Synonym
CG 3117; CG3117; CG-3117; Naproxen; Naposin; Napratec
IUPAC/Chemical Name
(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
InChi Key
CMWTZPSULFXXJA-VIFPVBQESA-N
InChi Code
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
SMILES Code
O=C(O)[C@@H](C)C1=CC=C2C=C(OC)C=CC2=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Naproxen is a COX-1 and COX-2 inhibitor with IC50s of 8.72 and 5.15 μM.
In vitro activity:
These findings indicate that naproxen could protect against IL-1β-induced damage by improving cell viability and preventing cell death. Additionally, naproxen suppressed the expression of the cytokines IL-6, IL-12, and tumor necrosis factor-α (TNF-α), and downregulated the expression of vascular endothelial growth factor (VEGF) and tissue factor (TF) induced by IL-1β. Importantly, naproxen also inhibited the attachment of monocytes to endothelial cells, which was achieved through Krüppel-like factor 6 (KLF6)-mediated reduced expression of intracellular adhesion molecule-1 (ICAM-1) and E-selectin.
Reference: Bioengineered. 2021 Dec;12(1):5361-5372. https://pubmed.ncbi.nlm.nih.gov/34427537/
In vivo activity:
Six-week-old transgenic KrasG12V mice (n = 20; male + female) were fed modified AIN-76A diets containing naproxen (0/400 ppm) for 30 wk and euthanized at 36 wk of age. Administration of naproxen (400 ppm) inhibited lung tumor multiplicity by ∼52% (9.4 ± 0.85; P < 0001) and adenocarcinoma by ∼64% (6.1 ± 0.6; P < 0001), compared with control-diet-fed mice. Biomarker analysis showed significantly reduced inflammation (COX-2, IL-10), reduced tumor cell proliferation (PCNA, cyclin D1), and increased apoptosis (p21, caspase-3) in the lung tumors exposed to naproxen. Decreased serum levels of PGE2 and CXCR4 were observed in naproxen diet fed KrasG12V mice.
Reference: Neoplasia. 2021 Jun;23(6):574-583. https://pubmed.ncbi.nlm.nih.gov/34091121/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
73.0 |
317.03 |
| PBS (pH 7.2) |
1.0 |
4.34 |
| Water |
75.0 |
325.72 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
230.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Wu Y, Hao R, Lan B, Mu Y, Dang F, Wang R. The protective effects of naproxen against interleukin-1β (IL-1β)- induced damage in human umbilical vein endothelial cells (HUVECs). Bioengineered. 2021 Dec;12(1):5361-5372. doi: 10.1080/21655979.2021.1955560. PMID: 34427537; PMCID: PMC8806478.
2. Terrier O, Dilly S, Pizzorno A, Chalupska D, Humpolickova J, Bouřa E, Berenbaum F, Quideau S, Lina B, Fève B, Adnet F, Sabbah M, Rosa-Calatrava M, Maréchal V, Henri J, Slama-Schwok A. Antiviral Properties of the NSAID Drug Naproxen Targeting the Nucleoprotein of SARS-CoV-2 Coronavirus. Molecules. 2021 Apr 29;26(9):2593. doi: 10.3390/molecules26092593. PMID: 33946802; PMCID: PMC8124269.
3. Paglia DN, Kanjilal D, Kadkoy Y, Moskonas S, Wetterstrand C, Lin A, Galloway J, Tompson J, Culbertson MD, O'Connor JP. Naproxen treatment inhibits articular cartilage loss in a rat model of osteoarthritis. J Orthop Res. 2021 Oct;39(10):2252-2259. doi: 10.1002/jor.24937. Epub 2020 Dec 15. PMID: 33274763; PMCID: PMC8175455.
4. Kumar G, Madka V, Singh A, Farooqui M, Stratton N, Lightfoot S, Mohammed A, Rao CV. Naproxen inhibits spontaneous lung adenocarcinoma formation in KrasG12V mice. Neoplasia. 2021 Jun;23(6):574-583. doi: 10.1016/j.neo.2021.05.010. Epub 2021 Jun 3. PMID: 34091121; PMCID: PMC8187931.
In vitro protocol:
1. Wu Y, Hao R, Lan B, Mu Y, Dang F, Wang R. The protective effects of naproxen against interleukin-1β (IL-1β)- induced damage in human umbilical vein endothelial cells (HUVECs). Bioengineered. 2021 Dec;12(1):5361-5372. doi: 10.1080/21655979.2021.1955560. PMID: 34427537; PMCID: PMC8806478.
2. Terrier O, Dilly S, Pizzorno A, Chalupska D, Humpolickova J, Bouřa E, Berenbaum F, Quideau S, Lina B, Fève B, Adnet F, Sabbah M, Rosa-Calatrava M, Maréchal V, Henri J, Slama-Schwok A. Antiviral Properties of the NSAID Drug Naproxen Targeting the Nucleoprotein of SARS-CoV-2 Coronavirus. Molecules. 2021 Apr 29;26(9):2593. doi: 10.3390/molecules26092593. PMID: 33946802; PMCID: PMC8124269.
In vivo protocol:
1. Paglia DN, Kanjilal D, Kadkoy Y, Moskonas S, Wetterstrand C, Lin A, Galloway J, Tompson J, Culbertson MD, O'Connor JP. Naproxen treatment inhibits articular cartilage loss in a rat model of osteoarthritis. J Orthop Res. 2021 Oct;39(10):2252-2259. doi: 10.1002/jor.24937. Epub 2020 Dec 15. PMID: 33274763; PMCID: PMC8175455.
2. Kumar G, Madka V, Singh A, Farooqui M, Stratton N, Lightfoot S, Mohammed A, Rao CV. Naproxen inhibits spontaneous lung adenocarcinoma formation in KrasG12V mice. Neoplasia. 2021 Jun;23(6):574-583. doi: 10.1016/j.neo.2021.05.010. Epub 2021 Jun 3. PMID: 34091121; PMCID: PMC8187931.
1: Ash MM, Jolly PS. Cholestatic hepatic injury associated with vismodegib, aspirin, and naproxen use: a case study and review of vismodegib safety. Int J Dermatol. 2015 Mar;54(3):370-4. doi: 10.1111/ijd.12543. Epub 2014 Jul 11. Review. PubMed PMID: 25039741.
2: Leung GJ, Rainsford KD, Kean WF. Osteoarthritis of the hand II: chemistry, pharmacokinetics and pharmacodynamics of naproxen, and clinical outcome studies. J Pharm Pharmacol. 2014 Mar;66(3):347-57. doi: 10.1111/jphp.12165. Epub 2013 Oct 31. Review. PubMed PMID: 24175972.
3: Law S, Derry S, Moore RA. Naproxen with or without an antiemetic for acute migraine headaches in adults. Cochrane Database Syst Rev. 2013 Oct 20;10:CD009455. doi: 10.1002/14651858.CD009455.pub2. Review. PubMed PMID: 24142263.
4: Law S, Derry S, Moore RA. Sumatriptan plus naproxen for acute migraine attacks in adults. Cochrane Database Syst Rev. 2013 Oct 21;10:CD008541. doi: 10.1002/14651858.CD008541.pub2. Review. PubMed PMID: 24142431.
5: Yang LP. Sumatriptan/naproxen sodium: a review of its use in adult patients with migraine. Drugs. 2013 Aug;73(12):1339-55. doi: 10.1007/s40265-013-0099-y. Review. PubMed PMID: 23912627.
6: Ali S, Pimentel JD, Ma C. Naproxen-induced liver injury. Hepatobiliary Pancreat Dis Int. 2011 Oct;10(5):552-6. Review. PubMed PMID: 21947732.
7: Allais G, Castagnoli Gabellari I, Rolando S, Benedetto C. Evaluation of the use of sumatriptan-naproxen sodium for menstrual migraine and dysmenorrhea. Expert Rev Neurother. 2011 Oct;11(10):1383-7. doi: 10.1586/ern.11.123. Review. PubMed PMID: 21955195.
8: Dhillon S. Naproxen/esomeprazole fixed-dose combination: for the treatment of arthritic symptoms and to reduce the risk of gastric ulcers. Drugs Aging. 2011 Mar 1;28(3):237-48. doi: 10.2165/11207150-000000000-00000. Review. PubMed PMID: 21329403.
9: Suthisisang CC, Poolsup N, Suksomboon N, Lertpipopmetha V, Tepwitukgid B. Meta-analysis of the efficacy and safety of naproxen sodium in the acute treatment of migraine. Headache. 2010 May;50(5):808-18. doi: 10.1111/j.1526-4610.2010.01635.x. Epub 2010 Mar 5. Review. PubMed PMID: 20236345.
10: Khoury CK, Couch JR. Sumatriptan-naproxen fixed combination for acute treatment of migraine: a critical appraisal. Drug Des Devel Ther. 2010 Feb 18;4:9-17. Review. PubMed PMID: 20368903; PubMed Central PMCID: PMC2846149.
11: Cleves C, Tepper SJ. Sumatriptan/naproxen sodium combination for the treatment of migraine. Expert Rev Neurother. 2008 Sep;8(9):1289-97. doi: 10.1586/14737175.8.9.1289. Review. PubMed PMID: 18759540.
12: Naproxen sodium/metoclopramide: metoclopramide/naproxen-sodium, MT 100, naproxen-sodium/metoclopramide. Drugs R D. 2006;7(4):259-61. Review. PubMed PMID: 16784251.
13: Curran MP, Wellington K. Delayed-release lansoprazole plus naproxen. Drugs. 2004;64(17):1915-9; discussion 1920-1. Review. PubMed PMID: 15329041.
14: Kovacevic L, Bernstein J, Valentini RP, Imam A, Gupta N, Mattoo TK. Renal papillary necrosis induced by naproxen. Pediatr Nephrol. 2003 Aug;18(8):826-9. Epub 2003 May 28. Review. PubMed PMID: 12774222.
15: Kalksma R, Jansen TL, Bruyn GA. Severe neutropenia due to naproxen therapy in rheumatoid arthritis: a case report and review of literature. Neth J Med. 2002 Aug;60(7):289-91. Review. PubMed PMID: 12430576.
16: Schapira D, Balbir-Gurman A, Nahir AM. Naproxen-induced leukocytoclastic vasculitis. Clin Rheumatol. 2000;19(3):242-4. Review. PubMed PMID: 10870665.
17: Bjarnason I, Thjodleifsson B. Gastrointestinal toxicity of non-steroidal anti-inflammatory drugs: the effect of nimesulide compared with naproxen on the human gastrointestinal tract. Rheumatology (Oxford). 1999 May;38 Suppl 1:24-32. Review. PubMed PMID: 10369403.
18: Sutton LB. Naproxen sodium. J Am Pharm Assoc (Wash). 1996 Nov;NS36(11):663-7. Review. PubMed PMID: 8952254.
19: Lossos IS, Yossepowitch O, Amir G, Orren R. [Leukocytoclastic vasculitis associated with naproxen]. Harefuah. 1996 May 1;130(9):600-1, 655. Review. Hebrew. PubMed PMID: 8794637.
20: Gamst ON. Enteric coated naproxen tablets. Eur J Rheumatol Inflamm. 1992;12(2):5-8. Review. PubMed PMID: 1364940.
