| Identification | Back Directory | [Name]
Lamevudine | [CAS]
443642-29-3 | [Synonyms]
MK-608
MK-0608
Lamevudine
7-deaza-2C-Me-A
2'--C-Meth yltubercidin
2'-b-C-methyl tubercidin
7-Deaza-2'-C-methyladenosine
7H-PYRROLO[2,3-D]PYRIMIDIN-4-A
2’-b-C-Methyl-7-deazaadenosine
(2R,3R,4R,5R)-2-(4-aMino-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-5-(hyd
7-(2-C-Methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
4-Amino-7-(2--C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-(2-C-methyl-β-D-ribofuranosyl)-
7-(2-C-Methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
4-Amino-7-(2-beta-C-methyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
2’-b-C-Methyl tubercidin,2’-b-C-Methyl-7-deazaadenosine, MKR608, antiviral, HCV inhibitor
(2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
(2R,3R,4R,5R)-2-(4-Aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol
2’-beta-C-methyl tubercidin, 4-Amino-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo [2,3-d]pyrimidine, MRK608
(2R,3R,4R,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol | [EINECS(EC#)]
200-001-2 | [Molecular Formula]
C12H16N4O4 | [MDL Number]
MFCD14584964 | [MOL File]
443642-29-3.mol | [Molecular Weight]
280.28 |
| Chemical Properties | Back Directory | [Melting point ]
222 °C(Solv: methanol (67-56-1); acetonitrile (75-05-8)) | [Boiling point ]
620.7±55.0 °C(Predicted) | [density ]
1.75±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: Slightly soluble: 0.1-1 mg/ml | [form ]
Solid | [pka]
12.51±0.70(Predicted) | [color ]
White to off-white | [InChI]
InChI=1/C12H16N4O4/c1-12(19)8(18)7(4-17)20-11(12)16-3-2-6-9(13)14-5-15-10(6)16/h2-3,5,7-8,11,17-19H,4H2,1H3,(H2,13,14,15)/t7-,8-,11-,12-/s3 | [InChIKey]
IRZRJANZDIOOIF-ULJXVLPWNA-N | [SMILES]
C[C@]1([C@@H]([C@@H](CO)O[C@H]1N1C=CC2=C(N=CN=C12)N)O)O |&1:1,2,3,7,r| |
| Hazard Information | Back Directory | [Uses]
7-Deaza-2''-C-methyladenosine is a hepatitis C virus (HCV) polymerase inhibitor. | [Definition]
MK 0608 (7-Deaza-2'-C-methyladenosine) is an anti-viral agent against Hepatitis C Virus (HCV). It has been shown to inhibit viral RNA replication in the subgenomic HCV genotype 1b replicon, with a 50% effective concentration (EC50) of 0.3 μM (EC90 = 1.3 μM). To determine efficacy in vivo, MK-0608 was administered to HCV-infected chimpanzees, resulting in dose- and time-dependent decreases in plasma viral loads. In separate experiments, chimpanzees dosed for 7 days with MK-0608 at 0.2 and 2 mg per kg of body weight per day by intravenous administration experienced average reductions in viral load of 1.0 and >5 log10 IU/ml, respectively.
| [in vivo]
Oral dosing of MK-0608 results in a potent antiviral effect. In preclinical pharmacokinetic experiments with rats, dogs, and rhesus monkeys, MK-0608 demonstrates good to excellent oral bioavailability (50 to 100%) and long plasma half-lives in dogs and rhesus macaques (9 and 14 h, respectively)[1]. | Animal Model: | The HCV-infected chimpanzees[1] | | Dosage: | 1 mg/kg | | Administration: | Administered orally; once daily for 37 days | | Result: | Chimpanzee X6 had a baseline viral load that varied from 1,110 to 12,900 IU/mL, and chimpanzee X4 had a baseline viral load of 3×106 to 9×106 IU/mL. |
| [Solubility in organics]
Soluble in DMSO, not in water.
| [storage]
Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20 ℃ for long term (months to years).
| [References]
[1] DAVID B OLSEN. A 7-deaza-adenosine analog is a potent and selective inhibitor of hepatitis C virus replication with excellent pharmacokinetic properties.[J]. Antimicrobial Agents and Chemotherapy, 2004, 48 10: 3944-3953. DOI: 10.1128/aac.48.10.3944-3953.2004
[2] JOANNA ŻMURKO. The Viral Polymerase Inhibitor 7-Deaza-2’-C-Methyladenosine Is a Potent Inhibitor of In Vitro Zika Virus Replication and Delays Disease Progression in a Robust Mouse Infection Model[J]. PLoS Neglected Tropical Diseases, 2016, 10 1. DOI: 10.1101/041905 |
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