Identification
- Summary
Suprofen is an NSAID used to prevent pupil constriction in ocular surgery.
- Brand Names
- Profenal
- Generic Name
- Suprofen
- DrugBank Accession Number
- DB00870
- Background
An ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. It is no longer approved for use in the United States.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Suprofen (DB00870)
- Weight
- Average: 260.308
Monoisotopic: 260.05071494 - Chemical Formula
- C14H12O3S
- Synonyms
- (±)-2-(p-(2-thenoyl)phenyl)propionic acid
- 2-(4-(2-Thenoyl)phenyl)propionsäure
- 2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic acid
- 4-(2-Thenoyl)hydratropsäure
- p-2-thenoylhydratropic acid
- Suprofen
- Suprofene
- Suprofeno
- Suprofenum
- Sutoprofen
- α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid
- External IDs
- R 25061
- TN 762
Pharmacology
- Indication
Used as eye drops to inhibit the miosis (pupil constriction) that may occur during ocular surgery.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Reversal of Intraoperative miosis •••••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Suprofen is a non-steroidal anti-inflammatory analgesic and antipyretic. Ophthalmic anti-inflammatory medicines are used in the eye to lessen problems that can occur during or after some kinds of eye surgery. Sometimes, the pupil of the eye gets smaller during an operation (pupil constriction), making it more difficult for the surgeon to reach some areas of the eye. Suprofen is used to help prevent this.
- Mechanism of action
Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A2). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
20%
- Metabolism
Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include bleeding in the eye or redness or swelling of the eye or the eyelid, blurred vision or other change in vision, fever or chills, itching or tearing, nausea or vomiting, pain, sensitivity to light, shortness of breath, sticky or matted eyelashes, swelling of face, throbbing pain, tightness in chest, troubled breathing, and wheezing.
- Pathways
Pathway Category Suprofen Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The risk or severity of adverse effects can be increased when Suprofen is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Suprofen is combined with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Acetylsalicylic acid can be decreased when used in combination with Suprofen. Alclofenac The risk or severity of adverse effects can be increased when Suprofen is combined with Alclofenac. Aminophenazone The risk or severity of adverse effects can be increased when Suprofen is combined with Aminophenazone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Srendam (Pola Pharma) / Sulprotin (Taiyo Pharmaceutical) / Topalgic (Alfresa Pharma)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Profenal Solution 10 mg/1 Ophthalmic ALCON LABORATORIES, INC. 2007-06-23 Not applicable US 
Categories
- ATC Codes
- M01AE07 — Suprofen
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Phenylpropionates
- Propionates
- Sensory System Agents
- UGT1A1 Substrates
- UGT2B7 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Aryl-phenylketones
- Alternative Parents
- Phenylpropanoic acids / Monocyclic monoterpenoids / Aromatic monoterpenoids / Thiophene carboxylic acids and derivatives / Benzoyl derivatives / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 2-phenylpropanoic-acid / Aromatic heteromonocyclic compound / Aromatic monoterpenoid / Aryl-phenylketone / Benzenoid / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid, thiophenes, aromatic ketone (CHEBI:9362)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 988GU2F9PE
- CAS number
- 40828-46-4
- InChI Key
- MDKGKXOCJGEUJW-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)
- IUPAC Name
- 2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid
- SMILES
- CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1
References
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Alcon laboratories inc
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 10 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 124.3 °C PhysProp water solubility limited solubility Not Available logP 2.2 Not Available pKa 3.91 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.0422 mg/mL ALOGPS logP 3.16 ALOGPS logP 3.53 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 4.01 Chemaxon pKa (Strongest Basic) -7.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 69.41 m3·mol-1 Chemaxon Polarizability 26.84 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9927 Blood Brain Barrier + 0.9289 Caco-2 permeable + 0.6039 P-glycoprotein substrate Non-substrate 0.7298 P-glycoprotein inhibitor I Non-inhibitor 0.9534 P-glycoprotein inhibitor II Non-inhibitor 0.9664 Renal organic cation transporter Non-inhibitor 0.8998 CYP450 2C9 substrate Non-substrate 0.6293 CYP450 2D6 substrate Non-substrate 0.9226 CYP450 3A4 substrate Non-substrate 0.8098 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.8607 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.8958 CYP450 3A4 inhibitor Non-inhibitor 0.9526 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.9398 Carcinogenicity Non-carcinogens 0.7568 Biodegradation Ready biodegradable 0.7714 Rat acute toxicity 3.1892 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9869 hERG inhibition (predictor II) Non-inhibitor 0.9716
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.1462316 predictedDarkChem Lite v0.1.0 [M-H]- 153.3026 predictedDeepCCS 1.0 (2019) [M+H]+ 169.2073316 predictedDarkChem Lite v0.1.0 [M+H]+ 155.69817 predictedDeepCCS 1.0 (2019) [M+Na]+ 169.0855316 predictedDarkChem Lite v0.1.0 [M+Na]+ 161.92946 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Loll PJ, Picot D, Ekabo O, Garavito RM: Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site. Biochemistry. 1996 Jun 11;35(23):7330-40. [Article]
- Bender A, Scheiber J, Glick M, Davies JW, Azzaoui K, Hamon J, Urban L, Whitebread S, Jenkins JL: Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem. 2007 Jun;2(6):861-73. [Article]
- Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [Article]
- Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR: Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci U S A. 1999 Jun 22;96(13):7563-8. [Article]
- NIH DailyMed: Suprofen [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [Article]
- Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR: Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci U S A. 1999 Jun 22;96(13):7563-8. [Article]
- NIH DailyMed: Suprofen [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Hutzler JM, Balogh LM, Zientek M, Kumar V, Tracy TS: Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection. Drug Metab Dispos. 2009 Jan;37(1):59-65. doi: 10.1124/dmd.108.023358. Epub 2008 Oct 6. [Article]
- O'Donnell JP, Dalvie DK, Kalgutkar AS, Obach RS: Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab Dispos. 2003 Nov;31(11):1369-77. doi: 10.1124/dmd.31.11.1369. [Article]
- Mancy A, Broto P, Dijols S, Dansette PM, Mansuy D: The substrate binding site of human liver cytochrome P450 2C9: an approach using designed tienilic acid derivatives and molecular modeling. Biochemistry. 1995 Aug 22;34(33):10365-75. [Article]
- Wang JF, Yan JY, Wei DQ, Chou KC: Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism. Med Chem. 2009 May;5(3):263-70. [Article]
- Alexander Alex, C. John Harris, Dennis A. Smith (2016). Attrition in the Pharmaceutical industry: reasons, implications, and pathways forward. Wiley.
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Moser J, Hye A, Lovell WW, Earl LK, Castell JV, Miranda MA: Mechanisms of drug photobinding to proteins: photobinding of suprofen to human serum albumin. Toxicol In Vitro. 2001 Aug-Oct;15(4-5):333-7. doi: 10.1016/s0887-2333(01)00033-9. [Article]
- Hasegawa J, Nakayama T, Nozaki M, Fujimura H: [Interaction of suprofen and serum albumin]. Nihon Yakurigaku Zasshi. 1984 Jan;83(1):85-91. [Article]
- Noctor TA, Wainer IW, Hage DS: Allosteric and competitive displacement of drugs from human serum albumin by octanoic acid, as revealed by high-performance liquid affinity chromatography, on a human serum albumin-based stationary phase. J Chromatogr. 1992 Jun 10;577(2):305-15. doi: 10.1016/0378-4347(92)80252-l. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Urate transmembrane transporter activity
- Specific Function
- Required for efficient urate re-absorption in the kidney. Regulates blood urate levels. Mediates saturable urate uptake by facilitating the exchange of urate against organic anions.
- Gene Name
- SLC22A12
- Uniprot ID
- Q96S37
- Uniprot Name
- Solute carrier family 22 member 12
- Molecular Weight
- 59629.57 Da
References
- Alexander Alex, C. John Harris, Dennis A. Smith (2016). Attrition in the Pharmaceutical industry: reasons, implications, and pathways forward. Wiley.
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:45