Bulaquine

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

MedKoo CAT#: 571287

CAS#: 79781-00-3

Description: Bulaquine is a derivative of 8-aminoquinoline. It possesses potent activity against hepatic stages of plasmodia and hypnozoites of Plasmodium vivax and Plasmodium ovale. There were gene expression alterations in transcription, protein biosynthesis, intracellular signalling, cell division, protein ubiquitination, transcription regulation and steroid biosynthesis. The chemical showed an absence of traditional markers of hepatic stress.


Price and Availability

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Bulaquine 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#: 571287
Name: Bulaquine
CAS#: 79781-00-3
Chemical Formula: C21H27N3O3
Exact Mass: 369.2052
Molecular Weight: 369.47
Elemental Analysis: C, 68.27; H, 7.37; N, 11.37; O, 12.99


Synonym:

IUPAC/Chemical Name: 2(3H)-Furanone, dihydro-3-(1-((4-((6-methoxy-8-quinolinyl)amino)pentyl)amino)ethylidene)-

InChi Key: ADCOUXIGWFEYJP-SDXDJHTJSA-N

InChi Code: InChI=1S/C21H27N3O3/c1-14(6-4-9-22-15(2)18-8-11-27-21(18)25)24-19-13-17(26-3)12-16-7-5-10-23-20(16)19/h5,7,10,12-14,22,24H,4,6,8-9,11H2,1-3H3/b18-15-

SMILES Code: O=C1OCC/C1=C(NCCCC(NC2=C3N=CC=CC3=CC(OC)=C2)C)\C


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

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).

Harmonized System Code:
293490


References

1: Dwivedi AK, Saxena D, Singh S. HPLC and HPTLC assays for the antimalarial agents chloroquine, primaquine and bulaquine. J Pharm Biomed Anal. 2003 Nov 24;33(4):851-8. PubMed PMID: 14623615.

2: Mehrotra N, Lal J, Puri SK, Madhusudanan KP, Gupta RC. In Vitro and In Vivo pharmacokinetic studies of bulaquine (analogue of primaquine), a novel antirelapse antimalarial, in rat, rabbit and monkey--highlighting species similarities and differences. Biopharm Drug Dispos. 2007 Jul;28(5):209-27. PubMed PMID: 17410524.

3: Noel S, Sharma S, Shankar R, Rath SK. Identification of differentially expressed genes after acute exposure to bulaquine (CDRI 80/53) in mice liver. Basic Clin Pharmacol Toxicol. 2008 Dec;103(6):522-9. doi: 10.1111/j.1742-7843.2008.00279.x. Epub 2008 Jul 18. PubMed PMID: 18684221.

4: Gogtay NJ, Kamtekar KD, Dalvi SS, Mehta SS, Chogle AR, Aigal U, Kshirsagar NA. A randomized, parallel study of the safety and efficacy of 45 mg primaquine versus 75 mg bulaquine as gametocytocidal agents in adults with blood schizonticide-responsive uncomplicated falciparum malaria [ISCRTN50134587]. BMC Infect Dis. 2006 Feb 1;6:16. PubMed PMID: 16448575; PubMed Central PMCID: PMC1389708.

5: Nitin M, Rajanikanth M, Lal J, Madhusudanan KP, Gupta RC. Liquid chromatography-tandem mass spectrometric assay with a novel method of quantitation for the simultaneous determination of bulaquine and its metabolite, primaquine, in monkey plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Aug 15;793(2):253-63. PubMed PMID: 12906899.

6: Lal J, Mehrotra N, Gupta RC. Analysis and pharmacokinetics of bulaquine and its major metabolite primaquine in rabbits using an LC-UV method--a pilot study. J Pharm Biomed Anal. 2003 Apr 24;32(1):141-50. PubMed PMID: 12852456.

7: Gogtay NJ, Kamtekar KD, Dalvi SS, Chogle AR, Aigal U, Kshirsagar NA. Preliminary report of the evaluation of the gametocytocidal action of bulaquine, in adult patients with acute, Plasmodium falciparum malaria. Ann Trop Med Parasitol. 2004 Jul;98(5):525-8. PubMed PMID: 15257802.

8: Adak T, Valecha N, Sharma VP. Plasmodium vivax polymorphism in a clinical drug trial. Clin Diagn Lab Immunol. 2001 Sep;8(5):891-4. PubMed PMID: 11527798; PubMed Central PMCID: PMC96166.

9: Krudsood S, Wilairatana P, Tangpukdee N, Chalermrut K, Srivilairit S, Thanachartwet V, Muangnoicharoen S, Luplertlop N, Brittenham GM, Looareesuwan S. Safety and tolerability of elubaquine (bulaquine, CDRI 80/53) for treatment of Plasmidium vivax malaria in Thailand. Korean J Parasitol. 2006 Sep;44(3):221-8. PubMed PMID: 16969059; PubMed Central PMCID: PMC2532664.

10: Graves PM, Gelband H, Garner P. Primaquine or other 8-aminoquinoline for reducing Plasmodium falciparum transmission. Cochrane Database Syst Rev. 2015 Feb 19;(2):CD008152. doi: 10.1002/14651858.CD008152.pub4. Review. PubMed PMID: 25693791; PubMed Central PMCID: PMC4455224.

11: Puri SK, Dutta GP. Plasmodium cynomolgi: gametocytocidal activity of the anti-malarial compound CDRI 80/53 (elubaquine) in rhesus monkeys. Exp Parasitol. 2005 Sep;111(1):8-13. PubMed PMID: 16005457.

12: Graves PM, Gelband H, Garner P. Primaquine or other 8-aminoquinoline for reducing P. falciparum transmission. Cochrane Database Syst Rev. 2014 Jun 30;(6):CD008152. doi: 10.1002/14651858.CD008152.pub3. Review. Update in: Cochrane Database Syst Rev. 2015;(2):CD008152. PubMed PMID: 24979199; PubMed Central PMCID: PMC4456193.

13: Rajgor DD, Gogtay NJ, Kadam VS, Kamtekar KD, Dalvi SS, Chogle AR, Aigal U, Bichile LS, Kain KC, Kshirsagar NA. Efficacy of a 14-day primaquine regimen in preventing relapses in patients with Plasmodium vivax malaria in Mumbai, India. Trans R Soc Trop Med Hyg. 2003 Jul-Aug;97(4):438-40. PubMed PMID: 15259476.

14: Puri SK, Srivastava R, Pandey VC, Sethi N, Dutta GP. Methemoglobin toxicity and hematological studies on malaria anti-relapse compound CDRI 80/53 in dogs. Am J Trop Med Hyg. 1989 Dec;41(6):638-42. PubMed PMID: 2641641.

15: Pandey VC, Puri SK, Sahni SK, Srivastava P, Dutta GP. Effect of anti-relapse antimalarial compound CDRI 80/53 and primaquine on hepatic mixed function oxidase system of rhesus monkey. Pharmacol Res. 1990 Nov-Dec;22(6):701-7. PubMed PMID: 2075158.

16: Tekwani BL, Walker LA. 8-Aminoquinolines: future role as antiprotozoal drugs. Curr Opin Infect Dis. 2006 Dec;19(6):623-31. Review. PubMed PMID: 17075340.

17: Srivastava P, Singh S, Jain GK, Puri SK, Pandey VC. A simple and rapid evaluation of methemoglobin toxicity of 8-aminoquinolines and related compounds. Ecotoxicol Environ Saf. 2000 Mar;45(3):236-9. PubMed PMID: 10702341.

18: Paliwal JK, Gupta RC. A rapid and sensitive high performance liquid chromatographic assay of the new antimalarial compound 80/53 in serum with a novel sample clean-up method and its pharmacokinetics in rabbits. J Pharm Biomed Anal. 1998 Aug;17(4-5):775-83. PubMed PMID: 9682162.

19: Kshirsagar NA. Malaria: anti malarial resistance and policy ramifications and challenges. J Postgrad Med. 2006 Oct-Dec;52(4):291-3. Review. PubMed PMID: 17102549.

20: Puri SK, Dutta GP. Causal prophylactic activity of a new 8-aminoquinoline derivative against Plasmodium cynomolgi B in rhesus monkeys. Indian J Med Res. 1990 May;91:197-9. PubMed PMID: 2397941.