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