NPS

(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid

Created:	2007-10-04
Last modified:	2020-06-05

Find Related PDB Entry
11 entries where NPS is found as a standalone ligand

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	31
Chiral Atom Count	1
Bond Count	32
Aromatic Bond Count	11

Toggle Hydrogen Toggle Labels

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

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