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