WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H327014
CAS#: 1445385-02-3
Description: Lumicitabine, also known as ALS-8176, is an orally bioavailable prodrug of the novel RSV replication inhibitor ALS-8112. In nonclinical studies, ALS-008112 enters various types of epithelial cells in the respiratory tract and is subsequently phosphorylated to form an intracellular nucleoside triphosphate with a half-life of approximately 29 hours. The nucleoside triphosphate analogue inhibits RSV replication by means of chain termination.
Hodoodo Cat#: H327014
Name: Lumicitabine
CAS#: 1445385-02-3
Chemical Formula: C18H25ClFN3O6
Exact Mass: 433.14
Molecular Weight: 433.861
Elemental Analysis: C, 49.83; H, 5.81; Cl, 8.17; F, 4.38; N, 9.69; O, 22.13
Synonym: Lumicitabine; ALS-8176; ALS8176； ALS 8176; JNJ 64041575; JNJ64041575; JNJ-64041575; AL 8176; AL8176; AL-8176; ALS 008176; ALS 008176; ALS008176.
IUPAC/Chemical Name: (2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-(chloromethyl)-4-fluoro-2-((isobutyryloxy)methyl)tetrahydrofuran-3-yl isobutyrate
InChi Key: MJVKYGMNSQJLIN-KYZVSKTDSA-N
InChi Code: InChI=1S/C18H25ClFN3O6/c1-9(2)15(24)27-8-18(7-19)13(28-16(25)10(3)4)12(20)14(29-18)23-6-5-11(21)22-17(23)26/h5-6,9-10,12-14H,7-8H2,1-4H3,(H2,21,22,26)/t12-,13+,14-,18-/m1/s1
SMILES Code: O=C(N=C(C=C1)N)N1[C@H](O2)[C@H](F)[C@H](OC(C(C)C)=O)[C@@]2(CCl)COC(C(C)C)=O
Appearance: Solid powder
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
More Info:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 433.86 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Fearns R, Deval J. New antiviral approaches for respiratory syncytial virus and other mononegaviruses: Inhibiting the RNA polymerase. Antiviral Res. 2016 Aug 26. pii: S0166-3542(16)30352-7. doi: 10.1016/j.antiviral.2016.08.006. [Epub ahead of print] Review. PubMed PMID: 27575793.
2: Deval J, Fung A, Stevens SK, Jordan PC, Gromova T, Taylor JS, Hong J, Meng J, Wang G, Dyatkina N, Prhavc M, Symons JA, Beigelman L. Biochemical Effect of Resistance Mutations against Synergistic Inhibitors of RSV RNA Polymerase. PLoS One. 2016 May 10;11(5):e0154097. doi: 10.1371/journal.pone.0154097. eCollection 2016. PubMed PMID: 27163448; PubMed Central PMCID: PMC4862670.
3: DeVincenzo JP, McClure MW, Symons JA, Fathi H, Westland C, Chanda S, Lambkin-Williams R, Smith P, Zhang Q, Beigelman L, Blatt LM, Fry J. Activity of Oral ALS-008176 in a Respiratory Syncytial Virus Challenge Study. N Engl J Med. 2015 Nov 19;373(21):2048-58. doi: 10.1056/NEJMoa1413275. PubMed PMID: 26580997.
4: Deval J, Hong J, Wang G, Taylor J, Smith LK, Fung A, Stevens SK, Liu H, Jin Z, Dyatkina N, Prhavc M, Stoycheva AD, Serebryany V, Liu J, Smith DB, Tam Y, Zhang Q, Moore ML, Fearns R, Chanda SM, Blatt LM, Symons JA, Beigelman L. Molecular Basis for the Selective Inhibition of Respiratory Syncytial Virus RNA Polymerase by 2'-Fluoro-4'-Chloromethyl-Cytidine Triphosphate. PLoS Pathog. 2015 Jun 22;11(6):e1004995. doi: 10.1371/journal.ppat.1004995. eCollection 2015 Jun. PubMed PMID: 26098424; PubMed Central PMCID: PMC4476725.
5: Wang G, Deval J, Hong J, Dyatkina N, Prhavc M, Taylor J, Fung A, Jin Z, Stevens SK, Serebryany V, Liu J, Zhang Q, Tam Y, Chanda SM, Smith DB, Symons JA, Blatt LM, Beigelman L. Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection. J Med Chem. 2015 Feb 26;58(4):1862-78. doi: 10.1021/jm5017279. Epub 2015 Feb 10. PubMed PMID: 25667954.
