Valacyclovir hydrochloride
- Iupac Name：2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate;hydrochloride
- CAS No.: 124832-27-5
- Molecular Weight：360.8
- Modify Date.: 2022-12-06 15:25
1. Names and Identifiers
- 1.1 Name
- Valacyclovir hydrochloride
- 1.2 Synonyms
(S)-2-((2-AMINO-6-OXO-1H-PURIN-9(6H)-YL)METHOXY)ETHYL 2-AMINO-3-METHYLBUTANOATE HYDROCHLORIDE 2-[(2-azanyl-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-azanyl-3-methyl-butanoate hydrochloride 9-((2-Hydroxy-ethoxy)methyl)guanine L-valine ester hydrochloride L-Valacyclovir Hydrochloride L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, monohydrochloride (9CI) Valacyclovir Hydrochloride (200 mg) VALACYCLOVIR HYDROCHLORIDE [9-((2-HYDROXY-ETHOXY)MET HYL)GUANINE L-VALINE ESTER HYDROCHLORIDE] Valtrex
- 1.3 CAS No.
- 124832-27-5
- 1.4 EINECS(EC#)
- 641-092-8
- 1.5 Molecular Formula
- C13H21ClN6O4 (isomer)
- 1.6 Inchi
- InChI=1S/C13H20N6O4.ClH/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20;/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20);1H/t8-;/m0./s1
- 1.7 InChkey
- ZCDDBUOENGJMLV-UHFFFAOYNA-N
- 1.8 Canonical Smiles
- CC(C)C(C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N.Cl
- 1.9 Isomers Smiles
- CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N.Cl
2. Properties
- 2.1 Melting point
- 170-172°C
- 2.1 StorageTemp
- Keep in dark place,Sealed in dry,Store in freezer, under -20°C
3. Safety and Handling
- 3.1 Hazard Codes
- Xi,Xn
- 3.1 Risk Statements
- 36/37/38-22
- 3.1 Safety Statements
- 26-36-24/25
- 3.1 RIDADR
- 3077
- 3.1 WGK Germany
- 3
4. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
5. Synthesis Route
124832-27-5Total: 4 Synthesis Route
6. Other Information
- 6.0 Merck
- 14,9899
- 6.1 Description
- Valacyclovir hydrochloride, an orally active L-valyl ester of the potent antiviral agent aciclovir, was launched in 1995 in the United Kingdom for the treatment of herpes simplex virus (HSV) infections of the skin and mucous membranes, including initial and recurrent genital herpes. As a prodrug, valaciclovir has an improved pharmacokinetic profile to aciclovir. It is rapidly absorbed after oral administration and extensively converted to aciclovir via first-pass metabolism to achieve plasma levels of aciclovir comparable to those seen with aciclovir via i.v. route. Valacyclovir is then activated selectively in virus-infected cells by viral thymidine kinase to form aciclovir triphosphate in a stepwise fashion. This active species inhibits viral DNA polymerase via irreversible binding to the active site of the enzyme. Once aciclovir is incorporated into the elongating viral DNA, it terminates replication of the viral DNA strand, an antiviral mechanism unique to aciclovir. Valacyclovir is reportedly in clinical trials for the suppression of cytomegalovirus infection and disease in renal transplant patients.
- 6.2 Chemical Properties
- White Crystalline Powder
- 6.3 Originator
- Glaxo Wellcome (United Kingdom)
- 6.4 Uses
- Acyclovir (A192400) impurity. The L-Valine ester prodrug of Acyclovir.
- 6.5 Uses
- Valaciclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.
- 6.6 Brand name
- Valtrex (GlaxoSmithKline).
- 6.7 General Description
- Valacyclovir (Valtrex) is the hydrochloride salt of the Lvalylester of acyclovir. The compound is a water-solublecrystalline solid, and it is a prodrug intended to increase thebioavailability of acyclovir by increasing lipophilicity.Valacyclovir is hydrolyzed rapidly and almost completely toacyclovir following oral administration.
Valacyclovir has been approved for the treatment of herpeszoster (shingles) in immunocompromised patients. Theside effect profile observed in valacyclovir is comparablewith bioequivalent doses of acyclovir.
- 6.8 Pharmacokinetics
- The binding of valacyclovir to human plasma proteins ranges between 13.5 to 17.9%. The plasma elimination half-life of acyclovir is 2.5 to 3.3 hours. The bioavailability of valacyclovir hydrochloride is 54%, compared to approximately 20% for oral acyclovir, and it is as effective as acyclovir in decreasing the duration of pain associated with posttherapeutic neuralgia and episodes of genital lesion healing.
- 6.9 Side effects
- The adverse effects are similar to acyclovir, which include nausea, headache, vomiting, constipation, and anorexia.
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