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Home> Encyclopedia >   /  Pharmaceutical Intermediates  /  Organic Intermediate  /  Chemical Auxiliary Agent
Valganciclovir hydrochloride structure
Valganciclovir hydrochloride structure

Valganciclovir hydrochloride

Iupac Name:[2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-3-hydroxypropyl] (2S)-2-amino-3-methylbutanoate;hydrochloride
CAS No.: 175865-59-5
Molecular Weight:390.825
Modify Date.: 2022-11-22 15:43
Introduction: Valganciclovir hydrochloride, a prodrug of the antiviral ganciclovir, was launched in theUS for the oral treatment of cytemegalovirus (CMV) retinitis, a sight-threateningcomplication in patients with AIDS. This L-Valyl ester prodrug can be prepared in threesteps from the nucleoside analog ganciclovir by trimethylsilyl-protection of the aminogroup, coupling with N-benzyloxycarbonyl-L-valine-N-carboxyanhydride, hydrolysis withhydrochloric acid and hydrogenolysis of the Cbz-protecting group. Valganciclovir is wellabsorbed and rapidly hydrolyzed to ganciclovir by intracellular esterases in the intestinalmucosal cells and by hepatic esterases. Unlike ganciclovir, valganciclovir wasdemonstrated to be actively transported by the intestinal peptide transporter PEPT1 inCaco-2 cells. As a consequence, its absolute bioavailability in human was 10-fold highercompared to ganciclovir (6%). In clinical trials, it was shown that a twice-daily 900 mg doseof valganciclovir resulted in similar systemic ganciclovir exposure to 5 mg/kg twice-dailyintravenous injection of ganciclovir. Valganciclovir concentrations could not be quantified inmost patients within three to four hours. In a randomized non-blind phase III clinical trial,oral valganciclovir (900 mg twice daily for three weeks then 900 mg once daily for oneweek) was as effective as intravenous ganciclovir (5 mg/kg twice daily for three weeksthen 5 mg/kg once daily). Oral treatment with valganciclovir avoided catheter-relatedinfection that sometimes occurred with intravenous ganciclovir. View more+
1. Names and Identifiers
1.1 Name
Valganciclovir hydrochloride
1.2 Synonyms

2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride hydrate L-Valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl Ester Monohydrochloride L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, hydrochloride (1:1) L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, monohydrochloride L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, monohydrochloride hydrate Ro 107-9070/194 Rs 079070-194 Unii-4p3T9qf9nz Valcyt Valcyte Valganciclovir hydrochloride hydrate

1.3 CAS No.
175865-59-5
1.4 CID
135413534
1.5 EINECS(EC#)
1308068-626-2
1.6 Molecular Formula
C14H23ClN6O5 (isomer)
1.7 Inchi
InChI=1S/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8?,9-;/m0./s1
1.8 InChkey
ZORWARFPXPVJLW-MTFPJWTKSA-N
1.9 Canonical Smiles
CC(C)C(C(=O)OCC(CO)OCN1C=NC2=C1N=C(NC2=O)N)N.Cl
1.10 Isomers Smiles
CC(C)[C@@H](C(=O)OCC(CO)OCN1C=NC2=C1N=C(NC2=O)N)N.Cl
2. Properties
2.1 Melting point
162-164°C
2.1 Boiling point
629.1 °C at 760 mmHg
2.1 Flash Point
334.3 °C
2.1 Precise Quality
390.14200
2.1 PSA
171.37000
2.1 logP
0.64680
2.1 Solubility
H2O: ≥8mg/mL
2.2 Appearance
White Crystalline Solid
2.3 Chemical Properties
White Crystalline Solid
2.4 Color/Form
white to tan
3. Use and Manufacturing
3.1 Usage
A pro-drug of ganciclovir. Used in treatment of retro-virus?
4. Safety and Handling
4.1 Hazard Declaration
H340
4.1 RIDADR
NONH for all modes of transport
4.1 Caution Statement
P201, P202, P260, P264, P270, P281, P308+P313, P314, P405, P501
4.1 WGK Germany
3
4.1 Specification

  L-Valine,2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester,hydrochloride (1:1) (CAS NO.175865-59-5), its Synonyms are Valganciclovir hydrochloride ; L-Valine, ester with 9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)guanine, monohydrochloride ; Valcyt ; Valcyte ; Valganciclovir HCl .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 1A

Carcinogenicity, Category 1A

Reproductive toxicity, Category 1A

Specific target organ toxicity \u2013 repeated exposure, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H340 May cause genetic defects

H350 May cause cancer

H360 May damage fertility or the unborn child

H372 Causes damage to organs through prolonged or repeated exposure

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

P314 Get medical advice/attention if you feel unwell.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. Other Information
6.0 Chemical Properties
White Crystalline Solid
6.1 Uses
A pro-drug of ganciclovir. Used in treatment of retro-virus?
6.2 Uses
antibacterial, inhibits protein synthesis
6.3 Uses
Valganciclovir is the valyl ester prodrug of ganciclovir , an antiviral agent used for the treatment of HIV associated retinitis and for the prevention of post transplant cytomegalovirus (CMV) infections. Upon oral administration, intestinal and hepatic esterases rapidly convert valganciclovir to ganciclovir, which can inhibit viral DNA synthesis (IC50 = 0.95 μM) by targeting the CMV polymerase.
6.4 Brand name
Valcyte (Roche).
7. Computational chemical data
  • Molecular Weight: 390.825g/mol
  • Molecular Formula: C14H23ClN6O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 390.1418455
  • Monoisotopic Mass: 390.1418455
  • Complexity: 528
  • Rotatable Bond Count: 9
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 8
  • Topological Polar Surface Area: 167
  • Heavy Atom Count: 26
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADceBzuAAEAAAAAAAAAAAAAAAAAWAAAAAgAAAAAAAAAEABgAAAHgAQCAAADTzhlgYHuBfMFgCoAQfxfACAgC0XEKABUIGoVECDWBhASCAfQIgNEQJDAGAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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