Valacyclovir
- valacyclovir
- Valaciclovir
- 124832-26-4
- ValACV
- Zelitrex
- Create:2019-01-15
- Modify:2025-01-18
- 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl L-valinate
- 256U87
- Acyclovir, L valyl Ester
- acyclovir, L-valyl ester
- BW256U87
- D- Valacyclovir
- L Valylacyclovir
- L-valyl Ester Acyclovir
- L-valylacyclovir
- valaciclovir
- valacyclovir
- valacyclovir hydrochloride
- valacyclovir hydrochloride, (DL)-isomer
- valacyclovir, (D)-isomer
- valacyclovir, (DL)-isomer
- valacyclovir, (L)-isomer
- Valacyclovir, D-
- valacyclovir, x-hydrochloride, (D)-isomer
- valacyclovir, x-hydrochloride, (DL)-isomer
- Valtrex
- valacyclovir
- Valaciclovir
- 124832-26-4
- ValACV
- Zelitrex
- Valcivir
- Valcyclovir
- Val-ACV
- L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine
- UNII-MZ1IW7Q79D
- MZ1IW7Q79D
- L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester
- Valaciclovir (INN)
- CHEBI:35854
- HSDB 8084
- Valtrex (TN)
- CHEMBL1349
- 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate
- 256U87 HCl
- DTXSID1023732
- (S)-2-[(2-Amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl-2-amino-3-methylbutanoate
- BW 256U87
- MFCD01861507
- VALACICLOVIR [INN]
- 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
- L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester
- 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
- Valaciclovir [INN:BAN]
- Talavir
- Virval
- L-VALINE, ESTER WITH 9-((2-HYDROXYETHOXY)METHYL)GUANINE
- Valacyclover Hydrochloric
- Acyclovir-valine
- (S)-2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl 2-amino-3-methylbutanoate
- 2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
- VACV
- Valaciclovir, Valtrex
- BW256U87
- NCGC00159520-02
- Valaciclovirum
- 2-((2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)ethyl L-valinate
- BW-256U
- TXC
- Valtrex (TM)
- Valcyclovir [INN:BAN]
- L-Valine ester with 9-
- VALACYCLOVIR [MI]
- 2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
- 256U87
- VALACYCLOVIR [VANDF]
- SCHEMBL28644
- BSPBio_002474
- MLS001304747
- MLS006011776
- VALACICLOVIR [WHO-DD]
- DTXCID403732
- GTPL4824
- J05AB11
- HMS2090D20
- HMS2234I15
- BCP28415
- BBL033701
- BDBM50162073
- STK802272
- STL535579
- ZB0748
- 2-{[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]oxy}ethyl L-valinate
- AKOS005622706
- AKOS007930693
- AKOS025149468
- AKOS037496964
- CS-1356
- DB00577
- valacyclovir hydrochloride (monohydrate)
- NCGC00178638-04
- NCGC00178638-05
- NCGC00178638-15
- Valaciclovir;Val-ACV; Valtrex; Zelitrex
- AC-11128
- HY-17425
- SMR000752514
- SMR004703478
- SBI-0206711.P001
- NS00009305
- D08664
- EN300-150220
- G78316
- AB00698497-11
- AB01275525-01
- AB01275525_02
- AB01275525_03
- Q418594
- W-200980
- BRD-K46435977-003-01-2
- BRD-K46435977-003-03-8
- BRD-K46435977-003-11-1
- BRD-K46435977-003-12-9
- 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl L-valinate
- 2-[(2-amino-1,6-dihydro-6-oxo-9h-purin-9-yl)methoxy]ethyl-l-valinate
- (S)-2-((2-amino-6-oxo-3H-purin-9(6H)-yl)methoxy)ethyl 2-amino-3-methylbutanoate
- 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methyl-butanoate
- L-VALINE 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER
- (S)-2-Amino-3-methyl-butyric acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester
164.19 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.89 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
152.055618 100
135.027756 37.83
146.116974 15.29
144.103165 7.77
67.901878 7.64
152.0562 100
72.08053 17.74
135.0295 10.59
84.08189 7.78
146.11731 6.32
116.07042 100
176.05684 25.82
323.14694 21.14
206.06767 14.54
162.04108 3.88
152.0562 100
72.08053 17.74
135.0295 10.59
84.08189 7.78
146.11731 6.32
- Acyclovir (has active moiety)
- Valacyclovir Hydrochloride (has salt form)
- Valacyclovir hydrochloride monohydrate (active moiety of)
- Cytoplasm
- Membrane
Use (kg; approx.) in Germany (2009): >750
Use (kg) in USA (2002): 63500
Consumption (g per capita; approx.) in Germany (2009): 0.00916
Consumption (g per capita) in the USA (2002): 0.225
Excretion rate: 0.01
Calculated removal (%): 22
P264, P270, P301+P317, P330, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
Oral therapy with valacyclovir is associated with a low rate of mild-to-moderate serum aminotransferase elevations, but these abnormalities are usually asymptomatic and self-limited even with continuation of therapy. Complicating the attribution of liver test abnormalities to valacyclovir therapy is the fact that enzyme elevations are not uncommon during the course of varicella-zoster infection (both chickenpox and shingles) and can progress to clinically apparent hepatitis and even acute liver failure. Clinically apparent liver disease due to valacyclovir itself is rare, but isolated reports have been published. The time to onset was short (1 to 2 weeks) and the course mild, with few symptoms and rapid resolution (Case 1). The pattern of liver injury described was mixed hepatocellular-cholestatic. Immunoallergic features and autoantibodies were absent.
Likelihood score: D (possible rare cause of clinically apparent liver injury).
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
The dosage of acyclovir in milk after valacyclovir is less than 1% of a typical infant dosage and would not be expected to cause any adverse effects in breastfed infants. No special precautions are required when using valacyclovir during breastfeeding. In one study, administration of valacyclovir to mothers with concurrent herpes simplex type 2 and HIV infections reduced breastmilk shedding of the HIV virus in breastmilk at 6 and 14 weeks postpartum, but not later. In another study in HIV-positive mothers, valacyclovir did not reduced breastmilk shedding of cytomegalovirus (CMV) or infant CMV acquisition.
◉ Effects in Breastfed Infants
In a study of pregnant women with concurrent HIV and Herpes simplex infections, mothers received zidovudine 300 mg daily from week of pregnancy until 12 months postpartum and nevirapine at delivery. Half of the women (n = 74) also received valacyclovir 500 mg orally twice daily from 34 weeks gestation until 12 months postpartum. At 6 weeks postpartum, all infants who received acyclovir in breastmilk had normal serum creatinine (<0.83 mg/dL). Their median serum creatinine and alanine aminotransferase (ALT) values, and growth were no different from those of unexposed infants, with the exception of one infant with an ALT level of 70.1 units/L. Infants whose mothers received valacyclovir generally had adverse effects that were similar to the placebo group, except that treated infants had a lower risk of eczema and oral thrush than infants in the placebo arm.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=HDOVUKNUBWVHOX-QMMMGPOBSA-N
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