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ISOPRINOSINE structure
ISOPRINOSINE structure

ISOPRINOSINE

Iupac Name:4-acetamidobenzoic acid;9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one;1-(dimethylamino)propan-2-ol
CAS No.: 36703-88-5
Molecular Weight:550.569
Modify Date.: 2022-12-08 12:20
1. Names and Identifiers
1.1 Name
ISOPRINOSINE
1.2 Synonyms

)(1:3) aviral delimmun imunovir inosine,compd.with1-(dimethylamino)-2-propanol4-(acetylamino)benzoate(salt inosinepranobex inosiplex

1.3 CAS No.
36703-88-5
1.4 CID
135449284
1.5 EINECS(EC#)
253-162-1
1.6 Molecular Formula
C24H34N6O9 (isomer)
1.7 Inchi
PBJNZCQJMWVIRT-WCYUCLFNNA-N
1.8 InChkey
PBJNZCQJMWVIRT-WCYUCLFNNA-N
1.9 Canonical Smiles
CC(O)CN(C)C.CC(=O)NC1=CC=C(C=C1)C(O)=O.OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
1.10 Isomers Smiles
CC(O)CN(C)C.CC(=O)NC1=CC=C(C=C1)C(O)=O.OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
2. Properties
2.1 Melting point
140-142°C
2.1 StorageTemp
Inert atmosphere,Room Temperature
3. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

5. Other Information
5.0 Merck
14,4976
5.1 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 therapy1,2. 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 vivo4,5.
5.2 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
5.3 Chemical Properties
White Solid
5.4 Uses
Isoprinosine
5.5 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
5.6 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.
5.7 Clinical Use
Treatment of mucocutaneous herpes simplex, genital warts, subacute sclerosing panencephalitis
5.8 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].
5.9 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].
5.10 Drug interactions
Potentially hazardous interactions with other drugs
None known
5.11 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
5.12 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.
6. Computational chemical data
  • Molecular Weight: 550.569g/mol
  • Molecular Formula: C24H34N6O9
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 1114.55464106
  • Monoisotopic Mass: 1114.55464106
  • Complexity: 658
  • Rotatable Bond Count: 14
  • Hydrogen Bond Donor Count: 13
  • Hydrogen Bond Acceptor Count: 22
  • Topological Polar Surface Area: 399
  • Heavy Atom Count: 79
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count: 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 7
  • CACTVS Substructure Key Fingerprint: AAADcfB//gAAAAAAAAAAAAAAAAAAAWJAAAAwYMEAAAAAAEAB1AAAHgAQCAAADBzhngY3+JfMFgCoAyfzfACCgC03EqAJ2IGofMiLfjrA3bGecYhv1gPb2ef4+SOeCAAAAAAAAAAQAAAAAAAAAAAAAAAAAA==
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