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