Idoxuridine
- CAS No.
- 54-42-2
- Chemical Name:
- Idoxuridine
- Synonyms
- IDU;1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-iodopyriMidine-2,4(1H,3H)-dione;ldoxuridine;IUDR;Stoxil;Herplex;DENDRID;Iododeoxyuridine;5-Indo-2ˊ-deoxyuridine;2'-DEOXY-5-IODOURIDINE
- CBNumber:
- CB7482614
- Molecular Formula:
- C9H11IN2O5
- Molecular Weight:
- 354.1
- MOL File:
- 54-42-2.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/4/9 22:15:29
| Melting point | 194 °C (lit.) |
|---|---|
| alpha | 280 º (c=1,1M NaOH) |
| Density | 1.7911 (estimate) |
| refractive index | 30 ° (C=1, 1mol/L NaOH) |
| storage temp. | 2-8°C |
| solubility | DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated) |
| form | Crystalline Powder |
| pka | 8.25(at 25℃) |
| color | White to slightly beige |
| Water Solubility | 1.6 g/L (20 ºC) |
| Sensitive | Air & Light Sensitive |
| Merck | 14,4891 |
| BRN | 30397 |
| InChIKey | XQFRJNBWHJMXHO-FSDSQADBSA-N |
| CAS DataBase Reference | 54-42-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Uridine, 2'-deoxy-5-iodo-(54-42-2) |
| EPA Substance Registry System | Uridine, 2'-deoxy-5-iodo- (54-42-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335-H341-H361 | |||||||||
| Precautionary statements | P201-P302+P352-P305+P351+P338-P308+P313 | |||||||||
| Hazard Codes | T,Xn | |||||||||
| Risk Statements | 45-46-61-40-68-62-36/37/38-63 | |||||||||
| Safety Statements | 53-45-36-22-36/37-26 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | YU7700000 | |||||||||
| F | 8-23 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29389090 | |||||||||
| Toxicity | LD50 i.p. in mice: 2.5 g/kg (Prusoff, 1979) | |||||||||
| NFPA 704 |
|
Idoxuridine price More Price(11)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | I7125 | 5-Iodo-2′-deoxyuridine ≥99% (HPLC) | 54-42-2 | 5G | ₹21422.68 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR2884 | Idoxuridine pharmaceutical secondary standard, certified reference material | 54-42-2 | 500MG | ₹25817.63 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | I7125 | 5-Iodo-2′-deoxyuridine ≥99% (HPLC) | 54-42-2 | 25G | ₹85582.45 | 2022-06-14 | Buy |
| TCI Chemicals (India) | I0258 | 5-Iodo-2'-deoxyuridine | 54-42-2 | 1G | ₹5900 | 2022-05-26 | Buy |
| TCI Chemicals (India) | I0258 | 5-Iodo-2'-deoxyuridine | 54-42-2 | 5G | ₹11200 | 2022-05-26 | Buy |
Idoxuridine Chemical Properties,Uses,Production
Chemical Properties
Crystalline Solid
Uses
Idoxuridine is an antiviral agent effective against herpes-simplex infections; in ophthalmie eyedrops, ointments, and solutions.
Indications
Idoxuridine (Herplex) is a water-soluble iodinated derivative of deoxyuridine that inhibits several DNA viruses including HSV, VZV, vaccinia, and polyoma virus. The triphosphorylated metabolite of idoxuridine inhibits both viral and cellular DNA synthesis and is also incorporated into DNA. Such modified DNA is susceptible to strand breakage and causes aberrant viral protein synthesis. Because of its significant host cytotoxicity, idoxuridine cannot be used to treat systemic viral infections. The development of resistance to this drug is common.
Definition
ChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-iodouracil as the nucleobase; used as an antiviral agent.
Pharmaceutical Applications
A halogenated pyrimidine analog originally synthesized as an
anticancer agent. Formulated in dimethylsulfoxide for topical
application and as a solution for ophthalmic use.
Activity is largely limited to DNA viruses, primarily HSV-1,
HSV-2 and VZV. HSV-1 plaque formation in BHK 21 cells
is sensitive to 6.25–25 mg/L; type 2 microplaques required
62.5–125 mg/L. RNA viruses are not affected, with the exception
of oncogenic RNA viruses such as Rous sarcoma virus.
Drug resistance is easily generated in vitro, and may be an
obstacle to treatment. However, there is little or no crossresistance
with newer nucleoside analogs.
It is poorly soluble in water, and aqueous solutions are
ineffective against infections other than those localized to the
eye. In animals, therapeutic levels are achieved in the cornea
within 30 min of ophthalmic application and persist for 4 h.
Penetration is otherwise poor, with only the biologically inactive
dehalogenated metabolite uracil entering the eye.
The drug is too toxic for systemic administration. Contact
dermatitis, punctate epithelial keratopathy, follicular conjunctivitis,
ptosis, stenosis and occlusion of the puncta and keratinization
of the lid margins occur in up to 14% of those
receiving ophthalmic preparations.
It is used in herpes keratitis, but has largely been superseded
by trifluridine or aciclovir.
Mechanism of action
Idoxuridine is a nucleoside containing a halogenated pyrimidine and is an analogue of thymidine. It acts as an antiviral agent against DNA viruses by interfering with their replication based on the similarity of structure between thymidine and idoxuridine. Idoxuridine is first phosphorylated by the host cell virusencoded enzyme thymidine kinase to an active triphosphate form. The phosphorylated drug inhibits cellular DNA polymerase to a lesser extent than HSV DNA polymerase, which is necessary for the synthesis of viral DNA. The triphosphate form of the drug is then incorporated during viral nucleic acid synthesis by a false pairing system that replaces thymidine. When transcription occurs, faulty viral proteins are formed, resulting in defective viral particles.
Clinical Use
The only FDA-approved use of idoxuridine is in the treatment of herpes simplex infections of the eyelid, conjunctiva conjunctiva, and cornea. It is most effective against surface infections because it has little ability to penetrate the tissues of the eye. intravenous idoxuridine was designated an orphan drug for the treatment of soft tissue sarcoma.
Side effects
Idoxuridine may cause local irritation, mild edema, itching, and photophobia. Corneal clouding and small punctate defects in the corneal epithelium have been reported. Allergic reactions are rare.
Safety Profile
Moderately toxic by intraperitoneal route. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Iand NOx.
Metabolism
Idoxuridine is metabolized rapidly in the body to iodouracil, uracil, and iodide. Metabolites are excreted in the urine.
Idoxuridine Preparation Products And Raw materials
Raw materials
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| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Otto Chemie Pvt. Ltd. | +91 9820041841 | Mumbai, India | 5873 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Chem Genes India Private Limited | 08048372510Ext 250 | Uttar Pradesh, India | 16 | 58 | Inquiry |
| Anand Agencies | 91-20-24454597 | Maharashtra, India | 2337 | 58 | Inquiry |
| Sisco Research Laboratories Pvt. Ltd. | +91-22-4268 5800 | Mumbai, India | 4317 | 58 | Inquiry |
| Pharmaffiliates Analytics & Synthetics (P) Ltd. | 91-172-5066494 | Haryana, India | 631 | 58 | Inquiry |
Related articles
- What is Idoxuridine?
- Idoxuridine is an analog of the pyrimidine nucleoside thymidine. It was synthesized in 1959 by William Prusoff as a possible a....
- Apr 13，2022
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