Art. -Nr.: HY-187759

(R)-Buciclovir

(R)-Buciclovir is an orally active acyclic guanosine analog anti-herpetic agent that, following selective phosphorylation by HSV thymidine kinase, generates a triphosphate metabolite that inhibits viral DNA polymerase and DNA synthesis, thereby exerting anti-HSV activity. (R)-Buciclovir can be used for research on herpes simplex virus infection and genital herpes.

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CAS. Nr.: 86304-28-1
Formel: C₉H₁₃N₅O₃
Molecular Weight:239.24

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(R)-Buciclovir Chemical Structure

CAS. Nr.: 86304-28-1

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Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- Parmacokinetics
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

HSV-1

1.0 μM (IC₅₀, HEL cells)

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Cellular Effect

Cell Line	Type	Value	Description	References
Vero	IC50	2.1 μM	Inhibition of HSV-1 C-42 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-1 C-42 plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	230.0 μM	Inhibition of acyclovir-resistant HSV-1 C-42 Acvr plaque formation in Vero cells by plaque reduction assay. Inhibition of acyclovir-resistant HSV-1 C-42 Acvr plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	1.2 μM	Inhibition of HSV-1 7935-72 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-1 7935-72 plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	7.0 μM	Inhibition of HSV-1 KJ502 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-1 KJ502 plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	6.8 μM	Inhibition of HSV-1 C1(101) plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-1 C1(101) plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	5.0 μM	Inhibition of HSV-1 Sc16 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-1 Sc16 plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	4.0 μM	Inhibition of HSV-2 91075 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-2 91075 plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	≥ 250 μM	Inhibition of acyclovir-resistant HSV-2 91075 Acvr plaque formation in Vero cells by plaque reduction assay. Inhibition of acyclovir-resistant HSV-2 91075 Acvr plaque formation in Vero cells by plaque reduction assay.	3024562
Vero	IC50	11.0 μM	Inhibition of HSV-2 B4327 plaque formation in Vero cells by plaque reduction assay. Inhibition of HSV-2 B4327 plaque formation in Vero cells by plaque reduction assay.	3024562
HEL	IC50	1.0 μM	Inhibition of HSV-1 C-42 plaque formation in HEL cells by plaque reduction assay. Inhibition of HSV-1 C-42 plaque formation in HEL cells by plaque reduction assay.	3024562
HEL	IC50	5.9 μM	Inhibition of HSV-2 91075 plaque formation in HEL cells by plaque reduction assay. Inhibition of HSV-2 91075 plaque formation in HEL cells by plaque reduction assay.	3024562
Vero	IC50	2300 μM	Inhibition of cell proliferation in Vero cells after 48 h incubation by cell growth inhibition assay using a cell counter. Inhibition of cell proliferation in Vero cells after 48 h incubation by cell growth inhibition assay using a cell counter.	3024562
HEL	IC50	170 μM	Inhibition of cell proliferation in HEL cells after 48 h incubation by cell growth inhibition assay using a cell counter. Inhibition of cell proliferation in HEL cells after 48 h incubation by cell growth inhibition assay using a cell counter.	3024562

In Vitro

(R)-Buciclovir (compound BCV) effectively inhibits HSV-1 and HSV-2 replication in in vitro cell culture experiments^[1].
(R)-Buciclovir (5-500 μM) affects cell sensitivity to (R)-Buciclovir through the herpes simplex virus type 1 (HSV-1) DNA polymerase gene^[4].
(R)-Buciclovir (compound BCV) inhibits plaque formation by HSV-1 and HSV-2, with its inhibitory potency varying depending on the virus strain and host cell type. The highest activity is observed against HSV-1 C-42 in HEL cells, with an IC₅₀ of 1.0 μM^[2].
(R)-Buciclovir (500-1000 μM) induces a concentration-dependent clastogenic effect in cultured human lymphocytes in vitro, producing almost exclusively chromatid breaks, with abnormal metaphase figures reaching up to 44.0% at 1000 μM^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Parmacokinetics

Species	Dose	Route	Serum Concentration	AUC_0-∞	T_1/2 (Distribution)	T_1/2β	T_1/2 (Elimination)	CL	Bioavailability
Mice^[1]	150 mg/kg	i.p.	3.1 μM	/	/	/	/	/	/
Mice^[2]	62.8 μmol/L	i.v.	/	49.5 μM·h	6.4 min	19.7 min	143.4 min	21.1 mL/min/kg	/
Mice^[2]	63 μmol/Kg	p.o.	/	/	/	/	/	/	13 %

In Vivo

(R)-Buciclovir (compound BCV) (5-10% wt/wt topical administration; 200-400 mg/kg daily subcutaneous administration) exhibits potent anti-herpetic efficacy in Dunkin-Hartley guinea pigs intravaginally infected with HSV-2. When administered topically early in infection, 10% (R)-buciclovir reduces early vaginal viral titers by 99%, whereas even with delayed administration up to 72 h post-infection, subcutaneous doses as high as 400 mg/kg daily significantly reduce lesion scores^[1].
(R)-Buciclovir (5-20% wt/wt; topical application; 4 times daily for 5 days) reduces vaginal HSV-2 replication and decreases mortality in intravaginally infected NMRI mice, whereas systemic intraperitoneal administration of (R)-Buciclovir (37.5 mg/kg every 6 h for 5 days) has no effect on mortality or mean day of death, and systemic oral administration of (R)-Buciclovir (200-400 mg/kg daily; continuous dosing) fails to produce a statistically significant reduction in cumulative mortality across different HSV-2 strains and does not prevent viral spread to the nervous system^[1].
(R)-Buciclovir (compound BCV) (5-20 mg/kg per day; i.p.; twice daily; for 5 consecutive days) provides complete survival protection in mice with systemic HSV-1 C-42 infection at daily doses of 10 and 20 mg/kg^[2].
(R)-Buciclovir (10-400 mg/kg per day; i.p. or p.o.) significantly reduces the mortality rate and prolongs the average survival time of mice systemically infected with HSV-2 91075^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Dunkin-Hartley (Young, female, 225 to 250 g, intravaginal inoculation of HSV-2 strain MS at 7×10⁴ PFU following mild vaginal mucosa injury)^[1]
Dosage:

5% wt/wt topical cream; 10% wt/wt topical cream; 200 mg/kg per day (subcutaneous); 300 mg/kg per day (subcutaneous); 400 mg/kg per day (subcutaneous)
Administration:

topical; four times daily; 5 days (starting at 1 h, 24 h, 48 h, or 72 h post-infection); subcutaneous; twice daily; 5 days (starting at 1 h, 24 h, or 72 h post-infection)
Result:

Reduced cumulative lesion score by 73% with topical 5% (R)-buciclovir treatment starting 1 h post-infection.
Reduced mean intravaginal titers on days 1 to 3 post-infection by 99% or more with topical 10% (R)-buciclovir treatment starting 1 h post-infection, with titers of 1.30 log₁₀ PFU/mL at 24 h post-infection, 2.54 log₁₀ PFU/mL at 48 h post-infection, and 1.70 log₁₀ PFU/mL at 72 h post-infection, and a cumulative lesion score of 6.3.
Recorded a cumulative lesion score of 35.8 with topical 10% (R)-buciclovir treatment starting 24 h post-infection, with mean intravaginal titers of 4.90 log₁₀ PFU/mL at 24 h post-infection, 3.20 log₁₀ PFU/mL at 48 h post-infection, and 2.75 log₁₀ PFU/mL at 72 h post-infection.
Recorded a cumulative lesion score of 34.2 with topical 10% (R)-buciclovir treatment starting 48 h post-infection, with mean intravaginal titers of 4.69 log₁₀ PFU/mL at 24 h post-infection, 4.73 log₁₀ PFU/mL at 48 h post-infection, and 2.79 log₁₀ PFU/mL at 72 h post-infection.
Recorded a cumulative lesion score of 40.1 with topical 10% (R)-buciclovir treatment starting 72 h post-infection, with mean intravaginal titers of 5.13 log₁₀ PFU/mL at 24 h post-infection, 4.67 log₁₀ PFU/mL at 48 h post-infection, and 4.10 log₁₀ PFU/mL at 72 h post-infection.
Reduced cumulative lesion score by 48% (mean cumulative lesion score 25.0) with subcutaneous 200 mg/kg per day (R)-buciclovir treatment starting 1 h post-infection.
Reduced cumulative lesion score by 69% (mean cumulative lesion score 15.0) with subcutaneous 300 mg/kg per day (R)-buciclovir treatment starting 1 h post-infection.
Recorded a cumulative lesion score of 12.1 with subcutaneous 400 mg/kg per day (R)-buciclovir treatment starting 24 h post-infection.
Produced a 48% reduction in cumulative lesion score (17.8) with subcutaneous 400 mg/kg per day (R)-buciclovir treatment starting 72 h post-infection, with no animals progressing to the most severe disease stage 5, and only 1 of 8 animals progressing to stage 4.
Showed no effect on measured intravaginal virus titers with subcutaneous (R)-buciclovir treatments.

Animal Model:

NMRI (Female, 15 g, intravaginal inoculation with 7×10⁴ PFU of HSV-2 strain MS or 2×10⁴ PFU of HSV-2 strain 91075)^[1]
Dosage:

5% wt/wt topical cream; 10% wt/wt topical cream; 20% wt/wt topical cream; 37.5 mg/kg (intraperitoneal, every 6 h); 200 mg/kg per day (oral); 400 mg/kg per day (oral)
Administration:

topical; four times daily; 5 days (starting 1 h post-infection); intraperitoneal; every 6 h; 5 days (starting 1 h post-infection); oral; continuous; throughout the experiment after infection
Result:

Resulted in 8 deaths out of 15 mice (53% mortality) with a mean day of death of 9.5 days for HSV-2 strain MS infection with topical 5% (R)-Buciclovir treatment.
Resulted in 4 out of 15 deaths (27% mortality) with a mean day of death of 12.3 days for HSV-2 strain MS infection with topical 10% (R)-Buciclovir treatment.
Resulted in 1 out of 15 deaths (7% mortality) for HSV-2 strain MS infection with topical 20% (R)-Buciclovir treatment.
Resulted in 8 out of 15 deaths (53% mortality) with a mean day of death of 9.8 days for HSV-2 strain 91075 infection with topical 10% (R)-Buciclovir treatment.
Resulted in 4 out of 15 deaths (27% mortality) with a mean day of death of 10.8 days for HSV-2 strain 91075 infection with topical 20% (R)-Buciclovir treatment.
Reduced the mean genital virus titers from days 1 to 3 post-infection by 98% or more with topical (R)-Buciclovir treatment starting 1 h post-infection.
Showed no effect on cumulative mortality, mean day of death, or vaginal virus replication with intraperitoneal 150 mg/kg per day (R)-Buciclovir treatment.
Resulted in 15 out of 15 deaths (100% mortality) with a mean day of death of 8.3 days for HSV-2 strain MS infection with oral (R)-Buciclovir at 1 mg/mL.
Resulted in 12 out of 15 deaths (80% mortality) with a mean day of death of 8.8 days for HSV-2 strain MS infection with oral (R)-Buciclovir at 2 mg/mL.
Resulted in 12 out of 15 deaths (80% mortality) with a mean day of death of 7.3 days for HSV-2 strain 91075 infection with oral (R)-Buciclovir at 1 mg/mL.
Resulted in 12 out of 15 deaths (80% mortality) with a mean day of death of 9.0 days for HSV-2 strain 91075 infection with oral (R)-Buciclovir at 2 mg/mL.
Produced no statistically significant effects on the cumulative mortality rate for any oral (R)-Buciclovir dose.
Failed to prevent the spread of virus to the spinal cord and brain with systemic (R)-Buciclovir administration.

Animal Model:

NMRI mice (female, 14 to 15 g)^[2]
Dosage:

5 mg/kg per day; 10 mg/kg per day; 20 mg/kg per day
Administration:

i.p.; twice daily; 5 consecutive days
Result:

Recorded 5 out of 10 treated mice died, with a mean days to death of 9.2 at 5 mg/kg per day.
Recorded 0 out of 10 treated mice died at 10 mg/kg per day.
Recorded 0 out of 10 treated mice died at 20 mg/kg per day.

Animal Model:

NMRI mice (female, 14 to 15 g)^[2]
Dosage:

10 mg/kg per day (i.p.); 25 mg/kg per day (i.p.); 50 mg/kg per day (i.p.); 400 mg/kg per day (p.o.)
Administration:

i.p.; twice daily; 5 consecutive days; p.o. (via drinking water); 10 days
Result:

Recorded 2 out of 10 treated mice died, with a mean days to death of 11.0 at 10 mg/kg per day i.p.
Recorded 2 out of 10 treated mice died, with a mean days to death of 13.0 at 25 mg/kg per day i.p.
Recorded 1 out of 10 treated mice died, with a mean days to death of 13.0 at 50 mg/kg per day i.p.
Recorded 3 out of 16 treated mice died, with a mean days to death of 13.7 at 400 mg/kg per day p.o.

Chemical Information

CAS. Nr. 86304-28-1
Molecular Weight 239.24
Formel C₉H₁₃N₅O₃
SMILES

C(C[C@H](CO)O)N1C2=C(N=C1)C(=O)N=C(N)N2
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Handling Instructions (2659 KB)

Verweise

[1]. Lundgren B, et al. Efficacy of the acyclic guanosine analog buciclovir [(R)-9-(3,4-dihydroxybutyl)guanine] in experimental genital herpes. Antimicrobial agents and chemotherapy. 1986 Feb;29(2):294-7.

[2]. Larsson A, et al. Mode of action, toxicity, pharmacokinetics, and efficacy of some new antiherpesvirus guanosine analogs related to buciclovir. Antimicrobial agents and chemotherapy. 1986 Oct;30(4):598-605.

[3]. Qin T, et al. Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir. The Journal of organic chemistry. 2018 Dec 21;83(24):15512-15523.

[4]. Chiou HC, et al. Mutation within the herpes simplex virus DNA polymerase gene conferring resistance to (R)-9-(3,4-dihydroxybutyl)guanine. Antimicrobial agents and chemotherapy. 1986 Sep;30(3):502-4.

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

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(R)-Buciclovir

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