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Technical details about Rintatolimod, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 38640-92-5, [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-1h-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate;[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, Schembl27306, Dtxsid50191952
Molecular Formula
C28H40N9O25P3
Molecular Weight
995.6  g/mol
InChI Key
KNUXHTWUIVMBBY-JRJYXWDASA-N

Rintatolimod is a synthetic derivative of inosinic acid with antiretroviral and immunomodulatory properties. Atvogen acts through a number of pathways to stimulate intracellular antiviral activity of the immune system: it stimulates interferon production; activates the oligoadenylate synthase-RNase L pathway; stimulates natural killer cell activity; and acts as a non-mitogenic stimulator of the immune system. This agent also inhibits replication of human immunodeficiency virus (HIV) in vitro. (NCI04)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
2.1.2 InChI
InChI=1S/C10H13N4O8P.C9H14N3O8P.C9H13N2O9P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17;10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18;12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20);1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18);1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,10-;2*4-,6-,7-,8-/m111/s1
2.1.3 InChI Key
KNUXHTWUIVMBBY-JRJYXWDASA-N
2.1.4 Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)O)O)O.C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)O.C1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O
2.1.5 Isomeric SMILES
C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O.C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O.C1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. (ri(n).r(c(12)u)n)

2. Ampligen

3. Mismatched Double-stranded Rna

4. Poly(i)-poly(c12u)

5. Poly(i).poly(c12,u)

6. Poly(inosinic Acid) Poly(cytidylic(12), Uridylic)acid

2.2.2 Depositor-Supplied Synonyms

1. 38640-92-5

2. [(2r,3s,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate;[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-1h-purin-9-yl)oxolan-2-yl]methyl Dihydrogen Phosphate;[(2r,3s,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl Dihydrogen Phosphate

3. Schembl27306

4. Dtxsid50191952

2.3 Create Date
2019-01-15
3 Chemical and Physical Properties
Molecular Weight 995.6 g/mol
Molecular Formula C28H40N9O25P3
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count27
Rotatable Bond Count12
Exact Mass995.13481879 g/mol
Monoisotopic Mass995.13481879 g/mol
Topological Polar Surface Area517 Ų
Heavy Atom Count65
Formal Charge0
Complexity1600
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


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