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MedKoo Cat#: 584365 | Name: Coformycin

Description:

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

Coformycin is a ribonucleoside antibiotic synergist and adenosine deaminase inhibitor isolated from Nocardia interforma and Streptomyces kaniharaensis. It is proposed as an antineoplastic synergist and immunosuppressant.

Chemical Structure

Coformycin
CAS#11033-22-0

Theoretical Analysis

MedKoo Cat#: 584365

Name: Coformycin

CAS#: 11033-22-0

Chemical Formula: C11H16N4O5

Exact Mass: 284.1121

Molecular Weight: 284.27

Elemental Analysis: C, 46.48; H, 5.67; N, 19.71; O, 28.14

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 #
No Data
Synonym
Coformycin; NSC 277817
IUPAC/Chemical Name
Imidazo(4,5-d)(1,3)diazepin-8-ol, 3,4,7,8-tetrahydro-3-beta-D-ribofuranosyl-, (R)-
InChi Key
YOOVTUPUBVHMPG-LODYRLCVSA-N
InChi Code
InChI=1S/C11H16N4O5/c16-2-6-8(18)9(19)11(20-6)15-4-14-7-5(17)1-12-3-13-10(7)15/h3-6,8-9,11,16-19H,1-2H2,(H,12,13)/t5-,6-,8-,9-,11-/m1/s1
SMILES Code
O[C@H]1C2=C(N([C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O)O)C=N2)NC=NC1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 284.27 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: Bzowska A, Lassota P, Shugar D. Phosphorylation of coformycin and 2'-deoxycoformycin, and substrate and inhibitor properties of the nucleosides and nucleotides in several enzyme systems. Z Naturforsch C. 1985 Sep-Oct;40(9-10):710-4. PubMed PMID: 3002059. 2: Hanvey JC, Hawkins ES, Baker DC, Suhadolnik RJ. 8-Ketodeoxycoformycin and 8-ketocoformycin as intermediates in the biosynthesis of 2'-deoxycoformycin and coformycin. Biochemistry. 1988 Jul 26;27(15):5790-5. PubMed PMID: 3052586. 3: Danton MJ, Coleman MS. Isolation of mutant adenosine deaminase by coformycin affinity chromatography. Anal Biochem. 1986 Nov 15;159(1):233-9. PubMed PMID: 3492941. 4: Han BW, Bingman CA, Mahnke DK, Sabina RL, Phillips GN Jr. Crystallization and preliminary X-ray crystallographic analysis of adenosine 5'-monophosphate deaminase (AMPD) from Arabidopsis thaliana in complex with coformycin 5'-phosphate. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Aug 1;61(Pt 8):740-2. Epub 2005 Jul 8. PubMed PMID: 16511144; PubMed Central PMCID: PMC1952363. 5: Szentmiklósi AJ, Németh M, Cseppentö A, Szegi J, Papp JG, Szekeres L. Effects of hypoxia on the guinea-pig myocardium following inhibition of adenosine deaminase by coformycin. Arch Int Pharmacodyn Ther. 1984 Jun;269(2):287-94. PubMed PMID: 6476984. 6: Castro C, Britt BM. Binding thermodynamics of the transition state analogue coformycin and of the ground state analogue 1-deazaadenosine to bovine adenosine deaminase. J Enzyme Inhib. 2001;16(3):217-32. PubMed PMID: 11697042. 7: Szentmiklósi AJ, Németh M, Cseppentö A, Szegi J, Papp JG, Szekeres L. Potentiation of the myocardial actions of adenosine in the presence of coformycin, a specific inhibitor of adenosine deaminase. Arch Int Pharmacodyn Ther. 1982 Apr;256(2):236-52. PubMed PMID: 7103613. 8: Goday A, Simmonds HA, Webster DR, Levinsky RJ, Watson AR, Hoffbrand AV. Importance of platelet-free preparations for evaluating lymphocyte nucleotide levels in inherited or acquired immunodeficiency syndromes. Clin Sci (Lond). 1983 Dec;65(6):635-43. PubMed PMID: 6414755. 9: Ho MC, Cassera MB, Madrid DC, Ting LM, Tyler PC, Kim K, Almo SC, Schramm VL. Structural and metabolic specificity of methylthiocoformycin for malarial adenosine deaminases. Biochemistry. 2009 Oct 13;48(40):9618-26. doi: 10.1021/bi9012484. PubMed PMID: 19728741; PubMed Central PMCID: PMC2771402. 10: Matsumoto SS, Yu J, Yu AL. Inhibition of RNA synthesis by deoxyadenosine plus deoxycoformycin in resting lymphocytes. J Immunol. 1983 Dec;131(6):2762-6. PubMed PMID: 6196398. 11: Marongiu ME, Pani A, Tinti E, Grifantini M, Franchetti P, Cristalli G, La Colla P. Enhancement of the anti-HIV-1 activity of ddAdo by coformycin, EHNA and deaza-EHNA derivatives. New Microbiol. 1995 Oct;18(4):359-70. PubMed PMID: 8590388. 12: Brox LW, Pollock E, Belch A. Adenosine and deoxyadenosine toxicity in colony assay systems for human T-lymphocytes, B-lymphocytes, and granulocytes. Cancer Chemother Pharmacol. 1982;9(1):49-52. PubMed PMID: 6982786. 13: Kline PC, Schramm VL. Electrostatic potential surfaces of the transition state for AMP deaminase and for (R)-coformycin, a transition state inhibitor. J Biol Chem. 1994 Sep 2;269(35):22385-90. PubMed PMID: 8071366. 14: Lee SH, Thomas LK, Unger FM, Christian R, Sartorelli AC. Comparative antineoplastic activity against P388 leukemia of 9-beta-D-arabinofuranosyladenine (araA) and 9-beta-(2'-azido-2'-deoxy-D-arabinofuranosyl) adenine (arazide). Int J Cancer. 1981 May 15;27(5):703-8. PubMed PMID: 6974703. 15: Jackson RC, Leopold WR, Ross DA. The biochemical pharmacology of (2'-R)-chloropentostatin, a novel inhibitor of adenosine deaminase. Adv Enzyme Regul. 1986;25:125-39. PubMed PMID: 2433905. 16: Grever MR, Siaw MF, Coleman MS, Whisler RL, Balcerzak SP. Inhibition of K and NK lymphocyte cytotoxicity by an inhibitor of adenosine deaminase and deoxyadenosine. J Immunol. 1983 Jan;130(1):365-9. PubMed PMID: 6600187. 17: Kajander EO, Kubota M, Willis EH, Carson DA. S-adenosylmethionine metabolism as a target for adenosine toxicity. Adv Exp Med Biol. 1986;195 Pt B:221-6. PubMed PMID: 3490121. 18: Ashby B, Holmsen H. Platelet AMP deaminase. Regulation by Mg-ATP2- and inorganic phosphate and inhibition by the transition state analog coformycin. J Biol Chem. 1983 Mar 25;258(6):3668-72. PubMed PMID: 6601104. 19: Parks RE Jr, Dawicki DD, Agarwal KC, Chen SF, Stoeckler JD. Role of nucleoside transport in drug action. The adenosine deaminase inhibitor, deoxycoformycin, and the antiplatelet drugs, dipyridamole and dilazep. Ann N Y Acad Sci. 1985;451:188-203. PubMed PMID: 3878117. 20: Else M, Dearden CE, Matutes E, Forconi F, Lauria F, Ahmad H, Kelly S, Liyanage A, Ratnayake V, Shankari J, Whalley I, Catovsky D. Rituximab with pentostatin or cladribine: an effective combination treatment for hairy cell leukemia after disease recurrence. Leuk Lymphoma. 2011 Jun;52 Suppl 2:75-8. doi: 10.3109/10428194.2011.568650. Epub 2011 Apr 19. PubMed PMID: 21504288.