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MedKoo Cat#: 206983 | Name: Teglarinad chloride

Description:

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

Teglarinad chloride, also known as GMX-1777 and EB1627, is a potent NAMPT inhibitor. GMX1777 is a water-soluble prodrug of the cyanoguanidine compound GMX1778 with potential antineoplastic activity. In vivo, apoptosis inducer GMX1777 is rapidly converted into GMX1778 through hydrolytic cleavage of a carbonate ester bond. Although the exact mechanism of action has yet to be fully elucidated, GMX1778 appears to antagonize nuclear factor-kappa B (NF-kB) transcription, resulting in the induction of tumor cell apoptosis.

Chemical Structure

Teglarinad chloride
Teglarinad chloride
CAS#432037-57-5 (chloride)

Theoretical Analysis

MedKoo Cat#: 206983

Name: Teglarinad chloride

CAS#: 432037-57-5 (chloride)

Chemical Formula: C30H43Cl2N5O8

Exact Mass:

Molecular Weight: 672.60

Elemental Analysis: C, 53.57; H, 6.44; Cl, 10.54; N, 10.41; O, 19.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
766501-75-1 (cation) 432037-57-5 (chloride)
Synonym
GMX-1777 chloride; GMX 1777; GMX1777; Teglarinad chloride; EB1627; EB-1627; EB 1627;
IUPAC/Chemical Name
[4-[[N'-[6-(4-chlorophenoxy)hexyl]-N-cyanocarbamimidoyl]amino]pyridin-1-ium-1-yl]methyl 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl carbonate chloride
InChi Key
DAHMXVAETAAQOZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H42ClN5O8.ClH/c1-38-16-17-39-18-19-40-20-21-41-22-23-43-30(37)44-25-36-13-10-27(11-14-36)35-29(34-24-32)33-12-4-2-3-5-15-42-28-8-6-26(31)7-9-28;/h6-11,13-14H,2-5,12,15-23,25H2,1H3,(H,33,34);1H
SMILES Code
O=C(OC[N+]1=CC=C(N/C(NC#N)=N\CCCCCCOC2=CC=C(C=C2)Cl)C=C1)OCCOCCOCCOCCOC.[Cl-]
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 672.60 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
1: Preyat N, Leo O. Complex role of nicotinamide adenine dinucleotide in the regulation of programmed cell death pathways. Biochem Pharmacol. 2016 Feb 1;101:13-26. doi: 10.1016/j.bcp.2015.08.110. Epub 2015 Sep 3. PubMed PMID: 26343585. 2: Chan M, Gravel M, Bramoullé A, Bridon G, Avizonis D, Shore GC, Roulston A. Synergy between the NAMPT inhibitor GMX1777(8) and pemetrexed in non-small cell lung cancer cells is mediated by PARP activation and enhanced NAD consumption. Cancer Res. 2014 Nov 1;74(21):5948-54. doi: 10.1158/0008-5472.CAN-14-0809. Epub 2014 Aug 21. PubMed PMID: 25145669. 3: Olesen UH, Petersen JG, Garten A, Kiess W, Yoshino J, Imai S, Christensen MK, Fristrup P, Thougaard AV, Björkling F, Jensen PB, Nielsen SJ, Sehested M. Target enzyme mutations are the molecular basis for resistance towards pharmacological inhibition of nicotinamide phosphoribosyltransferase. BMC Cancer. 2010 Dec 12;10:677. doi: 10.1186/1471-2407-10-677. PubMed PMID: 21144000; PubMed Central PMCID: PMC3019212. 4: Bi TQ, Che XM. Nampt/PBEF/visfatin and cancer. Cancer Biol Ther. 2010 Jul 15;10(2):119-25. doi: 10.4161/cbt.10.2.12581. Epub 2010 Jul 3. Review. PubMed PMID: 20647743. 5: Fuchs D, Rodriguez A, Eriksson S, Christofferson R, Sundberg C, Azarbayjani F. Metronomic administration of the drug GMX1777, a cellular NAD synthesis inhibitor, results in neuroblastoma regression and vessel maturation without inducing drug resistance. Int J Cancer. 2010 Jun 15;126(12):2773-89. doi: 10.1002/ijc.25206. PubMed PMID: 20112275. 6: Kato H, Ito E, Shi W, Alajez NM, Yue S, Lee C, Chan N, Bhogal N, Coackley CL, Vines D, Green D, Waldron J, Gullane P, Bristow R, Liu FF. Efficacy of combining GMX1777 with radiation therapy for human head and neck carcinoma. Clin Cancer Res. 2010 Feb 1;16(3):898-911. doi: 10.1158/1078-0432.CCR-09-1945. Epub 2010 Jan 26. PubMed PMID: 20103674. 7: Watson M, Roulston A, Bélec L, Billot X, Marcellus R, Bédard D, Bernier C, Branchaud S, Chan H, Dairi K, Gilbert K, Goulet D, Gratton MO, Isakau H, Jang A, Khadir A, Koch E, Lavoie M, Lawless M, Nguyen M, Paquette D, Turcotte E, Berger A, Mitchell M, Shore GC, Beauparlant P. The small molecule GMX1778 is a potent inhibitor of NAD+ biosynthesis: strategy for enhanced therapy in nicotinic acid phosphoribosyltransferase 1-deficient tumors. Mol Cell Biol. 2009 Nov;29(21):5872-88. doi: 10.1128/MCB.00112-09. Epub 2009 Aug 24. PubMed PMID: 19703994; PubMed Central PMCID: PMC2772749. 8: Beauparlant P, Bédard D, Bernier C, Chan H, Gilbert K, Goulet D, Gratton MO, Lavoie M, Roulston A, Turcotte E, Watson M. Preclinical development of the nicotinamide phosphoribosyl transferase inhibitor prodrug GMX1777. Anticancer Drugs. 2009 Jun;20(5):346-54. doi: 10.1097/CAD.0b013e3283287c20. PubMed PMID: 19369827.