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