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Rintatolimod

Rintatolimod

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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

Rintatolimod

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 Formula	C₂₈H₄₀N₉O₂₅P₃
Molecular Weight	995.6 g/mol
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	27
Rotatable Bond Count	12
Exact Mass	995.13481879 g/mol
Monoisotopic Mass	995.13481879 g/mol
Topological Polar Surface Area	517 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1600
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

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.)