Tebuquine

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MedKoo CAT#: 526427

CAS#: 74129-03-6

Description: Tebuquine, also known CI-897 and WR-228258, is an antimalarial agent. WR-225,448 is active against P. falciparum in vitro. WR 228,258 in vitro shows a chloroquine-like effect, but not in vivo, suggesting that its mode of action in vivo is different from that of chloroquine. WR 225,448 has no action in the CIPC in vitro and affects primarily mitochondria of the parasites in vivo. It probably acts through a metabolite. Both pre-erythrocytic and erythrocytic stages of rodent malaria parasites are affected by WR 225,448.

Chemical Structure

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Tebuquine
CAS# 74129-03-6
Instruction

Theoretical Analysis

MedKoo Cat#: 526427
Name: Tebuquine
CAS#: 74129-03-6
Chemical Formula: C26H25Cl2N3O
Exact Mass: 465.14
Molecular Weight: 466.406
Elemental Analysis: C, 66.96; H, 5.40; Cl, 15.20; N, 9.01; O, 3.43

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.

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Synonym: Tebuquine; CI-897; CI897; CI 897; WR-228,258; WR 228,258; WR228,258; WR-228258; WR 228258; WR228258.

IUPAC/Chemical Name: (1,1'-Biphenyl)-2-ol, 4'-chloro-5-((7-chloro-4-quinolinyl)amino)-3-(((1,1-dimethylethyl)amino)methyl)-

InChi Key: BCHMRNALCJISMZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H25Cl2N3O/c1-26(2,3)30-15-17-12-20(14-22(25(17)32)16-4-6-18(27)7-5-16)31-23-10-11-29-24-13-19(28)8-9-21(23)24/h4-14,30,32H,15H2,1-3H3,(H,29,31)

SMILES Code: OC1=C(CNC(C)(C)C)C=C(NC2=CC=NC3=CC(Cl)=CC=C23)C=C1C4=CC=C(Cl)C=C4

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 466.41 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:
In vitro protocol:
In vivo protocol:

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1: Romero AH, Acosta ME, Gamboa N, Charris JE, Salazar J, López SE. Synthesis, β-hematin inhibition studies and antimalarial evaluation of dehydroxy isotebuquine derivatives against Plasmodium berghei. Bioorg Med Chem. 2015 Aug 1;23(15):4755-62. doi: 10.1016/j.bmc.2015.05.040. PubMed PMID: 26081761.

2: Casagrande M, Basilico N, Parapini S, Romeo S, Taramelli D, Sparatore A. Novel amodiaquine congeners as potent antimalarial agents. Bioorg Med Chem. 2008 Jul 15;16(14):6813-23. doi: 10.1016/j.bmc.2008.05.068. PubMed PMID: 18562202.

3: Sharma P, Chhabra S, Rai N, Ghoshal N. Exploration of rate-limiting conformational state for 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N(omega)-oxides (tebuquine analogues) for antimalarial activity using molecular shape analysis and molecular field analysis studies. J Chem Inf Model. 2007 May-Jun;47(3):1087-96. PubMed PMID: 17425301.

4: Miroshnikova OV, Hudson TH, Gerena L, Kyle DE, Lin AJ. Synthesis and antimalarial activity of new isotebuquine analogues. J Med Chem. 2007 Feb 22;50(4):889-96. PubMed PMID: 17266295.

5: Naisbitt DJ, Williams DP, O'Neill PM, Maggs JL, Willock DJ, Pirmohamed M, Park BK. Metabolism-dependent neutrophil cytotoxicity of amodiaquine: A comparison with pyronaridine and related antimalarial drugs. Chem Res Toxicol. 1998 Dec;11(12):1586-95. PubMed PMID: 9860505.

6: Ruscoe JE, Tingle MD, O'Neill PM, Ward SA, Park BK. Effect of disposition of mannich antimalarial agents on their pharmacology and toxicology. Antimicrob Agents Chemother. 1998 Sep;42(9):2410-6. PubMed PMID: 9736572; PubMed Central PMCID: PMC105842.

7: O'Neill PM, Willock DJ, Hawley SR, Bray PG, Storr RC, Ward SA, Park BK. Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues. J Med Chem. 1997 Feb 14;40(4):437-48. PubMed PMID: 9046333.

8: Peters W, Robinson BL. The chemotherapy of rodent malaria. XLVII. Studies on pyronaridine and other Mannich base antimalarials. Ann Trop Med Parasitol. 1992 Oct;86(5):455-65. PubMed PMID: 1288426.

9: Werbel LM, Cook PD, Elslager EF, Hung JH, Johnson JL, Kesten SJ, McNamara DJ, Ortwine DF, Worth DF. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides. J Med Chem. 1986 Jun;29(6):924-39. PubMed PMID: 3712383.

10: Peters W, Robinson BL. The chemotherapy of rodent malaria, XXXVII. The in vivo action of two Mannich bases, WR 194,965 and WR 228,258 and an 8-aminoquinoline WR 225,448. Ann Trop Med Parasitol. 1984 Dec;78(6):561-5. PubMed PMID: 6532327.

11: Peters W, Irare SG, Ellis DS, Warhurst DC, Robinson BL. The chemotherapy of rodent malaria, XXXVIII. Studies on the activity of three new antimalarials (WR 194,965, WR 228,258 and WR 225,448) against rodent and human malaria parasites (Plasmodium berghei and P. falciparum). Ann Trop Med Parasitol. 1984 Dec;78(6):567-79. PubMed PMID: 6398032.