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Also known as: 394730-60-0, Victrelis, Sch 503034, Ebp 520, Sch-503034, Sch503034

Molecular Formula

C₂₇H₄₅N₅O₅

Molecular Weight

519.7 g/mol

InChI Key

LHHCSNFAOIFYRV-DOVBMPENSA-N

FDA UNII

89BT58KELH

Boceprevir is an orally bioavailable, synthetic tripeptide inhibitor of the nonstructural protein 3 and 4A complex (NS3/NS4A), with potential activity against hepatitis C virus (HCV) genotype 1. Upon administration, boceprevir reversibly binds to the active center of the HCV NS3/NS4A and prevents NS3/NS4A protease-mediated polyprotein maturation. This disrupts the processing of viral proteins and the formation of a viral replication complex, which inhibits viral replication in HCV genotrype 1-infected host cells. NS3, a serine protease, is essential for the proteolytic cleavages within the HCV polyprotein and plays a key role during HCV viral RNA replication. NS4A is an activating factor for NS3. HCV is a small, enveloped, single-stranded RNA virus belonging to the Flaviviridae family.

Boceprevir is a Hepatitis C Virus NS3/4A Protease Inhibitor. The mechanism of action of boceprevir is as a HCV NS3/4A Protease Inhibitor, and Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 3A5 Inhibitor.

1 2D Structure

Boceprevir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

2.1.2 InChI

InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1

2.1.3 InChI Key

LHHCSNFAOIFYRV-DOVBMPENSA-N

2.1.4 Canonical SMILES

CC1(C2C1C(N(C2)C(=O)C(C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C

2.1.5 Isomeric SMILES

CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C

2.2 Other Identifiers

2.2.1 UNII

89BT58KELH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. N-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-(2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexan-2-carboxamide

2. Sch 503034

3. Sch-503034

4. Sch503034

5. Victrelis

2.3.2 Depositor-Supplied Synonyms

1. 394730-60-0

2. Victrelis

3. Sch 503034

4. Ebp 520

5. Sch-503034

6. Sch503034

7. Ebp-520

8. 89bt58kelh

9. Chebi:68621

10. 3-{[(1r,2s,5s)-3-[(2s)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-cyclobutyl-2-oxobutanamide

11. (1r,2s,5s)-n-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-((s)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

12. (1r,2s,5s)-n-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-((2s)-2-(((1,1-dimethylethyl)carbamoyl)amino)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexane-2-carboxamide

13. (1r,2s,5s)-n-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[(2s)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

14. (1r,2s,5s)-n-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[n-(tert-butylcarbamoyl)-3-methyl-l-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

15. (1s,4s,5r)-n-[3-amino-1-(cyclobutylmethyl)-2,3-dioxo-propyl]-3-[(2s)-2-(tert-butylcarbamoylamino)-3,3-dimethyl-butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-4-carboxamide

16. Boceprevir [usan]

17. Boceprevir [usan:inn]

18. Unii-89bt58kelh

19. Hsdb 8081

20. Victrelis(tm)

21. Victrelis (tn)

22. 3-azabicyclo(3.1.0)hexane-2-carboxamide, N-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-((2s)-2-((((1,1-dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6-dimethyl-, (1r,2s,5s)-

23. 3-azabicyclo[3.1.0]hexane-2-carboxamide, N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2s)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-, (1r,2s,5s)-

24. Boceprevir & Nm107

25. Boceprevir [mi]

26. Boceprevir [inn]

27. Boceprevir (inn/usan)

28. Boceprevir [vandf]

29. Boceprevir [mart.]

30. Boceprevir [who-dd]

31. Boceprevir [ema Epar]

32. Schembl640836

33. Chembl218394

34. Ebp520

35. Gtpl7876

36. Boceprevir [orange Book]

37. Bdbm12311

38. Dtxsid30960103

39. Bcp02502

40. Ex-a1336

41. Mfcd22208555

42. S3733

43. Akos005145787

44. Ebp-520;sch503034

45. Ccg-269852

46. Cs-0361

47. Db08873

48. Dt-0021

49. Ncgc00378631-01

50. Boc

51. Hy-10237

52. Sch 503034 & Nm107

53. D08876

54. Q410551

55. J-519910

56. (1r,5s)-n-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(s)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(s)-carboxamide

57. 3-azabicyclo(3.1.0)hexane-2-carboxamide, N-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-((2s)-2-((((1,1- Dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6- Dimethyl-, (1r,2s,5s)-

58. N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

59. N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-{n-[(tert-butylamino)(hydroxy)methylidene]-3-methylvalyl}-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboximidic Acid

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₄₅N₅O₅
Molecular Weight	519.7 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	519.34206955 g/mol
Monoisotopic Mass	519.34206955 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	959
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Victrelis
PubMed Health	Boceprevir (By mouth)
Drug Classes	Antiviral
Drug Label	VICTRELIS (boceprevir) is an inhibitor of the hepatitis C virus (HCV) non-structural protein 3 (NS3) serine protease.Boceprevir has the following chemical name: (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)am...
Active Ingredient	Boceprevir
Dosage Form	Capsule
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Merck Sharp Dohme

2 of 2
Drug Name	Victrelis
PubMed Health	Boceprevir (By mouth)
Drug Classes	Antiviral
Drug Label	VICTRELIS (boceprevir) is an inhibitor of the hepatitis C virus (HCV) non-structural protein 3 (NS3) serine protease.Boceprevir has the following chemical name: (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)am...
Active Ingredient	Boceprevir
Dosage Form	Capsule
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Merck Sharp Dohme

4.2 Therapeutic Uses

Boceprevir is indicated for the treatment of chronic hepatitis C genotype 1 infection, in combination with peginterferon alfa and ribavirin, in adult patients (18 years and older) with compensated liver disease, including cirrhosis, who are previously untreated or who have failed previous interferon and ribavirin therapy. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VICTRELIS (boceprevir) capsule (July 2012). Available from, as of November 13, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=ae879ebe-b620-4829-b6f8-74b58da1c771

Boceprevir must not be used as monotherapy and should only be used in combination with peginterferon alfa and ribavirin. /Included in US product label/

4.3 Drug Warning

FDA notified healthcare professionals that the boceprevir (Victrelis) drug label has been revised to state that co-administration of boceprevir, a hepatitis C virus (HCV) protease inhibitor, along with certain ritonavir-boosted human immunodeficiency virus (HIV) protease inhibitors, is not recommended. The findings of a drug-drug interaction study and clinical trial showed that co-administration increased of the possibility of reducing the effectiveness of the medicines, permitting the amount of HCV or HIV virus in the blood to increase. Ritonavir-boosted HIV protease inhibitors include ritonavir-boosted atazanavir (Reyataz), ritonavir-boosted darunavir (Prezista), and lopinavir/ritonavir (Kaletra).

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012

FDA notified healthcare professionals of updates to the prescribing information concerning interactions between protease inhibitors and certain statin drugs. Protease inhibitors and statins taken together may raise the blood levels of statins and increase the risk for muscle injury (myopathy). The most serious form of myopathy, called rhabdomyolysis, can damage the kidneys and lead to kidney failure, which can be fatal. BACKGROUND: Statins are a class of prescription drugs used together with diet and exercise to reduce blood levels of low-density lipoprotein (LDL) cholesterol ("bad cholesterol"). HIV protease inhibitors are a class of prescription anti-viral drugs used to treat HIV. HCV protease inhibitors are a class of prescription anti-viral drugs used to treat hepatitis C infection. RECOMMENDATION: Healthcare professionals should follow the recommendations in the prescribing information (drug labels) when prescribing HIV or HCV protease inhibitors with statins.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012

FDA notified healthcare professionals and patients that drug interactions between the hepatitis C virus (HCV) protease inhibitor boceprevir (Victrelis) and certain ritonavir-boosted human immunodeficiency virus (HIV) protease inhibitors (atazanavir, lopinavir, darunavir) can potentially reduce the effectiveness of these medicines when they are used together. A drug interaction study showed that taking boceprevir (Victrelis) with ritonavir (Norvir) in combination with atazanavir (Reyataz) or darunavir (Prezista), or with Kaletra (lopinavir/ritonavir) reduced the blood levels of the HIV medicines and boceprevir in the body. FDA will be updating the boceprevir drug label to include information about these drug interactions. BACKGROUND: Boceprevir is a hepatitis C virus (HCV) protease inhibitor used with the medicines peginterferon alfa and ribavirin to treat chronic (long-lasting) hepatitis C infection in adults. HIV protease inhibitors are a class of anti-viral drugs used to treat HIV infection. Ritonavir is an HIV protease inhibitor used to "boost" other HIV protease inhibitors, increasing their levels in the blood and making them more effective. RECOMMENDATION: Patients should not stop taking any of their medicines without talking to their healthcare professional. Patients should contact their healthcare professional if they have any questions or concerns. Healthcare professionals who have started patients infected with both chronic HCV and HIV on boceprevir and antiretroviral therapy containing a ritonavir-boosted protease inhibitor should closely monitor patients for HCV treatment response and for potential HCV and HIV virologic rebound.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012

Because boceprevir must be used in conjunction with peginterferon alfa and ribavirin, it is contraindicated in women who are or may become pregnant and in male partners of pregnant women. The contraindications, warnings, and precautions for all 3 drugs should be considered.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 849

For more Drug Warnings (Complete) data for Boceprevir (21 total), please visit the HSDB record page.

4.4 Drug Indication

Boceprevir, when used in combination with [DB00811], [DB00008], and [DB00022] is indicated for use in the treatment of chronic HCV genotype 1 infection in adults.

FDA Label

Victrelis is indicated for the treatment of chronic hepatitis-C (CHC) genotype-1 infection, in combination with peginterferon alfa and ribavirin, in adult patients with compensated liver disease who are previously untreated or who have failed previous therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Boceprevir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotype 1.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

BOCEPREVIR

5.2.2 FDA UNII

89BT58KELH

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Cytochrome P450 3A5 Inhibitors

5.3 ATC Code

J05AE

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AP - Antivirals for treatment of hcv infections

J05AP03 - Boceprevir

5.4 Absorption, Distribution and Excretion

Absorption

Boceprevir reaches peak plasma concentration 2 hours after administration. Absolute bioavailability has not been determined. When taken with food exposure increases up to 65%. In capsule, Boceprevir consists of two diaseromers in a 1:1 ratio. In plasma this ratio changes to 2:1 favoring the active diastereomer.

Route of Elimination

Boceprevir is mainly eliminated in the feces (79%) with a small amount eliminated in the urine (9%). Approximately 8% and 3% is excreted as the parent compound in the feces and urine respectively.

Volume of Distribution

The mean apparent volume of distribution for Bocepravir is 772 litres at steady state.

Clearance

Boceprevir has a mean total body clearance of 161 liters per hour.

In healthy subjects who received 800 mg three times daily alone, boceprevir drug exposure was characterized by AUC(T) of 5408 ng. hr per mL (n=71), Cmax of 1723 ng per mL (n=71), and Cmin of 88 ng per mL (n=71). Pharmacokinetic results were similar between healthy subjects and HCV-infected subjects.

Boceprevir was absorbed following oral administration with a median Tmax of 2 hours. Steady state AUC, Cmax, and Cmin increased in a less-than-dose-proportional manner and individual exposures overlapped substantially at 800 mg and 1200 mg, suggesting diminished absorption at higher doses. Accumulation is minimal (0.8- to 1.5-fold) and pharmacokinetic steady state is achieved after approximately 1 day of three times daily dosing.

Boceprevir should be administered with food. Food enhanced the exposure of boceprevir by up to 65% at the 800 mg three times daily dose, relative to the fasting state. The bioavailability of boceprevir was similar regardless of meal type (e.g., high-fat vs. low-fat) or whether taken 5 minutes prior to eating, during a meal, or immediately following completion of the meal. Therefore, boceprevir may be taken without regard to either meal type or timing of the meal.

Boceprevir has a mean apparent volume of distribution (Vd/F) of approximately 772 L at steady state in healthy subjects.

For more Absorption, Distribution and Excretion (Complete) data for Boceprevir (10 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Bocepravir is primarily metabolized via the aldo-ketoreductase-mediated pathway producing a diastereomeric mix of metabolites at a 4 fold greater exposure than the parent compound. Boceprevir also undergoes oxidative metabolism via CYP3A4/5, although to a lesser extent.

Studies in vitro indicate that boceprevir primarily undergoes metabolism through the aldo-ketoreductase (AKR)-mediated pathway to ketone-reduced metabolites that are inactive against HCV. After a single 800-mg oral dose of (14)C-boceprevir, the most abundant circulating metabolites were a diasteriomeric mixture of ketone-reduced metabolites with a mean exposure approximately 4-fold greater than that of boceprevir. Boceprevir also undergoes, to a lesser extent, oxidative metabolism mediated by CYP3A4/5.

5.6 Biological Half-Life

Boceprevir has a mean half-life of elimination of 3.4 hours.

Boceprevir is eliminated with a mean plasma half-life (t1/2) of approximately 3.4 hours.

5.7 Mechanism of Action

Boceprevir is a NS3/4a protease inhibitor used to inhibit viral HCV replication. NS3/4a protease is an integral part of viral replication and mediates the cleavage the virally encoded polyprotein to mature proteins (NS4A, NS4B, NS5A and NS5B). Boceprevir covalently but reversibly binds the serine (S139) resiude in the active site via a ()-ketoamide functional group. This inhibits the proteolytic acitvity of the HCV 1a and 1b encoded enzyme.

Boceprevir is a selective hepatitis C virus (HCV) nonstructural (NS) 3/4A protease inhibitor. The drug is a direct-acting antiviral agent with activity against HCV. Boceprevir contains an alpha-ketoamide functional group that selectively, covalently, and reversibly binds the active serine site of HCV NS3 protease. By blocking proteolytic cleavage of NS4A, NS4B, NS5A, and NS5B from the HCV-encoded polyprotein, the drug inhibits HCV replication in host cells. Boceprevir has in vitro activity against HCV genotypes 1a and 1b, but is less active against genotypes 2, 2a, and 3a.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 851

Boceprevir is an inhibitor of the HCV NS3/4A protease that is necessary for the proteolytic cleavage of the HCV encoded polyprotein into mature forms of the NS4A, NS4B, NS5A and NS5B proteins. Boceprevir covalently, yet reversibly, binds to the NS3 protease active site serine (S139) through an (alpha)-ketoamide functional group to inhibit viral replication in HCV-infected host cells. In a biochemical assay, boceprevir inhibited the activity of recombinant HCV genotype 1a and 1b NS3/4A protease enzymes, with Ki values of 14 nM for each subtype.

... Boceprevir is a ketoamide protease inhibitor that binds reversibly to the HCV nonstructural NS3 protease active site inhibiting intracellular viral replication. Phase III clinical studies have demonstrated that, in combination with the current standard of care, boceprevir significantly increases the a sustained virological response rate in both treatment-naive and previously treated patients with genotype 1 CHC. ...

PMID:22397560 Trembling PM et al; Expert Rev Anti Infect Ther 10 (3): 269-79 (2012)

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ACTIVE PHARMA INGREDIENTS

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