Thioinosinic acid

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

MedKoo CAT#: 463937

CAS#: 53-83-8

Description: Thioinosinic acid is an intermediate metabolite of azathioprine, an immunosuppressive drug.

Chemical Structure

img
Thioinosinic acid
CAS# 53-83-8
Instruction

Theoretical Analysis

MedKoo Cat#: 463937
Name: Thioinosinic acid
CAS#: 53-83-8
Chemical Formula: C10H13N4O7PS
Exact Mass: 364.02
Molecular Weight: 364.269
Elemental Analysis: C, 32.97; H, 3.60; N, 15.38; O, 30.74; P, 8.50; S, 8.80

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Thioinosinic-acid; Thio-IMP; ThioIMP; Thio IMP; NSC 520722; NSC520722; NSC-520722;

IUPAC/Chemical Name: ((2R,3S,4R,5R)-3,4-dihydroxy-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate

InChi Key: ZKRFOXLVOKTUTA-KQYNXXCUSA-N

InChi Code: InChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1

SMILES Code: O[C@H]1[C@H]([C@H](n(cn2)c3c2c(S)ncn3)O[C@@H]1COP(O)(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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 364.27 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Aboul-Fadl T, Agrawal VK, Buckheit RW Jr, Broom AD. An unusual "senseless" 2',5'-oligoribonucleotide with potent anti-HIV activity. Nucleosides Nucleotides Nucleic Acids. 2004;23(3):545-54. doi: 10.1081/NCN-120030713. PMID: 15113022.

2: Hyde RM, Broom AD, Buckheit RW Jr. Antiviral amphipathic oligo- and polyribonucleotides: analogue development and biological studies. J Med Chem. 2003 May 8;46(10):1878-85. doi: 10.1021/jm0203276. PMID: 12723951.

3: Buckheit RW Jr, Lackman-Smith C, Snow MJ, Halliday SM, White EL, Ross LJ, Agrawal VK, Broom AD. PMTI, a broadly active unusual single-stranded polyribonucleotide, inhibits human immunodeficiency virus replication by multiple mechanisms. Antivir Chem Chemother. 1999 Jan;10(1):23-32. doi: 10.1177/095632029901000103. PMID: 10079876.

4: Lennard L, Hale JP, Lilleyman JS. Red blood cell hypoxanthine phosphoribosyltransferase activity measured using 6-mercaptopurine as a substrate: a population study in children with acute lymphoblastic leukaemia. Br J Clin Pharmacol. 1993 Oct;36(4):277-84. doi: 10.1111/j.1365-2125.1993.tb00365.x. PMID: 12959304; PMCID: PMC1364679.

5: Lennard L, Singleton HJ. High-performance liquid chromatographic assay of the methyl and nucleotide metabolites of 6-mercaptopurine: quantitation of red blood cell 6-thioguanine nucleotide, 6-thioinosinic acid and 6-methylmercaptopurine metabolites in a single sample. J Chromatogr. 1992 Nov 27;583(1):83-90. doi: 10.1016/0378-4347(92)80347-s. PMID: 1484095.

6: Ha T, Morgan SL, Vaughn WH, Eto I, Baggott JE. Detection of inhibition of 5-aminoimidazole-4-carboxamide ribotide transformylase by thioinosinic acid and azathioprine by a new colorimetric assay. Biochem J. 1990 Dec 1;272(2):339-42. doi: 10.1042/bj2720339. PMID: 2268263; PMCID: PMC1149705.

7: Bishop GA, Hall BM. Effects of immunosuppressive drugs on functions of activated T lymphocytes. Cyclosporine inhibition of gamma interferon production in the presence of interleukin. Transplantation. 1988 May;45(5):967-72. doi: 10.1097/00007890-198805000-00026. PMID: 3130699.

8: Lennard L. Assay of 6-thioinosinic acid and 6-thioguanine nucleotides, active metabolites of 6-mercaptopurine, in human red blood cells. J Chromatogr. 1987 Dec 25;423:169-78. doi: 10.1016/0378-4347(87)80340-7. PMID: 3443647.

9: Tomasovic SP, Higashikubo R, Cohen AM, Broom AD. Comparative kinetics of poly(6-thioinosinic acid) and 6-mercaptopurine treated L1210 cells. Cytometry. 1982 Jul;3(1):48-54. doi: 10.1002/cyto.990030111. PMID: 6889485.