Carboxyamidotriazole orotate

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

MedKoo CAT#: 204830

CAS#: 187739-60-2

Description: Carboxyamidotriazole orotate (CTO) is t he orotate salt form of carboxyamidotriazole (CAI), an orally bioavailable small molecule with potential antiangiogenic and antiproliferative activities. Carboxyamidotriazole binds to and inhibits non-voltage-operated calcium channels, blocking both Ca2+ influx into cells and Ca2+ release from intracellular stores, resulting in the disruption of calcium channel-mediated signal transduction. CAI inhibits PI3 activity and vascular endothelial growth factor (VEGF) signaling. This may inhibit endothelial proliferation, tumor cell growth, invasion and metastasis.


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Carboxyamidotriazole orotate, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 204830
Name: Carboxyamidotriazole orotate
CAS#: 187739-60-2
Chemical Formula: C23H16Cl3IN7O6
Exact Mass:
Molecular Weight: 719.68
Elemental Analysis: C, 38.38; H, 2.24; Cl, 14.78; I, 17.63; N, 13.62; O, 13.34


Synonym: Carboxyamidotriazole orotate CTO.

IUPAC/Chemical Name: 4-carbamoyl-1-(3,5-dichloro-4-(4-chlorobenzoyl)benzyl)-1H-1,2,3-triazol-5-aminium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate (1:1)

InChi Key: MNWOBDDXRRBONM-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H12Cl3N5O2.C5H4N2O4/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;8-3-1-2(4(9)10)6-5(11)7-3/h1-6H,7,21H2,(H2,22,27);1H,(H,9,10)(H2,6,7,8,11)

SMILES Code: [NH3+]C1=C(C(N)=O)N=NN1CC2=CC(Cl)=C(C(C3=CC=C(Cl)C=C3)=O)C(Cl)=C2.O=C(C(NC4=O)=CC(N4)=O)[O-]


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
187739-60-2 (Carboxyamidotriazole orotate)
99519-84-3 (Carboxyamidotriazole)


References

1: 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. 2011 Jul 16. [Epub ahead of print] PubMed PMID: 21767946.

2: 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. Epub 2010 Oct 30. PubMed PMID: 21041018.

3: 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. Epub 2009 Aug 11. PubMed PMID: 19679174.

4: 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.

5: 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. PubMed PMID: 18464258.

6: Guo L, Ye C, Chen W, Ye H, Zheng R, Li J, Yang H, Yu X, Zhang D. Anti-inflammatory and analgesic potency of carboxyamidotriazole, a tumorostatic agent. J Pharmacol Exp Ther. 2008 Apr;325(1):10-6. Epub 2008 Jan 8. PubMed PMID: 18182559.

7: Alessandro R, Fontana S, Giordano M, Corrado C, Colomba P, Flugy AM, Santoro A, Kohn EC, De Leo G. Effects of carboxyamidotriazole on in vitro models of imatinib-resistant chronic myeloid leukemia. J Cell Physiol. 2008 Apr;215(1):111-21. PubMed PMID: 17924401.

8: Mignen O, Brink C, Enfissi A, Nadkarni A, Shuttleworth TJ, Giovannucci DR, Capiod T. Carboxyamidotriazole-induced inhibition of mitochondrial calcium import blocks capacitative calcium entry and cell proliferation in HEK-293 cells. J Cell Sci. 2005 Dec 1;118(Pt 23):5615-23. PubMed PMID: 16306224.

9: Dutcher JP, Leon L, Manola J, Friedland DM, Roth B, Wilding G; Eastern Cooperative Oncology Group. Phase II study of carboxyamidotriazole in patients with advanced renal cell carcinoma refractory to immunotherapy: E4896, an Eastern Cooperative Oncology Group Study. Cancer. 2005 Dec 1;104(11):2392-9. PubMed PMID: 16222691.

10: Enfissi A, Prigent S, Colosetti P, Capiod T. The blocking of capacitative calcium entry by 2-aminoethyl diphenylborate (2-APB) and carboxyamidotriazole (CAI) inhibits proliferation in Hep G2 and Huh-7 human hepatoma cells. Cell Calcium. 2004 Dec;36(6):459-67. PubMed PMID: 15488595.