Cidofovir

Anti-CMV drug;inhibitor of viral DNA syntheis CAS# 113852-37-2

Cidofovir

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Chemical structure

Cidofovir

3D structure

Chemical Properties of Cidofovir

Cas No. 113852-37-2 SDF Download SDF
PubChem ID 466146 Appearance Powder
Formula C8H14N3O6P M.Wt 279.19
Type of Compound N/A Storage Desiccate at -20°C
Synonyms GS 0504; HPMPC; (S)-HPMPC
Solubility Soluble to 12 mg/mL (42.98 mM) in Water
Chemical Name [1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid
SMILES C1=CN(C(=O)N=C1N)CC(CO)OCP(=O)(O)O
Standard InChIKey VWFCHDSQECPREK-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Cidofovir

DescriptionCidofovir is an anti-CMV drug which can suppress CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription. IC50 Value: Target: CMV DNA polymerase in vitro: The minimum concentrations of (S)-HPMPC required to inhibit CMV plaque formation by 50% was microgram/ml. The selectivity indices of (S)-HPMPC, as determined by the ratio of the 50% inhibitory concentration for cell growth to the 50% inhibitory concentration for plaque formation for CMV (AD-169 strain), was 1,500 [1]. The time course of uptake of HPMPC into Vero cells was linear between 10 and 75 min and proportional to the concentration in the medium from 10(-6) to 10(-2) M. HPMPC uptake was temperature sensitive and the rate of uptake was considerably lower at 27 degrees than at 37 degrees and almost totally inhibited at 4 degrees [2]. in vivo: Levels of cidofovirin serum following intravenous infusion were dose proportional over the dose range of 1.0 to 10.0 mg/kg of body weight and declined biexponentially with an overall mean +/- standard deviation terminal half-life of 2.6 +/- 1.2 h (n = 25). Approximately 90% of the intravenous dose was recovered unchanged in the urine in 24 h. The overall mean +/- standard deviation total clearance of the drug from serum (148 +/- 25 ml/h/kg; n = 25) approximated renal clearance (129 +/- 42 ml/h/kg; n = 25), which was significantly higher (P < 0.001) than the baseline creatinine clearance in the same patients (83 +/- 21 ml/h/kg; n = 12) [3]. Positive CMV urine cultures reverted to negative in 2 of 8 patients receiving doses of < or = 1.5 mg/kg twice weekly and 11 of 13 patients receiving higher doses. Cidofovir has in vivo anti-CMV activity demonstrated by prolonged clearing of CMV viruria, although this observation is tempered by the fact that clearance of viremia could not be demonstrated [4]. Toxicity: Patients receiving 0.5 or 1.5 mg/kg twice weekly experienced no serious toxicity. The first two patients who received 5 mg/kg twice weekly developed glycosuria and 2+ proteinuria. Subsequent patients received concomitant probenecid to attempt to ameliorate renal toxicity [4]. Clinical trial: FDA approved drug

References:
[1]. Snoeck R, et al. (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. Antimicrob Agents Chemother. 1988 Dec;32(12):1839-44. [2]. Connelly MC, et al. Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in Vero cells. Biochem Pharmacol. 1993 Sep 14;46(6):1053-7. [3]. Cundy KC, et al. Clinical pharmacokinetics of cidofovir in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 1995 Jun;39(6):1247-52. [4]. Polis MA, et al. Anticytomegaloviral activity and safety of cidofovir in patients with human immunodeficiency virus infection and cytomegalovirus viruria. Antimicrob Agents Chemother. 1995 Apr;39(4):882-6.

Cidofovir Dilution Calculator

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Cidofovir Molarity Calculator

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Preparing Stock Solutions of Cidofovir

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5818 mL 17.909 mL 35.8179 mL 71.6358 mL 89.5448 mL
5 mM 0.7164 mL 3.5818 mL 7.1636 mL 14.3272 mL 17.909 mL
10 mM 0.3582 mL 1.7909 mL 3.5818 mL 7.1636 mL 8.9545 mL
50 mM 0.0716 mL 0.3582 mL 0.7164 mL 1.4327 mL 1.7909 mL
100 mM 0.0358 mL 0.1791 mL 0.3582 mL 0.7164 mL 0.8954 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Cidofovir

Cidofovir(Vistide) is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis. (IC50= 0.94 μM) A wild type HCMV laboratory strain (AD 169) and 3 ganciclovir-resistant clinical isolates(generated as a result of Ganciclovir t

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References on Cidofovir

Reduced cell viability and apoptosis induction in human thyroid carcinoma and mesothelioma cells exposed to cidofovir.[Pubmed:28223140]

Toxicol In Vitro. 2017 Jun;41:49-55.

Besides its well-recognized antiviral activity, Cidofovir (CDV) has been shown to exert anticancer properties both within in vitro and in vivo models. The aim of this study was to evaluate the effects of CDV on still unexplored cultured cancer cells from human mesothelioma as well as breast, colon, liver, lung, prostate, and thyroid carcinomas. Overall, a dose- and time-dependent inhibition of cell viability was observed after CDV exposure. To clarify the mechanisms underlying CDV action, apoptotic cell death was investigated in two infected cell lines [Ist-Mes1 and Ist-Mes2 mesothelioma cells (SV40+)] and in two uninfected cell lines (NCI-H2425 mesothelioma cells and FTC-133 thyroid cancer cells), which resulted the most sensitive to CDV treatment. Reduced expression of procaspase-3 and increased expression of PARP p85 fragment were observed in both infected and uninfected mesothelioma cells, indicating apoptosis induction by CDV in a virus-independent manner. Similarly, the increase of the pro-apoptotic proteins p53, cytochrome c and caspase-3, the decrease of the survival protein Bcl-x, and the increment of Bax/Bcl-2 ratio revealed the occurrence of apoptosis in CDV-treated FTC-133. The presence of nuclear DNA fragmentation confirmed apoptotic cell death by CDV. Overall, our findings warrant further investigations to explore the therapeutic potential of CDV for human mesothelioma and follicular thyroid carcinoma.

Comparison of cidofovir and the measles, mumps, and rubella vaccine in the treatment of recurrent respiratory papillomatosis.[Pubmed:28231366]

Ear Nose Throat J. 2017 Feb;96(2):69-74.

We conducted a retrospective study of the use of Cidofovir and the measles, mumps, and rubella (MMR) vaccineas adjunctive treatments to lesion debridement in patients with recurrent respiratory papillomatosis (RRP). Our study population was made up of 15 children-7 boys and 8 girls, aged 1 to 16 years at diagnosis (mean: 6.2)-with pathologically confirmed RRP who had been followed for at least 1 year. In addition to demographic data, we compiled information on disease severity, the type of adjunctive treatment administered to each patient, the frequency of debridements, the length of observation, and remission rates. Of the 15 patients, 5 had been treated with Cidofovirafter debridement (Cidofovir-only group), 6 were treated with MMR vaccine after debridement (MMR-only group), 3 were treated with one and later switched to the other based on parental preference, and 1 received neither treatment, only debridement. The initial mean Derkay disease severity scores were 12.6 for the Cidofovir-only group and 11.0 for the MMR-only group (p = 0.61). The Cidofovir-only patients underwent an average of 11.8 adjunctive treatments and the MMR-only patients an average of 17.7 (p = 0.33). The average duration of observation was 44.0 months in the Cidofovir-only group and 64.7 months in the MMR-only group (p = 0.29). Remission rates were 20% in the Cidofovir-only group and 50% in the MMR-only group (p = 0.54). Our study found insufficient evidence of any significant differences between Cidofovir and the MMR vaccinein terms of the number and frequency of adjunctive treatments and the rates of remission.

Description

Cidofovir suppresses virus replication by selective inhibition of viral DNA synthesis.

Keywords:

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