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K1136

Sigma-Aldrich

Ketorolac tris salt

≥99%, crystalline

Synonym(s):

(±)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid tris salt, Toradol

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About This Item

Empirical Formula (Hill Notation):
C15H13NO3 · C4H11NO3
CAS Number:
74103-07-4
Molecular Weight:
376.40
MDL number:
MFCD00887595
UNSPSC Code:
12352202
PubChem Substance ID:
24278503
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

assay

≥99%

form

crystalline

solubility

H2O: soluble 15 mg/mL, clear, colorless to faintly yellow (stable at least one month at −20 °C.)

storage temp.

room temp

SMILES string

NC(CO)(CO)CO.OC(=O)C1CCn2c1ccc2C(=O)c3ccccc3

InChI

1S/C15H13NO3.C4H11NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13;5-4(1-6,2-7)3-8/h1-7,11H,8-9H2,(H,18,19);6-8H,1-3,5H2

InChI key

BWHLPLXXIDYSNW-UHFFFAOYSA-N

Gene Information

human ... PTGS1(5742) , PTGS2(5743)

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Application

Ketorolac has been used:
  • as an intraperitoneal injection in mice to study the effect of ketorolac on expression of c-Fos (a human proto-oncogene) in ARC (arcuate nucleus of the hypothalamus) POMC (proopiomelanocortin) -EGFP (enhanced green fluorescent protein) neurons
  • to treat mice in order to show that this treatment does not prevent IL-1β-mediated inhibition of Agouti-related protein (AgRP) secretion from murine hypothalamic explants
  • as an analgesic medication to treat rats induced with acute inflammatory joint injury by injecting carrageenan into the ankle

Biochem/physiol Actions

Ketorolac is a non-steroidal agent that possesses moderate anti-inflammatory activity and is also a potent analgesic. It shows superior analgesic efficacy to that of the opioid analgesics like morphine in patients with moderate to severe postsurgical pain. It inhibits prostaglandin synthesis and platelet aggregation induced by arachidonic acid and collagen. It is a dual COX-1/COX-2 inhibitor.

Caution

Stable at least 2 years if stored at room temperature.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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G Cirino et al.
British journal of pharmacology, 117(7), 1421-1426 (1996-04-01)
1. The effects of novel nitric oxide-releasing nonsteroidal anti-inflammatory compounds (NO-NSAIDs) on induction of nitric oxide (NO) synthase by bacterial lipopolysaccharide (LPS) were examined in a murine cultured macrophage cell line, J774. 2. LPS-induced nitrite production was markedly attenuated by
R A Dionne et al.
Clinical and experimental rheumatology, 19(6 Suppl 25), S63-S70 (2001-11-07)
While non-steroidal anti-inflammatory drugs (NSAIDs) are the mainstay of therapy for the management of acute pain and rheumatoid arthritis, toxicity associated with chronic administration limits their benefit-to-risk relationship in many patients. A series of studies is reviewed that assesses the
Rachel L Ruhlen et al.
The Journal of the American Osteopathic Association, 113(10), 738-752 (2013-10-03)
Animal models can be used to investigate manual therapy mechanisms, but testing manipulation in animal models is problematic because animals cannot directly report their pain. To develop a rat model of inflammatory joint injury to test the efficacy of manual
M M Buckley et al.
Drugs, 39(1), 86-109 (1990-01-01)
Ketorolac is a non-steroidal agent with potent analgesic and moderate anti-inflammatory activity. It is administered as the tromethamine salt orally, intramuscularly, intravenously, and as a topical ophthalmic solution. Clinical studies indicate single-dose efficacy greater than that of morphine, pethidine (meperidine)
O Laneuville et al.
The Journal of pharmacology and experimental therapeutics, 271(2), 927-934 (1994-11-01)
We developed an in vitro expression system for accurate kinetic analyses of the inhibition of the human prostaglandin H synthase isozymes (hPGHS-1 and -2) by nonsteroidal anti-inflammatory drugs (NSAIDs). Assays of instantaneous inhibition in which enzyme, 10 microM arachidonate, and
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