SR4554

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

MedKoo CAT#: 206027

CAS#: 167648-73-9

Description: SR4554 is a fluorine-containing 2-nitroimidazole, designed as a hypoxia marker detectable with 19F magnetic resonance spectroscopy (MRS). SR-4554 has plasma pharmacokinetic and toxicity profiles suitable for use as a hypoxia probe. It can be detected in tumors by unlocalized MRS. Additional clinical studies are warranted.


Chemical Structure

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SR4554
CAS# 167648-73-9

Theoretical Analysis

MedKoo Cat#: 206027
Name: SR4554
CAS#: 167648-73-9
Chemical Formula: C8H9F3N4O4
Exact Mass: 282.05759
Molecular Weight: 282.18
Elemental Analysis: C, 34.05; H, 3.21; F, 20.20; N, 19.86; O, 22.68

Size Price Shipping out time Quantity
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Pricing updated 2021-03-02. Prices are subject to change without notice.

Optional 3: SR4554, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received.

Synonym: SR4554; SR4554; SR 4554.

IUPAC/Chemical Name: 2-(2-nitro-1H-imidazol-1-yl)-N-(3,3,3-trifluoro-2-hydroxypropyl)acetamide

InChi Key: BTLNRJMECFTISR-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H9F3N4O4/c9-8(10,11)5(16)3-13-6(17)4-14-2-1-12-7(14)15(18)19/h1-2,5,16H,3-4H2,(H,13,17)

SMILES Code: O=C(NCC(O)C(F)(F)F)CN1C=CN=C1[N+]([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, not in water

Shelf Life:
>5 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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 282.18 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Lee CP, Payne GS, Oregioni A, Ruddle R, Tan S, Raynaud FI, Eaton D, Campbell MJ, Cross K, Halbert G, Tracy M, McNamara J, Seddon B, Leach MO, Workman P, Judson I. A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy. Br J Cancer. 2009 Dec 1;101(11):1860-8. doi: 10.1038/sj.bjc.6605425. PubMed PMID: 19935799; PubMed Central PMCID: PMC2788261.

2: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Dec;28(10):719-40. PubMed PMID: 17235418.

3: Seddon BM, Workman P. The role of functional and molecular imaging in cancer drug discovery and development. Br J Radiol. 2003;76 Spec No 2:S128-38. Review. PubMed PMID: 15572335.

4: Seddon BM, Payne GS, Simmons L, Ruddle R, Grimshaw R, Tan S, Turner A, Raynaud F, Halbert G, Leach MO, Judson I, Workman P. A phase I study of SR-4554 via intravenous administration for noninvasive investigation of tumor hypoxia by magnetic resonance spectroscopy in patients with malignancy. Clin Cancer Res. 2003 Nov 1;9(14):5101-12. Review. PubMed PMID: 14613987.

5: Workman P. Challenges of PK/PD measurements in modern drug development. Eur J Cancer. 2002 Nov;38(16):2189-93. Review. PubMed PMID: 12387843.

6: Seddon BM, Maxwell RJ, Honess DJ, Grimshaw R, Raynaud F, Tozer GM, Workman P. Validation of the fluorinated 2-nitroimidazole SR-4554 as a noninvasive hypoxia marker detected by magnetic resonance spectroscopy. Clin Cancer Res. 2002 Jul;8(7):2323-35. PubMed PMID: 12114437.

7: Busch TM, Hahn SM, Evans SM, Koch CJ. Depletion of tumor oxygenation during photodynamic therapy: detection by the hypoxia marker EF3 [2-(2-nitroimidazol-1[H]-yl)-N-(3,3,3-trifluoropropyl)acetamide ]. Cancer Res. 2000 May 15;60(10):2636-42. PubMed PMID: 10825135.

8: Aboagye EO, Kelson AB, Tracy M, Workman P. Preclinical development and current status of the fluorinated 2-nitroimidazole hypoxia probe N-(2-hydroxy-3,3,3-trifluoropropyl)-2-(2-nitro-1-imidazolyl) acetamide (SR 4554, CRC 94/17): a non-invasive diagnostic probe for the measurement of tumor hypoxia by magnetic resonance spectroscopy and imaging, and by positron emission tomography. Anticancer Drug Des. 1998 Sep;13(6):703-30. Review. Erratum in: Anticancer Drug Des 1998 Dec;13(8):1009-10. PubMed PMID: 9755726.

9: McSheehy PM, Robinson SP, Ojugo AS, Aboagye EO, Cannell MB, Leach MO, Judson IR, Griffiths JR. Carbogen breathing increases 5-fluorouracil uptake and cytotoxicity in hypoxic murine RIF-1 tumors: a magnetic resonance study in vivo. Cancer Res. 1998 Mar 15;58(6):1185-94. PubMed PMID: 9515804.

10: Aboagye EO, Maxwell RJ, Horsman MR, Lewis AD, Workman P, Tracy M, Griffiths JR. The relationship between tumour oxygenation determined by oxygen electrode measurements and magnetic resonance spectroscopy of the fluorinated 2-nitroimidazole SR-4554. Br J Cancer. 1998;77(1):65-70. PubMed PMID: 9459147; PubMed Central PMCID: PMC2151248.

11: Aboagye EO, Lewis AD, Tracy M, Workman P. Bioreductive metabolism of the novel fluorinated 2-nitroimidazole hypoxia probe N-(2-hydroxy-3,3,3-trifluoropropyl)-2-(2-nitroimidazolyl) acetamide (SR-4554). Biochem Pharmacol. 1997 Dec 1;54(11):1217-24. PubMed PMID: 9416972.

12: Aboagye EO, Maxwell RJ, Kelson AB, Tracy M, Lewis AD, Graham MA, Horsman MR, Griffiths JR, Workman P. Preclinical evaluation of the fluorinated 2-nitroimidazole N-(2-hydroxy-3,3,3-trifluoropropyl)-2-(2-nitro-1-imidazolyl) acetamide (SR-4554) as a probe for the measurement of tumor hypoxia. Cancer Res. 1997 Aug 1;57(15):3314-8. PubMed PMID: 9242466.

13: Aboagye EO, Lewis AD, Graham MA, Tracy M, Kelson AB, Ryan KJ, Workman P. The pharmacokinetics, bioavailability and biodistribution in mice of a rationally designed 2-nitroimidazole hypoxia probe SR-4554. Anticancer Drug Des. 1996 Apr;11(3):231-42. PubMed PMID: 8663910.

14: Aboagye EO, Graham MA, Lewis AD, Workman P, Kelson AB, Tracy M. Development and validation of a solid-phase extraction and high-performance liquid chromatographic assay for a novel fluorinated 2-nitroimidazole hypoxia probe (SR-4554) in Balb/c mouse plasma. J Chromatogr B Biomed Appl. 1995 Oct 6;672(1):125-32. PubMed PMID: 8590924.

15: Aboagye EO, Lewis AD, Johnson A, Workman P, Tracy M, Huxham IM. The novel fluorinated 2-nitroimidazole hypoxia probe SR-4554: reductive metabolism and semiquantitative localisation in human ovarian cancer multicellular spheroids as measured by electron energy loss spectroscopic analysis. Br J Cancer. 1995 Aug;72(2):312-8. PubMed PMID: 7640211; PubMed Central PMCID: PMC2034013.



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