Details of the Drug

General Information of Drug (ID: DMZ5RGV)

Drug Name

Naproxen

Synonyms

NAPROXEN; 22204-53-1; (S)-Naproxen; Naproxene; Naprosyn; (+)-Naproxen; Equiproxen; Laraflex; Naproxenum; Naproxeno; d-Naproxen; (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid; (S)-(+)-Naproxen; Calosen; Nycopren; Naprosyne; Bonyl; Reuxen; Naixan; Axer; (+)-(S)-Naproxen; Ec-Naprosyn; (S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; Flexipen; Clinosyn; Artrixen; Anexopen; Acusprain; Novonaprox; Arthrisil; Leniartil; Danaprox; Bipronyl; Artroxen; Napren; Naposin; Napflam; Genoxen; Daprox; Atiflan; Artagen; Apronax; Naprius; Nalyxan; Lefaine; Congex

Indication

Disease Entry	ICD 11	Status	REF
Bursitis	N.A.	Approved	[1]
Dysmenorrhea	GA34.3	Approved	[1]
Fever	MG26	Approved	[1]
Gout	FA25	Approved	[1]
Headache	8A80-8A84	Approved	[1]
Migraine disorder	N.A.	Approved	[1]
Osteoarthritis	FA00-FA05	Approved	[2]
Pain	MG30-MG3Z	Phase 2	[3]
Endometriosis	GA10	Investigative	[4]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

230.26

Logarithm of the Partition Coefficient (xlogp)

3.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1 h [5]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [6]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [7]
Clearance: The clearance of drug is 0.13 mL/min/kg [8]
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 [9]
Half-life: The concentration or amount of drug in body reduced by one-half in 12 - 17 hours [10]
Metabolism: The drug is metabolized via the liver [8]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 108.568 micromolar/kg/day [11]
Unbound Fraction: The unbound fraction of drug in plasma is 0.002% [12]
Vd: The volume of distribution (Vd) of drug is 0.16 L/kg [8]
Water Solubility: The ability of drug to dissolve in water is measured as 0.115 mg/mL [6]

Chemical Identifiers

Formula: C14H14O3
IUPAC Name: (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Canonical SMILES: C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
InChI: 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

Cross-matching ID

PubChem CID: 156391
ChEBI ID: CHEBI:7476
CAS Number: 22204-53-1
DrugBank ID: DB00788
TTD ID: D0DJ1B
VARIDT ID: DR00603
INTEDE ID: DR1130
ACDINA ID: D00456

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Prostaglandin G/H synthase 1 (COX-1)	TT8NGED	PGH1_HUMAN	Inhibitor	[13]
Prostaglandin G/H synthase 2 (COX-2)	TTVKILB	PGH2_HUMAN	Inhibitor	[13]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[14]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[15]
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[16]
Cytochrome P450 2C8 (CYP2C8)_{Main DME}	DES5XRU	CP2C8_HUMAN	Substrate	[16]
UDP-glucuronosyltransferase 2B7 (UGT2B7)	DEB3CV1	UD2B7_HUMAN	Substrate	[17]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[18]
UDP-glucuronosyltransferase 1A10 (UGT1A10)	DEL5N6Y	UD110_HUMAN	Substrate	[18]
UDP-glucuronosyltransferase 1A6 (UGT1A6)	DESD26P	UD16_HUMAN	Substrate	[18]
UDP-glucuronosyltransferase 1A3 (UGT1A3)	DEF2WXN	UD13_HUMAN	Substrate	[18]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[19]
Aldo-keto reductase family 1 member C1 (AKR1C1)	OTQKR4CM	AK1C1_HUMAN	Gene/Protein Processing	[20]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[20]
Aldo-keto reductase family 1 member C3 (AKR1C3)	OTU2SXBA	AK1C3_HUMAN	Gene/Protein Processing	[20]
Angiotensin-converting enzyme 2 (ACE2)	OTTRZGU7	ACE2_HUMAN	Gene/Protein Processing	[21]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[22]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[23]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2)	OTW8V2V1	ABCG2_HUMAN	Gene/Protein Processing	[22]
Cytochrome P450 2C9 (CYP2C9)	OTGLBN29	CP2C9_HUMAN	Biotransformations	[24]
Cytochrome P450 4A11 (CYP4A11)	OTPU5J0S	CP4AB_HUMAN	Gene/Protein Processing	[25]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Bursitis

ICD Disease Classification

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Prostaglandin G/H synthase 2 (COX-2)	DTT	PTGS2	1.64E-44	1.57	1.7
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DME	UGT1A1	3.70E-05	-8.48E-02	-3.30E-01
Cytochrome P450 2C8 (CYP2C8)	DME	CYP2C8	2.66E-04	-1.21E-01	-5.72E-01
Cytochrome P450 1A2 (CYP1A2)	DME	CYP1A2	7.40E-09	-1.57E-01	-6.38E-01
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	1.35E-09	-5.03E-01	-6.35E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Naproxen (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[26]
Sodium bicarbonate	DMMU6BJ	Minor	Decreased absorption of Naproxen due to altered gastric pH caused by Sodium bicarbonate.	Acidosis [5C73]	[27]
Repaglinide	DM5SXUV	Moderate	Increased risk of hypoglycemia by the combination of Naproxen and Repaglinide.	Acute diabete complication [5A2Y]	[28]
Glibenclamide	DM8JXPZ	Moderate	Increased risk of hypoglycemia by the combination of Naproxen and Glibenclamide.	Acute diabete complication [5A2Y]	[28]
Tolazamide	DMIHRNA	Moderate	Increased risk of hypoglycemia by the combination of Naproxen and Tolazamide.	Acute diabete complication [5A2Y]	[28]
Glipizide	DMZA5PQ	Moderate	Increased risk of hypoglycemia by the combination of Naproxen and Glipizide.	Acute diabete complication [5A2Y]	[28]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Naproxen caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[29]
Inotersen	DMJ93CT	Major	Increased risk of bleeding by the combination of Naproxen and Inotersen.	Amyloidosis [5D00]	[29]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[30]
Cilostazol	DMZMSCT	Moderate	Increased risk of bleeding by the combination of Naproxen and Cilostazol.	Arterial occlusive disease [BD40]	[31]
Budesonide	DMJIBAW	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Budesonide.	Asthma [CA23]	[32]
Ofloxacin	DM0VQN3	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Ofloxacin.	Bacterial infection [1A00-1C4Z]	[33]
Kanamycin	DM2DMPO	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Kanamycin.	Bacterial infection [1A00-1C4Z]	[34]
Sparfloxacin	DMB4HCT	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Sparfloxacin.	Bacterial infection [1A00-1C4Z]	[33]
Streptomycin	DME1LQN	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Streptomycin.	Bacterial infection [1A00-1C4Z]	[34]
Gemifloxacin	DMHT34O	Moderate	Additive CNS depression effects by the combination of Naproxen and Gemifloxacin.	Bacterial infection [1A00-1C4Z]	[33]
Norfloxacin	DMIZ6W2	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Norfloxacin.	Bacterial infection [1A00-1C4Z]	[33]
ABT-492	DMJFD2I	Moderate	Additive CNS depression effects by the combination of Naproxen and ABT-492.	Bacterial infection [1A00-1C4Z]	[33]
Gentamicin	DMKINJO	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Gentamicin.	Bacterial infection [1A00-1C4Z]	[34]
Rabeprazole	DMMZXIW	Moderate	Decreased absorption of Naproxen due to altered gastric pH caused by Rabeprazole.	Bacterial infection [1A00-1C4Z]	[35]
Netilmicin	DMRD1QK	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Netilmicin.	Bacterial infection [1A00-1C4Z]	[34]
Levofloxacin	DMS60RB	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Levofloxacin.	Bacterial infection [1A00-1C4Z]	[33]
Lomefloxacin	DMVRH9C	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Lomefloxacin.	Bacterial infection [1A00-1C4Z]	[33]
Risedronate	DM5FLTY	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Risedronate.	Bone paget disease [FB85]	[36]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Naproxen and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[37]
Lapatinib	DM3BH1Y	Moderate	Decreased metabolism of Naproxen caused by Lapatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[38]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Naproxen caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[39]
Trastuzumab Emtansine	DMU1LXS	Moderate	Increased risk of bleeding by the combination of Naproxen and Trastuzumab Emtansine.	Breast cancer [2C60-2C6Y]	[31]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Naproxen and Iodipamide.	Cholelithiasis [DC11]	[40]
Levomilnacipran	DMV26S8	Moderate	Increased risk of bleeding by the combination of Naproxen and Levomilnacipran.	Chronic pain [MG30]	[41]
Regorafenib	DMHSY1I	Major	Increased risk of bleeding by the combination of Naproxen and Regorafenib.	Colorectal cancer [2B91]	[29]
Drospirenone	DM1A9W3	Moderate	Increased risk of hyperkalemia by the combination of Naproxen and Drospirenone.	Contraceptive management [QA21]	[42]
Methoxyflurane	DML0RAE	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Methoxyflurane.	Corneal disease [9A76-9A78]	[29]
Ardeparin	DMYRX8B	Major	Increased risk of bleeding by the combination of Naproxen and Ardeparin.	Coronary thrombosis [BA43]	[43]
Mifepristone	DMGZQEF	Moderate	Decreased metabolism of Naproxen caused by Mifepristone mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[44]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Naproxen caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[45]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Naproxen caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[46]
MK-8228	DMOB58Q	Moderate	Increased metabolism of Naproxen caused by MK-8228 mediated induction of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[47]
Danaparoid	DM6CLBN	Major	Increased risk of bleeding by the combination of Naproxen and Danaparoid.	Deep vein thrombosis [BD71]	[43]
Rivaroxaban	DMQMBZ1	Major	Increased risk of bleeding by the combination of Naproxen and Rivaroxaban.	Deep vein thrombosis [BD71]	[48]
Sertraline	DM0FB1J	Moderate	Increased risk of bleeding by the combination of Naproxen and Sertraline.	Depression [6A70-6A7Z]	[41]
Vortioxetine	DM6F1PU	Moderate	Increased risk of bleeding by the combination of Naproxen and Vortioxetine.	Depression [6A70-6A7Z]	[41]
Milnacipran	DMBFE74	Moderate	Increased risk of bleeding by the combination of Naproxen and Milnacipran.	Depression [6A70-6A7Z]	[41]
Escitalopram	DMFK9HG	Moderate	Increased risk of bleeding by the combination of Naproxen and Escitalopram.	Depression [6A70-6A7Z]	[41]
Clomipramine	DMINRKW	Moderate	Increased risk of bleeding by the combination of Naproxen and Clomipramine.	Depression [6A70-6A7Z]	[41]
PMID28870136-Compound-49	DMTUC9E	Moderate	Increased risk of bleeding by the combination of Naproxen and PMID28870136-Compound-49.	Discovery agent [N.A.]	[49]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Cannabidiol.	Epileptic encephalopathy [8A62]	[29]
Tazemetostat	DMWP1BH	Moderate	Increased risk of bleeding by the combination of Naproxen and Tazemetostat.	Follicular lymphoma [2A80]	[31]
Dexlansoprazole	DM1DBV5	Moderate	Decreased absorption of Naproxen due to altered gastric pH caused by Dexlansoprazole.	Gastro-oesophageal reflux disease [DA22]	[35]
Ripretinib	DM958QB	Moderate	Decreased clearance of Naproxen due to the transporter inhibition by Ripretinib.	Gastrointestinal stromal tumour [2B5B]	[26]
Avapritinib	DMK2GZX	Major	Increased risk of bleeding by the combination of Naproxen and Avapritinib.	Gastrointestinal stromal tumour [2B5B]	[29]
Chlorothiazide	DMLHESP	Moderate	Antagonize the effect of Naproxen when combined with Chlorothiazide.	Heart failure [BD10-BD1Z]	[50]
Bumetanide	DMRV7H0	Moderate	Antagonize the effect of Naproxen when combined with Bumetanide.	Heart failure [BD10-BD1Z]	[50]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Naproxen caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[51]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[52]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Naproxen caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[53]
Fenofibrate	DMFKXDY	Moderate	Decreased metabolism of Naproxen caused by Fenofibrate mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[26]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Naproxen and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[54]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Naproxen and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[55]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Naproxen and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[56]
Indapamide	DMGN1PW	Moderate	Antagonize the effect of Naproxen when combined with Indapamide.	Hypertension [BA00-BA04]	[50]
Trichlormethiazide	DMHAQCO	Moderate	Antagonize the effect of Naproxen when combined with Trichlormethiazide.	Hypertension [BA00-BA04]	[50]
Dipyridamole	DMXY30O	Moderate	Increased risk of bleeding by the combination of Naproxen and Dipyridamole.	Hypertension [BA00-BA04]	[31]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Naproxen caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[57]
Balsalazide	DM7I1T9	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Balsalazide.	Indeterminate colitis [DD72]	[58]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Naproxen caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[26]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Naproxen caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[59]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Naproxen caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[29]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of bleeding by the combination of Naproxen and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[60]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Idelalisib.	Mature B-cell leukaemia [2A82]	[61]
Acalabrutinib	DM7GCVW	Major	Increased risk of bleeding by the combination of Naproxen and Acalabrutinib.	Mature B-cell lymphoma [2A85]	[62]
Ibrutinib	DMHZCPO	Major	Increased risk of bleeding by the combination of Naproxen and Ibrutinib.	Mature B-cell lymphoma [2A85]	[63]
Ponatinib	DMYGJQO	Major	Increased risk of bleeding by the combination of Naproxen and Ponatinib.	Mature B-cell lymphoma [2A85]	[64]
Arry-162	DM1P6FR	Moderate	Decreased clearance of Naproxen due to the transporter inhibition by Arry-162.	Melanoma [2C30]	[26]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Naproxen caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[26]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Naproxen caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[29]
Exjade	DMHPRWG	Major	Increased risk of nephrotoxicity by the combination of Naproxen and Exjade.	Mineral absorption/transport disorder [5C64]	[65]
Panobinostat	DM58WKG	Major	Increased risk of bleeding by the combination of Naproxen and Panobinostat.	Multiple myeloma [2A83]	[26]
Deflazacort	DMV0RNS	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Deflazacort.	Muscular dystrophy [8C70]	[32]
Ruxolitinib	DM7Q98D	Moderate	Increased risk of bleeding by the combination of Naproxen and Ruxolitinib.	Myeloproliferative neoplasm [2A20]	[31]
Dasatinib	DMJV2EK	Major	Increased risk of bleeding by the combination of Naproxen and Dasatinib.	Myeloproliferative neoplasm [2A20]	[66]
Omacetaxine mepesuccinate	DMPU2WX	Major	Increased risk of bleeding by the combination of Naproxen and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[67]
Prasugrel	DM7MT6E	Major	Increased risk of bleeding by the combination of Naproxen and Prasugrel.	Myocardial infarction [BA41-BA43]	[29]
Vorapaxar	DMA16BR	Major	Increased risk of bleeding by the combination of Naproxen and Vorapaxar.	Myocardial infarction [BA41-BA43]	[68]
Sibutramine	DMFJTDI	Moderate	Increased risk of bleeding by the combination of Naproxen and Sibutramine.	Obesity [5B80-5B81]	[41]
Dexfenfluramine	DMJ7YDS	Moderate	Increased risk of bleeding by the combination of Naproxen and Dexfenfluramine.	Obesity [5B80-5B81]	[41]
Polythiazide	DMCH80F	Moderate	Antagonize the effect of Naproxen when combined with Polythiazide.	Oedema [MG29]	[50]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Naproxen caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[69]
MK-4827	DMLYGH4	Moderate	Increased risk of bleeding by the combination of Naproxen and MK-4827.	Ovarian cancer [2C73]	[29]
Aspirin	DM672AH	Moderate	Increased risk of bleeding by the combination of Naproxen and Aspirin.	Pain [MG30-MG3Z]	[70]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Naproxen caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[71]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Naproxen caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[72]
Iloprost	DMVPZBE	Moderate	Increased risk of bleeding by the combination of Naproxen and Iloprost.	Pulmonary hypertension [BB01]	[73]
Everolimus	DM8X2EH	Major	Increased risk of nephrotoxicity by the combination of Naproxen and Everolimus.	Renal cell carcinoma [2C90]	[74]
Temsirolimus	DMS104F	Major	Increased risk of nephrotoxicity by the combination of Naproxen and Temsirolimus.	Renal cell carcinoma [2C90]	[74]
Gatifloxacin	DMSL679	Moderate	Additive CNS stimulant effects by the combination of Naproxen and Gatifloxacin.	Respiratory infection [CA07-CA4Z]	[33]
Sulfasalazine	DMICA9H	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Sulfasalazine.	Rheumatoid arthritis [FA20]	[58]
Dexamethasone	DMMWZET	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Dexamethasone.	Rheumatoid arthritis [FA20]	[32]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Naproxen and Leflunomide.	Rheumatoid arthritis [FA20]	[55]
Methylprednisolone	DM4BDON	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Methylprednisolone.	Solid tumour/cancer [2A00-2F9Z]	[32]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Naproxen and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[29]
Prednisolone	DMQ8FR2	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Prednisolone.	Solid tumour/cancer [2A00-2F9Z]	[32]
Pitolisant	DM8RFNJ	Moderate	Increased risk of GI mucosal injury/bleeding risk by the combination of Naproxen and Pitolisant.	Somnolence [MG42]	[29]
Lusutrombopag	DMH6IKO	Moderate	Decreased clearance of Naproxen due to the transporter inhibition by Lusutrombopag.	Thrombocytopenia [3B64]	[69]
Caplacizumab	DMPUKA7	Moderate	Increased risk of bleeding by the combination of Naproxen and Caplacizumab.	Thrombocytopenia [3B64]	[31]
Apixaban	DM89JLN	Major	Increased risk of bleeding by the combination of Naproxen and Apixaban.	Thrombosis [DB61-GB90]	[29]
Cangrelor	DM8JRH0	Moderate	Increased risk of bleeding by the combination of Naproxen and Cangrelor.	Thrombosis [DB61-GB90]	[31]
Brilinta	DMBR01X	Moderate	Increased risk of bleeding by the combination of Naproxen and Brilinta.	Thrombosis [DB61-GB90]	[29]
Cabozantinib	DMIYDT4	Major	Increased risk of bleeding by the combination of Naproxen and Cabozantinib.	Thyroid cancer [2D10]	[75]
Tacrolimus	DMZ7XNQ	Major	Increased risk of nephrotoxicity by the combination of Naproxen and Tacrolimus.	Transplant rejection [NE84]	[74]
Olsalazine	DMZW9HA	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Olsalazine.	Ulcerative colitis [DD71]	[58]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Naproxen and Plazomicin.	Urinary tract infection [GC08]	[34]
Betrixaban	DM2C4RF	Major	Increased risk of bleeding by the combination of Naproxen and Betrixaban.	Venous thromboembolism [BD72]	[76]
-----------


⏷ Show the Full List of 113 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Fumaric acid	E00420	444972	Acidulant; Antioxidant; Complexing agent; Flavoring agent; Solubilizing agent
Glyceryl monostearate	E00310	24699	Emollient; Emulsifying agent; Emulsion stabilizing agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Kyselina citronova	E00014	311	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Lactic acid	E00020	612	Acidulant
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Carmellose sodium	E00625	Not Available	Disintegrant
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Crospovidone	E00626	Not Available	Disintegrant
Edetate disodium	E00186	8759	Complexing agent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Magnesium sulfate	E00281	24083	Vaccine adjuvant
Polyethylene glycol 1000	E00647	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water	E00035	962	Solvent
--------------------


⏷ Show the Full List of 40 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Naproxen 220 mg capsule	220 mg	Oral Capsule	Oral
Naproxen 220 mg tablet	220 mg	Oral Tablet	Oral
Naproxen 550 mg tablet	550 mg	Oral Tablet	Oral
Naproxen 750 mg tablet	750 mg	24 HR Extended Release Oral Tablet	Oral
Naproxen 500 mg tablet	500 mg	24 HR Extended Release Oral Tablet	Oral
Naproxen 200 mg tablet	200 mg	Oral Tablet	Oral
Naproxen 275 mg tablet	275 mg	Oral Tablet	Oral
Naproxen 375 mg tablet	375 mg	24 HR Extended Release Oral Tablet	Oral
Naproxen 250 mg tablet	250 mg	Oral Tablet	Oral
Naproxen 375 mg tablet	375 mg	Oral Tablet	Oral
Naproxen 500 mg tablet	500 mg	Oral Tablet	Oral
Naproxen 375 mg tablet	375 mg	Delayed Release Oral Tablet	Oral
Naproxen 500 mg tablet	500 mg	Delayed Release Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Naproxen FDA Label
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5230).
4	New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202.
5	Todd PA, Clissold SP: Naproxen. A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs. 1990 Jul;40(1):91-137. doi: 10.2165/00003495-199040010-00006.
6	BDDCS applied to over 900 drugs
7	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
8	Naprelan FDA Label
9	Falany CN, Strom P, Swedmark S: Sulphation of o-desmethylnaproxen and related compounds by human cytosolic sulfotransferases. Br J Clin Pharmacol. 2005 Dec;60(6):632-40. doi: 10.1111/j.1365-2125.2005.02506.x.
10	Naproxen .
11	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
12	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
13	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.
14	Drug interactions in dentistry: the importance of knowing your CYPs. J Am Dent Assoc. 2004 Mar;135(3):298-311.
15	Influence of mutations associated with Gilbert and Crigler-Najjar type II syndromes on the glucuronidation kinetics of bilirubin and other UDP-glucuronosyltransferase 1A substrates. Pharmacogenet Genomics. 2007 Dec;17(12):1017-29.
16	Involvement of multiple cytochrome P450 isoforms in naproxen O-demethylation. Eur J Clin Pharmacol. 1997;52(4):293-8.
17	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.
18	S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33.
19	Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen. J Inorg Biochem. 2012 Feb;107(1):54-64. doi: 10.1016/j.jinorgbio.2011.10.014. Epub 2011 Nov 3.
20	Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
21	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
22	Cyclooxygenase inhibitors down regulate P-glycoprotein in human colorectal Caco-2 cell line. Pharm Res. 2008 Sep;25(9):1991-2001. doi: 10.1007/s11095-008-9596-1. Epub 2008 Jun 26.
23	Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43.
24	Differential activation of CYP2C9 variants by dapsone. Biochem Pharmacol. 2004 May 15;67(10):1831-41.
25	Effects of acidic non-steroidal anti-inflammatory drugs on human cytochrome P450 4A11 activity: Roles of carboxylic acid and a sulfur atom in potent inhibition by sulindac sulfide. Chem Biol Interact. 2023 Sep 1;382:110644. doi: 10.1016/j.cbi.2023.110644. Epub 2023 Jul 25.
26	Cerner Multum, Inc. "Australian Product Information.".
27	Brogden RN, Heel RC, Speight TM, Avery GS "Naproxen up to date: a review of its pharmacological properties and therapeutic efficacy and use in rheumatic diseases and pain states." Drugs 18 (1979): 241-77. [PMID: 387372]
28	Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
29	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
30	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
31	Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA.
32	Buchman AL, Schwartz MR "Colonic ulceration associated with the systemic use of nonsteroidal antiinflammatory medication." J Clin Gastroenterol 22 (1996): 224-6. [PMID: 8724264]
33	Product Information. Factive (gemifloxacin). GeneSoft Inc, San Francisco, CA.
34	Assael BM, Chiabrando C, Gagliardi L, Noseda A, Bamonte F, Salmona M "Prostaglandins and aminoglycoside nephrotoxicity." Toxicol Appl Pharmacol 78 (1985): 386-94. [PMID: 4049389]
35	Product Information. Naprosyn (naproxen). Syntex Laboratories Inc, Palo Alto, CA.
36	Product Information. Actonel (risedronate). Procter and Gamble Pharmaceuticals, Cincinnati, OH.
37	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
38	Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ.
39	Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
40	Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
41	Alderman CP, Moritz CK, Ben-Tovim DI "Abnormal platelet aggregation associated with fluoxetine therapy." Ann Pharmacother 26 (1992): 1517-9. [PMID: 1482806]
42	Product Information. Yasmin (drospirenone-ethinyl estradiol) Berlex Laboratories, Richmond, CA.
43	Bang CJ, Riedel B, Talstad I, Berstad A "Interaction between heparin and acetylsalicylic acid on gastric mucosal and skin bleeding in humans." Scand J Gastroenterol 27 (1992): 489-94. [PMID: 1321488]
44	Product Information. Korlym (mifepristone). Corcept Therapeutics Incorporated, Menlo Park, CA.
45	Product Information. Isturisa (osilodrostat). Recordati Rare Diseases Inc, Lebanon, NJ.
46	Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
47	Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
48	Product Information. Xarelto (rivaroxaban). Bayer Inc, Toronto, IA.
49	Canadian Pharmacists Association.
50	Muller FO, Schall R, Devaal AC, Groenewoud G, Hundt HKL, Middle MV "Influence of meloxicam on furosemide pharmacokinetics and pharmacodynamics in healthy volunteers." Eur J Clin Pharmacol 48 (1995): 247-51. [PMID: 7589049]
51	Product Information. Priftin (rifapentine). Hoechst Marion-Roussel Inc, Kansas City, MO.
52	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
53	Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
54	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
55	EMEA "EMEA public statement on leflunomide (ARAVA) - severe and serious hepatic reactions.".
56	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
57	Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
58	Novis BH, Korzets Z, Chen P, Bernheim J "Nephrotic syndrome after treatment with 5-aminosalicylic acid." Br Med J (Clin Res Ed) 296 (1988): 1442. [PMID: 3132281]
59	Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
60	Caruso V, Iacoviello L, Di Castelnuovo A, et.al "Thrombotic complications in childhood acute lymphoblastic leukemia: a meta-analysis of 17 prospective studies comprising 1752 pediatric patients." Blood 108 (2006): 2216-22. [PMID: 16804111]
61	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
62	Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
63	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
64	Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
65	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
66	Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ.
67	Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA.
68	Product Information. Zontivity (vorapaxar). Merck & Company Inc, Whitehouse Station, NJ.
69	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
70	Concomitant use of ibuprofen and aspirin. J Pain Palliat Care Pharmacother 21 (2007): 73-4. [PMID: 17844731]
71	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
72	Benoist G, van Oort I, et al "Drug-drug interaction potential in men treated with enzalutamide: Mind the gap." Br J Clin Pharmacol 0 (2017): epub. [PMID: 28881501]
73	Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC.
74	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
75	Product Information. Cometriq (cabozantinib). Exelixis Inc, S San Francisco, CA.
76	Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA.