Cat. No.: 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.

For research use only. We do not sell to patients.

CAS No.: 86304-28-1
Formula: C₉H₁₃N₅O₃
Molecular Weight:239.24

Storage:

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

(R)-Buciclovir Chemical Structure

CAS No.: 86304-28-1

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Use of MCE Products

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

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- Parmacokinetics
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

HSV-1

1.0 μM (IC₅₀, HEL cells)

All HSV Isoforms :

All DNA/RNA Synthesis Isoforms :

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 No. 86304-28-1
Molecular Weight 239.24
Formula C₉H₁₃N₅O₃
SMILES

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

Room temperature in continental US; may vary elsewhere.
Storage

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

Purity & Documentation

Handling Instructions (2659 KB)

References

[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.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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(R)-Buciclovir

All HSV Isoforms

All DNA/RNA Synthesis Isoforms