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MedKoo Cat#: 598463 | Name: Formycin B

Description:

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

Formycin B is a model nucleoside analogue.

Chemical Structure

Formycin B
Formycin B
CAS#13877-76-4

Theoretical Analysis

MedKoo Cat#: 598463

Name: Formycin B

CAS#: 13877-76-4

Chemical Formula: C10H12N4O5

Exact Mass: 268.0808

Molecular Weight: 268.22

Elemental Analysis: C, 44.78; H, 4.51; N, 20.89; O, 29.82

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Formycin B; Laurusin; Ohyamycin; NSC 106486; NSC-106486; NSC106486;
IUPAC/Chemical Name
3-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
InChi Key
MTCJZZBQNCXKAP-KSYZLYKTSA-N
InChi Code
InChI=1S/C10H12N4O5/c15-1-3-7(16)8(17)9(19-3)5-4-6(14-13-5)10(18)12-2-11-4/h2-3,7-9,15-17H,1H2,(H,13,14)(H,11,12,18)/t3-,7-,8-,9+/m1/s1
SMILES Code
O=C1C(NN=C2[C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O)O)=C2NC=N1
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 268.22 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: Wu X, Hui AC, Giacomini KM. Formycin B elimination from the cerebrospinal fluid of the rat. Pharm Res. 1993 Apr;10(4):611-5. PubMed PMID: 8483848. 2: Borgland SL, Parkinson FE. Uptake and release of [3H]formycin B via sodium-dependent nucleoside transporters in mouse leukemic L1210/MA27.1 cells. J Pharmacol Exp Ther. 1997 Apr;281(1):347-53. PubMed PMID: 9103516. 3: Burke T, Lee S, Ferguson PJ, Hammond JR. Interaction of 2',2'-difluorodeoxycytidine (gemcitabine) and formycin B with the Na+-dependent and -independent nucleoside transporters of Ehrlich ascites tumor cells. J Pharmacol Exp Ther. 1998 Sep;286(3):1333-40. PubMed PMID: 9732397. 4: Robinson N, Kaur K, Emmett K, Iovannisci DM, Ullman B. Biochemical genetic analysis of formycin B action in Leishmania donovani. J Biol Chem. 1984 Jun 25;259(12):7637-43. PubMed PMID: 6203896. 5: Spector T, Jones TE, LaFon SW, Nelson DJ, Berens RL, Marr JJ. Monophosphates of formycin B and allopurinol riboside. Interactions with leishmanial and mammalian succino-AMP synthetase and GMP reductase. Biochem Pharmacol. 1984 May 15;33(10):1611-7. PubMed PMID: 6732835. 6: Berman JD, Rainey P, Santi DV. Metabolism of formycin B by Leishmania amastigotes in vitro. Comparative metabolism in infected and uninfected human macrophages. J Exp Med. 1983 Jul 1;158(1):252-7. PubMed PMID: 6190980; PubMed Central PMCID: PMC2187072. 7: Nolan LL, Berman JD, Giri L. The effect of formycin B on mRNA translation and uptake of purine precursors in Leishmania mexicana. Biochem Int. 1984 Aug;9(2):207-18. PubMed PMID: 6207832. 8: Mehta KD, Gupta RS. Involvement of adenosine kinase in the phosphorylation of formycin B in CHO cells. Biochem Biophys Res Commun. 1985 Jul 31;130(2):910-7. PubMed PMID: 2992490. 9: Plagemann PG, Aran JM, Woffendin C. Na(+)-dependent, active and Na(+)-independent, facilitated transport of formycin B in mouse spleen lymphocytes. Biochim Biophys Acta. 1990 Feb 16;1022(1):93-102. PubMed PMID: 2302407. 10: Croft SL, Neal RA. The effect of allopurinol ribonucleoside and formycin B on Trypanosoma cruzi infections in mice. Trans R Soc Trop Med Hyg. 1985;79(4):517-8. PubMed PMID: 3936241. 11: Plagemann PG, Woffendin C. Use of formycin B as a general substrate for measuring facilitated nucleoside transport in mammalian cells. Biochim Biophys Acta. 1989 Jan 17;1010(1):7-15. PubMed PMID: 2909251. 12: McCabe RE, Remington JS, Araujo FG. In vitro and in vivo activities of formycin B against Trypanosoma cruzi. Antimicrob Agents Chemother. 1985 Apr;27(4):491-4. PubMed PMID: 3923921; PubMed Central PMCID: PMC180081. 13: Rojas T, Avila JL. American Leishmania spp: formycin B treatment of cutaneous leishmaniasis in mice. Parasitology. 1987 Jun;94 ( Pt 3):467-74. PubMed PMID: 3614989. 14: Plagemann PG. Mycoplasma contamination greatly enhances the apparent transport and concentrative accumulation of formycin B by mammalian cell culture. Biochim Biophys Acta. 1991 Apr 26;1064(1):162-4. PubMed PMID: 1902747. 15: Borgland SL, Parkinson FE. Effect of adenosine receptor agonists on release of the nucleoside analogue [3H]formycin B from cultured smooth muscle DDT1 MF-2 cells. Eur J Pharmacol. 1998 Apr 10;346(2-3):339-44. PubMed PMID: 9652378. 16: Berman JD. Leishmania tropica: quantitation of in vitro activity of antileishmanial agents by Giemsa staining, viability, and 3H-formycin B incorporation. J Parasitol. 1984 Aug;70(4):561-2. PubMed PMID: 6502359. 17: Neal RA, Croft SL, Nelson DJ. Anti-leishmanial effect of allopurinol ribonucleoside and the related compounds, allopurinol, thiopurinol, thiopurinol ribonucleoside, and of formycin B, sinefungin and the lepidine WR6026. Trans R Soc Trop Med Hyg. 1985;79(1):122-8. PubMed PMID: 3992630. 18: Berman JD, Hanson WL, Chapman WL, Waits VB, Cox RH. Toxicity of formycin B to hamster and dog. J Parasitol. 1987 Dec;73(6):1267-8. PubMed PMID: 3437362. 19: Wierzchowski J, Iwanska B, Bzowska A, Shugar D. Interactions of calf spleen purine nucleoside phosphorylase with formycin B and its aglycone - spectroscopic and kinetic studies. Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):849-54. PubMed PMID: 18066912. 20: Hofflin JM, Guptill DR, Araujo FG, Remington JS. Difluoromethylornithine and formycin B in toxoplasmosis. J Infect Dis. 1985 Nov;152(5):1101. PubMed PMID: 3930627.

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