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MedKoo Cat#: 526858 | Name: DDD107498
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Description:

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

DDD107498, also known as DDD 498 and Cabamiquine, is a multiple-stage antimalarial agent that inhibits protein synthesis. DDD107498 demonstrates potential to address a variety of clinical needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening programme against blood-stage malaria parasites; its molecular target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along messenger RNA, and is essential for protein synthesis. This discovery of eEF2 as a viable antimalarial drug target opens up new possibilities for drug discovery.

Chemical Structure

DDD107498
DDD107498
CAS#1469439-69-7

Theoretical Analysis

MedKoo Cat#: 526858

Name: DDD107498

CAS#: 1469439-69-7

Chemical Formula: C27H31FN4O2

Exact Mass: 462.2431

Molecular Weight: 462.57

Elemental Analysis: C, 70.11; H, 6.76; F, 4.11; N, 12.11; O, 6.92

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to Ship
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,350.00 Ready to ship
500mg USD 2,950.00 Ready to ship
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Related CAS #
No Data
Synonym
Cabamiquine; DDD-107498; DDD 107498; DDD 498; DDD-498; DDD498; MMV121; MMV-121; MMV 121; M-5717; M5717; M 5717;
IUPAC/Chemical Name
6-fluoro-2-(4-(morpholinomethyl)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide
InChi Key
BENUHBSJOJMZEE-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H31FN4O2/c28-22-7-8-25-23(17-22)24(27(33)29-9-12-31-10-1-2-11-31)18-26(30-25)21-5-3-20(4-6-21)19-32-13-15-34-16-14-32/h3-8,17-18H,1-2,9-16,19H2,(H,29,33)
SMILES Code
O=C(NCCN1CCCC1)C2=CC(C3=CC=C(CN4CCOCC4)C=C3)=NC5=CC=C(F)C=C52
Appearance
Solid powder
Purity
>99% (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
More Info
Related: CAS# CAS 1469439-69-7 (DDD107498 free base) CAS 1469439-71-1 (DDD107498 SUCCINATE)
Biological target:
DDD107498 (M-5717, DDD-498) is a P. falciparum translation elongation factor 2 inhibitor.
In vitro activity:
Furthermore, DDD107498 was more potent than artesunate in ex vivo assays against a range of clinical isolates of both P. falciparum (median EC50 = 0.81 [Range 0.29-3.29] nM, n=44) and P. vivax (median EC50 = 0.51 [Range 0.25-1.39] nM, n=28), collected from patients with malaria from Southern Papua, Indonesia, a region where high-grade multidrug-resistant malaria is endemic for both species (Extended Data Fig. 2b). In contrast the compound was not toxic to human cells (MRC5 and Hep-G2 cells) at much higher concentrations (> 20,000 fold selectivity, Extended Data Fig. 2c). Reference: Nature. 2015 Jun 18; 522(7556): 315–320. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4700930/
In vivo activity:
DDD107498 was very active in several mouse models of malaria, with comparable or greater efficacy than current antimalarials (Extended Data Table 1b). DDD107498 had an ED90 (90% reduction in parasitaemia) of 0.57 mg/kg after a single oral dose in mice infected with the rodent parasite P. berghei. Efficacy was also tested in NOD-scid IL-2R_null mice engrafted with human erythrocytes and infected with P. falciparum strain 3D70087/N9 (Fig. 2a)9. When dosed orally daily for 4 days, the ED90 on day 7 after infection was 0.95 mg/kg per day. Blood sampling from the infected SCID mice suggested a minimum parasiticidal concentration (MPC) for DDD107498 of 10-13 ng/mL for asexual blood stage infections. Reference: Nature. 2015 Jun 18; 522(7556): 315–320. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4700930/
Solvent mg/mL mM
Solubility
DMSO 93.0 201.05
Water 93.0 201.05
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 462.57 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
Formulation protocol:
1. Baragaña B, Hallyburton I, Lee MC, Norcross NR, Grimaldi R, Otto TD, Proto WR, Blagborough AM, Meister S, Wirjanata G, Ruecker A, Upton LM, Abraham TS, Almeida MJ, Pradhan A, Porzelle A, Luksch T, Martínez MS, Luksch T, Bolscher JM, Woodland A, Norval S, Zuccotto F, Thomas J, Simeons F, Stojanovski L, Osuna-Cabello M, Brock PM, Churcher TS, Sala KA, Zakutansky SE, Jiménez-Díaz MB, Sanz LM, Riley J, Basak R, Campbell M, Avery VM, Sauerwein RW, Dechering KJ, Noviyanti R, Campo B, Frearson JA, Angulo-Barturen I, Ferrer-Bazaga S, Gamo FJ, Wyatt PG, Leroy D, Siegl P, Delves MJ, Kyle DE, Wittlin S, Marfurt J, Price RN, Sinden RE, Winzeler EA, Charman SA, Bebrevska L, Gray DW, Campbell S, Fairlamb AH, Willis PA, Rayner JC, Fidock DA, Read KD, Gilbert IH. A novel multiple-stage antimalarial agent that inhibits protein synthesis. Nature. 2015 Jun 18;522(7556):315-20. doi: 10.1038/nature14451. Erratum in: Nature. 2016 Sep 1;537(7618):122. PMID: 26085270; PMCID: PMC4700930.
In vitro protocol:
1. Baragaña B, Hallyburton I, Lee MC, Norcross NR, Grimaldi R, Otto TD, Proto WR, Blagborough AM, Meister S, Wirjanata G, Ruecker A, Upton LM, Abraham TS, Almeida MJ, Pradhan A, Porzelle A, Luksch T, Martínez MS, Luksch T, Bolscher JM, Woodland A, Norval S, Zuccotto F, Thomas J, Simeons F, Stojanovski L, Osuna-Cabello M, Brock PM, Churcher TS, Sala KA, Zakutansky SE, Jiménez-Díaz MB, Sanz LM, Riley J, Basak R, Campbell M, Avery VM, Sauerwein RW, Dechering KJ, Noviyanti R, Campo B, Frearson JA, Angulo-Barturen I, Ferrer-Bazaga S, Gamo FJ, Wyatt PG, Leroy D, Siegl P, Delves MJ, Kyle DE, Wittlin S, Marfurt J, Price RN, Sinden RE, Winzeler EA, Charman SA, Bebrevska L, Gray DW, Campbell S, Fairlamb AH, Willis PA, Rayner JC, Fidock DA, Read KD, Gilbert IH. A novel multiple-stage antimalarial agent that inhibits protein synthesis. Nature. 2015 Jun 18;522(7556):315-20. doi: 10.1038/nature14451. Erratum in: Nature. 2016 Sep 1;537(7618):122. PMID: 26085270; PMCID: PMC4700930.
In vivo protocol:
1. Baragaña B, Hallyburton I, Lee MC, Norcross NR, Grimaldi R, Otto TD, Proto WR, Blagborough AM, Meister S, Wirjanata G, Ruecker A, Upton LM, Abraham TS, Almeida MJ, Pradhan A, Porzelle A, Luksch T, Martínez MS, Luksch T, Bolscher JM, Woodland A, Norval S, Zuccotto F, Thomas J, Simeons F, Stojanovski L, Osuna-Cabello M, Brock PM, Churcher TS, Sala KA, Zakutansky SE, Jiménez-Díaz MB, Sanz LM, Riley J, Basak R, Campbell M, Avery VM, Sauerwein RW, Dechering KJ, Noviyanti R, Campo B, Frearson JA, Angulo-Barturen I, Ferrer-Bazaga S, Gamo FJ, Wyatt PG, Leroy D, Siegl P, Delves MJ, Kyle DE, Wittlin S, Marfurt J, Price RN, Sinden RE, Winzeler EA, Charman SA, Bebrevska L, Gray DW, Campbell S, Fairlamb AH, Willis PA, Rayner JC, Fidock DA, Read KD, Gilbert IH. A novel multiple-stage antimalarial agent that inhibits protein synthesis. Nature. 2015 Jun 18;522(7556):315-20. doi: 10.1038/nature14451. Erratum in: Nature. 2016 Sep 1;537(7618):122. PMID: 26085270; PMCID: PMC4700930.
1: Baragaña B, Hallyburton I, Lee MC, Norcross NR, Grimaldi R, Otto TD, Proto WR, Blagborough AM, Meister S, Wirjanata G, Ruecker A, Upton LM, Abraham TS, Almeida MJ, Pradhan A, Porzelle A, Martínez MS, Bolscher JM, Woodland A, Norval S, Zuccotto F, Thomas J, Simeons F, Stojanovski L, Osuna-Cabello M, Brock PM, Churcher TS, Sala KA, Zakutansky SE, Jiménez-Díaz MB, Sanz LM, Riley J, Basak R, Campbell M, Avery VM, Sauerwein RW, Dechering KJ, Noviyanti R, Campo B, Frearson JA, Angulo-Barturen I, Ferrer-Bazaga S, Gamo FJ, Wyatt PG, Leroy D, Siegl P, Delves MJ, Kyle DE, Wittlin S, Marfurt J, Price RN, Sinden RE, Winzeler EA, Charman SA, Bebrevska L, Gray DW, Campbell S, Fairlamb AH, Willis PA, Rayner JC, Fidock DA, Read KD, Gilbert IH. A novel multiple-stage antimalarial agent that inhibits protein synthesis. Nature. 2015 Jun 18;522(7556):315-20. doi: 10.1038/nature14451. PubMed PMID: 26085270; PubMed Central PMCID: PMC4700930.

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