Find Maribavir manufacturers, exporters & distributors on PharmaCompass

Maribavir

Maribavir

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

2 API Suppliers, 1 KDMF, 1 NDC API, 2 Listed Suppliers

DEVELOPMENTS

9 Drug(s) in Development

9 Drug(s) in Development

DOSSIERs // Finished Dosage Formulations

2 Dossiers, 1 FDA Orange Book, 1 Canada

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions

1 US Medicaid Prescriptions

PATENTS

1 US Patents, 2 US Exclusivities

DIGITAL CONTENT

26 News

26 News

Product Search

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

Other Certificates

Other Suppliers

API REF. PRICE (USD / KG)

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: 176161-24-3, Benzimidavir, 1263w94, Livtencity, (2s,3s,4r,5s)-2-(5,6-dichloro-2-(isopropylamino)-1h-benzo[d]imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, Camvia

Molecular Formula

C₁₅H₁₉Cl₂N₃O₄

Molecular Weight

376.2 g/mol

InChI Key

KJFBVJALEQWJBS-XUXIUFHCSA-N

FDA UNII

PTB4X93HE1

Maribavir is an orally available benzimidazole riboside compound with activity against cytomegalovirus (CMV). Maribavir is a selective ATP competitor of viral UL97 kinase, which is involved in viral nuclear maturation events, such as viral DNA assembly and movement of viral capsids from the nucleus of infected cells. Maribavir has activity against strains of CMV that are resistant to standard anti-CMV agents.

Maribavir is a Cytomegalovirus pUL97 Kinase Inhibitor. The mechanism of action of maribavir is as a Cytomegalovirus pUL97 Kinase Inhibitor, and Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.

1 2D Structure

Maribavir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4R,5S)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol

2.1.2 InChI

InChI=1S/C15H19Cl2N3O4/c1-6(2)18-15-19-9-3-7(16)8(17)4-10(9)20(15)14-13(23)12(22)11(5-21)24-14/h3-4,6,11-14,21-23H,5H2,1-2H3,(H,18,19)/t11-,12-,13-,14-/m0/s1

2.1.3 InChI Key

KJFBVJALEQWJBS-XUXIUFHCSA-N

2.1.4 Canonical SMILES

CC(C)NC1=NC2=CC(=C(C=C2N1C3C(C(C(O3)CO)O)O)Cl)Cl

2.1.5 Isomeric SMILES

CC(C)NC1=NC2=CC(=C(C=C2N1[C@@H]3[C@H]([C@H]([C@@H](O3)CO)O)O)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

PTB4X93HE1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1263-w-94

2. 1263w94

3. 5,6-dichloro-2-(isopropylamino)-1-beta-l-ribofuranosylbenzimidazole

4. Benzimidavir

5. Bw 1263w94

6. Bw-1263w94

7. Gw 1263

8. Gw 257406x

9. Gw-1263

10. Gw-257406x

11. Gw257406x

2.3.2 Depositor-Supplied Synonyms

1. 176161-24-3

2. Benzimidavir

3. 1263w94

4. Livtencity

5. (2s,3s,4r,5s)-2-(5,6-dichloro-2-(isopropylamino)-1h-benzo[d]imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

6. Camvia

7. Bw-1263w94

8. Gw-257406x

9. Gw-1263

10. Ptb4x93he1

11. (2s,3s,4r,5s)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol

12. 5,6-dichloro-2-(isopropylamino)-1-beta-l-ribofuranosyl-1h-benzimidazole

13. 1263-w-94

14. Gw257406x

15. G1263

16. Maribavir [usan]

17. Unii-ptb4x93he1

18. Maribavir [usan:inn:ban]

19. Camvia(tm)

20. Camvia (tn)

21. Bw 1263w94

22. Maribavir [inn]

23. Maribavir (usan/inn)

24. Maribavir [who-dd]

25. Schembl791309

26. Chembl515408

27. Gtpl12049

28. Dtxsid60170091

29. Zinc3824412

30. Bw1263w94

31. 5,6-dichloro-2-(isopropylamino)-1-(beta-l-ribofuranosyl)-1h-benzimidazole

32. Akos015962194

33. Db06234

34. Gw 1263

35. Gw 257406x

36. 5,6-dichloro-n-(1-methylethyl)-1-beta-l-ribofuranosyl-1h-benzimidazol-2-amine

37. Ncgc00378559-03

38. Ac-22286

39. As-49903

40. Hy-16305

41. Vp-41263

42. D04859

43. O10059

44. Q6762512

45. Maribavir (1263w94, Benzimidazole D-ribose Derivative)

46. 5,6-dichloro-2-(isopropylamino)-1-beta-l-ribofuranosylbenzimidazole

47. 5,6-dichloro-2-(isopropylamino)-1-(.beta.-l-ribofuranosyl)benzimidazole

48. 5,6-dichloro-2-isopropylamino-1-(beta-l-ribofuranosyl)-1h-benzimidazole

49. 1h-benzimidazol-2-amine, 5,6-dichloro-n-(1-methylethyl)-1-.beta.-l-ribofuranosyl-

50. 1h-benzimidazol-2-amine, 5,6-dichloro-n-(1-methylethyl)-1-beta-l-ribofuranosyl-

51. 5,6-dichloro-2-(isopropylamino)-1-.beta.-l-ribofuranosylbenzimidazole

52. 5,6-dichloro-n-(1-methylethyl)-1-.beta.-l-ribofuranosyl-1h-benzimidazol-2-amine

53. (2s,3s,4r,5s)-2-(5,6-dichloro-2-(isopropylamino)-1h-benzo[d]-imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

54. (2s,3s,4r,5s)-2-[5,6-dichloro-2-(isopropylamino)benzimidazol-1-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₉Cl₂N₃O₄
Molecular Weight	376.2 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	375.0752615 g/mol
Monoisotopic Mass	375.0752615 g/mol
Topological Polar Surface Area	99.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	447
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Maribavir is indicated for the treatment of adult and pediatric patients (weighing >35kg and at least 12 years old) with post-transplant cytomegalovirus (CMV) infection which is refractory to standard treatment with [ganciclovir], [valganciclovir], [cidofovir], or [foscarnet].

Cytomegaloviral disease

Treatment of cytomegalovirus (CMV) infection

5 Pharmacology and Biochemistry

5.1 Pharmacology

Maribavir exerts its antiviral efficacy via an alternative target as compared to traditional CMV antivirals and is thus useful in the treatment of CMV infections that have proven resistant to standard therapy. Maribavir should not be used concomitantly with ganciclovir or valganciclovir, as these molecules both require activation via CMV pUL97 in order to exert their antiviral effect. Taking them alongside maribavir - an inhibitor of this same kinase - will therefore significantly reduce their antiviral activity.

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

MARIBAVIR

5.3.2 FDA UNII

PTB4X93HE1

5.3.3 Pharmacological Classes

Cytochrome P450 3A4 Inhibitors [MoA]; Cytomegalovirus pUL97 Kinase Inhibitor [EPC]; Cytomegalovirus pUL97 Kinase Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]

5.4 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX10 - Maribavir

5.5 Absorption, Distribution and Excretion

Absorption

Population pharmacokinetic modeling in patients receiving maribavir 400mg twice daily showed an AUC_0-tau and C_max of 128 g.h/mL and 17.2 g/mL, respectively. It has a median T_max of one to three hours.

Route of Elimination

Maribavir is eliminated primarily via hepatic metabolism. Following the oral administration of radiolabeled maribavir, 61% of the dose was excreted in the urine (<2% as unchanged drug) and 14% was excreted in the feces (5.7% as unchanged drug).

Volume of Distribution

The mean apparent steady-state volume of distribution for maribavir was 27.3 L.

Clearance

In post-transplant patients, the mean oral clearance of maribavir was 2.85 L/h.

5.6 Metabolism/Metabolites

Maribavir is extensively metabolized following oral administration, primarily by CYP3A4 and, to a lesser extent, by CYP1A2. Its major circulating metabolite is VP 44469, an inactive N-dealkylated metabolite.

5.7 Biological Half-Life

In post-transplant patients, the mean half-life of elimination was 4.32 hours.

5.8 Mechanism of Action

Human cytomegalovirus (CMV) is a herpesvirus commonly causing infection in patients following stem cell or organ transplants. As with other herpesviruses, CMV tends to persist in the host and become reactivated under immunosuppressive conditions - patients requiring multiple immunosuppressive medications to combat transplant rejection are thus at a much higher risk of developing serious CMV infections. Maribavir belongs to a class of anti-cytomegalovirus antivirals called benzimidazole ribosides. It competitively inhibits the human CMV pUL97 viral protein kinase, which results in viable but severely defective viruses upon replication, although the reasons for this remain poorly defined. In addition, maribavir also inhibits viral release from the nucleus to the cytoplasm by inhibiting pUL97-dependent phosphorylation of the nuclear lamina component lamin A/C, although the extent to which this activity contributes to its antiviral efficacy is unclear.