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    Chemistry

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    Also known as: 917389-32-3, Aic246, Prevymis, Aic-246, Aic 246, Mk-8228
    Molecular Formula
    C29H28F4N4O4
    Molecular Weight
    572.5  g/mol
    InChI Key
    FWYSMLBETOMXAG-QHCPKHFHSA-N
    FDA UNII
    1H09Y5WO1F
    Letermovir
    Letermovir is an orally bioavailable, non-nucleoside, 3,4-dihydroquinazolinyl acetic acid and inhibitor of the pUL56 subunit of the viral terminase complex of cytomegalovirus (CMV), with potential CMV-specific antiviral activity. Upon oral administration, letermovir binds to the pUL56 subunit of the viral terminase complex of CMV and prevents the cleavage of concatemeric DNA into monomeric genome length DNA. As this agent interferes with viral DNA processing and subsequent viral DNA packaging into procapsids, CMV replication is blocked and CMV infection is prevented.
    Letermovir is a Cytomegalovirus DNA Terminase Complex Inhibitor. The mechanism of action of letermovir is as a DNA Terminase Complex Inhibitor, and Cytochrome P450 3A Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer.
    1 2D Structure

    Letermovir

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(4S)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-4H-quinazolin-4-yl]acetic acid
    2.1.2 InChI
    InChI=1S/C29H28F4N4O4/c1-40-20-6-3-5-19(16-20)35-11-13-36(14-12-35)28-34-27-21(7-4-8-22(27)30)23(17-26(38)39)37(28)24-15-18(29(31,32)33)9-10-25(24)41-2/h3-10,15-16,23H,11-14,17H2,1-2H3,(H,38,39)/t23-/m0/s1
    2.1.3 InChI Key
    FWYSMLBETOMXAG-QHCPKHFHSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=C(C=C1)C(F)(F)F)N2C(C3=C(C(=CC=C3)F)N=C2N4CCN(CC4)C5=CC(=CC=C5)OC)CC(=O)O
    2.1.5 Isomeric SMILES
    COC1=C(C=C(C=C1)C(F)(F)F)N2[C@H](C3=C(C(=CC=C3)F)N=C2N4CCN(CC4)C5=CC(=CC=C5)OC)CC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    1H09Y5WO1F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aic246

    2. Prevymis

    2.3.2 Depositor-Supplied Synonyms

    1. 917389-32-3

    2. Aic246

    3. Prevymis

    4. Aic-246

    5. Aic 246

    6. Mk-8228

    7. 1h09y5wo1f

    8. 2-[(4s)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-4h-quinazolin-4-yl]acetic Acid

    9. 2-((4s)-8-fluoro-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3-(2-methoxy-5-(trifluoromethyl)phenyl)-4h-quinazolin-4-yl)acetic Acid

    10. 4-quinazolineacetic Acid, 8-fluoro-3,4-dihydro-2-(4-(3-methoxyphenyl)-1-piperazinyl)-3-(2-methoxy-5-(trifluoromethyl)phenyl)-, (4s)-

    11. Letermovir [inn]

    12. Letermovir [usan:inn]

    13. Unii-1h09y5wo1f

    14. Prevymis (tn)

    15. (s)-[8-fluoro-2-[4-(3-methoxyphenyl)piperazine-1-yl]-3-(2-methoxy-5-trifluoromethylphenyl)-3,4-dihydroquinazoline-4-yl]acetic Acid

    16. (s)-{8-fluoro-2-[4-(3-methoxyphenyl)piperazine-1-yl]-3-(2-methoxy-5-trifluoromethylphenyl)-3,4-dihydroquinazoline-4-yl}acetic Acid

    17. Mk-8828

    18. Letermovir(aic246)

    19. Letermovir [mi]

    20. Letermovir [jan]

    21. Letermovir [usan]

    22. Letermovir [who-dd]

    23. Letermovir (jan/usan/inn)

    24. Schembl379403

    25. Chembl1241951

    26. Letermovir [orange Book]

    27. Dtxsid40238683

    28. Ex-a1871

    29. S8873

    30. Zinc100369359

    31. Cs-1571

    32. Db12070

    33. Aic246;aic 246;aic-246

    34. Ncgc00378936-01

    35. Ncgc00378936-02

    36. Ac-35698

    37. As-56206

    38. Hy-15233

    39. J3.556.145e

    40. D10801

    41. D71052

    42. A902281

    43. Q15409407

    44. (4s)-2-(8-fluoro-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3-(2-methoxy-5-(trifluoromethyl)phenyl)-3,4-dihydroquinazolin-4-yl)acetic Acid

    45. (4s)-8-fluoro-3,4-dihydro-2-[4-(3-methoxyphenyl)-1-piperazinyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-4-quinazolineacetic Acid

    46. (s)-{8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-(2-methoxy-5-trifluoromethylphenyl)-3,4-dihydro-quinazolin-4-yl}acetic Acid

    47. (s)-{8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-(2-methoxy-5-trifluoromethylphenyl)-3,4-dihydroquinazolin-4-yl}acetic Acid

    48. (s)-2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetic Acid

    2.4 Create Date
    2010-04-26
    3 Chemical and Physical Properties
    Molecular Weight 572.5 g/mol
    Molecular Formula C29H28F4N4O4
    XLogP34.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count7
    Exact Mass572.20466804 g/mol
    Monoisotopic Mass572.20466804 g/mol
    Topological Polar Surface Area77.8 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity931
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For use in prophylaxis of cytomegalovirus (CMV) infection and disease in adult CMV-seropositive recipients of an allogeneic hematopoietic stem cell transplant (HSCT).

    FDA Label

    Prevymis is indicated for prophylaxis of cytomegalovirus (CMV) reactivation and disease in adult CMV-seropositive recipients [R+] of an allogeneic haematopoietic stem cell transplant (HSCT).

    Consideration should be given to official guidance on the appropriate use of antiviral agents.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Letermovir inhibits the activity of the DNA terminase complex of CMV thereby preventing the cutting of viral DNA into mature length genomes for packaging into viral particles. Letemovir inhibits the DNA terminase complex with an EC50 of 2.1nM.

    5.2 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

    Poly(ADP-ribose) Polymerase Inhibitors

    Chemicals and drugs that inhibit the action of POLY(ADP-RIBOSE)POLYMERASES. (See all compounds classified as Poly(ADP-ribose) Polymerase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    LETERMOVIR
    5.3.2 FDA UNII
    1H09Y5WO1F
    5.3.3 Pharmacological Classes
    Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2C9 Inducers [MoA]; Cytochrome P450 3A Inhibitors [MoA]; Cytomegalovirus DNA Terminase Complex Inhibitor [EPC]; DNA Terminase Complex Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]; Cytochrome P450 2C19 Inducers [MoA]
    5.4 ATC Code

    J05

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AX - Other antivirals

    J05AX18 - Letermovir

    5.5 Absorption, Distribution and Excretion

    Absorption

    Letermovir has a bioavailability of 94% in healthy subjects when administered without cyclosporin, 35% in HSCT recipients when administered without cyclosporin, and 85% in HSCT recipients when administered with cyclosporin. Letermovir's Tmax is 45 min to 2.25 h. Time to steady state has been observed to be 9-10 days. Taking Letermovir with food increases Cmax by an average of 129.82% (range of 104.35%-161.50%). No significant effect on AUC has been observed .

    Route of Elimination

    Letemovir is taken up by the liver through OATP1B1/3 transporters. 93% is excreted in the feces with 70% as the parent drug. <2% is excreted in the urine.

    Volume of Distribution

    The mean steady state volume of distrubution is 45.5L

    Clearance

    The mean clearance is 11.25 L/h in healthy subjects

    5.6 Metabolism/Metabolites

    Letermovir undergoes a minor degree of metabolism through UGT1A1/1A3.

    5.7 Biological Half-Life

    The mean terminal half-life was observed to be 12 hours following administration of Letemovir 480 mg IV once daily.

    5.8 Mechanism of Action

    CMV relies on a DNA terminase complex consisting of multiple subunits (pUL51, pUL56, and pUL89) for processing of viral DNA. Viral DNA is produced in a single repeating strand which is then cut by the DNA terminase complex into individual viral genomes which can then be packaged into mature viral particles. Letemovir inhibits the activity of this complex to prevent production of mature viral genomes and the production of viable viral particles. The exact nature of Letemovir's binding to this complex is not currently known. Initially, the observation of resistance-causing mutations in pUL56 suggested this subunit was the location of Letemovir binding. However, resistance mutations have now been observed in pUL51, pUL56, and pUL89. It is possible that changes in amino acid sequence in one subunit could result in conformational changes to interacting subunits affecting Letemovir binding or that Letemovir interacts with multiple subunits of the complex but evidence towards either of these distinctions has not yet been seen. pUL89 is known to contain the endonuclease activity of the complex but because all members of the complex are necessary for targeting as well as protection from proteosomal degradation, it is difficult to discern if Letemovir inhibits pUL89's activity directly.

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