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5 Gangwal Healthcare
6 Nanjing Well Pharmaceutical
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2 Alcedo Pharmachem
3 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd
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11 Gangwal Chemicals
1 Huzhou Sunflower Pharmaceutical
6 Ideal Cures Pvt Ltd
14 Kerry
3 Kima Chemical
6 Lonza Capsugel
4 Microlex e.U
1 Nanjing Bold Chemical
1 NEWEDGE Overseas
4 Novo Excipients
2 Pharmatrans-Sanaq
3 Pluviaendo
1 Prachin Chemical
1 Qianhao Chemical (Hebei) Co., Ltd
1 Qualicaps
3 Roquette
15 Seppic
2 Shanghai Shenmei Pharmaceutical Technology Co., Ltd
1 Shanghai Welltone Material Technology Co., Ltd
2 Sigachi Industries
2 The Dow Chemical Company
1 Ulanqab Kema New Material
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1 Zhejiang Huakang Pharmaceutical

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Synopsis

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Chemistry

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Also known as: 192725-17-0, Abt-378, Aluviran, Koletra, Abt 378, A 157378.0

Molecular Formula

C₃₇H₄₈N₄O₅

Molecular Weight

628.8 g/mol

InChI Key

KJHKTHWMRKYKJE-SUGCFTRWSA-N

FDA UNII

2494G1JF75

An HIV protease inhibitor used in a fixed-dose combination with RITONAVIR. It is also an inhibitor of CYTOCHROME P-450 CYP3A.

Lopinavir is a Protease Inhibitor. The mechanism of action of lopinavir is as a HIV Protease Inhibitor, and P-Glycoprotein Inhibitor, and Cytochrome P450 3A Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor.

1 2D Structure

Lopinavir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-N-[(2S,4S,5S)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide

2.1.2 InChI

InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1

2.1.3 InChI Key

KJHKTHWMRKYKJE-SUGCFTRWSA-N

2.1.4 Canonical SMILES

CC1=C(C(=CC=C1)C)OCC(=O)NC(CC2=CC=CC=C2)C(CC(CC3=CC=CC=C3)NC(=O)C(C(C)C)N4CCCNC4=O)O

2.1.5 Isomeric SMILES

CC1=C(C(=CC=C1)C)OCC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](C[C@H](CC3=CC=CC=C3)NC(=O)[C@H](C(C)C)N4CCCNC4=O)O

2.2 Other Identifiers

2.2.1 UNII

2494G1JF75

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A 157378.0

2. A-157378.0

3. A157378.0

4. Abt 378

5. Abt-378

6. Abt378

7. N-(4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2h)-pydrimidineacetamide

2.3.2 Depositor-Supplied Synonyms

1. 192725-17-0

2. Abt-378

3. Aluviran

4. Koletra

5. Abt 378

6. A 157378.0

7. A-157378.0

8. Lopinavir-

9. Rs-346

10. Chebi:31781

11. A-157378-0

12. Lopinavir (abt-378)

13. (alphas)-tetrahydro-n-((alphas)-alpha-((2s,3s)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-alpha-isopropyl-2-oxo-1(2h)-pyrimidineacetamide

14. Lpv

15. Lopinavir, (s-(2s,4s,5s))-

16. A 157378

17. 2494g1jf75

18. (2s)-n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide

19. (s)-n-((2s,4s,5s)-5-(2-(2,6-dimethylphenoxy)acetamido)-4-hydroxy-1,6-diphenylhexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

20. N-{1-benzyl-4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-5-phenyl-pentyl}-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide

21. Ncgc00164576-02

22. Dsstox_cid_26456

23. Dsstox_rid_81630

24. Dsstox_gsid_46456

25. (2s)-n-[(2s,4s,5s)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide

26. (2s)-n-[(1s,3s,4s)-1-benzyl-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-pentyl]-3-methyl-2-(2-oxohexahydropyrimidin-1-yl)butanamide

27. Ab1

28. Smr002529581

29. Cas-192725-17-0

30. Lopinavirum

31. Abt378

32. Unii-2494g1jf75

33. Hsdb 8138

34. 1mui

35. 2qhc

36. 2rkf

37. 2rkg

38. 3ogq

39. Lopinavir [usan:usp:inn:ban]

40. Aids032937

41. Lopinavir, Bio-x

42. (2s)-n-((1s,3s,4s)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

43. (2s)-n-[(1s,3s,4s)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

44. Lopinavir & Plga

45. Kaletra (lpv+rtv)

46. 2o4s

47. 2q5k

48. 4l1a

49. Lopinavir [inn]

50. Lopinavir [jan]

51. Lopinavir [mi]

52. Lopinavir [usan]

53. Lopinavir [vandf]

54. Chembl729

55. Lopinavir [mart.]

56. Lpv & Aag

57. Lopinavir [usp-rs]

58. Lopinavir [who-dd]

59. Lopinavir [who-ip]

60. Lopinavir (jan/usp/inn)

61. Schembl21775

62. Lopinavir [ema Epar]

63. (1s-(1r*(r*),3r*,4r*))-n-(4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2h)-pyrimidineacetamide

64. Mls003915624

65. Mls004774152

66. Mls006011206

67. Abt-378; Lopinavir

68. Lopinavir [orange Book]

69. Dtxsid8046456

70. Lopinavir [ep Monograph]

71. Gtpl11504

72. Lopinavir [usp Monograph]

73. Kaletra Component Lopinavir

74. Bcpp000184

75. Lopinavirum [who-ip Latin]

76. Ex-a4008

77. Zinc3951740

78. Tox21_112204

79. Bdbm50180655

80. Lopinavir & Alpha1-acid Glycoprotein

81. Mfcd22628840

82. S1380

83. Lopinavir Component Of Kaletra

84. Akos025243115

85. Lopinavir & Poly-lactide-co-glycolide

86. Tox21_112204_1

87. Bcp9000857

88. Ccg-270285

89. Cs-2077

90. Db01601

91. Ks-1436

92. Lopinavir 100 Microg/ml In Acetonitrile

93. Ncgc00164576-01

94. Ncgc00164576-03

95. Ncgc00164576-04

96. (2s)-n-[(2r,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenyl-hexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide

97. (alphas)-n-[(1s,3s,4s)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2h)-pyrimidineacetamide

98. 1(2h)-pyrimidineacetamide, N-((1s,3s,4s)-4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahyrdo-alpha-1-methylethyl)-2-oxo-, (alphas)-

99. Bl164636

100. Hy-14588

101. L0377

102. Sw219767-1

103. D01425

104. Ab01274785-01

105. Ab01274785_02

106. A813594

107. Q422585

108. Sr-01000931910

109. J-521653

110. Sr-01000931910-2

111. A-1573780

112. Brd-k99451608-001-02-4

113. (.alpha.s)-tetrahydro-n-((.alpha.s)-.alpha.-((2s,3s)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-.alpha.-isopropyl-2-oxo-1(2h)-pyrimidineacetamide

114. (1s-(1r*(r*),3r*,4r*))-n-(4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-.alpha.-(1-methylethyl)-2-oxo-1(2h)-pyrimidineacetamide

115. (2s)-n-[(2s,4s,5s)-5-{[(2,6-dimethylphenoxy)acetyl]amino}-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

116. 1(2h)-pyrimidineacetamide, N-[(1s,3s,4s)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-.alpha.-(1-methylethyl)-2-oxo-, (as)-

117. 1(2h)-pyrimidineacetamide, N-[(1s,3s,4s)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphas)- (9ci)

118. 1(2h)-pyrimidineacetamide, N-[(1s,3s,4s)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphas)-

119. 1(2h)-pyrimidineacetamide, N-[4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, [1s-[1r*(r*),3r*,4r*]]-

2.4 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₈N₄O₅
Molecular Weight	628.8 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	15
Exact Mass	628.36247064 g/mol
Monoisotopic Mass	628.36247064 g/mol
Topological Polar Surface Area	120 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	940
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 Therapeutic Uses

Anti-HIV Agents; HIV Protease Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2013)

The fixed combination of lopinavir and ritonavir (lopinavir/ritonavir) is used in conjunction with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in adults, adolescents, and pediatric patients 14 days of age and older. Lopinavir/ritonavir is used in patients who are antiretroviral naive (have not previously received antiretroviral therapy) or antiretroviral experienced (received prior antiretroviral therapy). /Included in US product label/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 633

The manufacturer advises that the following factors be considered when initiating lopinavir/ritonavir. Administration of lopinavir/ritonavir in conjunction with other active antiretroviral agents is associated with a greater likelihood of treatment response. Use of lopinavir/ritonavir should be guided by results of genotypic or phenotypic viral resistance testing and/or the individual's prior antiretroviral treatment. The number of lopinavir resistance-associated mutations at baseline affects virologic response to lopinavir/ritonavir. Once-daily administration of lopinavir/ritonavir is not recommended in adults infected with HIV-1 strains with 3 or more viral mutations associated with lopinavir resistance and is not recommended in pediatric patients.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 633

Lopinavir/ritonavir is used in conjunction with other antiretrovirals for postexposure prophylaxis of HIV infection in individuals who have had nonoccupational exposure to blood, genital secretions, or other potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission. /NOT included in US product label/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 634

For more Therapeutic Uses (Complete) data for Lopinavir (6 total), please visit the HSDB record page.

4.2 Drug Warning

Serious and/or life-threatening adverse effects, clinically important drug interactions, or loss of virologic effect can occur if the fixed combination of lopinavir and ritonavir (lopinavir/ritonavir) is used concomitantly with some drugs. The potential for drug interactions must be considered prior to and during lopinavir/ritonavir therapy. Clinicians should review all drugs the patient is receiving and should monitor for adverse effects during lopinavir/ritonavir therapy.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 635

Lopinavir/ritonavir oral solution contains 42.4% (v/v) alcohol and 15.3% (w/v) propylene glycol. When administered concomitantly with propylene glycol, ethanol competitively inhibits metabolism of propylene glycol, which may lead to elevated propylene glycol concentrations. Preterm neonates /NOT included in US product label/may be at increased risk of propylene glycol-associated adverse effects due to diminished ability to metabolize propylene glycol, thereby leading to accumulation and potential adverse events. Life-threatening cardiac toxicity (including complete atrioventricular [AV] block, bradycardia, cardiomyopathy), lactic acidosis, acute renal failure, CNS depression, and respiratory complications leading to death have been reported, predominantly in preterm neonates /NOT included in US product label/ receiving lopinavir/ritonavir oral solution. Neonates, especially those born prematurely, are at risk of lopinavir, ethanol, and/or propylene glycol toxicity if they receive lopinavir/ritonavir oral solution.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 635

Once-daily regimens of lopinavir/ritonavir have not been evaluated in pediatric patients, and are not recommended in patients younger than 18 years of age.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 636

A safe and effective dose of lopinavir/ritonavir oral solution has not been established in neonates younger than 14 days of age /NOT included in US product label/ (whether born prematurely or full term). If the benefits of the oral solution for the treatment of HIV infection in an infant immediately after birth are judged to outweigh potential risks, the infant should be monitored closely for increases in serum osmolality and serum creatinine and other signs of toxicity related to the oral solution. These toxicities include hyperosmolality with or without lactic acidosis, renal toxicity, CNS depression (including stupor, coma, apnea), seizures, hypotonia, cardiac arrhythmias, ECG changes, and hemolysis. If lopinavir/ritonavir oral solution is used in preterm neonates /NOT included in US product label/ or in pediatric patients 14 days to 6 months of age, total amounts of alcohol and propylene glycol from all drugs that the child is receiving should be taken into account to avoid toxicity associated with these excipients.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 636

For more Drug Warnings (Complete) data for Lopinavir (19 total), please visit the HSDB record page.

4.3 Drug Indication

The combination product lopinavir/ritonavir, marketed under the brand name Kaletra, is indicated in combination with other antiretrovirals for the treatment of HIV-1 infection in adults and pediatric patients 14 days old.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lopinavir inhibits the activity of an enzyme critical for the HIV viral lifecycle. It has a moderate duration of action necessitating once or twice daily dosing. Lopinavir, like other protease inhibitors, has a propensity for participating in drug interactions - use caution when administering lopinavir to patients maintained on other pharmaceutical agents as pharmacodynamic and pharmacokinetic interactions are common. Fatal hepatotoxicity and pancreatitis have been noted in patients undergoing therapy with lopinavir and patients with an increased baseline risk of these events should be monitored closely throughout therapy.

5.2 MeSH Pharmacological Classification

Cytochrome P-450 CYP3A Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)

HIV Protease Inhibitors

Inhibitors of HIV PROTEASE, an enzyme required for production of proteins needed for viral assembly. (See all compounds classified as HIV Protease Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LOPINAVIR

5.3.2 FDA UNII

2494G1JF75

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Organic Anion Transporting Polypeptide 1B1 Inhibitors

5.4 ATC Code

J05AR10

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

5.5 Absorption, Distribution and Excretion

Absorption

When administered alone, lopinavir has exceptionally low oral bioavailability (~25%) - for this reason, it is exclusively co-administered with ritonavir, which dramatically improves bioavailability, hinders drug metabolism, and allows for the attainment of therapeutic lopinavir concentrations. Following oral administration of lopinavir/ritonavir, maximal plasma concentrations are achieved at approximately 4.4 hours (T_max), and the C_max and AUC_tau are 9.8 3.7 - 11.8 3.7 g/mL and 92.6 36.7 - 154.1 61.4 gh/mL, respectively. Relative to administration in the fasted state, administration with a meal increases the AUC of the tablet formulation slightly (~19%) but dramatically increases the AUC of the oral solution formulation (~130%).

Route of Elimination

Lopinavir is primarily eliminated in the feces. Following oral administration, approximately 10.4 2.3% of the administered dose is excreted in the urine and 82.6 2.5% is excreted in the feces. Unchanged parent drug accounted for 2.2% and 19.8% of the administered dose in urine and feces, respectively.

Volume of Distribution

The volume of distribution of lopinavir following oral administration is approximately 16.9 L.

Clearance

The estimated apparent clearance following oral administration is approximately 6-7 L/h.

At steady state, lopinavir is approximately 98-99% bound to plasma proteins. Lopinavir binds to both alpha-1-acid glycoprotein (AAG) and albumin; however, it has a higher affinity for AAG. At steady state, lopinavir protein binding remains constant over the range of observed concentrations after 400/100 mg KALETRA twice daily, and is similar between healthy volunteers and HIV-1 positive patients.

US Natl Inst Health; DailyMed. Current Medication Information for KALETRA (kaletra) tablet (September 2010). Available from, as of July 27, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=68e860d7-4adc-418a-ba12-233ccdf85d0a

In a pharmacokinetic study in HIV-1 positive subjects (n = 19), multiple dosing with 400/100 mg KALETRA twice daily with food for 3 weeks produced a mean SD lopinavir peak plasma concentration (Cmax) of 9.8 + or - 3.7 ug/mL, occurring approximately 4 hours after administration. The mean steady-state trough concentration prior to the morning dose was 7.1 + or - 2.9 ug/mL and minimum concentration within a dosing interval was 5.5 + or - 2.7 ug/mL. Lopinavir AUC over a 12 hour dosing interval averaged 92.6 + or - 36.7 ug*h/mL. The absolute bioavailability of lopinavir co-formulated with ritonavir in humans has not been established. Under nonfasting conditions (500 kcal, 25% from fat), lopinavir concentrations were similar following administration of KALETRA co-formulated capsules and oral solution. When administered under fasting conditions, both the mean AUC and Cmax of lopinavir were 22% lower for the KALETRA oral solution relative to the capsule formulation.

Lopinavir and ritonavir are distributed into milk in rats; it is not known whether the drugs are distributed into human milk.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 636

The pharmacokinetics of once daily Kaletra have been evaluated in HIV-1 infected subjects naive to antiretroviral treatment. Kaletra 800/200 mg was administered in combination with emtricitabine 200 mg and tenofovir DF 300 mg as part of a once daily regimen. Multiple dosing of 800/200 mg Kaletra once daily for 4 weeks with food (n = 24) produced a mean + or - 3.7 SD lopinavir peak plasma concentration (Cmax) of 11.8 + or - 3.7 ug/mL, occurring approximately 6 hours after administration. The mean steady-state lopinavir trough concentration prior to the morning dose was 3.2 + or - 3.7 2.1 ug/mL and minimum concentration within a dosing interval was 1.7 + or - 3.7 1.6 ug/mL. Lopinavir AUC over a 24 hour dosing interval averaged 154.1 + or - 3.7 61.4 ug* h/mL.

For more Absorption, Distribution and Excretion (Complete) data for Lopinavir (11 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Lopinavir undergoes extensive oxidative metabolism, almost exclusively via hepatic CYP3A isozymes. Co-administration with ritonavir, a potent inhibitor of CYP3A enzymes, helps to stave off lopinavir's biotransformation and increase plasma levels of active antiviral drug. Twelve metabolites have been identified _in vitro_, with the C-4 oxidation products M1, M3, and M4 being the predominant metabolites found in plasma. The structures of these primary metabolites have been identified, but precise structural information regarding the remaining minor metabolites has not been elucidated.

Lopinavir was metabolised in rat, dog and human primarily by hepatic CYP3A4 isoenzymes. Radioactivity in rat and dog faeces consisted largely of unchanged parent compound after oral administration. Although there were similarities in metabolite pattern between rat, dog and human, qualitative and quantitative differences were observed. The metabolism of lopinavir was sensitive to inhibition of ritonavir, which is in accordance with the inhibition of metabolic clearance of lopinavir by ritonavir observed in the rat.

European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Kaletra, Scientific Discussion p.5 (2006). Available from, as of July 27, 2013: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000368/WC500039040.pdf

In vitro experiments with human hepatic microsomes indicate that lopinavir primarily undergoes oxidative metabolism. Lopinavir is extensively metabolized by the hepatic cytochrome P450 system, almost exclusively by the CYP3A isozyme. Ritonavir is a potent CYP3A inhibitor which inhibits the metabolism of lopinavir, and therefore increases plasma levels of lopinavir. A (14)C-lopinavir study in humans showed that 89% of the plasma radioactivity after a single 400/100 mg Kaletra dose was due to parent drug. At least 13 lopinavir oxidative metabolites have been identified in man. Ritonavir has been shown to induce metabolic enzymes, resulting in the induction of its own metabolism. Pre-dose lopinavir concentrations decline with time during multiple dosing, stabilizing after approximately 10 to 16 days.

5.7 Biological Half-Life

The elimination half-life of lopinavir is 6.9 2.2 hours.

After single dose administration, mean elimination half-life ranged between 2 to 3 hours and seemed to be increased after multiple dose administration (about 4-6 hr).

European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Kaletra, Scientific Discussion p.10 (2006). Available from, as of July 27, 2013: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000368/WC500039040.pdf

5.8 Mechanism of Action

The HIV lifecycle is comprised of 3 distinct stages: assembly, involving creation and packaging of essential viral components; budding, wherein the viral particle crosses the host cell plasma membrane and forms a lipid envelope; and maturation, wherein the viral particle alters its structure and becomes infectious. At the center of this lifecycle is the Gag polyprotein which, along with the products of its proteolysis, coordinate these stages and function as the major structural proteins of the virus. The HIV-1 protease enzyme, a dimeric aspartic protease, is the enzyme responsible for cleaving the Gag polyprotein and thus plays a critical role in many aspects of the HIV viral lifecycle. Lopinavir is an inhibitor of the HIV-1 protease enzyme. Its design is based on the "peptidomimetic" principle, wherein the molecule contains a hydroxyethylene scaffold which mimics the normal peptide linkage (cleaved by HIV protease) but which itself cannot be cleaved. By preventing HIV-1 protease activity, and thus the proteolysis of the Gag polyprotein, lopinavir results in the production of immature, non-infectious viral particles.

/The researchers/ have previously shown that the HIV protease inhibitor lopinavir has selective toxicity against human papillomavirus (HPV)-positive cervical carcinoma cells via an unknown mechanism. SiHa cervical carcinoma cells were stably transfected with the proteasome sensor vector pZsProSensor-1 to confirm lopinavir inhibits the proteasome in these cells. The Panorama Xpress profiler 725 antibody array was then used to analyse specific changes in protein expression in lopinavir-treated versus control untreated SiHa cells followed by PCR and western blotting. Colorimetric growth assays of lopinavir-treated E6/E7 immortalised versus control human keratinocytes were performed. Targeted small interfering RNA gene silencing followed by growth assay comparison of lopinavir-treated/untreated SiHa cells was also used. Lopinavir induced an increase in the fluorescence of pZsProSensor-1 transfected SiHa cells, indicative of proteasomal inhibition. Ribonuclease L (RNASEL) protein was shown to be up-regulated in lopinavir-treated SiHa cells, which was confirmed by PCR and western blot. Targeted silencing of RNASEL reduced the sensitivity of SiHa cells to lopinavir. Selective toxicity against E6/E7 immortalised keratinocytes versus control cells was also seen with lopinavir and was associated with up-regulated RNASEL expression. These data are consistent with the toxicity of lopinavir against HPV-positive cervical carcinoma cells being related to its ability to block viral proteasome activation and induce an up-regulation of the antiviral protein RNASEL. This is supported by the drug's selective toxicity and up-regulation of RNASEL in E6/E7 immortalised keratinocytes combined with the increased resistance to lopinavir observed in SiHa cells following silencing of RNASEL gene expression.

PMID:21685539 Batman G et al; Antivir Ther 16 (4): 515-25 (2011)

Lopinavir inhibits replication of HIV type 1 (HIV-1) by interfering with HIV protease. During HIV replication, HIV protease cleaves viral polypeptide products of the gag and gag-pol genes to form structural proteins of the virion core and essential viral enzymes. By interfering with the formation of these essential proteins and enzymes, lopinavir blocks maturation of the virus and causes formation of nonfunctional, immature, noninfectious virions. Lopinavir also has some in vitro activity against HIV type 2 (HIV-2).

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 639

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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Drugs in Development

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 100MG;25MG

USFDA APPLICATION NUMBER - 21906

DOSAGE - TABLET;ORAL - 200MG;50MG

USFDA APPLICATION NUMBER - 21906

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Topical

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

29 API Suppliers

15 USDMF

6 CEP/COS

5 EU WC

2 KDMF

8 NDC API

16 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

12 Drugs in Development

INTERMEDIATES

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

56 FDF Dossiers

20 FDA Orange Book

14 Europe

3 Canada

10 South Africa

9 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

TABLET;ORAL - 100MG;25MG

TABLET;ORAL - 200MG;50MG

RELATED EXCIPIENT COMPANIES

1 Minakem

3 Rochem International Inc

1 SPI Pharma

4 DKSH

1 Pharm-RX Chemical

2 Faran Shimi Pharmaceutical

6 Boai NKY Pharmaceuticals Ltd

1 Chynops Pharma

5 Gangwal Healthcare

6 Nanjing Well Pharmaceutical

1 ACG Worldwide

7 Actylis

1 Aeon Procare

2 Alcedo Pharmachem

3 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

15 BASF

1 Bioplus Life Sciences

1 Clariant

11 Corel Pharma Chem

1 Finar

11 Gangwal Chemicals

1 Huzhou Sunflower Pharmaceutical

6 Ideal Cures Pvt Ltd

14 Kerry

3 Kima Chemical

6 Lonza Capsugel

4 Microlex e.U

1 Nanjing Bold Chemical

1 NEWEDGE Overseas

4 Novo Excipients

2 Pharmatrans-Sanaq

3 Pluviaendo

1 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

3 Roquette

15 Seppic

2 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shanghai Welltone Material Technology Co., Ltd

2 Sigachi Industries

2 The Dow Chemical Company

1 Ulanqab Kema New Material

2 Valens Pharmachem

1 Zhejiang Huakang Pharmaceutical

EXCIPIENTS BY APPLICATIONS

52 Coating Systems & Additives

29 Solubilizers

25 Controlled & Modified Release

23 Fillers, Diluents & Binders

21 Film Formers & Plasticizers

18 Parenteral