 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C151H185N49O83P14S14 |
| Molecular Weight | 4896.90576338768 |
| Exact Mass | 4894.421 |
| CAS # | 1072874-90-8 |
| PubChem CID | 56843415 |
| Appearance | Off-white to light yellow solid powder |
| LogP | -12.2 |
| Hydrogen Bond Donor Count | 32 |
| Hydrogen Bond Acceptor Count | 111 |
| Rotatable Bond Count | 86 |
| Heavy Atom Count | 311 |
| Complexity | 14200 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | S=P(O)(OCC12COC(C(N3C(NC(C(C)=C3)=O)=O)O1)C2OP(O)(OCC1C(CC(N2C(N=C(C=C2)N)=O)O1)OP(O)(OCC1C(CC(N2C=NC3C(N)=NC=NC2=3)O1)OP(O)(OCC12COC(C(N3C(N=C(C=C3)N)=O)O1)C2OP(O)(OCC1C(CC(N2C=NC3C(N)=NC=NC2=3)O1)OP(O)(OCC12COC(C(N3C(N=C(C=C3)N)=O)O1)C2OP(O)(OCC1C(CC(N2C(NC(C(C)=C2)=O)=O)O1)OP(O)(OCC12COC(C(N3C(N=C(C=C3)N)=O)O1)C2OP(O)(OCC12COC(C(N3C(N=C(C=C3)N)=O)O1)C2O)=S)=S)=S)=S)=S)=S)=S)=S)OC1C2C(N3C=NC4C(NC(N)=NC3=4)=O)OC1(COP(O)(OC1CC(N3C(NC(C(C)=C3)=O)=O)OC1COP(O)(OC1CC(N3C(NC(C(C)=C3)=O)=O)OC1COP(O)(OC1C3C(N4C=NC5C(N)=NC=NC4=5)OC1(COP(O)(OC1CC(N4C(N=C(C=C4)N)=O)OC1COP(O)(OC1C4C(N5C(N=C(C=C5)N)=O)OC1(CO)CO4)=S)=S)CO3)=S)=S)=S)CO2 |
| InChi Key | OSOOBMBDIGGTCP-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C151H185N49O83P14S14/c1-60-26-193(140(215)182-119(60)203)87-21-66(74(258-87)34-245-290(225,304)281-110-102-130(199-58-171-94-114(161)165-55-168-117(94)199)268-150(110,44-239-102)50-252-291(226,305)272-65-20-86(187-13-6-79(153)174-134(187)209)256-72(65)33-243-286(221,300)277-105-97-125(262-144(105,37-201)38-234-97)189-15-8-81(155)176-136(189)211)271-285(220,299)241-30-73-67(22-88(257-73)194-27-61(2)120(204)183-141(194)216)273-293(228,307)253-51-151-45-240-103(131(269-151)200-59-172-95-118(200)180-132(162)181-123(95)207)111(151)283-297(232,311)254-52-149-43-238-101(129(267-149)196-29-63(4)122(206)185-143(196)218)109(149)280-289(224,303)244-32-71-64(19-85(255-71)186-12-5-78(152)173-133(186)208)270-284(219,298)242-31-76-69(24-90(260-76)197-56-169-92-112(159)163-53-166-115(92)197)275-294(229,308)249-47-147-41-236-99(127(265-147)191-17-10-83(157)178-138(191)213)107(147)279-288(223,302)247-36-77-70(25-91(261-77)198-57-170-93-113(160)164-54-167-116(93)198)276-295(230,309)250-48-146-40-235-98(126(264-146)190-16-9-82(156)177-137(190)212)106(146)278-287(222,301)246-35-75-68(23-89(259-75)195-28-62(3)121(205)184-142(195)217)274-292(227,306)251-49-148-42-237-100(128(266-148)192-18-11-84(158)179-139(192)214)108(148)282-296(231,310)248-46-145-39-233-96(104(145)202)124(263-145)188-14-7-80(154)175-135(188)210/h5-18,26-29,53-59,64-77,85-91,96-111,124-131,201-202H,19-25,30-52H2,1-4H3,(H,219,298)(H,220,299)(H,221,300)(H,222,301)(H,223,302)(H,224,303)(H,225,304)(H,226,305)(H,227,306)(H,228,307)(H,229,308)(H,230,309)(H,231,310)(H,232,311)(H2,152,173,208)(H2,153,174,209)(H2,154,175,210)(H2,155,176,211)(H2,156,177,212)(H2,157,178,213)(H2,158,179,214)(H2,159,163,166)(H2,160,164,167)(H2,161,165,168)(H,182,203,215)(H,183,204,216)(H,184,205,217)(H,185,206,218)(H3,162,180,181,207) |
| Chemical Name | 1-[4-[[3-[[3-(2-amino-6-oxo-1H-purin-9-yl)-7-[[7-[[5-(4-amino-2-oxopyrimidin-1-yl)-3-[[3-[[3-(4-amino-2-oxopyrimidin-1-yl)-7-[[3-[[3-(4-amino-2-oxopyrimidin-1-yl)-7-[[3-[[3-(4-amino-2-oxopyrimidin-1-yl)-7-[[3-(4-amino-2-oxopyrimidin-1-yl)-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-[[[1-[[[5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[3-(4-amino-2-oxopyrimidin-1-yl)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-hydroxyphosphinothioyl]oxymethyl]oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-3-(6-aminopurin-9-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-hydroxyphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | miR-122[1] |
| ln Vitro | Miravirsen's primary mechanism of action is assumed to be hybridizing to mature miR-122 and preventing its interaction with HCV RNA; both pri- and pre-miR-122 include its target sequence[1]. With nanomolar affinity, miravirsen binds to the stem-loop structure of pri- and pre-miR-122, preventing Drosha and Dicer from processing miR-122 precursors[1]. |
| ln Vivo | In mice, miravirsen (SPC-3649; 2.5–25 mg/kg; intravenous; daily, for 3 days) suppresses miR-122 activity[2]. |
| Animal Protocol |
Animal/Disease Models: NMRI female mice (27 g)[2] Doses: 2.5, 6.25, 12.5, and 25 mg/kg Route of Administration: intravenous (iv)injection; daily, for 3 days Experimental Results: Inhibited miR-122 activity in a dose-dependent manner. |
| References |
[1]. Miravirsen (SPC3649) can inhibit the biogenesis of miR-122. Nucleic Acids Res. 2014 Jan;42(1):609-21. [2]. Antagonism of microRNA-122 in mice by systemically administered LNA-antimiR leads to up-regulation of a large set of predicted target mRNAs in the liver. Nucleic Acids Res. 2008 Mar;36(4):1153-62. |
| Additional Infomation | Miravirsen has been investigated for the treatment of Hepatitis C and Hepatitis C, Chronic. |
Solubility Data
| Solubility (In Vitro) | H2O : 100 mg/mL (20.13 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 14.29 mg/mL (2.88 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.2042 mL | 1.0211 mL | 2.0421 mL | |
| 5 mM | 0.0408 mL | 0.2042 mL | 0.4084 mL | |
| 10 mM | 0.0204 mL | 0.1021 mL | 0.2042 mL |