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The aim of the presented work is the comparison of aqueous and 1-octanol solubilities of different acyclovir derivatives and their hydroxypropyl-I?-cyclodextrin inclusion complexes. 1 IntroductionHerpes viruses are the most wide-spread DNA human viruses, so searching for new efficient drugs possessing good antiviral activity is very important. In our earlier work [16] we determined aqueous and 1-octanol solubility and partition coefficient between these two solvents of acyclovir and chosen acyclovir derivatives.
An aqueous solution at a concentration of one half of the solubility of the substance examined was prepared. The initial concentration in the aqueous solution and the final concentration of the substance after each measurement were determined by spectrophotometry. 3 Results and DiscussionAcyclovir derivatives which are the subject of this work are potential drugs, so it is necessary to know their solubility in aqueous solutions and partition coefficient between water and 1-octanol, which mimics cell membrane. Analysis of the results presented in Tables 1 and 2 indicates that very low aqueous solubility of acyclovir derivatives substituted by aromatic groups, compounds with good antiviral activity towards herpes viruses [15], which is a barrier for their use as drugs. One exception is acyclovir derivative 7 possessing a tert-butyl substituent (6-t-But-TACV) where this dependence is not linear over the whole range of cyclodextrin concentrations, showing an An type of solubility diagram.
0 is the solubility of the sample in solutions without cyclodextrin, obtained by determination of saturated solution concentration of acyclovir derivative solutions. Table 4 presents values of stability constants of cyclodextrin inclusion complexes and enhancement of aqueous solubility connected with the presence of cyclodextrin in the solutions. Jakarta, DeskripsiAcyclovir termasuk golongan obat antivirus yang digunakan untuk mengobati infeksi yang disebabkan oleh virus jenis tertentu.
Zovirax is used for treating chickenpox (varicella) or shingles (herpes zoster) and treating or suppressing genital herpes infections.
INDICATIONS Zovirax is used for treating chickenpox (varicella) or shingles (herpes zoster) and treating or suppressing genital herpes infections. Medicines that may harm the kidney (eg, aminoglycoside antibiotics [eg, gentamicin], amphotericin B, cyclosporine, nonsteroidal anti-inflammatory drugs [NSAIDs] [eg, ibuprofen], tacrolimus, vancomycin) because the risk of kidney side effects may be increased. Zovirax may cause dizziness, lightheadedness, or fainting; alcohol, hot weather, exercise, or fever may increase these effects.
Lab tests, including kidney function and serum urea nitrogen (BUN), may be performed while you use Zovirax. Use Zovirax with caution in the elderly; they may be more sensitive to its effects, especially confusion, drowsiness, or hallucinations. Zovirax is not recommended for use in children younger 2 years; safety and effectiveness in these children have not been confirmed. Lasuna or Garlic, as it is more commonly known, is a potent herb helpful in preventing hypercholesterolemia. Vermox is used to treat infections caused by worms such as whipworm, pinworm, roundworm, and hookworm.
The drug known by its generic name, Acyclovir, belongs to the synthetic nucleoside analogues group of drugs used primarily to treat particular viral infections. Manufactured by GlaxoSmithKline and marketed as Zovirax, it comes in liquid, capsule and tablet forms.
But acyclovir remains the oldest form of treatment for the herpes simplex 1 and simplex 2 viruses, or cold sores and genital herpes, which cause infections in those afflicted with HIV. When a virus takes over a living cell and reproduces itself, at the host cell’s expense, acyclovir is converted into an activated form by the same virus, enabling it to use acyclovir’s active form instead of the nucleoside which it normally uses in the manufacture of DNA; DNA is a crucial element in the replication of a virus. Simply put, cells which have been virally infected tend to absorb more of the acyclovir than their normal counterparts; therefore there is more conversion of it into active forms, a condition which helps prolong the anti-viral activity. Acyclovir is not a curative treatment for viral infections but it can shorten the duration of the infections and lessen their possibility of developing into more serious medical conditions.
In initial cases of genital herpes, acyclovir helps reduce lesions and decreases severity and frequency of infections which are recurrent. Depending on the severity of the genital herpes infection of an individual who has it for the first time, an oral dosage of acyclovir at 400mg thrice a day has been recommended by the CDCP or Center for Disease Control and Prevention; this dosage has to be ingested between seven and ten days. The patient may then choose to have daily or episodic therapy; the former is also known as suppressive therapy. Patients who have existing conditions of HIV should take 400mg of oral acyclovir thrice a day between five and ten days. While there haven’t been sufficient clinical studies on the use of acyclovir by pregnant women and subsequent adverse effects, nursing women are cautioned against ingesting acyclovir since this can be transferred to an infant as an excretion in breast milk. All prices provided on this website are estimates only and will vary depending on your insurance and location. The antiviral drugs have been used from 1960s, but new drugs with higher bioactivity and lower toxicity are continually being developed and tested. These factors have significant influence on absorption of drugs by cells and therapeutic effects.
On the other hand, the studied compounds have higher solubility in 1-octanol and in water saturated with 1-octanol than in pure water, which suggests that the drugs may have good permeation properties. Values of the correlation parameters a and b for tricyclic acyclovir derivatives complexed by cyclodextrin are presented in Table 3.
The highest values of stability constants and 3a€“7 fold enhancement of solubility are observed for compounds possessing aromatic groups, which may be bound inside the cyclodextrin cavity. Obat ini dapat mengobati luka ataupun benjolan berisi air di sekitar mulut yang disebabkan oleh herpes simpleks, herpes zoster dan cacar air.


Acyclovir is a prescriptive medication that prevents the division and multiplication of viruses responsible for said infections. When the active acyclovir is incorporated into a new virus in the DNA, production of DNA stops.
Taking acyclovir for treatment of genital herpes can help reduce its severity or prevent it from further recurrences. The latter is experienced as a painful rash which could develop several years after having had chicken pox with the reactivation of the virus. For shingles, acyclovir helps reduce pain, shorten the duration for healing, and halts the formation of more lesions and further spread of the virus. Acyclovir may be used intravenously for patients who have severe cases of genital herpes as well as those whose immune systems are compromised. Those who elected episodic therapy can choose to take acyclovir orally at 400mg thrice daily for a total of five days, 800mg thrice daily for a total of two days or 800mg twice a day for a total of five days.
For suppressive therapy, the CDCP recommends 400mg of oral acyclovir twice daily; those who are already infected with HIV should take it between 400mg and 800mg two or three times daily.
The aqueous solubilities of the compounds are very low but may be enhanced by complexation with hydroxypropyl-I?-cyclodextrin, especially if the acyclovir derivatives have aromatic groups which may be included in the cyclodextrin cavity. The first antiviral drugs: synthetic analogs of pyrimidinea€“idoxyuridine, trifluridine and vidarabine, were synthesized in 1960 [1]. The work showed extremely low aqueous solubilities (10a?’3 to 10a?’5 molA·dma?’3) for the main group of these compounds, especially with aromatic substituents. They were purified by recrystallization and the resulting compounds were homogenous according to HPLC and 1H NMR analysis.The hydroxypropyl-I?-cyclodextrin (HP-I?-CD) was purchased from Janssen Drug Delivery System (USA), R81216 no 30 221 54, and used without additional purification. For each complex energy optimization 100 cycles of molecular mechanic and molecular dynamic calculations were performed. Values of water and 1-octanol solubility of tricyclic acyclovir derivatives are shown in Table 1. The main reason for the low solubility of tricyclic acyclovir derivatives with aromatic groups in water is the high hydrophobicity of these substituents. The linearity of acyclovir derivative concentration versus cyclodextrin concentration in solutions and slope of line being lower than unity suggest 1:1 stoichiometry of acyclovir derivativea€”cyclodextrin complexes [29].
Obat ini juga dapat digunakan untuk mengobati herpes genital (herpes pada organ intim).Acyclovir merupakan obat antivirus, namun sebenarnya bukan obat untuk membunuh virus herpes ataupun cacar air. Check with your health care provider before you start, stop, or change the dose of any medicine. Use a sunscreen or wear protective clothing if you must be outside for more than a short time.
You can also be contagious and spread the herpes virus but not have any signs or symptoms at all. FDA (Food and Drug Administration) approved the drug for use against the virus known as varicella-zoster in the treatment of viral infections which caused shingles and chicken pox. A study published last year, however, revealed that herpes strains which are resistant to acyclovir could develop over a certain period of time. Aside from acyclovir’s availability in 200 mg capsules, 400mg and 800mg tablets, and 200mg and 5ml liquid suspension, it is also available as a 50mg or 40ml injection, a 500mg and 1000mg powder and as 5% ointment.
There have been reports of seizures, hepatitis, agitation, hypersensitivity reaction, muscle pain, and anemia, all of which must be reported to the patient’s doctor for advisement. The values of 1-octanola€“water partition coefficients of acyclovir derivatives, obtained using extraction experiments, showed a similar sequence as the solubility results in 1-octanol.
KH2PO4 and Na2HPO4 salts used for preparation of buffer solutions were of analytical grade (POCh, Gliwice, Poland). Then 10 optimized structures of complexes with the lowest energy of complexation were taken and average values of energy of complexation and surfaces of acyclovir derivative and cyclodextrin were determined.
Use of cyclodextrins, which can include aromatic groups into their cavity, may enhance the aqueous solubility of such compounds. Virus yang menyebabkan infeksi terus hidup dalam tubuh, namun obat ini dapat mengurangi keparahan dan mempercepat penyembuhan.Obat ini membantu menyembuhkan luka atau benjolan yang timbul dengan lebih cepat, mencegah munculnya luka atau benjolan baru, dan mengurangi rasa sakit serta gatal.
Doctors have also prescribed acyclovir in the treatment of the Epstein-Barr virus which causes mononucleosis. Additionally, some molecular mechanics and molecular dynamic calculations were performed to determine optimized structures of acyclovir derivative complexes with I?-cyclodextrin treated as a model. Acyclovir, 1, which is a substituted guanine, belongs to the next generation of antiviral drugs. Calculations were performed with I?-cyclodextrin because hydroxypropyl-I?-cyclodextrin used in experiments doesna€™t have an exactly defined structure.
Solubilities of the studied compounds in 1-octanol shows the opposite tendency, the solubility is smaller for compounds 1a€“7, substituted by alkyl or halogen group. For this purpose we used several cyclodextrins and hydroxypropyl-I?-cyclodextrin was chosen as being more efficient for complexating the tricyclic acyclovir derivatives [20]. The low concentration of acyclovir derivative in buffer saturated with 1-octanol and containing cyclodextrin is connected with complexation of 1-octanol in the cyclodextrin cavity that prevents complexation of 6-Ph-O-Me-TACV. Selain itu, pada orang dengan sistem kekebalan yang lemah, obat ini dapat mengurangi risiko virus menyebar ke bagian tubuh lain dan menyebabkan infeksi serius. This drug, synthesized in 1977 by Ellion and coworkers [2], was registered in 1982 and now is a well known, selective, antiviral agent [1].


The low aqueous solubility of tricyclic acyclovir derivatives is disadvantageous for drug application and absorption by cells, so enhancement of their solubility seems to be very important. Additionally, both solubility of compounds 1a€“12 in water saturated with 1-octanol, and in 1-octanol saturated with water, were determined and compared with the previous results. If it is almost time for your next dose, skip the missed dose and go back to your regular dosing schedule.
The toxicity of acyclovir is lower than other antiviral dugs, due to its acyclic sugar chain. One of the ways of enhancing solubility of tricyclic analogs of acyclovir in aqueous solutions can be the formation of inclusion complexes with cyclodextrins. Compounds for which the aqueous solubility is higher than the solubility in 1-octanol are less soluble if the water is saturated in 1-octanol and more soluble in 1-octanol saturated with water. Figure 4 shows the dependence of acyclovir derivative on cyclodextrin concentration for three compounds TACV, 2-Br-6-Me-TaCV and 6-Phe TACV. Complexation of such drugs by cyclodextrin enhances their aqueous solubility but in contact with 1-octanol, which mimics the cell membrane, the drug is easily released from the cyclodextrin complex as a result of competitive complexation of 1-octanol.
Acyclovir, after phosphorylation of the sugar chain, which takes place in infected cells, can inhibit replication of viruses HSV-1 and HSV-2. Natural and substituted cyclodextrins are known as solubilizing agents for many drugs used in pharmacy, acting by forming inclusion and non-inclusion complexes with them [19]. Solubilities of acyclovir derivatives with aromatic groups, which are more soluble in 1-octanol than in water, are higher if water is saturated with 1-octanol. Several derivatives of acyclovir, obtained by modification of acyclic chain, have been synthesized and registered as drugs [1, 3]. Native and substituted cyclodextrins are generally nontoxic and may be used in pharmacy, mainly as solubilizers, but sometimes as stabilizers or in order to enhance bioactivity or reduce local drug irritation [18]. Hydroxypropyl-derivatives of I±-, I?-, and I?-cyclodextrins are especially suitable for drug formulation due to their amorphous form in the solid state. Compounds 4a€“9 and 11a€“12 were chosen for these studies, because their aqueous solubility is very low and should be enhanced for pharmaceutical applications. Similar dependences of aqueous solubility of both groups of the studied compounds were observed at higher temperatures 35 and 45 A°C.
Other examples of acyclovir derivatives registered as antiviral drugs are prodrugs, which are bioactive only after disintegration to acyclovir in the human body.
Now, worldwide more than 40 different drugs are marketed in the form of native and substituted cyclodextrin complexes.Our study on complexation of chosen tricyclic acyclovir derivatives in aqueous buffered solutions indicates significant enhancement of solubility of the studied compounds, especially these possessing aromatic substituents [20]. Additionally, their structures suggested that these compounds may be come complexed by cyclodextrins, especially tricyclic acyclovir derivatives possessing aromatic substituents.
Application of antiviral drugs as acyclovir prodrugs, like valacyclovir or famciclovir, gives the possibility of enhancing the absorption of acyclovir in the human body. The increase of solubility is mainly caused by inclusion of hydrophobic groups inside the cyclodextrin cavity. In the case of application of valacyclovir, absorption is four times higher than by application of acyclovir [1].Some guanine substituted acyclovir derivatives were synthesized by De Clerq and coworkers [4, 5]. The complexation of alkyl and aromatic parts of tricyclic acyclovir derivatives in cyclodextrin cavities was confirmed by 1H NMR. Those derivatives have somewhat greater antiviral activity towards HSV viruses than the parent drug. Differential scanning calorimetry (DSC) experiments also indicate the existence of cyclodextrin complexes with studied compounds in the solid state [19].In the literature, there are only a few reports of acyclovir and their derivatives complexed with cyclodextrins [21a€“26]. Tricyclic acyclovir derivatives synthesized by Golankiewicz and coworkers have high antiviral activity and good fluorescent properties, important for monitoring their concentration in body fluids. Stability constants of these complexes and the enhancement of aqueous solubility are low, but results of in vitro experiments indicated that stability, absorption and permeation of drugs used as cyclodextrin complexes are higher than those of the pure drugs [25, 26].The aim of our work is the comparison of aqueous and 1-octanol solubilities of tricyclic acyclovir derivatives possessing high antiviral activity and their cyclodextrin complexes, and connecting these results with the values of their partition coefficients between water and 1-octanol determined by extraction experiments. After 7 days equilibrium was reached and then the suspensions were centrifuged and the absorbance of the studied compounds was measured by UVa€“Vis spectrophotometry using a Shimadzu UV 2401 PC Spectrometer equipped with a thermostatically controlled cell compartment.
Their synthesis, structures, antiviral and spectral properties have been the subject of many publications [6a€“14]. Additionally, molecular modeling and molecular dynamic optimizations of cyclodextrin inclusion complexes with tricyclic acyclovir analogs were performed in order to explain structures and the physicochemical properties of the complexes. During the measurement of absorbance, a buffered-solution of HP-I?-CD, of the same concentration as in the studied solution, was always put as the reference.
Pada pengobatan akut Hepes zoster800 mg setiap 4 jam, 5xsehari selama 7-10 hari per oral.2. The bioactivity and spectral properties of tricyclic acyclovir derivatives were summarized by Golankiewicz and Ostrowski in a mini review [15]; they found that, generally, substitution in appended rings enhanced the antiviral properties and selectivity of the studied compounds.
The magnitude of antiviral activity towards different viruses depends on the type, position of substituted group and the kind of acyclic sugar chain. In particular, substitution in the 6th position by a phenyl or 4-biphenylyl group afforded the greatest increase in antiviral activity [15].



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