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

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