2-Fluoroadenosine | CAS# 146-78-1 | Nucleosides

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

MedKoo CAT#: 122475

CAS#: 146-78-1

Description: 2-Fluoroadenosine is a nucleoside that has shown high resistance to the enzyme cyclase.

Chemical Structure

2-Fluoroadenosine

CAS# 146-78-1

Instruction

Theoretical Analysis

MedKoo Cat#: 122475
Name: 2-Fluoroadenosine
CAS#: 146-78-1
Chemical Formula: C10H12FN5O4
Exact Mass: 285.09
Molecular Weight: 285.240
Elemental Analysis: C, 42.11; H, 4.24; F, 6.66; N, 24.55; O, 22.44

Price and Availability

Size	Price	Availability
1g	USD 250	2 Weeks
5g	USD 550	2 Weeks
10g	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 2-Fluoroadenosine; (2R,3R,4S,5R)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol; ADENOSINE, 2-FLUORO-; 6-Amino-2-fluoro-9-beta-D-ribofuranosylpurine

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key: HBUBKKRHXORPQB-UUOKFMHZSA-N

InChi Code: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

SMILES Code: OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(F)=NC(N)=C3N=C2)O1

Appearance: To be determined

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 285.24 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ye S, Rezende MM, Deng WP, Herbert B, Daly JW, Johnson RA, Kirk KL. Synthesis
of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine:
potent P-site inhibitors of adenylyl cyclase. J Med Chem. 2004 Feb
26;47(5):1207-13. doi: 10.1021/jm0303599. PMID: 14971900.

2: Zimmerman TP, Rideout JL, Wolberg G, Duncan GS, Elion GB. 2-Fluoroadenosine
3':5'-monophosphate. A metabolite of 2-fluoroadenosine in mouse cytotoxic
lymphocytes. J Biol Chem. 1976 Nov 10;251(21):6757-66. PMID: 185217.

3: Ye S, Rezende MM, Deng WP, Kirk KL. Convenient synthesis of
2'-deoxy-2-fluoroadenosine from 2-fluoroadenine. Nucleosides Nucleotides Nucleic
Acids. 2003 Oct;22(10):1899-905. doi: 10.1081/NCN-120025237. PMID: 14609229.

4: PITTILLO RF, MONCRIEF C, BROCKMAN RW, CHAMBERS P. ANTIMICROBIAL ACTIVITY OF
2-FLUOROADENOSINE AND 2-FLUOROADENINE. Antimicrob Agents Chemother (Bethesda).
1964;10:474-84. PMID: 14287979.

5: Ishihama A, Enami M, Nishijima Y, Fukui T, Ohtsuka E, Ikehara M.
2'-Deoxy-2'-azidoadenosine triphosphate and 2'-deoxy-2'-fluoroadenosine
triphosphate as substrates and inhibitors for Escherichia coli DNA-dependent RNA
polymerase. J Biochem. 1980 Mar;87(3):825-30. doi:
10.1093/oxfordjournals.jbchem.a132812. PMID: 6156150.

6: Berzin VB, Dorofeeva EV, Leonov VN, Miroshnikova AI. [The preparative method
for 2-fluoroadenosine synthesis]. Bioorg Khim. 2009 Mar-Apr;35(2):210-4.
Russian. doi: 10.1134/s1068162009020071. PMID: 19537172.

7: Dickinson MJ, Holly FW, Walton E, Zimmerman M. 3'-deoxynucleosides. V.
3'-Deoxy-2-fluoroadenosine. J Med Chem. 1967 Nov;10(6):1165-6. doi:
10.1021/jm00318a042. PMID: 6056051.

8: Decking UK, Alves C, Spahr R, Schrader J. 2-Fluoroadenosine uptake by
erythrocytes and endothelial cells studied by 19F-NMR. Am J Physiol. 1994
Apr;266(4 Pt 2):H1596-603. doi: 10.1152/ajpheart.1994.266.4.H1596. PMID:
8184939.

9: Ohrui H, Kohgo S, Hayakawa H, Kodama E, Matsuoka M, Nakata T, Mitsuya H.
2'-deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase
inhibitor with highly potent activity against wide spectrum of HIV-1 strains,
favorable toxic profiles, and stability in plasma. Nucleosides Nucleotides
Nucleic Acids. 2007;26(10-12):1543-6. doi: 10.1080/15257770701545218. PMID:
18066823.

10: Ohrui H. 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse
transcriptase inhibitor, is highly potent against all human immunodeficiency
viruses type 1 and has low toxicity. Chem Rec. 2006;6(3):133-43. doi:
10.1002/tcr.20078. PMID: 16795005.

11: Ohrui H, Kohgo S, Hayakawa H, Kodama E, Matsuoka M, Nakata T, Mitsuya H.
2'-Deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase
inhibitor with highly potent activity against all HIV-1 strains, favorable toxic
profiles and stability in plasma. Nucleic Acids Symp Ser (Oxf). 2006;(50):1-2.
doi: 10.1093/nass/nrl001. PMID: 17150787.

12: Agarwal KC, Parks RE Jr. Synergistic inhibition of platelet aggregation by
forskolin plus PGE1 or 2-fluoroadenosine: effects of 2',5'-dideoxyadenosine and
5'-methylthioadenosine. Biochem Pharmacol. 1982 Nov 15;31(22):3713-6. doi:
10.1016/0006-2952(82)90608-6. PMID: 6983882.

13: Kayushin AL, Tokunova JA, Fateev IV, Arnautova AO, Berzina MY, Paramonov AS,
Lutonina OI, Dorofeeva EV, Antonov KV, Esipov RS, Mikhailopulo IA, Miroshnikov
AI, Konstantinova ID. Radical Dehalogenation and Purine Nucleoside Phosphorylase
E. coli: How Does an Admixture of 2',3'-Anhydroinosine Hinder 2-fluoro-
cordycepin Synthesis. Biomolecules. 2021 Apr 7;11(4):539. doi:
10.3390/biom11040539. PMID: 33917025; PMCID: PMC8067715.

14: Gao ZG, Jacobson KA. Partial agonists for A(3) adenosine receptors. Curr Top
Med Chem. 2004;4(8):855-62. doi: 10.2174/1568026043450989. PMID: 15078216;
PMCID: PMC3425644.

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