liver enzymes		3 g 4 times / day multiple, intravenous Recommended	unhealthy, 19-91
Eosinophilia		3 g 4 times / day multiple, intravenous Recommended	unhealthy, 19-91
Rash	grade 1, 2.7% Disc. AE	3 g 4 times / day multiple, intravenous Recommended	unhealthy, 19-91
Nausea	grade 2, 2.7% Disc. AE	3 g 4 times / day multiple, intravenous Recommended	unhealthy, 19-91
Convulsions		3 g 5 times / day multiple, intravenous Overdose	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B15 84 ALDH 8 OAT1 725 OAT2 153 OATP1B3 961

Drug as perpetrator

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Target	Modality	Activity
ALDH 8	inhibitor 4,027	no
OAT2 155	inhibitor 4,027	no
OATP1B3 970	inhibitor 4,027	no
UGT2B15 84	inhibitor 4,027	no
OAT1 730	inhibitor 4,027	yes [IC50 1833 uM]

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9587	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9587
ChemicalBook	CB7224768	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7224768
eMolecules	29537804	https://www.emolecules.com/cgi-bin/more?vid=29537804
ZINC	ZINC000003831540	http://zinc15.docking.org/substances/ZINC000003831540

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PubMed

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Title	Date	PubMed
Bacteroides fragilis arthritis in a patient with sickle cell disease.	2001 Aug	11501546
The relationships and susceptibilities of some industrial, laboratory and clinical isolates of Pseudomonas aeruginosa to some antibiotics and biocides.	2001 Dec	11851804
[Identification and susceptibility to antimicrobial agents of strictly anaerobic bacteria isolated from hospitalized patients].	2002	12632658
Severe cellulitis/myositis caused by Stenotrophomonas maltophilia.	2002 Jan	11816260
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.	2002 Nov	12569987

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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.

Show entries

Name

Type

Language

TICARCILLIN CRESYL SODIUM

Official Name

English

BRL 12594

Preferred Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-((3-(4-METHYLPHENOXY)-1,3-DIOXO-2-(3-THIENYL)PROPYL)AMINO)-7-OXO-, MONOSODIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-

Common Name

English

P-TOLYL (R)-N-((2S,5R,6R)-(2-CARBOXY-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-6-YL))-3-THIOPHENEMALONAMATE SODIUM SALT

Common Name

English

TICARCILLIN CRESYL SODIUM [USAN]

Common Name

English

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Classification Tree

Code System

Code

Penicillin Antibiotic

NCI_THESAURUS

C1558

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Code System

Code

Type

Description

CAS

59070-06-3

PRIMARY

SMS_ID

300000055358

PRIMARY

ChEMBL

CHEMBL2111017

PRIMARY

FDA UNII

0EVR7Q3336

PRIMARY

PUBCHEM

23671017

PRIMARY

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ACTIVE MOIETY


					F93UJX4SWT

TICARCILLIN

PARENT (SALT/SOLVATE)


					569624Y431

TICARCILLIN CRESYL

SUBSTANCE RECORD


					0EVR7Q3336

TICARCILLIN CRESYL SODIUM

SMILES

InChI

CNS Activity

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator