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Penciclovir

CAS No.
39809-25-1
Chemical Name:
Penciclovir
Synonyms
PCV;CL200;VSA 671;Vectavir;BRL-39123;BRL-39123A;Penciceovir;PENCICLOVIR;PENCICLOVIR-D4;Penciclovir >
CBNumber:
CB7731886
Molecular Formula:
C10H15N5O3
Molecular Weight:
253.26
MDL Number:
MFCD00866931
MOL File:
39809-25-1.mol
MSDS File:
SDS
Last updated:2023-09-18 15:08:07

Penciclovir Properties

Melting point 275-277°C
Boiling point 653.4±65.0 °C(Predicted)
Density 1.68±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 0.02 M potassium phosphate: soluble2mg/mL
pka 14.42±0.10(Predicted)
form White solid
color White to Off-White
λmax 253nm(H2O)(lit.)
Merck 14,7083
CAS DataBase Reference 39809-25-1(CAS DataBase Reference)
FDA UNII 359HUE8FJC
NCI Dictionary of Cancer Terms PCV
ATC code D06BB06,J05AB13
EPA Substance Registry System 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]- (39809-25-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS02
Signal word  Danger
Hazard statements  H315-H319-H225
Precautionary statements  P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Hazard Codes  Xi
Risk Statements  36
Safety Statements  26
WGK Germany  3
RTECS  UP0789400
HS Code  2933.99.8290
NFPA 704
0
2 0

Penciclovir price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P0035 Penciclovir 39809-25-1 100mg $157.2 2024-03-01 Buy
Sigma-Aldrich 516090-M Penciclovir - CAS 39809-25-1 - Calbiochem A carba analog of Ganciclovir. Active against several herpes viruses. Induces apoptosis effectively without exerting much genotoxicity. 39809-25-1 100mg $201 2022-05-15 Buy
Sigma-Aldrich 516090-M Penciclovir - CAS 39809-25-1 - Calbiochem A carba analog of Ganciclovir. Active against several herpes viruses. Induces apoptosis effectively without exerting much genotoxicity. 39809-25-1 516090-100MG $220 2022-05-15 Buy
TCI Chemical P2164 Penciclovir >98.0%(HPLC)(T) 39809-25-1 200mg $186 2024-03-01 Buy
TCI Chemical P2164 Penciclovir >98.0%(HPLC)(T) 39809-25-1 1g $585 2023-06-20 Buy
Product number Packaging Price Buy
P0035 100mg $157.2 Buy
516090-M 100mg $201 Buy
516090-M 516090-100MG $220 Buy
P2164 200mg $186 Buy
P2164 1g $585 Buy

Penciclovir Chemical Properties,Uses,Production

Description

Vectavir was launched in the UK for herpes labialis. Penciclovir is synthetically available by two routes of four steps each from 2- (hydroxymethyl)butane-l,4-diol and is active against HSV-1, HSV-2 VZV but has limited activity against CMV. Vectavir is an acyclic guanosine analog that acts as a competitive inhibitor of DNA polymerase. It is a metabolic product of famcyclovir that is preferentially phosphorylated by viral infected cells (by thymidine kinases) over normal cells. The triphosphate has a low activity against cellular DNA polymerase which is one possible explanation for its low toxicity. While its spectrum of activity is similar to acyclovir, it is longer acting because its triphosphate is 20 times more stable and is not metabolized.

Chemical Properties

White Cyrstalline Solid

Originator

SmithKline Beecham (UK)

Uses

An antiviral.

Uses

A deuterated version of Penciclovir, an antiviral

Definition

ChEBI: A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclo ir, is used for oral administration.

Indications

Penciclovir has activity against HSV-1, HSV-2, VZV, and HBV. After oral administration, famciclovir is converted to penciclovir by first-pass metabolism. Penciclovir has a mechanism of action similar to that of acyclovir. It is first monophosphorylated by viral thymidine kinase; then it is converted to a triphosphate by cellular kinases.

Manufacturing Process

To a suspension of lithium aluminum hydride (2.87 g, 76 mmol) in tetrahydrofuran (125 ml), a solution of triethyl 1,1,2-ethanetricarboxylate (9.2 ml, 9.85 g, 40 mmol) in tetrahydrofuran (25 ml) was added dropwise with stirring over 2 hours. The inorganic salts were filtered off and washed with ethanol (100 ml). The filtrate and washings were combined and the solvent was evaporated under reduced pressure to afford a colourless oil (4.85 g). To a suspension of this oil in acetone (100 ml) 2,2-dimethoxypropane (25 ml) and p-toluenesulphonic acid monohydrate (2.3 g, 12 mmol) were added. The mixture was stirred for 1 hour. The resulting solution was neutralised with Amberlite IR 45 (methanol washed), filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with chloroform-methanol mixtures (40:1 and 25:1) to afford 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan as a colourless liquid (3.01 g, 47%).
To an ice-cooled solution of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan (1.92 g, 12 mmol) and carbon tetrabromide (7.96 g, 24 mmol) in dimethylformamide (100 ml) triphenylphosphine (6.30 g, 24 mmol) was added and the solution was left at 4°C overnight. To this solution methanol (20 ml) was added and the solvent was then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane-acetone (12:1) to afford 5-(2-bromoethyl)-2,2-dimethyl1,3-dioxan as a clear colourless liquid (0.89 g, 40%).
To a solution of 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxan (0.75 g, 3.7 mmol) in dry dimethylformamide (12 ml) 2-amino-6-chloropurine (0.68 g, 4.0 mmol) and then anhydrous potassium carbonate (0.83, 6.0 mmol) were added. The solution was stirred at room temperature for 5 hours and left at 4°C overnight. The solution was filtered and the solvent removed. The residue was purified by column chromatography on silica gel, eluting with chloroformmethanol mixtures (80:1 and 60:1) to afford 2-amino-6-chloro-9-[2-(2,2dimethyl-1,3-dioxan-5-yl)ethyl]purine as a white crystalline solid (0.74 g, 64%), melting point 125°-126°C.
2-Amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)-ethyl]purine (0.59 g, 1.9 mmol) in hydrochloric acid (1.0 M, 4 ml) was stirred at 60°C for 24 hours. The solution was diluted with water and neutralised with Amberlite IR 45. The mixture was filtered, the resin washed with water and the solvent evaporated under reduced pressure. The residue was recrystallised from water to afford 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (238 mg, 49%), melting point 275°-277°C.

brand name

Denavir (SmithKline Beecham).

Therapeutic Function

Antiviral

Acquired resistance

Penciclovir is inactive against thymidine kinase-deficient strains of HSV.

Pharmaceutical Applications

A synthetic acyclic purine nucleoside analog, usually administered orally as the diacetyl ester, famciclovir, which acts as a prodrug undergoing rapid first-pass metabolism to release the active compound in vivo. The parent compound has virtually no oral bioavailability, but is supplied as a topical formulation.

Pharmacokinetics

Oral absorption, penciclovir: 5%
famciclovir: 77%
Cmax famciclovir 250 mg oral: 1.6 mg/L after 0.5–1.5 h
famciclovir 500 mg oral: 3.3 mg/L after 0.5–1.5 h
famciclovir 750 mg oral: 5.1 mg/L after 0.5–1.5 h
Plasma half-life: 2.1–2.7 h
Volume of distribution: c. 1.5 L/kg
Plasma protein binding: <20%
Following absorption famciclovir is converted rapidly by enzyme-mediated deacetylation and oxidation to penciclovir. Food does not lead to any significant change in the availability or elimination.
The pharmacokinetics in elderly subjects are similar to those seen in younger subjects, although small increases in AUC and plasma half-lives were seen, consistent with slightly decreased renal clearance.
Renal excretion is the major route of elimination, 50–60% of an oral dose being recovered in the urine. After intravenous infusion, about 70% is excreted unchanged in the urine. After oral administration of famciclovir, penciclovir accounts for 82% of urinary drug-related material. The remainder includes metabolites, of which the largest is the 6-deoxy precursor of penciclovir. Renal clearance exceeds glomerular filtration, indicating renal tubular secretion.

Clinical Use

Herpes zoster and genital herpes
Orolabial herpes (topical)

Clinical Use

Penciclovir is approved as a topical formulation for the treatment of herpes labialis. In immunocompetent individuals, penciclovir shortens the duration of lesion presence and pain by approximately half a day when it is initiated within an hour of lesion development and applied every 2 hours during waking hours for 4 days.

Side effects

In clinical trials the incidence of adverse events after famciclovir, aciclovir and placebo were similar, the most common adverse events being headache and nausea.

References

[1] boyd m r, bacon t h, sutton d, et al. antiherpesvirus activity of 9-(4-hydroxy-3-hydroxy-methylbut-1-yl) guanine (brl 39123) in cell culture. antimicrobial agents and chemotherapy, 1987, 31(8): 1238-1242.
[2] hodge r a, perkins r m. mode of action of 9-(4-hydroxy-3-hydroxymethylbut-1-yl) guanine (brl 39123) against herpes simplex virus in mrc-5 cells. antimicrobial agents and chemotherapy, 1989, 33(2): 223-229.

97845-60-8
39809-25-1
Synthesis of Penciclovir from 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine
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View Lastest Price from Penciclovir manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Penciclovir pictures 2024-03-19 Penciclovir
39809-25-1
US $0.00 / Kg/Bag 2Kg/Bag GMP/ 99% up 20 tons Sinoway Industrial co., ltd.
Penciclovir pictures 2023-09-18 Penciclovir
39809-25-1
US $0.00-0.00 / kg 25kg 99% 1000kg Wuhan Marco Pharmaceutical Technology Co., Ltd.
Penciclovir pictures 2023-03-06 Penciclovir
39809-25-1
US $1.90 / KG 1KG 99% 10 ton Hebei Guanlang Biotechnology Co,.LTD
  • Penciclovir pictures
  • Penciclovir
    39809-25-1
  • US $0.00 / Kg/Bag
  • GMP/ 99% up
  • Sinoway Industrial co., ltd.
  • Penciclovir pictures
  • Penciclovir
    39809-25-1
  • US $0.00-0.00 / kg
  • 99%
  • Wuhan Marco Pharmaceutical Technology Co., Ltd.
  • Penciclovir pictures
  • Penciclovir
    39809-25-1
  • US $1.90 / KG
  • 99%
  • Hebei Guanlang Biotechnology Co,.LTD

Penciclovir Spectrum

9-[4-hychoxy-3-(hydvoxymethyl)butyl]guanine BRL-39123 BRL-39123A Vectavir PENCICLOVIR-D4 Penciceovir 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]- 9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine 2-[2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin)-9-yl]ethyl]propane-1,3-diol 2-Amino-9-(4-hydroxy-3-hydroxymethylbutyl)-9H-purin-6(1H)-one 2'-Carba-ganciclovir VSA 671 2-aMino-9-(4-hydroxy-3-(hydroxyMethyl)butyl)-3H-purin-6(9H)-one Penciclovir(BRL-39123) Famciclovir Penciclovir Impurity (USP) 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one 2-AMINO-1,9-DIHYDRO-9-[4-HYDROXY-3-(HYDROXYMETHYL)BUTYL]-6H-PURIN-6-ONE 2-AMINO-1,9-DIHYDRO-9-[4-HYDROXY-3-(HYDROXYMETHYL)BUTYL]-6H-PURIN-6-ONE-D4 PENCICLOVIR 2-Amino-9-(4-hydroxy-3-(hydroxymethyl)butyl)-1,9-dihydro-6H-purin-6-one 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one CL200 Penciclovir - CAS 39809-25-1 - Calbiochem VSA-671;BRL-39123 Penciclovir > Penciclovir Penciclovir Famciclovir Penciclovir Impurity 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6-one Penciclovir USP/EP/BP Antiviral drug Penciclovir 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1Hpurin-6(9H)-one PenciclovirQ: What is Penciclovir Q: What is the CAS Number of Penciclovir Q: What is the storage condition of Penciclovir Q: What are the applications of Penciclovir 2-amino-9-[1,1,2,2-tetradeuterio-4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one PCV 39809-25-1 39805-25-1 9809-25-1 C10H11N5O3D4 C10H15N5O3 C10H11D4N5O3 DENAVIR Bases & Related Reagents Intermediates & Fine Chemicals Nucleotides Pharmaceuticals Isotope Labeled Compounds API's 39809-25-1