CAS 66635-83-4|CAS 74103-06-3|Ketorolacum [Latin]|Ketorolaco [Spanish]|ketorolac|Acular Preservative Free|Ketoralac|Ketorolac|5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid|Acular LS|Acular|...

General Information

Structure

Molecular Formula

C₁₅H₁₃NO₃

Molecular Mass

255.26862

Exact Mass

255.08954328

Charge

InChI

InChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)

InChIKey

OZWKMVRBQXNZKK-UHFFFAOYSA-N

Canonic Smiles

OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1

Isomeric Smiles

OC(=O)C1CCn2c1ccc2C(=O)c1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.96

LogD (pH = 5.5)

0.62

Log P

2.28

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.84

Polar Surface Area

59.30

Polarizability

26.88

Molar Refractivity

70.19

LOG S

-2.74

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC name

5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

Synonyms

Ketorolaco [Spanish]KetoralacKetorolacKetorolacum [Latin]Ketorolac Tromethaminerac-ketorolac(+-)-ketorolac(+-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acidketorolac5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

IUPAC Traditional name

ketorolac

Brand Name

Acular Preservative FreeAcular LSToradolAcular

API Name

Ketorolac

International Nonproprietary Name (INN)

ketorolacumketorolacoketorolac

Names and Identifiers

Registration numbers

PubChem SID

16096381146507019170474140170474430

PubChem CID

CAS Number

DrugBank ID

ACToR Database

CHEBI ID

CHEBI:6129CHEBI:76223

HMDB Database

HMDB0014608

PubMed Citation Links

9549656230889942365303223447046235620342312643710593468192819962816621710223774231795622370243517456651234733802411267010027870232982502402264322191998

KEGG ID

C07062

Reaxys Registry

413572

MetaboLights Database

MTBLS2878MTBLS1622MTBLS2145

BRENDA Ligand Database

Wikipedia Title

CHEMBL

CompTox Database

BRENDA Database

BKMS React Database

Patent number

BE856681US4347186US4089969

KEGG DRUG Database

D08104

SureChEMBL Database

SCHEMBL14891

LINCS Database

LSM-1526

Registration numbers

Properties

Physical Property

Solubility

25 mg/mL (tromethamine salt)

Hydrophobicity(logP)

2.1

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00465

Drug Groups

approved

Description

A pyrrolizine carboxylic acid derivative structurally related to indomethacin. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed)

Indication

For the short-term (~5 days) management of moderately severe acute pain that requires analgesia at the opioid level, usually in a postoperative setting.

Pharmacology

Ketorolac, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain. It is a peripherally acting analgesic. The biological activity of ketorolac tromethamine is associated with the S-form. Ketorolac tromethamine possesses no sedative or anxiolytic properties.

Toxicity

LD₅₀ = 189 mg/kg (rat, oral).

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic. Less than 50% of a dose is metabolized. The major metabolites are a glucuronide conjugate, which may also be formed in the kidney, and p-hydroxy ketorolac. Neither metabolite has significant analgesic activity.

Absorption

Rapidly and completely absorbed after oral administration

Half Life

2.5 hours for the S-enantiomer compared with 5 hours for the R-enantiomer

Protein Binding

99%

Elimination

The principal route of elimination of ketorolac and its metabolites is renal. Approximately 6% of a dose is excreted in the feces.

Distribution

* 0.26 ± 0.08 L/kg [children 4 to 8 years old]

Clearance

* 0.042 +/- 0.01 L/hr/kg [Pediatric Patients]
* 0.02 L/h/kg [Normal Subjects IM]
* 0.03 L/h/kg [Normal Subjects oral]
* 0.02 L/h/kg [Healthy Elderly Subjects IM]
* 0.02 L/h/kg [Healthy Elderly Subjects oral]
* 0.03 L/h/kg [Patients with Hepatic Dysfunction IM]
* 0.03 L/h/kg [Patients with Hepatic Dysfunction oral]
* 0.02 L/h/kg [Patients with Renal Impairment IM]
* 0.02 L/h/kg [Patients with Renal Impairment oral]
* 0.02 L/h/kg [Renal Dialysis Patients IM]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

ChEBI

CHEBI:6129

A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.

CHEBI:76223

A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity

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