Idoxuridine | CAS#54-42-2 | MedKoo Biosciences

Idoxuridine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 120207

CAS#: 54-42-2

Description: Idoxuridine is an anti-herpesvirus antiviral and anticancer drug. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the iodine atom added to the uracil component blocks base pairing. It is used only topically due to cardiotoxicity. It was synthesized by William Prusoff in the late 1950s. Initially developed as an anticancer drug, idoxuridine became the first antiviral agent in 1962.

Chemical Structure

Idoxuridine

CAS# 54-42-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 120207
Name: Idoxuridine
CAS#: 54-42-2
Chemical Formula: C9H11IN2O5
Exact Mass: 353.97
Molecular Weight: 354.101
Elemental Analysis: C, 30.53; H, 3.13; I, 35.84; N, 7.91; O, 22.59

Price and Availability

Size	Price	Availability
1g	USD 250	2 Weeks
5g	USD 550	2 Weeks
10g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym:

IUPAC/Chemical Name: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione

InChi Key: XQFRJNBWHJMXHO-RRKCRQDMSA-N

InChi Code: InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

SMILES Code: O=C1NC(C(I)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Idoxuridine (5-Iodo-2′-deoxyuridine, 5-IUdR, IdUrd) is an iodinated thymidine analogue that competitively inhibits phosphorylases.
In vitro activity:	The model is used to perform a drug-repurposing study, with the main aim to identify existing drugs with the highest 3CLpro inhibition power. Among antiviral agents, lopinavir, idoxuridine, paritaprevir, and favipiravir showed the highest inhibition potential. Reference: Mol Divers. 2022 Oct;26(5):2631-2645. https://pubmed.ncbi.nlm.nih.gov/35001230/
In vivo activity:	Subsets of IdU+ cells expressed the osteoblast-lineage markers Runx2 and osteocalcin. The IdU+ cells expressing osteocalcin were lining the bone and were negative for the MSC marker p75. In conclusion, mouse periosteum contains nucleoside-label-retaining cells with a phenotype compatible with MSCs that are distinct from pericytes and osteoblasts. Reference: Eur Cell Mater. 2014 Mar 11;27:185-95; discussion 195. https://pubmed.ncbi.nlm.nih.gov/24614984/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	56.7	160.03
	PBS (pH 7.2)	5.0	14.12

Preparing Stock Solutions

The following data is based on the product molecular weight 354.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Novak J, Potemkin VA. A new glimpse on the active site of SARS-CoV-2 3CLpro, coupled with drug repurposing study. Mol Divers. 2022 Oct;26(5):2631-2645. doi: 10.1007/s11030-021-10355-8. Epub 2022 Jan 10. PMID: 35001230; PMCID: PMC8743077. 2. Almalki SA, Bawazeer TM, Asghar B, Alharbi A, Aljohani MM, Khalifa ME, El-Metwaly N. Synthesis and characterization of new thiazole-based Co(II) and Cu(II) complexes; therapeutic function of thiazole towards COVID-19 in comparing to current antivirals in treatment protocol. J Mol Struct. 2021 Nov 15;1244:130961. doi: 10.1016/j.molstruc.2021.130961. Epub 2021 Jun 24. PMID: 34188314; PMCID: PMC8222988. 3. Cherry HM, Roelofs AJ, Kurth TB, De Bari C. In vivo phenotypic characterisation of nucleoside label-retaining cells in mouse periosteum. Eur Cell Mater. 2014 Mar 11;27:185-95; discussion 195. doi: 10.22203/ecm.v027a14. PMID: 24614984.
In vitro protocol:	1. Novak J, Potemkin VA. A new glimpse on the active site of SARS-CoV-2 3CLpro, coupled with drug repurposing study. Mol Divers. 2022 Oct;26(5):2631-2645. doi: 10.1007/s11030-021-10355-8. Epub 2022 Jan 10. PMID: 35001230; PMCID: PMC8743077. 2. Almalki SA, Bawazeer TM, Asghar B, Alharbi A, Aljohani MM, Khalifa ME, El-Metwaly N. Synthesis and characterization of new thiazole-based Co(II) and Cu(II) complexes; therapeutic function of thiazole towards COVID-19 in comparing to current antivirals in treatment protocol. J Mol Struct. 2021 Nov 15;1244:130961. doi: 10.1016/j.molstruc.2021.130961. Epub 2021 Jun 24. PMID: 34188314; PMCID: PMC8222988.
In vivo protocol:	1. Cherry HM, Roelofs AJ, Kurth TB, De Bari C. In vivo phenotypic characterisation of nucleoside label-retaining cells in mouse periosteum. Eur Cell Mater. 2014 Mar 11;27:185-95; discussion 195. doi: 10.22203/ecm.v027a14. PMID: 24614984.

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1: Otto SE. Radiopharmaceuticals (Strontium 89) and radiosensitizers (idoxuridine). J Intraven Nurs. 1998 Nov-Dec;21(6):335-7. Review. PubMed PMID: 10392098.

2: Sondak VK, Robertson JM, Sussman JJ, Saran PA, Chang AE, Lawrence TS. Preoperative idoxuridine and radiation for large soft tissue sarcomas: clinical results with five-year follow-up. Ann Surg Oncol. 1998 Mar;5(2):106-12. PubMed PMID: 9527262.

3: Teshima H, Koi S, Yamakawa Y, Katase K, Umezawa S, Kato T, Hasumi K. [Treatment of genital condyloma acuminatum and vaginal intraepithelial neoplasia (VAIN) with topical idoxuridine and acrarubicin]. Nihon Sanka Fujinka Gakkai Zasshi. 1994 Oct;46(10):1065-8. Japanese. PubMed PMID: 7814938.

4: Pressacco J, Hedley DW, Erlichman C. ICI D1694 and idoxuridine: a synergistic antitumor combination. Cancer Res. 1994 Jul 15;54(14):3772-8. PubMed PMID: 8033097.

5: Greene RF, Collins JM. Effects of leucovorin on idoxuridine cytotoxicity and DNA incorporation. Cancer Res. 1990 Oct 15;50(20):6652-6. PubMed PMID: 2208128.

6: Happonen HP, Lassus A, Santalahti J, ForsstrÃ¶m S, Lassus J. Topical idoxuridine for treatment of genital warts in males. A double-blind comparative study of 0.25% and 0.5% cream. Genitourin Med. 1990 Aug;66(4):254-6. PubMed PMID: 2202655; PubMed Central PMCID: PMC1194524.

7: Happonen HP, Lassus A, Santalahti J, Forsstrom S, Lassus J. Combination of laser-therapy with 0.5% idoxuridine cream in the treatment of therapy-resistant genital warts in male patients: an open study. Sex Transm Dis. 1990 Jul-Sep;17(3):127-9. PubMed PMID: 2174190.

8: Hasumi K. A trial of topical idoxuridine for vulvar condyloma acuminatum. Br J Obstet Gynaecol. 1987 Apr;94(4):366-8. PubMed PMID: 3555605.

9: Hasumi K, Kobayashi T, Ata M, Saka N. [Topical idoxuridine for vulvar condyloma acuminatum]. Nihon Sanka Fujinka Gakkai Zasshi. 1986 Feb;38(2):277-9. Japanese. PubMed PMID: 3958525.

10: Hasumi K, Kobayashi T, Ata M. Topical idoxuridine for genital condyloma acuminatum. Lancet. 1984 Apr 28;1(8383):968. PubMed PMID: 6143908.

11: Koppang HS, Aas E. Squamous carcinoma induced by topical idoxuridine therapy? Br J Dermatol. 1983 Apr;108(4):501-3. PubMed PMID: 6838777.

12: Brun Ugstad M. [Cancer development after idoxuridine therapy?]. Tidsskr Nor Laegeforen. 1982 Nov 20;102(32):1732-3. Norwegian. PubMed PMID: 7167946.

13: Silvestri DL, Corey L, Holmes KK. Ineffectiveness of topical idoxuridine in dimethyl sulfoxide for therapy for genital herpes. JAMA. 1982 Aug 27;248(8):953-9. PubMed PMID: 7047788.

14: Graczyk J, Kowalczyk K, Pakulska W, Szadowska A. [Effect of selected piperazine derivatives on the metabolic clearance rate of idoxuridine-I-125 in mice with transplanted leukemia L1210]. Acta Pol Pharm. 1981;38(6):717-21. Polish. PubMed PMID: 7348532.

15: Heineman HS, Breen FA. Herpes simplex encephalitis in Hodgkins disease. Isolation of drug-sensitive virus from brain following unsuccessful treatment with idoxuridine. Cancer. 1975 Oct;36(4):1344-7. PubMed PMID: 169986.

16: Griswold DE, Heppner GH, Calabresi P. Stimulation of hemolysin plaque-forming cells by idoxuridine. Cancer Res. 1975 Jan;35(1):88-92. PubMed PMID: 1089043.

17: DvorÃ¡k O, AndrÃ½sek O, StrÃ¡nskÃ¡ E. [The possibility of selective chemotherapy of progressive recurring ovarian carcinoma with the aid of cytodiagnosis and incorporation of tagged idoxuridine]. Geburtshilfe Frauenheilkd. 1969 Jul;29(7):648-53. German. PubMed PMID: 5799686.

18: Porschen W, Feinendegen L. [In vivo determination of the cell loss rate in experimental neoplasms using radioactively marked idoxuridine]. Strahlentherapie. 1969 Jun;137(6):718-23. German. PubMed PMID: 5355170.

19: Waltuch G, Sachs F. Herpes zoster in a patient with Hodgkin's disease. Treatment with idoxuridine. Arch Intern Med. 1968 May;121(5):458-62. PubMed PMID: 5645723.

20: JOHNSON RO, KISKEN WA, CURRERI AR. SQUAMOUS CELL CARCINOMA OF ORAL CAVITY; INTRA-ARTERIAL INFUSION WITH FLUOROURACIL AND IDOXURIDINE. Arch Surg. 1965 May;90:760-3. PubMed PMID: 14280239.

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