Carboxyamidotriazole
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MedKoo CAT#: 206732

CAS#: 99519-84-3

Description: Carboxyamidotriazole, also known as CAI; RFE-007; NSC-609974; and L-651582, is a novel inhibitor of both cAMP-phosphodiesterases and GMP-phosphodiesterases. Carboxyamidotriazole inhibits oxidative phosphorylation in cancer cells and exerts synergistic anti-cancer effect with glycolysis inhibition. Carboxyamidotriazole ameliorates experimental colitis by inhibition of cytokine production, nuclear factor-κB activation, and colonic fibrosis.


Chemical Structure

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Carboxyamidotriazole
CAS# 99519-84-3

Theoretical Analysis

MedKoo Cat#: 206732
Name: Carboxyamidotriazole
CAS#: 99519-84-3
Chemical Formula: C17H12Cl3N5O2
Exact Mass: 423.0057
Molecular Weight: 424.67
Elemental Analysis: C, 48.08; H, 2.85; Cl, 25.04; N, 16.49; O, 7.53

Price and Availability

Size Price Availability Quantity
5.0mg USD 285.0 2 Weeks
10.0mg USD 450.0 2 Weeks
25.0mg USD 850.0 2 Weeks
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Synonym: CAI; RFE-007; NSC-609974; L-651582; RFE007; NSC609974; L651582; RFE 007; NSC 609974; L 651582; Carboxyamidotriazole

IUPAC/Chemical Name: 5-amino-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazole-4-carboxamide

InChi Key: WNRZHQBJSXRYJK-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H12Cl3N5O2/c18-10-3-1-9(2-4-10)15(26)13-11(19)5-8(6-12(13)20)7-25-16(21)14(17(22)27)23-24-25/h1-6H,7,21H2,(H2,22,27)

SMILES Code: O=C(C1=C(N)N(CC2=CC(Cl)=C(C(C3=CC=C(Cl)C=C3)=O)C(Cl)=C2)N=N1)N

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 424.67 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

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1: Toman O, Kabickova T, Vit O, Fiser R, Polakova KM, Zach J, Linhartova J, Vyoral D, Petrak J. Proteomic analysis of imatinib-resistant CML-T1 cells reveals calcium homeostasis as a potential therapeutic target. Oncol Rep. 2016 Sep;36(3):1258-68. doi: 10.3892/or.2016.4945. Epub 2016 Jul 18. PubMed PMID: 27430982; PubMed Central PMCID: PMC4968618.

2: Zhu L, Li J, Guo L, Yu XL, Wu DW, Chen W, Chen C, Du XW, Zhang DC, Ye CY. Therapeutic Effect of Carboxyamidotriazole on Adjuvant Arthritis in Rats. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2016 Feb;38(1):49-54. doi: 10.3881/j.issn.1000-503X.2016.01.009. PubMed PMID: 26956856.

3: Ju R, Guo L, Li J, Zhu L, Yu X, Chen C, Chen W, Ye C, Zhang D. Carboxyamidotriazole inhibits oxidative phosphorylation in cancer cells and exerts synergistic anti-cancer effect with glycolysis inhibition. Cancer Lett. 2016 Jan 28;370(2):232-41. doi: 10.1016/j.canlet.2015.10.025. Epub 2015 Oct 29. PubMed PMID: 26522259.

4: Beedie SL, Peer CJ, Pisle S, Gardner ER, Mahony C, Barnett S, Ambrozak A, Gütschow M, Chau CH, Vargesson N, Figg WD. Anticancer Properties of a Novel Class of Tetrafluorinated Thalidomide Analogues. Mol Cancer Ther. 2015 Oct;14(10):2228-37. doi: 10.1158/1535-7163.MCT-15-0320. Epub 2015 Aug 12. PubMed PMID: 26269604; PubMed Central PMCID: PMC4596783.

5: Zhu L, Li J, Guo L, Yu X, Wu D, Luo L, Zhu L, Chen W, Chen C, Ye C, Zhang D. Activation of NALP1 inflammasomes in rats with adjuvant arthritis; a novel therapeutic target of carboxyamidotriazole in a model of rheumatoid arthritis. Br J Pharmacol. 2015 Jul;172(13):3446-59. doi: 10.1111/bph.13138. Epub 2015 May 5. PubMed PMID: 25799914; PubMed Central PMCID: PMC4500378.

6: Guo L, Luo L, Ju R, Chen C, Zhu L, Li J, Yu X, Ye C, Zhang D. Carboxyamidotriazole: a novel inhibitor of both cAMP-phosphodiesterases and cGMP-phosphodiesterases. Eur J Pharmacol. 2015 Jan 5;746:14-21. doi: 10.1016/j.ejphar.2014.10.018. Epub 2014 Nov 11. PubMed PMID: 25446933.

7: Dragoni S, Turin I, Laforenza U, Potenza DM, Bottino C, Glasnov TN, Prestia M, Ferulli F, Saitta A, Mosca A, Guerra G, Rosti V, Luinetti O, Ganini C, Porta C, Pedrazzoli P, Tanzi F, Montagna D, Moccia F. Store-operated Ca2+ entry does not control proliferation in primary cultures of human metastatic renal cellular carcinoma. Biomed Res Int. 2014;2014:739494. doi: 10.1155/2014/739494. Epub 2014 Jul 9. PubMed PMID: 25126575; PubMed Central PMCID: PMC4119920.

8: Lodola F, Laforenza U, Bonetti E, Lim D, Dragoni S, Bottino C, Ong HL, Guerra G, Ganini C, Massa M, Manzoni M, Ambudkar IS, Genazzani AA, Rosti V, Pedrazzoli P, Tanzi F, Moccia F, Porta C. Store-operated Ca2+ entry is remodelled and controls in vitro angiogenesis in endothelial progenitor cells isolated from tumoral patients. PLoS One. 2012;7(9):e42541. doi: 10.1371/journal.pone.0042541. Epub 2012 Sep 25. PubMed PMID: 23049731; PubMed Central PMCID: PMC3458053.

9: Corrado C, Flugy AM, Taverna S, Raimondo S, Guggino G, Karmali R, De Leo G, Alessandro R. Carboxyamidotriazole-orotate inhibits the growth of imatinib-resistant chronic myeloid leukaemia cells and modulates exosomes-stimulated angiogenesis. PLoS One. 2012;7(8):e42310. doi: 10.1371/journal.pone.0042310. Epub 2012 Aug 3. PubMed PMID: 22879938; PubMed Central PMCID: PMC3411738.

10: Guo L, Ye C, Hao X, Zheng R, Ju R, Wu D, Luo L, Wang C, Li J, Yu X, Zhu L, Zhang D. Carboxyamidotriazole ameliorates experimental colitis by inhibition of cytokine production, nuclear factor-κB activation, and colonic fibrosis. J Pharmacol Exp Ther. 2012 Aug;342(2):356-65. doi: 10.1124/jpet.112.192849. Epub 2012 May 2. PubMed PMID: 22553216.

11: Ju R, Wu D, Guo L, Li J, Ye C, Zhang D. Inhibition of pro-inflammatory cytokines in tumour associated macrophages is a potential anti-cancer mechanism of carboxyamidotriazole. Eur J Cancer. 2012 May;48(7):1085-95. doi: 10.1016/j.ejca.2011.06.050. Epub 2011 Jul 20. PubMed PMID: 21767946.

12: Corrado C, Raimondo S, Flugy AM, Fontana S, Santoro A, Stassi G, Marfia A, Iovino F, Arlinghaus R, Kohn EC, Leo GD, Alessandro R. Carboxyamidotriazole inhibits cell growth of imatinib-resistant chronic myeloid leukaemia cells including T315I Bcr-Abl mutant by a redox-mediated mechanism. Cancer Lett. 2011 Jan 28;300(2):205-14. doi: 10.1016/j.canlet.2010.10.007. Epub 2010 Oct 30. PubMed PMID: 21041018.

13: Fiorio Pla A, Genova T, Pupo E, Tomatis C, Genazzani A, Zaninetti R, Munaron L. Multiple roles of protein kinase a in arachidonic acid-mediated Ca2+ entry and tumor-derived human endothelial cell migration. Mol Cancer Res. 2010 Nov;8(11):1466-76. doi: 10.1158/1541-7786.MCR-10-0002. Epub 2010 Sep 24. PubMed PMID: 20870737.

14: Hillman SL, Mandrekar SJ, Bot B, DeMatteo RP, Perez EA, Ballman KV, Nelson H, Buckner JC, Sargent DJ. Evaluation of the value of attribution in the interpretation of adverse event data: a North Central Cancer Treatment Group and American College of Surgeons Oncology Group investigation. J Clin Oncol. 2010 Jun 20;28(18):3002-7. doi: 10.1200/JCO.2009.27.4282. Epub 2010 May 17. PubMed PMID: 20479400; PubMed Central PMCID: PMC2903334.

15: Azad N, Perroy A, Gardner E, Imamura CK, Graves C, Sarosy GA, Minasian L, Kotz H, Raggio M, Figg WD, Kohn EC. A phase I study of paclitaxel and continuous daily CAI in patients with refractory solid tumors. Cancer Biol Ther. 2009 Oct;8(19):1800-5. Epub . PubMed PMID: 19738417; PubMed Central PMCID: PMC3104675.

16: Afzal A, Caballero S, Palii SS, Jurczyk S, Pardue M, Geroski D, Edelhauser H, Hochhaus G, Kim M, Franklin A, Shapiro G, Grant MB. Targeting retinal and choroid neovascularization using the small molecule inhibitor carboxyamidotriazole. Brain Res Bull. 2010 Feb 15;81(2-3):320-6. doi: 10.1016/j.brainresbull.2009.08.001. Epub 2009 Aug 11. PubMed PMID: 19679174; PubMed Central PMCID: PMC3635673.

17: Guo L, Li J, Ye H, Zheng R, Hao XJ, Chen WY, Jü R, Yao YR, Yang HF, Yu XL, Ye CY, Zhang DC. [Anti-inflammatory and analgesic potency of carboxyamidotriazole, a tumoristatic agent]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2009 Jun;31(3):315-21. Chinese. PubMed PMID: 19621516.

18: Tomillero A, Moral MA. Gateways to clinical trials. July-August 2008. Methods Find Exp Clin Pharmacol. 2008 Jul-Aug;30(6):459-95. PubMed PMID: 18850047.

19: Yang JL, Qu XJ, Yu Y, Kohn EC, Friedlander ML. Selective sensitivity to carboxyamidotriazole by human tumor cell lines with DNA mismatch repair deficiency. Int J Cancer. 2008 Jul 15;123(2):258-63. doi: 10.1002/ijc.23535. PubMed PMID: 18464258.

20: Fiorio Pla A, Grange C, Antoniotti S, Tomatis C, Merlino A, Bussolati B, Munaron L. Arachidonic acid-induced Ca2+ entry is involved in early steps of tumor angiogenesis. Mol Cancer Res. 2008 Apr;6(4):535-45. doi: 10.1158/1541-7786.MCR-07-0271. PubMed PMID: 18403634.



Additional Information

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