NPS

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

Created:	2007-10-04
Last modified:	2020-06-05

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11 entries where NPS is found as a standalone ligand

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

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Chemical Component Summary
Name	(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Synonyms	NAPROXEN
Systematic Name (OpenEye OEToolkits)	(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
Formula	C₁₄ H₁₄ O₃
Molecular Weight	230.259
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(c1ccc2c(c1)ccc(OC)c2)C
SMILES	CACTVS	3.341	COc1ccc2cc(ccc2c1)[CH](C)C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	CC(c1ccc2cc(ccc2c1)OC)C(=O)O
Canonical SMILES	CACTVS	3.341	COc1ccc2cc(ccc2c1)[C@H](C)C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O
InChI	InChI	1.03	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	InChI	1.03	CMWTZPSULFXXJA-VIFPVBQESA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00788
Name	Naproxen
Groups	vet_approved 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	(+)-Naproxen (+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid (S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid (S)-Naproxen (S)-2-(6-Methoxy-2-naphthyl)propionic acid Naproxène (+)-2-(Methoxy-2-naphthyl)-propionic acid (S)-2-(6-Methoxy-2-naphthyl)propanoic acid (+)-2-(Methoxy-2-naphthyl)-propionsäure Naproxen sodium (+)-2-(6-Methoxy-2-naphthyl)propionic acid Naprolag (S)-(+)-Naproxen Naproxen Naproxeno Naproxenum (+)-(S)-Naproxen (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid
Brand Names	All Day Pain Relief Naproxen Sodium Careone Naproxen Sodium Naproxen delayed release Apo-naproxen EC Pain and Fever Relief Naproxen-NA DF Equate Sinus and Cold D Health Mart Naproxen Sodium Equate Naproxen Sodium Naprosyn 500 Mg Tablets Naprosyn E Tab 250mg Rx Act all day pain relief Headache Pain All Night Pain Relief PM Simply Right Naproxen Sodium Sudafed 12 Hour Pressure And Pain Aleve, TRAVEL BASIX Nu-naprox Tab 375mg Desinflamax - Naproxen Sodium Naproxen-NA Naproxen Caplets Naproxen Sodium Caplets Theraproxen-90 Topcare Naproxen Sodium Comfort Pac with Naproxen Medique at Home Mediproxen Sinus and Cold D Teva-naproxen SR Naprosyn 375mg Apo-napro-NA Dg Health Naproxen Sodium Menstridol Topcare Sinus and Cold D Naproxen Sodium and Diphenhydramine Hydrochloride Suvexx Equaline Naproxen Sodium PM Anaprox Medique Mediproxen Napropak Good Sense All Day Pain Relief Naproxen Delayed Release Pain Relief Aleve Caplets Napropak Cool All Day Pain Relief Good Neighbor Pharmacy Sinus and Cold D Naproxen and Esomeprazole Magnesium Naproxen Back and Muscle Pain Sound Body Naproxen Sodium ShopRite Naproxen Sodium Teva-naproxen Sodium DS Pro-naproxen EC - 375 Naproxen and esomeprazole magnesium 7 Select Naproxen Sodium Pain Reliever & Sleep Aid Dg Health Naproxen Sodium PM Equaline Naproxen Sodium Formucare Naproxen Sodium Pain Reliever Fever Reducer Signature Care Pain Relief Waymade-naproxen Nu-naprox Tab 125mg Nu-naprox EC Naprosyn Sup 500mg Signature Care Naproxen Sodium Naprosyn 250mg Exchange Select Naproxen Sodium PMS-naproxen EC Up and Up Naproxen Sodium PM Pediapharm Naproxen Suspension Aleve Healthy Accents Naproxen Sodium Ntp-naproxen Sodium Preferred Plus Sinus and Cold D Ntp-naproxen Sodium DS Equate All Night Pain Relief Aleve liquid gels Naproxen Caplets All day relief for pain Ana-Dent PAIN RELIEF Ava-naproxen EC Waymade-naproxen Sodium Naproxen Sodium and Pseudoephedrine Hydrochloride Sinus and Cold Naproxen - 250 Naproxen Sodium Naproxen-375 Aleve-D Sinus and Headache Flanax Pain Relief Kit Naproxen - 500 PMS-naproxen Naprosyn E 250mg Tablets - Ect Aleve Caplets - Easy Open Arthritis Cap Naproxen Sodium and Diphenhydramine HCL Naproxen Sodium Headache Pain Naproxen EC Teva-naproxen Naproxen Menstrual Pain Relief Pain Zero Smart Sense Naproxen Sodium Mylan-naproxen/esomeprazole Mr Basic Care Naproxen Sodium PM Naproxen Sodium Tablets TopCare All Day Pain Relief Motrimax 12 Hour Tablets Rugby All Day Relief Amazon Basic Care Naproxen Sodium Proxen Np 660 Pain Relief All Day Flanax Pain Reliever/Fever reducer Aleve Nighttime Flanax Pain Reliever Up and Up Sinus and Cold D Rx Act All Day Pain Relief Leader All Day Sinus and Cold D Health Mart Sinus and Cold D Topcare All Day Pain Relief EC-naproxen Good Neighbor Pharmacy Naproxen Sodium Treximet Rexall All Day Pain Relief Topcare Back and Muscle Pain Naproxen Tablets Betr Headache Pain Relief Apo Naproxen Tab 125mg Bayer Aleve Equaline All Day Pain Relief Nu-napro-NA DS Flanax Menstrual Pain Reliever Naprosyn E Tab 500mg CareOne Naproxen Sodium Theraproxen Vicks Sinex D Severe Sinus and Cold Flanax Naproxen Sab-naproxen All Day Pain Relief Back and Muscle Pain Naproxen Sodium Back and Muscle Pain Caplets Nu-naprox Tab 250mg Berkley and Jensen Naproxen Sodium Naproxen Oral Suspension Ratio-naproxen E PREVACID NapraPAC 500 Nu-naprox Tab 500mg Leader All Day Pain Relief Prevacid Naprapac First Aid Direct All Day Pain Relief Aleve Headache Pain Belmora Flanax Humana Pharmacy All Day Pain Relief Care One Naproxen Sodium Naproxen Sodium HEADACHE PAIN Riva-naproxen Sodium Sunmark All Day Relief Naproxen NaproxenPax CAREALL Naproxen EC-Naprosyn Midol Extended Relief Naprosyn Naproxen Sodium 220mg Naproxen 125 Tab 125mg Pro-naproxen EC Synflex DS Tab 550mg Sunmark Sinus and Cold D Aleve Easy Open Arthritis Cap Caring Mill All Day Pain Relief Sunmark Naproxen Sodium Apo-napro-NA DS Equate All Day Pain Relief Rx Act Naproxen Sodium Aleve Back and Muscle Pain Riva-naproxen Sodium DS Vimovo Anaprox DS Tab 550mg Healthy Accents All Day Pain Relief Naproxen Sodium Capsules Good Neighbor Pharmacy Pain Relief All Day Naprosyn Sus 25mg/ml Leader Sinus and Cold-D AnaDent NaproPax Aleve PM Naproxen Sodium All Day Pain Relief Sumatriptan and Naproxen Sodium Lil Drug Store Pain Relief All Day Maxidol Liquid Gels Aleve Gelcaps Ana-Dent Toothache Relief Naproxen Capsules 200 mg Rhodiaprox - 500mg/sup Sudafed Sinus and Pain 12 Hour Theraproxen-500 Naproxen sodium Naprosyn 500 Mg Suppositories Naproxen Sodium DS Kirkland Signature Naproxen Sodium Naprosyn E Tab 375mg Back and Muscle Pain Naproxen Sodium PM Smart Sense naproxen sodium Sudafed Sinus 12 Hour Pressure plus Pain Up and Up Naproxen sodium Flanax Pain and Fever Reliever Naprelan Foster and Thrive All Day Pain Relief Care One All Day Pain Relief Naproxen Kit Naproxen Sodium Diphenhydramine Hydrochloride Basic Care Naproxen Sodium Naproxen Liquid Gels Leader Sinus and Cold D Being Well all day pain relief DG Health Naproxen Sodium Naproxen Sodium BACK AND MUSCLE PAIN Equipto - Naproxen External Cream Compounding Kit Ntp-naproxen SALLUS Pain Relief Collection with Naproxen Family Wellness Naproxen Sodium Members Mark Naproxen Sodium Synflex Tab 275mg First Aid Direct Naproxen Sodium PREVACID NapraPAC 375 Naprosyn 250mg Tablets Rapidol Naproxen Topcare All Night Pain Relief PM Naprotin Flanax Pain Reliever/Fever Reducer Aleve-D Sinus and Cold Dg Health All Day Pain Relief Leader All Day Ratio-naproxen Anaprox DS Waymade-naproxen Sodium DS Pain Reliever Naproxen Pain Relief Naproxen Sodium and Diphenhydramine HCl All Day Back and Muscle Pain Relief Sumatriptan Succinate and Naproxen Sodium Naproxen Sodium Diphenhydramine HCl Fulton Street Market Naproxen Sodium Nx 12 Hour Naproxen Sodium Back and Muscle Pain Naprosyn-SR Tab 750mg Naproxen Delayed-release Cold FAid Teva-naproxen Sodium Naproxen Sodium (NSAID) Fever Reducer/ Pain Reliever Apo-naproxen Xpect Naproxen Sodium Flanax CAREALL Naproxen Sodium Leader Naproxen Sodium Careone Naproxen Sodium PM All Day Sinus and Cold D Aleve Back and Body Pain Apo-naproxen EC Tablets Clear Choice Naproxen Sodium Naproxen Sodium and Pseudoephedrine Hydrochloride Cold and Sinus Naproxen Sodium and Pseudoephedrine Hydrochloride Sinus and Headache Trepoxen-250 Naproxen Sodium Diphenhydramine HCL Good Neighbor Pharmacy naproxen sodium Teva-naproxen EC Naproxen Headache Pain Up and Up Naproxen Sodium Riva-naproxen Naproxen All day relief for pain Apo-naproxen SR Tablets 750mg Naproxen Sodium Headache Pain Caplets Motrimax 12 Hour Nu-napro-NA Calmadol Pain Reliever All Day Relief Novo-naprox Tab 125mg Good Sense Naproxen Sodium Naproxen PM Naprosyn 375mg Tablets Mylan-naproxen EC Signature Care Naproxen Sodium PM Ntp-naproxen EC PREVACID NapraPAC 250
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 Antimigraine Preparations Antirheumatic Agents Arylpropionic acid NSAIDS 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 Nervous System 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	M01AE02 M01AE57 G02CC02 M02AA12 M01AE56 M01AE52 N02CC51
CAS number	22204-53-1

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Pancreatic triacylglycerol lipase	MLPLWTLSLLLGAVAGKEVCYERLGCFSDDSPWSGITERPLHILPWSPKD...	unknown	inhibitor
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 1A3	MATGLQVPLPWLATGLLLLLSVQPWAESGKVLVVPIDGSHWLSMREVLRE...	unknown	substrate
UDP-glucuronosyltransferase 1-6	MACLLRSFQRISAGVFFLALWGMVVGDKLLVVPQDGSHWLSMKDIVEVLS...	unknown	substrate
UDP-glucuronosyltransferase 1A7	MARAGWTGLLPLYVCLLLTCGFAKAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1A8	MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1A9	MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...	unknown	substrate
UDP-glucuronosyltransferase 1A10	MARAGWTSPVPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
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
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Organic anion transporter 3	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