Isoprinosine Chemical Properties

Melting point:

140-142°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated), Water (Slightly)

form 

Solid

color 

White to Off-White

Merck 

14,4976

InChI

InChI=1/C10H12N4O5.C9H9NO3.C5H13NO/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18;1-6(11)10-8-4-2-7(3-5-8)9(12)13;1-5(7)4-6(2)3/h2-4,6-7,10,15-17H,1H2,(H,11,12,18);2-5H,1H3,(H,10,11)(H,12,13);5,7H,4H2,1-3H3/t4-,6-,7-,10-;;/s3

InChIKey

PBJNZCQJMWVIRT-JHVGCDEENA-N

SMILES

O[C@@H]1[C@@H]([C@@H](CO)O[C@H]1N1C=NC2C(N=CNC1=2)=O)O.C(N(C)C)C(O)C.N(C1C=CC(C(=O)O)=CC=1)C(=O)C |&1:1,2,3,7,r|

Safety Information

HS Code 

2934.99.9001

Toxicity

LD50 in mice and rats (mg/kg): >4000 orally and i.p. (Gordon)

Isoprinosine Usage And Synthesis

Description

ISOPRINOSINE (also known as inosine pranobex) an antiviral drug combing of inosine and dimepranol acedoben (a salt of acetamidobenzoic acid and dimethylaminoisopropanol) in a ratio of 1 to 3. It is mainly used for treating the rare measles complication subacute sclerosing panencephalitis in conjunction with intrathecal interferon therapy^1,2. In UK, it is also indicated for mucocutaneous infections due to herpes simplex virus (type 1 and type 2) and for treatment of genital warts as adjunctive therapy to podophyllin or carbon dioxide laser1. It also has certain efficacy in the treatment of AIDS and some other acquired immunodeficiency such as aged patients, cancer patients, severely burned patients, ill patients, and surgery patients³. Preclinical studies have demonstrated that isoprinosine can inhibit the growth of both DNA and RNA viruses as well as potentiate cell-mediated immune response both in vitro and in vivo^4,5.

Sources

1. https://en.wikipedia.org/wiki/Inosine_pranobex
2. Waldman, R. H., and R. Ganguly. "Therapeutic efficacy of inosiplex (Isoprinosine) in rhinovirus infection. " Annals of the New York Academy of Sciences 284.1(1977):153–160.
3. https://www.ncbi.nlm.nih.gov/pubmed/2446760
4. https://www.ncbi.nlm.nih.gov/pubmed/83189
5. https://www.drugbank.ca/drugs/DB13156

Chemical Properties

White powder, odorless and tasteless. Soluble in water.

Uses

Isoprinosine is a new combination of active substances for the treatment of chronic systemic diseases such as cancer. Isoprinosine is an immunomodulator; antiviral. The ratio is between 1: 2 : 2 to 1 : 3 : 3

Biological Activity

isoprinosine is a complex of acetaminobenzoic acid, dimethylaminoisopropanol, and inosine in a 3:3:1 ratio with immunomodulatory effects.immunotherapy is the treatment of disease by inducing, enhancing, or suppressing an immune response. immunomodulatory regimens usually have fewer side effects than existing drugs, such as less potential for creating resistance when treating microbial disease.

Mechanism of action

Isoprinosine is thought to act through a receptor for an inosine-like compound on T cell precursors. In vivo it appears to induce the production of more mature T cells and there is some evidence that it can increase the CD4:CD8 ratio in a variety of conditions. In addition, Isoprinosine enhances B-lymphocyte activity, possibly through effects on helper T cells. It also increases macrophage phagocytosis, releases cytokines that induce macrophage proliferation, including immune interferon and interleukin-1 (IL-1) and IL-2, and potentiates T-cell mitogens.

Clinical Use

Treatment of mucocutaneous herpes simplex, genital warts, subacute sclerosing panencephalitis

in vitro

previous study found that increasing concentrations of isoprinosine (50-400 μg/ml) could produce progressively growing inhibitory effect on hhv-1 replication. the combination of 1000 iu/ml ifn-α and isoprinosine could result in enhanced anti-hhv activity [1].

in vivo

previous study demonstrated the positive effect of isoprinosine treatment on persistent infection of balb/c mice with murine gammaherpesvirus 68. increased number of leukocytes, increased percentage of neutrophils, elevated levels of virus-neutralizing antibodies, reduced number of atypical lymphocytes and reduced virus titers were detected in the examined organs after a 14-day treatment. the positive effect of isoprinosine therapy vanished after 120-150 days [2].

Metabolism

Hepatically metabolised. The major excretion product of the inosine moiety is uric acid, while the p-acetamidobenzoic acid and N,N-dimethylamino- 2-propanol components are excreted in the urine as glucuronidated and oxidised products, respectively, as well as being excreted unchanged

References

[1] majewska a, lasek w, janyst m, mynarczyk g. in vitro infibition of hhv-1 replication by inosine pranobex and interferon-α. acta pol pharm. 2016 may-jun;73(3):637-44.
[2] janíková o, anicová l, briestenská k, mistríková j. the effect of isoprinosine treatment on persistent infection of balb/c mice infected with murine gammaherpesvirus 68. acta virol. 2017;61(1):32-38. doi: 10.4149/av_2017_01_32.
[3] beran j, alapová e, pajdel m; isoprinosine study (ewo iso-2014/1) team. inosine pranobex is safe and effective for the treatment of subjects with confirmed acute respiratory viral infections: analysis and subgroup analysis from a phase 4, randomised, placebo-controlled, double-blind study. bmc infect dis. 2016 nov 7;16(1):648.

Isoprinosine(36703-88-5)Related Product Information

• Aluminium isopropoxide
• Sodium propan-2-olate
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Ethopabate
• IPTG
• Shikimic acid
• Ribavirin
• Acyclovir
• Polyinosinic acid-polycytidylic acid
• 1-Dimethylamino-2-propanol
• Inosine
• Isoprinosine