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