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MedKoo Cat#: 330136 | Name: Rifalazil
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Description:

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

lRifalazil (also known as KRM-1648 and AMI-1648) is an antibiotic. Rifalazil kills bacterial cells by blocking off the β-subunit in RNA polymerase. Rifalazil is used as treatments for many different diseases. Of the most common are Chlamydia infection, Clostridium difficile associated diarrhea (CDAD), and tuberculosis (TB).

Chemical Structure

Rifalazil
Rifalazil
CAS#129791-92-0

Theoretical Analysis

MedKoo Cat#: 330136

Name: Rifalazil

CAS#: 129791-92-0

Chemical Formula: C51H64N4O13

Exact Mass: 940.4470

Molecular Weight: 941.09

Elemental Analysis: C, 65.09; H, 6.86; N, 5.95; O, 22.10

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
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Synonym
Rifalazil; ABI 1648; ABI1648; ABI -648; Krm-1648; Krm 1648; Krm1648;
IUPAC/Chemical Name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-Tetrahydroxy-30-(4-isobutyl-1-piperazinyl)-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11;.1.14,7.05,36.026,35.028,33]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate
InChi Key
UEFHFKKWYKVLDC-HTQYORAHSA-N
InChi Code
InChI=1S/C51H64N4O13/c1-24(2)23-54-16-18-55(19-17-54)32-21-33(57)39-35(22-32)67-48-40(52-39)36-37-44(60)30(8)47-38(36)49(62)51(10,68-47)65-20-15-34(64-11)27(5)46(66-31(9)56)29(7)43(59)28(6)42(58)25(3)13-12-14-26(4)50(63)53-41(48)45(37)61/h12-15,20-22,24-25,27-29,34,42-43,46,57-60H,16-19,23H2,1-11H3,(H,53,63)/b13-12+,20-15+,26-14-/t25-,27+,28+,29+,34-,42-,43+,46+,51-/m0/s1
SMILES Code
CC(O[C@@H]([C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C/C=C1/C)[C@H](C)[C@@H](OC)/C=C/O[C@](O2)(C)C(C3=C2C(C)=C(O)C(C4=O)=C3C5=NC6=C(O)C=C(N7CCN(CC(C)C)CC7)C=C6OC5=C4NC1=O)=O)=O
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
Using rifalazil and the effects that coincide with taking rifalazil for treating a bacterial disease vary from person to person, as does any drug put into the human body. Food interactions and genetic variation are a few causes for the variation in side effects from the use of rifalazil. Its development was terminated in 2013 due to severe side effects.

Preparing Stock Solutions

The following data is based on the product molecular weight 941.09 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
1: Geisler WM, Pascual ML, Mathew J, Koltun WD, Morgan F, Batteiger BE, Mayes A, Tao S, Hurwitz SJ, Sayada C, Schinazi RF. Randomized, double-blind, multicenter safety and efficacy study of rifalazil compared with azithromycin for treatment of uncomplicated genital Chlamydia trachomatis infection in women. Antimicrob Agents Chemother. 2014 Jul;58(7):4014-9. doi: 10.1128/AAC.02521-14. Epub 2014 May 5. PubMed PMID: 24798277; PubMed Central PMCID: PMC4068607. 2: Jaff MR, Dale RA, Creager MA, Lipicky RJ, Constant J, Campbell LA, Hiatt WR. Anti-chlamydial antibiotic therapy for symptom improvement in peripheral artery disease: prospective evaluation of rifalazil effect on vascular symptoms of intermittent claudication and other endpoints in Chlamydia pneumoniae seropositive patients (PROVIDENCE-1). Circulation. 2009 Jan 27;119(3):452-8. doi: 10.1161/CIRCULATIONAHA.108.815308. Epub 2009 Jan 12. PubMed PMID: 19139383. 3: Rothstein DM, Suchland RJ, Xia M, Murphy CK, Stamm WE. Rifalazil retains activity against rifampin-resistant mutants of Chlamydia pneumoniae. J Antibiot (Tokyo). 2008 Aug;61(8):489-95. doi: 10.1038/ja.2008.65. PubMed PMID: 18997387. 4: Rothstein DM, Mullin S, Sirokman K, Söndergaard KL, Johnson S, Gwathmey JK, van Duzer J, Murphy CK. Rifalazil and derivative compounds show potent efficacy in a mouse model of H. pylori colonization. J Antibiot (Tokyo). 2008 Aug;61(8):485-8. doi: 10.1038/ja.2008.64. PubMed PMID: 18997386. 5: Mozhaev VV, Mozhaeva LV, Michels PC, Khmelnitsky YL. Extractive biotransformation for production of metabolites of poorly soluble compounds: synthesis of 32-hydroxy-rifalazil. Drug Metab Dispos. 2008 Oct;36(10):1998-2004. doi: 10.1124/dmd.108.021832. Epub 2008 Jul 7. PubMed PMID: 18606743. 6: Rifalazil. Tuberculosis (Edinb). 2008 Mar;88(2):148-50. doi: 10.1016/S1472-9792(08)70023-4. Review. PubMed PMID: 18486057. 7: Pregnolato M. Rifalazil(Kaneka corp). IDrugs. 1998 Sep;1(5):599-604. PubMed PMID: 18465600. 8: Larsson M, Han F. Determination of rifalazil in dog plasma by liquid-liquid extraction and LC-MS/MS: quality assessment by incurred sample analysis. J Pharm Biomed Anal. 2007 Nov 30;45(4):616-24. Epub 2007 Sep 12. PubMed PMID: 17942263. 9: Larsson M, Michaelis AF, Zhu Y, Ramu K. Determination of rifalazil, a potent antibacterial agent, in human plasma by liquid-liquid extraction and LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Nov 1;859(1):103-10. Epub 2007 Sep 15. PubMed PMID: 17936092. 10: Rothstein DM, van Duzer J, Sternlicht A, Gilman SC. Rifalazil and other benzoxazinorifamycins in the treatment of chlamydia-based persistent infections. Arch Pharm (Weinheim). 2007 Oct;340(10):517-29. Review. PubMed PMID: 17912677. 11: Chen YX, Cabana B, Kivel N, Pieniaszek H, Gilman S, Michaelis A. Lack of effect of rifalazil on ethinyl estradiol pharmacokinetics in healthy postmenopausal women. Int J Clin Pharmacol Ther. 2007 Jul;45(7):418-22. PubMed PMID: 17725249. 12: Chen YX, Cabana B, Kivel N, Michaelis A. Effect of food on the pharmacokinetics of rifalazil, a novel antibacterial, in healthy male volunteers. J Clin Pharmacol. 2007 Jul;47(7):841-9. Epub 2007 Apr 26. PubMed PMID: 17463218. 13: Stamm WE, Batteiger BE, McCormack WM, Totten PA, Sternlicht A, Kivel NM; Rifalazil Study Group. A randomized, double-blind study comparing single-dose rifalazil with single-dose azithromycin for the empirical treatment of nongonococcal urethritis in men. Sex Transm Dis. 2007 Aug;34(8):545-52. PubMed PMID: 17297383. 14: Osburne MS, Murphy CK, Rothstein DM. Enhanced activity of rifalazil in combination with levofloxacin, linezolid, or mupirocin against Staphylococcus aureus in vitro. J Antibiot (Tokyo). 2006 May;59(5):303-8. PubMed PMID: 16883781. 15: Rothstein DM, Shalish C, Murphy CK, Sternlicht A, Campbell LA. Development potential of rifalazil and other benzoxazinorifamycins. Expert Opin Investig Drugs. 2006 Jun;15(6):603-23. Review. PubMed PMID: 16732714. 16: Osburne MS, Rothstein DM, Farquhar R, Murphy CK. In vitro time-kill activities of rifalazil, alone and in combination with vancomycin, against logarithmic and stationary cultures of Staphylococcus aureus. J Antibiot (Tokyo). 2006 Feb;59(2):80-5. PubMed PMID: 16629407. 17: Suchland RJ, Brown K, Rothstein DM, Stamm WE. Rifalazil pretreatment of mammalian cell cultures prevents subsequent Chlamydia infection. Antimicrob Agents Chemother. 2006 Feb;50(2):439-44. PubMed PMID: 16436694; PubMed Central PMCID: PMC1366910. 18: Labro MT, Ollivier V, Babin-Chevaye C. Interaction of rifalazil with oxidant-generating systems of human polymorphonuclear neutrophils. Antimicrob Agents Chemother. 2005 Dec;49(12):5018-23. PubMed PMID: 16304167; PubMed Central PMCID: PMC1315961. 19: Suchland RJ, Bourillon A, Denamur E, Stamm WE, Rothstein DM. Rifampin-resistant RNA polymerase mutants of Chlamydia trachomatis remain susceptible to the ansamycin rifalazil. Antimicrob Agents Chemother. 2005 Mar;49(3):1120-6. PubMed PMID: 15728912; PubMed Central PMCID: PMC549232. 20: Kutlin A, Kohlhoff S, Roblin P, Hammerschlag MR, Riska P. Emergence of resistance to rifampin and rifalazil in Chlamydophila pneumoniae and Chlamydia trachomatis. Antimicrob Agents Chemother. 2005 Mar;49(3):903-7. PubMed PMID: 15728882; PubMed Central PMCID: PMC549234.