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