NPS

(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

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is present as a standalone ligand in 11 entries

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Chemical Component Summary
Name	(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Synonyms	NAPROXEN
Identifiers	(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Formula	C₁₄ H₁₄ O₃
Molecular Weight	230.259
Type	NON-POLYMER
Isomeric SMILES	C[C@@H](c1ccc2cc(ccc2c1)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

Chemical Details
Formal Charge	0
Atom Count	31
Chiral Atom Count	1
Bond Count	32
Aromatic Bond Count	11

Drug Info: DrugBank

DrugBank ID	DB00788
Name	Naproxen
Groups	approved vet_approved
Description	Naproxen is classified as a nonsteroidal anti-inflammatory dug (NSAID) and was initially approved for prescription use in 1976 and then for over-the-counter (OTC) use in 1994.[A178975] It can effectively manage acute pain as well as pain related to rheumatic diseases, and has a well studied adverse effect profile.[A179098] Given its overall tolerability and effectiveness, naproxen can be considered a first line treatment for a variety of clinical situations requiring analgesia.[A179098] Naproxen is available in both immediate and delayed release formulations, in combination with sumatriptan to treat migraines, and in combination with esomeprazole to lower the risk of developing gastric ulcers.[L6582][L6583][L7309][L7312]
Synonyms	(+)-2-(6-Methoxy-2-naphthyl)propionic acid (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid Naprolag (+)-2-(Methoxy-2-naphthyl)-propionic acid Naproxen sodium Naproxenum (S)-Naproxen (+)-2-(Methoxy-2-naphthyl)-propionsäure Naproxen (S)-2-(6-Methoxy-2-naphthyl)propanoic acid (+)-(S)-Naproxen (S)-2-(6-Methoxy-2-naphthyl)propionic acid (S)-(+)-Naproxen (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid (+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid Naproxeno (+)-Naproxen Naproxène
Brand Names	Topcare Sinus and Cold D First Aid Direct All Day Pain Relief Aleve, TRAVEL BASIX Apo-naproxen EC DG Health Naproxen Sodium Good Sense Naproxen Sodium Signature Care Pain Relief Members Mark Naproxen Sodium Flanax Pain Reliever/Fever Reducer Sunmark Sinus and Cold D Naproxen Aleve Easy Open Arthritis Cap Equaline All Day Pain Relief Naproxen-NA Aleve Nighttime Pro-naproxen EC - 375 Anaprox DS Tab 550mg Theraproxen Naproxen Sodium Headache Pain Caplets Naproxen sodium Health Mart Naproxen Sodium Bayer Aleve Up and Up Sinus and Cold D Naproxen Oral Suspension Flanax Naproxen Naproxen Sodium Careone Naproxen Sodium Exchange Select Naproxen Sodium Naproxen - 500 Trepoxen-250 Naprosyn Sup 500mg Naproxen Sodium Headache Pain Naproxen Sodium Back and Muscle Pain Sumatriptan and Naproxen Sodium CareOne Naproxen Sodium Naproxen and esomeprazole magnesium Nu-naprox Tab 375mg Naprosyn 250mg Tablets Menstridol Naproxen Menstrual Pain Relief Sudafed Sinus 12 Hour Pressure plus Pain Naprosyn 500 Mg Suppositories Flanax Pain and Fever Reliever Sunmark All Day Relief Naproxen Sodium Capsules All Day Pain Relief Naproxen Sodium Fulton Street Market Naproxen Sodium Pro-naproxen EC Theraproxen-500 Caring Mill All Day Pain Relief Pain and Fever Relief Mylan-naproxen EC Equate All Day Pain Relief Rx Act All Day Pain Relief Teva-naproxen SR Formucare Naproxen Sodium Pain Reliever Fever Reducer Naproxen Sodium PM Dg Health All Day Pain Relief Ntp-naproxen Sodium DS Naproxen Delayed-release Topcare Naproxen Sodium First Aid Direct Naproxen Sodium Equaline Naproxen Sodium PM Naprosyn E Tab 250mg Rugby All Day Relief Naproxen-NA DF Pediapharm Naproxen Suspension Aleve liquid gels Naproxen - 250 Napropak Cool Belmora Flanax Naprosyn E 250mg Tablets - Ect PREVACID NapraPAC 500 Rexall All Day Pain Relief Naproxen Kit Naproxen Sodium and Diphenhydramine Hydrochloride Leader All Day Pain Relief Naproxen Sodium (NSAID) Fever Reducer/ Pain Reliever Equipto - Naproxen External Cream Compounding Kit Naproxen Sodium DS Basic Care Naproxen Sodium PM Naproxen Capsules 200 mg Pain Reliever AnaDent Anaprox DS Leader Sinus and Cold-D Naprosyn E Tab 375mg Naproxen Delayed Release Sumatriptan Succinate and Naproxen Sodium Family Wellness Naproxen Sodium Naprosyn Rx Act all day pain relief Headache Pain EC-Naprosyn Healthy Accents Naproxen Sodium Naprosyn-SR Tab 750mg Naproxen EC Naproxen Liquid Gels Aleve Caplets - Easy Open Arthritis Cap PMS-naproxen EC Sudafed Sinus and Pain 12 Hour Nx 12 Hour Naproxen PM Apo-naproxen SR Tablets 750mg Nu-naprox Tab 250mg PREVACID NapraPAC 375 Sudafed 12 Hour Pressure And Pain Synflex DS Tab 550mg Rx Act Naproxen Sodium NaproxenPax Topcare All Day Pain Relief Aleve Back and Muscle Pain Waymade-naproxen Sodium DS ShopRite Naproxen Sodium Basic Care Naproxen Sodium Simply Right Naproxen Sodium 7 Select Naproxen Sodium Aleve Caplets Vimovo Suvexx PMS-naproxen Naproxen Sodium Diphenhydramine HCl Nu-napro-NA Riva-naproxen Sodium Midol Extended Relief Leader Naproxen Sodium Ntp-naproxen Proxen Np 660 Apo-naproxen Flanax Pain Reliever/Fever reducer Riva-naproxen Xpect Naproxen Sodium Nu-naprox Tab 125mg Aleve Gelcaps Equate Naproxen Sodium CAREALL Naproxen Rapidol Naproxen Sab-naproxen Good Neighbor Pharmacy Sinus and Cold D Naprotin Naproxen Sodium Diphenhydramine Hydrochloride Teva-naproxen Sodium Back and Muscle Pain Naproxen Sodium 220mg Mylan-naproxen/esomeprazole Mr Humana Pharmacy All Day Pain Relief Napropak Naproxen Headache Pain Prevacid Naprapac Medique at Home Mediproxen Flanax Pain Reliever Good Neighbor Pharmacy Naproxen Sodium Ana-Dent Toothache Relief Waymade-naproxen Sodium Naproxen Sodium HEADACHE PAIN Aleve PM Desinflamax - Naproxen Sodium Medique Mediproxen All Day Pain Relief Signature Care Naproxen Sodium All Night Pain Relief PM Aleve-D Sinus and Headache Leader All Day Lil Drug Store Pain Relief All Day Motrimax 12 Hour Tablets Motrimax 12 Hour Flanax Menstrual Pain Reliever Being Well all day pain relief Naprosyn E Tab 500mg Naproxen Sodium and Pseudoephedrine Hydrochloride Sinus and Headache Pain Reliever & Sleep Aid Smart Sense naproxen sodium Apo-napro-NA Comfort Pac with Naproxen Good Sense All Day Pain Relief Naproxen All day relief for pain Pain Zero PREVACID NapraPAC 250 Care One All Day Pain Relief Naproxen Sodium All Day Pain Relief Apo-napro-NA DS Naprosyn 375mg Naprosyn Sus 25mg/ml Naprosyn 375mg Tablets Nu-napro-NA DS Preferred Plus Sinus and Cold D Ntp-naproxen EC Ana-Dent PAIN RELIEF Naproxen Sodium Tablets Naproxen and Esomeprazole Magnesium Naproxen Sodium Caplets Up and Up Naproxen Sodium PM Pain Relief All Day Leader Sinus and Cold D Naprelan Naprosyn 500 Mg Tablets Naproxen Sodium and Diphenhydramine HCl Rhodiaprox - 500mg/sup Teva-naproxen EC All Day Pain Relief Back and Muscle Pain Good Neighbor Pharmacy Pain Relief All Day Ratio-naproxen E Nu-naprox Tab 500mg Health Mart Sinus and Cold D Dg Health Naproxen Sodium Kirkland Signature Naproxen Sodium Healthy Accents All Day Pain Relief Flanax Naproxen Sodium and Diphenhydramine HCL Teva-naproxen Sodium DS Riva-naproxen Sodium DS Naproxen delayed release Flanax Pain Relief Kit Naproxen Tablets Sound Body Naproxen Sodium Synflex Tab 275mg Dg Health Naproxen Sodium PM Good Neighbor Pharmacy naproxen sodium Leader All Day Sinus and Cold D TopCare All Day Pain Relief Aleve Ratio-naproxen Topcare Back and Muscle Pain Berkley and Jensen Naproxen Sodium Naproxen-375 All Day Relief Cold FAid Vicks Sinex D Severe Sinus and Cold Aleve Back and Body Pain Naproxen Back and Muscle Pain Theraproxen-90 Treximet Naproxen Sodium Back and Muscle Pain Caplets Apo-naproxen EC Tablets Naproxen Caplets All day relief for pain Clear Choice Naproxen Sodium NaproPax Careone Naproxen Sodium PM Equate Sinus and Cold D Topcare All Night Pain Relief PM Apo Naproxen Tab 125mg Betr Headache Pain Relief Up and Up Naproxen sodium Pain Relief Care One Naproxen Sodium Equaline Naproxen Sodium Foster and Thrive All Day Pain Relief Naproxen 125 Tab 125mg EC-naproxen Naproxen Pain Relief Sunmark Naproxen Sodium Naproxen Caplets Maxidol Liquid Gels Nu-naprox EC Aleve Headache Pain Equate All Night Pain Relief All Day Back and Muscle Pain Relief Signature Care Naproxen Sodium PM Sinus and Cold D Naproxen Sodium and Pseudoephedrine Hydrochloride Sinus and Cold Novo-naprox Tab 125mg Ava-naproxen EC Calmadol Pain Reliever Aleve-D Sinus and Cold Naproxen Sodium Diphenhydramine HCL Anaprox Naprosyn 250mg Teva-naproxen Up and Up Naproxen Sodium Smart Sense Naproxen Sodium SALLUS Pain Relief Collection with Naproxen Ntp-naproxen Sodium Waymade-naproxen Naproxen Sodium BACK AND MUSCLE PAIN All Day Sinus and Cold D
Indication	Naproxen is indicated for the management of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and for the relief of mild to moderate pain.[L6582][L6583][A178975] Further, it is first-line therapy for osteoarthritis, acute gouty arthritis, dysmenorrhea, and musculoskeletal inflammation and pain.[A178975]
Categories	Agents causing hyperkalemia Agents that produce hypertension Analgesics Analgesics, Non-Narcotic Anti-Inflammatory Agents Anti-Inflammatory Agents, Non-Steroidal Anti-Inflammatory Agents, Non-Steroidal (Non-Selective) Antigout Preparations Antiinflammatory and Antirheumatic Products Antiinflammatory and Antirheumatic Products, Non-Steroids Antiinflammatory Preparations, Non-Steroids for Topical Use Antiinflammatory Products for Vaginal Administration Antirheumatic Agents BSEP/ABCB11 Substrates Central Nervous System Agents Cyclooxygenase Inhibitors Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Enzyme Inhibitors Genito Urinary System and Sex Hormones Musculo-Skeletal System Naphthaleneacetic Acids Naphthalenes Nephrotoxic agents Non COX-2 selective NSAIDS OAT1/SLC22A6 inhibitors Other Nonsteroidal Anti-inflammatory Agents P-glycoprotein inhibitors Peripheral Nervous System Agents Photosensitizing Agents Propionates Sensory System Agents Topical Products for Joint and Muscular Pain UGT1A1 Substrates UGT1A3 substrates UGT1A6 substrate UGT1A9 Substrates UGT2B7 substrates
ATC-Code	G02CC02 M02AA12 M01AE56 M01AE52 M01AE02
CAS number	22204-53-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Prostaglandin G/H synthase 1	MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...	unknown	inhibitor
Prostaglandin G/H synthase 2	MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...	unknown	inhibitor
Peptostreptococcal albumin-binding protein	MKLNKKLLMAALAGAIVVGGGVNTFAADEPGAIKVDKAPEAPSQELKLTK...	unknown
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	substrate
UDP-glucuronosyltransferase 1-3	MATGLQVPLPWLATGLLLLLSVQPWAESGKVLVVPIDGSHWLSMREVLRE...	unknown	substrate
UDP-glucuronosyltransferase 1-6	MACLLRSFQRISAGVFFLALWGMVVGDKLLVVPQDGSHWLSMKDIVEVLS...	unknown	substrate
UDP-glucuronosyltransferase 1-7	MARAGWTGLLPLYVCLLLTCGFAKAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1-8	MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1-9	MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1-10	MARAGWTSPVPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource Name	Reference
Pharos	CHEMBL154
PubChem	156391
ChEMBL	CHEMBL154
ChEBI	CHEBI:7476
CCDC/CSD	COYRUD12, QIMBIA, COYRUD14, COYRUD13, AFOPIX, FEVZUD, QILZIX, COYRUD11, QILZAP, RODSUA, AFOPOD, PAPTUX, RODSOU, QILZOD, TERYEU, QIMCOH, RODSEK, PAMQAX, QIMBEW01, BEYTUW, COYRUD, QIMBAS01, SAJCOY, MICFEJ, COZYAS, QIMBAS, QIMCUN, FEVZUD01, TOBMAA, RODSIO, JULJEH, KETKUT, KETKIH, KETKON
COD	7221751, 4501397, 4513532, 7215887, 7215888, 7216530, 7205534, 7218004, 7218005, 2020783, 7209753, 7209755, 4509150

RCSB PDB Core Operations are funded by the U.S. National Science Foundation (DBI-2321666), the US Department of Energy (DE-SC0019749), and the National Cancer Institute, National Institute of Allergy and Infectious Diseases, and National Institute of General Medical Sciences of the National Institutes of Health under grant R01GM157729.

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NPS

(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

Chemical Component Summary

Chemical Details

Drug Info: DrugBank

Drug Targets

Related Resource References