Synonym
25-Desacetylrifapentine; L-14583; L 14583; L14583;
IUPAC/Chemical Name
Rifamycin, 3-(((4-cyclopentyl-1-piperazinyl)imino)methyl)-25-O-deacetyl-
InChi Key
LPUNEQQTZOWCNO-WHXRYXKQSA-N
InChi Code
InChI=1S/C45H62N4O11/c1-23-12-11-13-24(2)44(57)47-35-30(22-46-49-19-17-48(18-20-49)29-14-9-10-15-29)40(54)32-33(41(35)55)39(53)28(6)42-34(32)43(56)45(7,60-42)59-21-16-31(58-8)25(3)37(51)27(5)38(52)26(4)36(23)50/h11-13,16,21-23,25-27,29,31,36-38,50-55H,9-10,14-15,17-20H2,1-8H3,(H,47,57)/b12-11+,21-16+,24-13+,46-22+/t23-,25+,26+,27-,31-,36-,37+,38+,45-/m0/s1
SMILES Code
CO[C@H]1/C=C/O[C@]2(Oc(c(C)c3O)c(C2=O)c4c3c(O)c(NC(/C(C)=C/C=C/[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)O)C)O)C)O)C)=O)c(/C=N/N5CCN(C6CCCC6)CC5)c4O)C
Purity
>95% (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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
835.00
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: Egelund EF, Weiner M, Singh RP, Prihoda TJ, Gelfond JA, Derendorf H, Mac Kenzie WR, Peloquin CA. Protein binding of rifapentine and its 25-desacetyl metabolite in patients with pulmonary tuberculosis. Antimicrob Agents Chemother. 2014 Aug;58(8):4904-10. doi: 10.1128/AAC.01730-13. Epub 2014 May 19. PubMed PMID: 24841270; PubMed Central PMCID: PMC4136068.
2: Keung AC, Owens RC Jr, Eller MG, Weir SJ, Nicolau DP, Nightingale CH. Pharmacokinetics of rifapentine in subjects seropositive for the human immunodeficiency virus: a phase I study. Antimicrob Agents Chemother. 1999 May;43(5):1230-3. PubMed PMID: 10223941; PubMed Central PMCID: PMC89138.
3: Keung AC, Eller MG, Weir SJ. Pharmacokinetics of rifapentine in patients with varying degrees of hepatic dysfunction. J Clin Pharmacol. 1998 Jun;38(6):517-24. PubMed PMID: 9650541.
4: Riva E, Merati R, Cavenaghi L. High-performance liquid chromatographic determination of rifapentine and its metabolite in human plasma by direct injection into a shielded hydrophobic phase column. J Chromatogr. 1991 Aug 16;553(1-2):35-40. PubMed PMID: 1787163.
5: Ratti B, Toselli A, Rosina Parenti R. Method for determination of DL 473-IT and its metabolite L 14583 in plasma of humans, monkeys and rats. Farmaco Prat. 1981 Jul;36(7):319-28. PubMed PMID: 6791958.
