Antrafenine
Identification
- Generic Name
- Antrafenine
- DrugBank Accession Number
- DB01419
- Background
Antrafenine is a piperazine derivative drug that acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen. It is not widely used as it has largely been replaced by newer drugs.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 588.5435
Monoisotopic: 588.195995326 - Chemical Formula
- C30H26F6N4O2
- Synonyms
- Antrafenine
Pharmacology
- Indication
Antrafenine is used as an anti-inflammatory and analgesic agent for the relief of mild to moderate pain.
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- Pharmacodynamics
Its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
- Mechanism of action
Antrafenine is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity.
Target Actions Organism UProstaglandin G/H synthase 1 inhibitorHumans UProstaglandin G/H synthase 2 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- 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
Not Available
- Pathways
Pathway Category Antrafenine 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 softwareAbacavir Antrafenine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Antrafenine is combined with Abciximab. Acebutolol Antrafenine may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Antrafenine is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Antrafenine is combined with Acemetacin. - Food Interactions
- Not Available
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
- Stakane
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Phenylpiperazines
- Alternative Parents
- N-arylpiperazines / 4-aminoquinolines / Aminobenzoic acids and derivatives / Benzoic acid esters / Trifluoromethylbenzenes / Aniline and substituted anilines / Dialkylarylamines / Benzoyl derivatives / Aminopyridines and derivatives / N-alkylpiperazines show 14 more
- Substituents
- 4-aminoquinoline / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminopyridine / Aminoquinoline / Aniline or substituted anilines / Aromatic heteropolycyclic compound show 31 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 21FS93Y6OE
- CAS number
- 55300-29-3
- InChI Key
- NWGGKKGAFZIVBJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)
- IUPAC Name
- 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
- SMILES
- FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1
References
- Synthesis Reference
Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015488
- PubChem Compound
- 68723
- PubChem Substance
- 46507354
- ChemSpider
- 61973
- ChEBI
- 135841
- ChEMBL
- CHEMBL345524
- ZINC
- ZINC000053073961
- PharmGKB
- PA164784000
- Wikipedia
- Antrafenine
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
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 88-90 Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229. - Predicted Properties
Property Value Source Water Solubility 0.00284 mg/mL ALOGPS logP 6.3 ALOGPS logP 8.39 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 16.69 Chemaxon pKa (Strongest Basic) 7.04 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 57.7 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 147.01 m3·mol-1 Chemaxon Polarizability 55.48 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9969 Blood Brain Barrier + 0.9132 Caco-2 permeable - 0.5721 P-glycoprotein substrate Substrate 0.5792 P-glycoprotein inhibitor I Inhibitor 0.8917 P-glycoprotein inhibitor II Inhibitor 0.9464 Renal organic cation transporter Non-inhibitor 0.5702 CYP450 2C9 substrate Non-substrate 0.8703 CYP450 2D6 substrate Non-substrate 0.6674 CYP450 3A4 substrate Non-substrate 0.5172 CYP450 1A2 substrate Inhibitor 0.7622 CYP450 2C9 inhibitor Inhibitor 0.7438 CYP450 2D6 inhibitor Non-inhibitor 0.7155 CYP450 2C19 inhibitor Inhibitor 0.7394 CYP450 3A4 inhibitor Inhibitor 0.6383 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9305 Ames test Non AMES toxic 0.6823 Carcinogenicity Non-carcinogens 0.8812 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7506 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8133 hERG inhibition (predictor II) Inhibitor 0.8583
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 226.7468279 predictedDarkChem Lite v0.1.0 [M-H]- 226.0748279 predictedDarkChem Lite v0.1.0 [M-H]- 219.58025 predictedDeepCCS 1.0 (2019) [M+H]+ 226.2416279 predictedDarkChem Lite v0.1.0 [M+H]+ 226.3008279 predictedDarkChem Lite v0.1.0 [M+H]+ 221.97581 predictedDeepCCS 1.0 (2019) [M+Na]+ 226.4043279 predictedDarkChem Lite v0.1.0 [M+Na]+ 226.3518279 predictedDarkChem Lite v0.1.0 [M+Na]+ 227.88835 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Hassan SM, Olivesi A, Fish A, Turner P: A comparison of antrafenine and aspirin on platelet aggregation and frusemide-induced diuresis. Postgrad Med J. 1982 Jan;58(675):17-9. [Article]
- Berry H, Coquelin JP, Gordon A, Seymour D: Antrafenine, naproxen and placebo in osteoarthritis: a comparative study. Br J Rheumatol. 1983 May;22(2):89-94. [Article]
- James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 inhibitors, eicosanoid synthesis and clinical outcomes: a case study of system failure. Lipids. 2007 Sep;42(9):779-85. Epub 2007 Jun 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. [Article]
- Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Dec;16(8):691-7. Epub 2007 Jul 2. [Article]
- Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. [Article]
- White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. [Article]
- Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at July 24, 2007 08:34 / Updated at February 21, 2021 18:51