Drug Details

General Information of the Drug (ID: DR8439)
Name
Naproxen
Synonyms
NAPROXEN; 22204-53-1; (S)-Naproxen; (+)-Naproxen; Naprosyn; Equiproxen; Naproxene; Aleve; (S)-(+)-Naproxen; (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid; Laraflex; (S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; d-Naproxen; Naproxenum; Calosen; Naprosyne; Naproxeno; Nycopren; Bonyl; Naixan; Reuxen; Axer; (+)-(S)-Naproxen; Ec-Naprosyn; naproxen(+); Acusprain; Anexopen; Arthrisil; Artrixen; Artroxen; Bipronyl; Clinosyn; Danaprox; Flexipen; Leniartil; Novonaprox; Anaprox; Apronax; Artagen; Atiflan; Congex; Daprox; Genoxen; Lefaine; Nafasol; Nalyxan; Napflam; Napmel; Naposin; Napren; Naprius; Veradol; Fuxen; Naxen; Naxyn; Xenar; Dysmenalgit N; Apo-Naproxen; (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; Floginax; (S)-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-2-(Methoxy-2-naphthyl)-propionic acid; RS-3540; Naprelan; (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid; Dysmenalgit; Diocodal; (S)-2-(6-Methoxy-2-naphthyl)propanoic acid; Prexan; Apo-Napro-NA; d-2-(6-Methoxy-2-naphthyl)propionic acid; (+)-2-(Methoxy-2-naphthyl)-propionsaeure; UNII-57Y76R9ATQ; (+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid; (S)-(+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid; Proxen; CG 3117; CHEBI:7476; (2S)-2-(6-methoxy-2-naphthyl)propanoic acid; MFCD00010500; CHEMBL154; (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid; Laser; 57Y76R9ATQ; d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure; Naprium; Naprux; Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)-; Duk; Headlon; Napratec; Naprontag; Narocin; Naxopren; Prafena; Priaxen; Pronaxen; Rheumaflex; Saritilron; Sinartrin; Soproxen; Sutolin; Tohexen; Traumox; Flexen; Napxen; Noflam; Patxen; Rahsen; Sinton; Sutony; Velsay; Vinsen; Narma; Roxen; Anax; CAS-22204-53-1; Flanax Forte; Napren E; Naprosyn LLE; Proxen LE; Naxen F; Proxen LLE; U-Ritis; Naprosyn LLE Forte; (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid; Naproxi 250; Naproxi 500; (alphas)-6-methoxy-alpha-methyl-2-naphthaleneacetic acid; (S)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid; Naxyn 250; Naxyn 500; Equiproxen (Veterinary); Naproxene [INN-French]; Naproxenum [INN-Latin]; Naproxeno [INN-Spanish]; 26159-31-9; Xenar-CR; CCRIS 5265; HSDB 3369; EINECS 244-838-7; RS 3540; (S)-(+)-6-Methoxy-alp.-methyl-2-naphthalene acetic acid; 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (S)-; Naprolag; Naprosine; Naprosy; Panoxen; Proxine; Mnpa; SR-01000075977; 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)-; DL Naproxen; Naprosyn (TN); Naproxen,(S); NPS; Prestwick_349; (+)-2-(Methoxy-2-naphthyl)-propionsaeure [German]; Naproxen [USAN:USP:INN:BAN:JAN]; d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure [German]; PubChem8102; 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)-; 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (S)-; Spectrum_000977; 4or0; 4po0; (S)-(+)-Naproxene; Prestwick0_000791; Prestwick1_000791; Prestwick2_000791; Spectrum2_001043; Spectrum3_000514; Spectrum4_000069; Spectrum5_001327; (+)NAPROXEN; Naproxen2-(6-Methoxy-naphthalen-2-yl)-propionic acid; Epitope ID:139974; UPCMLD-DP001; 2-(6-Methoxy-naphthalen-2-yl)-propionic acid(Naproxen); EC 244-838-7; SCHEMBL3046; DSSTox_CID_20686; DSSTox_RID_79542; DSSTox_GSID_40686; Lopac0_000792; BSPBio_002067; KBioGR_000597; KBioSS_001457; ARONIS24306; BIDD:GT0062; DivK1c_000242; SPECTRUM1500425; Naproxen (JP17/USP/INN); SPBio_000966; SPBio_002861; GTPL5230; DTXSID4040686; UPCMLD-DP001:001; CMWTZPSULFXXJA-VIFPVBQESA-; HMS500M04; KBio1_000242; KBio2_001457; KBio2_004025; KBio2_006593; KBio3_001567; Naproxen 1.0 mg/ml in Methanol; PN400 COMPONENT NAPROXEN; NINDS_000242; HMS1920P13; HMS2089N21; HMS2091H12; HMS3649M13; HMS3886C15; Pharmakon1600-01500425; ZINC105216; ACT02593; Tox21_301953; ANW-24773; BDBM50339185; CCG-40130; NSC750183; NSC757239; AKOS005267223; AC-1363; DB00788; MCULE-2589082817; ME-0100; NSC 750183; NSC 757239; NSC-750183; NSC-757239; SDCCGSBI-0050769.P005; IDI1_000242; Naproxen 100 microg/mL in Acetonitrile; Naproxen solution 1.0 mg/ml in methanol; NCGC00016759-01; NCGC00016759-02; NCGC00016759-03; NCGC00021127-01; NCGC00161591-01; NCGC00255562-01; HY-15030; Naproxen, meets USP testing specifications; SBI-0050769.P004; AM20060551; M1021; S5177; W4580; Naproxen, VETRANAL(TM), analytical standard; (2S)-2-(6-Methoxynaphth-2-yl)propanoic acid; (S)-2-(6-methoxy-2-naphthyl)-propionic acid; 04N531; C01517; D00118; J10145; M-5280; (2S)-2-(6-methoxy(2-naphthyl))propanoic acid; AB00052049-04; AB00052049_05; (+)(S)2-(6-methoxy-2-naphthyl)-propionic acid; 2-(6-Methoxy-2-naphthyl)propanoic acid , (+)-; SR-01000003110; Q-201447; Q1215575; SR-01000003110-5; SR-01000075977-3; SR-01000075977-4; (+)-6-Methoxy-.alpha.-methyl-2-napthaleneacetic acid; BRD-K59197931-001-02-9; BRD-K59197931-001-03-7; BRD-K59197931-236-09-6; SR-01000075977-10; (+)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid; (S)-(+)-2-(6-methoxy-naphthalen-2-yl)-propionic acid; (S)-6-Methoxy-.alpha.-methyl-2-naphthalene acetic acid; Naproxen, British Pharmacopoeia (BP) Reference Standard; Naproxen, European Pharmacopoeia (EP) Reference Standard; (S)-(+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid, 98%; 2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (+)-; Naproxen, United States Pharmacopeia (USP) Reference Standard; 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)- (8CI); Naproxen, Pharmaceutical Secondary Standard; Certified Reference Material; Naproxen solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material; 131991-52-1; d-Naproxen; (2S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid; (S)-6-Methoxy-?-methyl-2-naphthaleneacetic Acid; d-2-(6-Methoxy-2-naphthyl)propionic Acid
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Molecular Type
Small molecule
Disease Osteoarthritis [ICD-11: FA00-FA05] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
99% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 0.13 mL/min/kg
Elimination
After oral administration, about 95% of naproxen and it's metabolites can be recovered in the urine with 66-92% recovered as conjugated metabolite and less than 1% recovered as naproxen or desmethylnaproxen
Half-life
The concentration or amount of drug in body reduced by one-half in 12 - 17 hours
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 108.568 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.002%
Vd
The volume of distribution (Vd) of drug is 0.16 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 0.115 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C14H14O3
PubChem CID
156391
Canonical SMILES
CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
InChI
1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1
InChIKey
CMWTZPSULFXXJA-VIFPVBQESA-N
CAS Number
CAS 22204-53-1
ChEBI ID
CHEBI:7476
TTD Drug ID
D0DJ1B
DrugBank ID
DB00788
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Omega-3 PUFAs      phytoplankton environmental sample     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression VCAM1  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Decrease Serum TG
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 Combining NX with omega-3 PUFAs increases their effectiveness in reducing serum TG and favorably altering AT gene expression and plasma bile acid profile.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Citral      Cymbogogon Citratus     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Male Wistar rats aged 7-9 weeks (weight range: 180-220 g) were used in this study.
                    Experimental
                    Result(s)		 The combination of naproxen and citral reduces nociception and gastric damage in rats.
Target and Pathway
Target(s) Prostaglandin G/H synthase 1 (COX-1)  Molecule Info  [4]
Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [4]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 NF-kappa B signaling pathway
4 VEGF signaling pathway
5 TNF signaling pathway
6 Retrograde endocannabinoid signaling
7 Serotonergic synapse
8 Ovarian steroidogenesis
9 Oxytocin signaling pathway
10 Regulation of lipolysis in adipocytes
11 Leishmaniasis
12 Pathways in cancer
13 Chemical carcinogenesis
14 MicroRNAs in cancer
15 Small cell lung cancer
16 Platelet activation
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Aryl Hydrocarbon Receptor
4 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
5 Spinal Cord Injury
6 Integrated Pancreatic Cancer Pathway
7 Eicosanoid Synthesis
8 Selenium Micronutrient Network
9 Phase 1 - Functionalization of compounds
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 A combination of Omega-3 PUFAs and COX inhibitors: A novel strategy to manage obesity-linked dyslipidemia and adipose tissue inflammation. J Diabetes Complications. 2020 Feb;34(2):107494.
Reference 3 The combination of naproxen and citral reduces nociception and gastric damage in rats. Arch Pharm Res. 2010 Oct;33(10):1691-7.
Reference 4 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
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