Synonym
Mirincamycin hydrochloride; U-24,729A; U 24,729A; U24,729A; U 24729 A; U-24729 A; U24729 A;
IUPAC/Chemical Name
(2S)-N-((1R,2R)-2-chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-4-pentylpyrrolidine-2-carboxamide dihydrochloride
InChi Key
VUGWNRKSMAIXJA-GUZBRATFSA-N
InChi Code
InChI=1S/C19H35ClN2O5S.2ClH/c1-4-5-6-7-11-8-12(21-9-11)18(26)22-13(10(2)20)17-15(24)14(23)16(25)19(27-17)28-3;;/h10-17,19,21,23-25H,4-9H2,1-3H3,(H,22,26);2*1H/t10-,11?,12+,13+,14+,15-,16-,17-,19-;;/m1../s1
SMILES Code
CCCCCC1C[C@@H](C(N[C@@H]([C@H](Cl)C)[C@@H]2[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O2)=O)NC1.Cl.Cl
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
511.92
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.
| 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: Fracisco S, Teja-isavadharm P, Gettayacamin M, Berman J, Li Q, Melendez V, Saunders D, Xie L, Ohrt C. Anti-relapse activity of mirincamycin in the Plasmodium cynomolgi sporozoite-infected Rhesus monkey model. Malar J. 2014 Oct 17;13:409. doi: 10.1186/1475-2875-13-409. PubMed PMID: 25326032; PubMed Central PMCID: PMC4209072.
2: Khemawoot P, Saunders D, Rasameesoraj M, Melendez V, Imerbsin R, Ohrt C, Fracisco S, Teja-Isavadharm P. Absolute bioavailability of cis-mirincamycin and trans-mirincamycin in healthy rhesus monkeys and ex vivo antimalarial activity against Plasmodium falciparum. Antimicrob Agents Chemother. 2011 Dec;55(12):5881-6. doi: 10.1128/AAC.01619-10. Epub 2011 Sep 26. PubMed PMID: 21947400; PubMed Central PMCID: PMC3232806.
3: Starzengruber P, Fuehrer HP, Swoboda P, Ganesh D, Haque R, Khan WA, Graninger W, Noedl H. Mirincamycin, an old candidate for malaria combination treatment and prophylaxis in the 21st century: in vitro interaction profiles with potential partner drugs in continuous culture and field isolates. Malar J. 2014 Jun 10;13:228. doi: 10.1186/1475-2875-13-228. PubMed PMID: 24916383; PubMed Central PMCID: PMC4059879.
4: Schmidt LH. Enhancement of the curative activity of primaquine by concomitant administration of mirincamycin. Antimicrob Agents Chemother. 1985 Feb;27(2):151-7. PubMed PMID: 3885847; PubMed Central PMCID: PMC176228.
5: Held J, Westerman R, Kremsner PG, Mordmüller B. In vitro activity of mirincamycin (U24729A) against Plasmodium falciparum isolates from Gabon. Antimicrob Agents Chemother. 2010 Jan;54(1):540-2. doi: 10.1128/AAC.01090-09. Epub 2009 Oct 19. PubMed PMID: 19841147; PubMed Central PMCID: PMC2798552.
6: Westblom TU, Midkiff BR, Czinn SJ. In vitro susceptibility of Helicobacter pylori to trospectomycin, pirlimycin (U-57930E), mirincamycin (U-24729A) and N-demethyl clindamycin (U-26767A). Eur J Clin Microbiol Infect Dis. 1993 Jul;12(7):560-2. PubMed PMID: 8404921.
