Apricoxib

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200273

CAS#: 197904-84-0

Description: Apricoxib, also known as Benzenesulfonamide 42(4ethoxyphenyl)4methyl1Hpyrrol1yl, is an orally bioavailable nonsteroidal anti-inflammatory agent (NSAID) with potential antiangiogenic and antineoplastic activities. Apricoxib binds to and inhibits the enzyme cyclooxygenase-2 (COX-2), thereby inhibiting the conversion of arachidonic acid into prostaglandins. Apricoxib-mediated inhibition of COX-2 may induce tumor cell apoptosis and inhibit tumor cell proliferation and tumor angiogenesis. COX-related metabolic pathways may represent crucial regulators of cellular proliferation and angiogenesis.


Chemical Structure

img
Apricoxib
CAS# 197904-84-0

Theoretical Analysis

MedKoo Cat#: 200273
Name: Apricoxib
CAS#: 197904-84-0
Chemical Formula: C19H20N2O3S
Exact Mass: 356.11946
Molecular Weight: 356.44
Elemental Analysis: C, 64.02; H, 5.66; N, 7.86; O, 13.47; S, 9.00

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: CS701; CS-701; CS 701 CS-706; CS706; CS 706; TG01; TG-01; TG01; R109339; R-109339; R 109339;TP-1001; TP-2001 Benzenesulfonamide 42(4ethoxyphenyl)4methyl1Hpyrrol1yl; Capoxigem

IUPAC/Chemical Name: 4-[2-(4-ethoxyphenyl)-4-methylpyrrol-1-yl]benzenesulfonamide

InChi Key: JTMITOKKUMVWRT-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20N2O3S/c1-3-24-17-8-4-15(5-9-17)19-12-14(2)13-21(19)16-6-10-18(11-7-16)25(20,22)23/h4-13H,3H2,1-2H3,(H2,20,22,23)

SMILES Code: O=S(C1=CC=C(N2C(C3=CC=C(OCC)C=C3)=CC(C)=C2)C=C1)(N)=O

Appearance: Solid powder

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 356.44 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.

Recalculate based on batch purity %
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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: St John MA, Wang G, Luo J, Dohadwala M, Hu D, Lin Y, Dennis M, Lee JM, Elashoff D, Lawhon T, Zaknoen SL, Burrows FJ, Dubinett SM. Apricoxib upregulates 15-PGDH and PGT in tobacco-related epithelial malignancies. Br J Cancer. 2012 Aug 7;107(4):707-12. doi: 10.1038/bjc.2012.203. Epub 2012 Jul 24. PMID: 22828609; PMCID: PMC3419945.

2: Kirane A, Toombs JE, Ostapoff K, Carbon JG, Zaknoen S, Braunfeld J, Schwarz RE, Burrows FJ, Brekken RA. Apricoxib, a novel inhibitor of COX-2, markedly improves standard therapy response in molecularly defined models of pancreatic cancer. Clin Cancer Res. 2012 Sep 15;18(18):5031-42. doi: 10.1158/1078-0432.CCR-12-0453. Epub 2012 Jul 24. PMID: 22829202; PMCID: PMC3777527.

3: Kirane A, Toombs JE, Larsen JE, Ostapoff KT, Meshaw KR, Zaknoen S, Brekken RA, Burrows FJ. Epithelial-mesenchymal transition increases tumor sensitivity to COX-2 inhibition by apricoxib. Carcinogenesis. 2012 Sep;33(9):1639-46. doi: 10.1093/carcin/bgs195. Epub 2012 Jun 7. PMID: 22678114; PMCID: PMC3514897.

4: Lee MH, Kachroo P, Pagano PC, Yanagawa J, Wang G, Walser TC, Krysan K, Sharma S, John MS, Dubinett SM, Lee JM. Combination Treatment with Apricoxib and IL-27 Enhances Inhibition of Epithelial-Mesenchymal Transition in Human Lung Cancer Cells through a STAT1 Dominant Pathway. J Cancer Sci Ther. 2014 Nov;6(11):468-477. doi: 10.4172/1948-5956.1000310. Epub 2014 Nov 15. PMID: 26523208; PMCID: PMC4624255.

5: Rao PN, Grover RK. Apricoxib, a COX-2 inhibitor for the potential treatment of pain and cancer. IDrugs. 2009 Nov;12(11):711-22. PMID: 19844858.

6: Mandal PK, Freiter EM, Bagsby AL, Robertson FM, McMurray JS. Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of inhibition of prostaglandin E2 production in inflammatory breast cancer cells. Bioorg Med Chem Lett. 2011 Oct 15;21(20):6071-3. doi: 10.1016/j.bmcl.2011.08.050. Epub 2011 Aug 19. PMID: 21903394; PMCID: PMC3310163.

7: Edelman MJ, Tan MT, Fidler MJ, Sanborn RE, Otterson G, Sequist LV, Evans TL, Schneider BJ, Keresztes R, Rogers JS, de Mayolo JA, Feliciano J, Yang Y, Medeiros M, Zaknoen SL. Randomized, double-blind, placebo-controlled, multicenter phase II study of the efficacy and safety of apricoxib in combination with either docetaxel or pemetrexed in patients with biomarker- selected non-small-cell lung cancer. J Clin Oncol. 2015 Jan 10;33(2):189-94. doi: 10.1200/JCO.2014.55.5789. Epub 2014 Dec 1. PMID: 25452446; PMCID: PMC4890680.

8: Ham M, Kaunitz JD. Gastroduodenal defense. Curr Opin Gastroenterol. 2007 Nov;23(6):607-16. doi: 10.1097/MOG.0b013e3282f02607. PMID: 17906436.

9: Reckamp K, Gitlitz B, Chen LC, Patel R, Milne G, Syto M, Jezior D, Zaknoen S. Biomarker-based phase I dose-escalation, pharmacokinetic, and pharmacodynamic study of oral apricoxib in combination with erlotinib in advanced nonsmall cell lung cancer. Cancer. 2011 Feb 15;117(4):809-18. doi: 10.1002/cncr.25473. Epub 2010 Oct 4. PMID: 20922800.

10: Gitlitz BJ, Bernstein E, Santos ES, Otterson GA, Milne G, Syto M, Burrows F, Zaknoen S. A randomized, placebo-controlled, multicenter, biomarker-selected, phase 2 study of apricoxib in combination with erlotinib in patients with advanced non-small-cell lung cancer. J Thorac Oncol. 2014 Apr;9(4):577-82. doi: 10.1097/JTO.0000000000000082. PMID: 24736085; PMCID: PMC4271824.

11: Carta F, Scozzafava A, Supuran CT. Sulfonamides: a patent review (2008 - 2012). Expert Opin Ther Pat. 2012 Jul;22(7):747-58. doi: 10.1517/13543776.2012.698264. Epub 2012 Jun 15. PMID: 22697257.

12: Dai P, Li J, Ma XP, Huang J, Meng JJ, Gong P. Efficacy and safety of COX-2 inhibitors for advanced non-small-cell lung cancer with chemotherapy: a meta- analysis. Onco Targets Ther. 2018 Feb 5;11:721-730. doi: 10.2147/OTT.S148670. PMID: 29440919; PMCID: PMC5804138.

13: Tokh M, Bathini V, Saif MW. First-line treatment of metastatic pancreatic cancer. JOP. 2012 Mar 10;13(2):159-62. PMID: 22406590.

14: Liu R, Xu KP, Tan GS. Cyclooxygenase-2 inhibitors in lung cancer treatment: Bench to bed. Eur J Pharmacol. 2015 Dec 15;769:127-33. doi: 10.1016/j.ejphar.2015.11.007. Epub 2015 Nov 5. PMID: 26548623.

15: Samore WR, Gondi CS. Brief overview of selected approaches in targeting pancreatic adenocarcinoma. Expert Opin Investig Drugs. 2014 Jun;23(6):793-807. doi: 10.1517/13543784.2014.902933. Epub 2014 Mar 27. PMID: 24673265.

16: Strimpakos AS, Syrigos KN, Saif MW. Translational research in pancreatic cancer. Highlights from the "2011 ASCO Gastrointestinal Cancers Symposium". San Francisco, CA, USA. January 20-22, 2011. JOP. 2011 Mar 9;12(2):120-2. PMID: 21386635.

17: Mathavan S, Kue CS, Kumar S. Identification of potential candidate genes for lip and oral cavity cancer using network analysis. Genomics Inform. 2021 Mar;19(1):e4. doi: 10.5808/gi.20062. Epub 2021 Mar 15. PMID: 33840168; PMCID: PMC8042300.

18: Rohatagi S, Kastrissios H, Gao Y, Zhang N, Xu J, Moberly J, Wada R, Yoshihara K, Takahashi M, Truitt K, Salazar D. Predictive population pharmacokinetic/pharmacodynamic model for a novel COX-2 inhibitor. J Clin Pharmacol. 2007 Mar;47(3):358-70. doi: 10.1177/0091270006296152. PMID: 17322148.

19: Kastrissios H, Rohatagi S, Moberly J, Truitt K, Gao Y, Wada R, Takahashi M, Kawabata K, Salazar D. Development of a predictive pharmacokinetic model for a novel cyclooxygenase-2 inhibitor. J Clin Pharmacol. 2006 May;46(5):537-48. doi: 10.1177/0091270006287122. PMID: 16638737.

20: Rohatagi S, Kastrissios H, Sasahara K, Truitt K, Moberly JB, Wada R, Salazar DE. Pain relief model for a COX-2 inhibitor in patients with postoperative dental pain. Br J Clin Pharmacol. 2008 Jul;66(1):60-70. doi: 10.1111/j.1365-2125.2008.03175.x. Epub 2008 Jun 3. PMID: 18522627; PMCID: PMC2485259.



Additional Information