Basic information
- CAS
74103-07-4- Standard SMILES
NC(CO)(CO)CO.O=C(c1ccccc1)c1ccc2n1CCC2C(=O)O- InChIKey
BWHLPLXXIDYSNW-UHFFFAOYSA-N- Molecular formula
- C19H24N2O6
- Average molar mass
- 376.4 g/mol
- Monoisotopic mass
- 376.16343649
Names & identifiers
- Preferred name
- Ketorolac Tromethamine
- IUPAC
- 2-amino-2-(hydroxymethyl)propane-1,3-diol;5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
- English name
- Ketorolac tromethamine
- Molecular formula
- C19H24N2O6
- Molecular weight
- 376.41
Names & synonyms
Show more names
Database identifiers
- CAS
74103-07-4- PubChem CID
- 84003
- DTXSID
DTXSID0045597- ChEMBL
CHEMBL1201124- UNII
- 4EVE5946BQ
- EC Number
- 620-545-3
Properties
Computed structural properties
- Topological polar surface area
- 146 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 6
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 430
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 160 · 160-161 C
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 15 mg/mL stable at least one month at −20 °C., soluble
- form
- crystalline
- color
- White to Light yellow
- biological source
- synthetic (organic)
- Water Solubility
- 2 O: · H2O: soluble 15mg/mL, clear, colorless to faintly yellow (stable at least one month at -20 °C.)
- λmax
- 322 nm · 322nm(MeOH)(lit.)
- Merck
- 14 · 14,5306
- Stability
- Hygroscopic
- InChI
- 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
- InChIKey
- BWHLPLXXIDYSNW-UHFFFAOYSA-N
- SMILES
- C(N)(CO)(CO)CO.C(C1C=CC=CC=1)(C1=CC=C2C(C(=O)O)CCN12)=O
- CAS DataBase Reference
- 74103 · 74103-07-4(CAS DataBase Reference)
- FDA UNII
- 4 EVE5946BQ · 4EVE5946BQ
- NCI Drug Dictionary
- ketorolac tromethamine
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H315-H319-H335
- Precautionary statements
- 301 · P301+P310+P330-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T
- Risk Statements
- 25 · 25-36/37/38-23/24/25
- Safety Statements
- 26 · 26-45-36/37/39
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 7759900 · UY7759900
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- HS Code
- 2933995500 · 2933995500
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralEye · Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (96.9%): Toxic if swallowed [Danger Acute toxicity, oral];H315 (93.8%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (93.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (92.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 64 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Ketorolac tromethamine
vLess-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Milk levels of ketorolac are low with the usual oral dosage, but milk levels have not been measured after higher injectable dosages or with the nasal spray. Ketorolac injection is used for a short time (typically 24 hours) after cesarean section in some hospital protocols with no evidence of harm to breastfed infants. However, the ketorolac dose an infant receives in colostrum is very low because of the small volume of colostrum produced. Some evidence suggests that IV ketorolac as part of a multimodal post-cesarean section analgesia reduces percentage of mothers who fail exclusive breastfeeding compared to patient-controlled IV morphine-based analgesia. Ketorolac has strong antiplatelet activity and can cause gastrointestinal bleeding. The manufacturer indicates that ketorolac is contraindicated during breastfeeding, so an alternate drug is preferred after the first 24 to 72 hours when larger volumes of milk are produced, especially while nursing a newborn or preterm infant.;Maternal use of ketorolac eye drops would not be expected to cause any adverse effects in breastfed infants. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue.;◉ Effects in Breastfed Infants;A randomized, double-blind study compared standard care of mothers receiving a cesarean section delivery (n = 60) to those receiving standard care plus multimodal pain management that included a single dose of 60 mg of intramuscular ketorolac given at the time of fascial closure (n = 60). No significant differences in abnormal neonatal growth, difficulty feeding, neonatal sedation, or respiratory depression rates between the two groups were seen during the first month postpartum.;◉ Effects on Lactation and Breastmilk;A randomized, double-blind study compared standard care of mothers receiving a cesarean section delivery (n = 60) to those receiving standard care plus multimodal pain management that included a single dose of 60 mg of intramuscular ketorolac given at the time of fascial closure (n = 60). No significant differences in breastfeeding rates (78% and 79%, respectively) were seen during the first month postpartum.;In a study comparing standard of care to enhanced recovery after cesarean section deliveries, a fixed dose of ketorolac 15 mg every 6 hours intravenously for 24 hours postpartum was part of the enhanced recovery protocol whereas as needed ketorolac 15 mg intravenously was part of the standard protocol. Patients in the enhanced recovery protocol (n = 58) had a greater frequency of exclusive breastfeeding (67%) than those in the standard protocol (48%; n = 60).;A retrospective study evaluated 1349 women who had undergone a cesarean section and were given ketorolac within 15 minutes of the end of surgery. The results indicated that there was no difference in pain control in the first 6 hours after surgery nor in the percentage of women who were breastfeeding at discharge.;A prospective cohort study of postcesarean pain control compared (1) morphine PCA and scheduled ibuprofen for the first 12 hours followed by continued scheduled ibuprofen with hydrocodone-acetaminophen as needed to a multimodal pain management regimen consisting of (2) acetaminophen 1000 mg orally every 8 hours, ketorolac 30 mg IV once initially, then 15 mg IV every 8 hours for 24 hours, then ibuprofen 600 mg orally every 8 hours for the remainder of the postoperative course with opioids given only as needed. Of women who planned to exclusively breastfeed on admission, fewer women used formula prior to discharge in the multimodal group compared to the traditional group (9% vs. 12%).
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- UY7759900
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 2933995500
- risk_code
- 25-36/37/38-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-45-36/37/39
- hazard_class
- 6.1(a)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H301-H315-H319-H335
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P301+P310+P330-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
ROX-888 is a intranasal formulation of the broadly used injectible analgesic, ketorolac. It has ability to provide effective analgesia in acute medical conditions resulting in moderate-severe pain, without the disabling side effects of opioid analgesics
FDA Pharmacological Classification
KETOROLAC TROMETHAMINE
Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]; Cyclooxygenase Inhibitor [EPC]; Cyclooxygenase Inhibitors [MoA]
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Applications
DescriptionKetorolac tromethamine is a nonsteroidal antiinflammatory agent that exhibits analgesic and antipyretic activity. The compound is effective in the management of moderate to severe postoperative pain. It is, however, the first of this type of agent to be administered parenterally as an analgesic and is specifically indicated for intramuscular injection. Ketorolac represents a useful alternative to the narcotic analgesics due to its lack of abuse potential.
DescriptionKetorolac is a non-steroidal anti-inflammatory drug (NSAID) and a non-selective COX inhibitor (IC50 = 20 nM for both COX-1 and COX-2). It prevents increases in paw swelling, increases paw withdrawal latency in a hot-plate test, and decreases prostaglandin E2 (PGE2) levels in paw tissue in a mouse model of carrageenan-induced inflammation when administered at a dose of 30 mg/kg. Ketorolac is a racemic mixture containing the active (S)-ketorolac and inactive (R)-ketorolac enantiomers. Formulations containing ketorolac have been used to manage postoperative pain and as ophthalmic solutions to treat ocular pain and inflammation.
UsesAnalgesic;Cyclooxygenase Inhibitor
UsesKetorolac is used primarily for its analgesic effects for short-term treatment of mild to moderate pain in dogs and rodents. The duration of analgesic effect in dogs is about 8 – 12 hours, but because of the availability of approved, safer NSAIDs for dogs, its use is questionable.
UsesCyclo-oxygenase inhibitor; analgesic; anti-inflammatory.
General DescriptionPharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Ketorolac Tromethamine belongs to the class of non-steroidal anti-inflammatory drugs, and its mode of action involves the inhibition of the bodily synthesis of prostagladins. It exhibits anti-inflammatory, antipyretic and analgesic effects.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: An organoammonium salt resulting from the mixture of equimolar amounts of ketorolac and tromethamine (tris). It has potent non-sedating analgesic and moderate anti-inflammatory effects. It is used in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.
Related reactions
Compound notes
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