Synonym
Bucyclovir triphosphate
IUPAC/Chemical Name
Guanine, 9-(3,4-dihydroxybutyl)-, triphosphate
InChi Key
CWMYQLUEXUJQIR-YFKPBYRVSA-N
InChi Code
InChI=1S/C9H16N5O12P3/c10-9-12-7-6(8(16)13-9)11-4-14(7)2-1-5(15)3-24-28(20,21)26-29(22,23)25-27(17,18)19/h4-5,15H,1-3H2,(H,20,21)(H,22,23)(H2,17,18,19)(H3,10,12,13,16)/t5-/m0/s1
SMILES Code
NC1=Nc2c(ncn2CC[C@H](O)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)C(=O)N1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
|
Solvent |
mg/mL |
mM |
| Solubility |
| Soluble in DMSO |
0.0 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
479.17
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Qin T, Li JP, Xie MS, Qu GR, Guo HM. Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir. J Org Chem. 2018 Dec 21;83(24):15512-15523. doi: 10.1021/acs.joc.8b02442. Epub 2018 Dec 5. PMID: 30468383.
2: Wu M, Hajszan T, Leranth C, Alreja M. Nicotine recruits a local glutamatergic circuit to excite septohippocampal GABAergic neurons. Eur J Neurosci. 2003 Sep;18(5):1155-68. doi: 10.1046/j.1460-9568.2003.02847.x. PMID: 12956714.
3: Reymen D, Naesens L, Balzarini J, Holý A, Dvoráková H, De Clercq E. Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. Antiviral Res. 1995 Dec;28(4):343-57. doi: 10.1016/0166-3542(95)00058-5. PMID: 8669893.
4: Balzarini J, Bohman C, Walker RT, de Clercq E. Comparative cytostatic activity of different antiherpetic drugs against herpes simplex virus thymidine kinase gene-transfected tumor cells. Mol Pharmacol. 1994 Jun;45(6):1253-8. PMID: 8022417.
5: Coen DM, Irmiere AF, Jacobson JG, Kerns KM. Low levels of herpes simplex virus thymidine- thymidylate kinase are not limiting for sensitivity to certain antiviral drugs or for latency in a mouse model. Virology. 1989 Feb;168(2):221-31. doi: 10.1016/0042-6822(89)90261-4. PMID: 2536980.
6: Abele G, Eriksson B, Harmenberg J, Wahren B. Inhibition of varicella-zoster virus-induced DNA polymerase by a new guanosine analog, 9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine triphosphate. Antimicrob Agents Chemother. 1988 Aug;32(8):1137-42. doi: 10.1128/aac.32.8.1137. PMID: 2847643; PMCID: PMC172365.
7: Kristofferson A, Ericson AC, Sohl-Akerlund A, Datema R. Limited efficacy of inhibitors of herpes simplex virus DNA synthesis in murine models of recrudescent disease. J Gen Virol. 1988 Jun;69 ( Pt 6):1157-66. doi: 10.1099/0022-1317-69-6-1157. PMID: 2838569.
8: Stenberg K, Lundström M, Olofsson S, Datema R. Incorporation into nucleic acids of the antiherpes guanosine analog buciclovir, and effects on DNA and protein synthesis. Biochem Pharmacol. 1988 May 15;37(10):1925-31. doi: 10.1016/0006-2952(88)90538-2. PMID: 2837218.
9: Bryson YJ. Promising new antiviral drugs. J Am Acad Dermatol. 1988 Jan;18(1 Pt 2):212-8. doi: 10.1016/s0190-9622(88)70031-6. PMID: 2448352.
10: Datema R, Ericson AC, Field HJ, Larsson A, Stenberg K. Critical determinants of antiherpes efficacy of buciclovir and related acyclic guanosine analogs. Antiviral Res. 1987 Jul;7(6):303-16. doi: 10.1016/0166-3542(87)90013-1. PMID: 2823702.
