ChemicalBook CAS DataBase List 443642-29-3

443642-29-3

Name	Lamevudine
CAS	443642-29-3
EINECS(EC#)	200-001-2
Molecular Formula	C12H16N4O4
MDL Number	MFCD14584964
Molecular Weight	280.28
MOL File	443642-29-3.mol

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

Chemical Properties

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\|

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P261-P280-P301+P312-P302+P352-P305+P351+P338

Hazard Information

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

Spectrum Detail

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