Acyclovir
- CAS No.
- 59277-89-3
- Chemical Name:
- Acyclovir
- Synonyms
- ACICLOVIR;ACV;Acyclovir USP;ACETYLTHIAZOLE;ACYCLOGUANOSINE;ovir;AcycL;Zoviax;Zyclir;Vimrax
- CBNumber:
- CB7126677
- Molecular Formula:
- C8H11N5O3
- Molecular Weight:
- 225.2
- MOL File:
- 59277-89-3.mol
- Modify Date:
- 2024/7/25 20:04:51
Melting point | 256-257°C |
---|---|
Boiling point | 366.71°C (rough estimate) |
Density | 1.3654 (rough estimate) |
refractive index | 1.8000 (estimate) |
storage temp. | 2-8°C |
solubility | H2O: 0.7 mg/mL |
form | powder |
pka | pKa 2.27 (Uncertain);9.25 (Uncertain) |
color | white |
Water Solubility | Soluble in 1M HCl at 50mg/ml. Soluble in water at 0.7mg/ml. Also soluble in DMSO |
Merck | 14,146 |
BCS Class | 4,3 |
Stability | Stable. Incompatible with strong oxidizing agents. |
InChIKey | MKUXAQIIEYXACX-UHFFFAOYSA-N |
LogP | -0.617 (est) |
CAS DataBase Reference | 59277-89-3(CAS DataBase Reference) |
IARC | 3 (Vol. 76) 2000 |
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H320 | |||||||||
Precautionary statements | P264-P305+P351+P338+P337+P313 | |||||||||
Hazard Codes | Xi,Xn | |||||||||
Risk Statements | 36/37/38-40-20/21/22 | |||||||||
Safety Statements | 22-24/25-36-26-23 | |||||||||
WGK Germany | 2 | |||||||||
RTECS | UP0791400 | |||||||||
HazardClass | IRRITANT | |||||||||
HS Code | 29335990 | |||||||||
Toxicity | LD50 in mice (mg/kg): >10,000 orally; 1000 i.p. (Schaeffer) | |||||||||
NFPA 704 |
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Acyclovir price More Price(7)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich(India) | A4669 | Acycloguanosine ≥99% (HPLC), powder | 59277-89-3 | 50MG | ₹11355.43 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | A4669 | Acycloguanosine ≥99% (HPLC), powder | 59277-89-3 | 100MG | ₹20015.43 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | PHR1254 | Acyclovir Pharmaceutical Secondary Standard; Certified Reference Material | 59277-89-3 | 1G | ₹8356.9 | 2022-06-14 | Buy |
Sigma-Aldrich(India) | A4669 | Acycloguanosine ≥99% (HPLC), powder | 59277-89-3 | 500MG | ₹79282.3 | 2022-06-14 | Buy |
TCI Chemicals (India) | A1915 | Acyclovir | 59277-89-3 | 1G | ₹3600 | 2022-05-26 | Buy |
Acyclovir Chemical Properties,Uses,Production
Description
As it is evident from the chemical structure, acyclovir looks like a nucleoside analog of guanosine in side chain of which, instead of the traditional cyclic sugar residue a 2-hydroxyethoxymethyl acyclic side chain is present. Acyclovir possesses antiviral activity with respect to types 1 and 2 of herpes simplex, shingles virus, Epstein–Barr virus, and cytomegalovirus.
Chemical Properties
white to light yellow crystal powder
Uses
Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered intravenously, orally, or topically.
Indications
Acyclovir (Zovirax) is a synthetic purine analog derived from guanine. It exerts
its effects on the herpes simplex virus (HSV) and varicella-zoster virus by interfering
with DNA synthesis through phosphorylation by viral thymidine kinase and
subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication.
It is effective against HSV-1 and 2, varicella-zoster virus, Epstein-Barr
virus, herpesvirus simiae, and cytomegalovirus. Acyclovir may be administered
intravenously, orally, or topically.
Acyclovir (400 mg PO b.i.d. or 200 mg PO five times a day) or other antiviral
antibiotics can suppress herpes-associated EM. It is of no value once the EM has
started. Not all episodes of a herpes simplex recurrence are associated with EM,
but in recurrent cases, a 6-month trial of suppressive therapy can be helpful.
Definition
ChEBI: An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9.
Antimicrobial activity
Activity is restricted to viruses of the herpes group. Herpes simplex virus (HSV) types 1 and 2, simian herpes virus B and varicella zoster viruses (VZV) are susceptible to concentrations readily attainable in human plasma. The 50% inhibitory concentration (ID50) is 0.1 μmol for HSV-1 and HSV-2 and 3 μmol for VZV, concentrations much below those toxic to cells. Valaciclovir is metabolized to aciclovir, and has the same antiviral profile. Thymidine-kinase-negative HSV mutants and cytomegalovirus (CMV) do not code for thymidine kinase and are generally resistant. Although Epstein–Barr virus (EBV) may have reduced thymidine kinase activity, its DNA polymerase is susceptible to aciclovir triphosphate and shows intermediate susceptibility. Human herpes viruses 6 and 7 are less susceptible than EBV.
Acquired resistance
Mutations in HSV that involve deficient thymidine kinase or an altered substrate are most common; alterations in the DNA polymerase gene also result in resistance. Resistant mutants may be found in wild virus populations; mutants lacking thymidine kinase activity may be readily induced by passage of HSV in the presence of the drug. Resistant strains have mostly been reported in immunocompromised patients, are generally thymidine-kinase negative, and have decreased virulence. Resistant mutants that retain thymidine kinase activity appear to retain virulence. Emergence of resistant HSV strains is less frequent in immunocompetent patients, occurring in about 2% of those receiving prolonged treatment.
General Description
Acyclovir, 9-[2-(hydroxyethoxy)methyl]-9H-guanine (Zovirax),is the most effective of a series of acyclic nucleosidesthat possess antiviral activity. In contrast with true nucleosidesthat have a ribose or a deoxyribose sugar attached to apurine or a pyrimidine base, the group attached to the basein acyclovir is similar to an open chain sugar, albeit lackingin hydroxyl groups. The clinically useful antiviral spectrumof acyclovir is limited to herpesviruses. It is most active (invitro) against HSV type 1, about two times less against HSVtype 2, and 10 times less potent against varicella–zostervirus (VZV).
The ultimate effect of acyclovir is the inhibition of viralDNA synthesis. Transport into the cell and monophosphorylationare accomplished by a thymidine kinase that is encodedby the virus itself.The affinity of acyclovir for the viralthymidine kinase is about 200 times that of the correspondingmammalian enzyme.
use: oral and parenteral. Oral acyclovir is used in the initialtreatment of genital herpes and to control mild recurrentepisodes. It has been approved for short-term treatment ofshingles and chickenpox caused by VZV. Intravenous administrationis indicated for initial and recurrent infectionsin immunocompromised patients and for the prevention andtreatment of severe episodes. The drug is absorbed slowlyand incompletely from the GI tract, and its oral bioavailabilityis only 15% to 30%. Nevertheless, acyclovir is distributedto virtually all body compartments.
Pharmaceutical Applications
A synthetic acyclic purine nucleoside analog of the natural nucleoside 2′ deoxyguanosine, formulated for oral and topical use, and as the sodium salt for intravenous infusion. Valaciclovir (the l-valyl ester) is a prodrug formulation supplied as the hydrochloride for oral use.
Biological Activity
Antiviral agent, active against herpes simplex viruses HSV-1 and HSV-2 (EC 50 values are 0.85 and 0.86 μ M respectively). Interferes with viral DNA polymerization through competitive inhibition with guanosine triphosphate. Induces apoptosis in cells transfected with HSV-TK (suicidal gene therapy).
Clinical Use
Aciclovir
Herpes simplex keratitis
Chickenpox and herpes zoster
Herpes simplex encephalitis and neonatal herpes
Prophylaxis of HSV infections in the severely immunocompromised
Valaciclovir
Herpes zoster and genital HSV infections
Acyclovir Preparation Products And Raw materials
Raw materials
1of3
chevron_rightPreparation Products
Supplier | Tel | Country | ProdList | Advantage | Inquiry |
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CHEMXTREE STANDARDS | +919872732255 | Punjab, India | 96 | 58 | Inquiry |
Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
Cadila Pharmaceuticals Ltd | +91-7069076657 +91-7069076657 | Ahmedabad, India | 54 | 58 | Inquiry |
AVD pharmaceuticals Pvt Ltd | +919860835260 | Pune, India | 102 | 58 | Inquiry |
Keminntek Laboratories | +91-040-29704569 +91-9515661451 | Hyderabad, India | 46 | 58 | Inquiry |
Anant Pharmaceuticals Pvt Ltd | +91-8550986868 +91-9485998001 | Haryana, India | 461 | 58 | Inquiry |
SNECOFRi Pvt Ltd | +91-9032850129 +91-9032850129 | Telangana, India | 404 | 58 | Inquiry |
Medi Pharma Drug House | +919930911911 | Mumbai, India | 143 | 58 | Inquiry |
Piramal Pharma Solutions | +919892735994 | Maharashtra, India | 48 | 58 | Inquiry |
Apotex Pharmachem India Pvt Ltd | +91-8022891034 +91-8022891000 | Karnataka, India | 109 | 58 | Inquiry |
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