lopinavir indications/contra

Stem definitionDrug idCAS RN
HIV protease inhibitors 1601 192725-17-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • lopinavir
  • aluviran
  • koletra
An HIV protease inhibitor used in a fixed-dose combination with RITONAVIR. It is also an inhibitor of CYTOCHROME P-450 CYP3A.
  • Molecular weight: 628.81
  • Formula: C37H48N4O5
  • CLOGP: 6.09
  • LIPINSKI: 2
  • HAC: 9
  • HDO: 4
  • TPSA: 120
  • ALOGS: -5.51
  • ROTB: 15

Drug dosage:

DoseUnitRoute
0.80 g O

Approvals:

DateAgencyCompanyOrphan
Sept. 15, 2000 FDA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Exposure during pregnancy 2619.87 41.43 690 4392 26873 3353904
Foetal exposure during pregnancy 2289.70 41.43 554 4528 14997 3365780
Premature baby 1125.01 41.43 271 4811 6982 3373795
Abortion spontaneous 821.26 41.43 229 4853 10556 3370221
Virologic failure 820.87 41.43 156 4926 1198 3379579
Immune reconstitution inflammatory syndrome 646.57 41.43 140 4942 2173 3378604
Stillbirth 628.60 41.43 128 4954 1447 3379330
Abortion induced 489.78 41.43 122 4960 3569 3377208
Maternal exposure during pregnancy 456.20 41.43 144 4938 10127 3370650
Lipodystrophy acquired 456.10 41.43 82 5000 441 3380336
Drug resistance 437.65 41.43 117 4965 4546 3376231
Premature delivery 425.22 41.43 101 4981 2404 3378373
Diarrhoea 383.51 41.43 255 4827 104093 3276684
Drug interaction 368.57 41.43 188 4894 46624 3334153
Anaemia 328.38 41.43 183 4899 54150 3326627
Kaposi's sarcoma 325.65 41.43 67 5015 795 3379982
Foetal death 325.40 41.43 78 5004 1928 3378849
Pyrexia 258.50 41.43 182 4900 80933 3299844
Mitochondrial toxicity 258.16 41.43 44 5038 162 3380615
Vomiting 251.36 41.43 186 4896 89345 3291432
Congenital anomaly 241.15 41.43 60 5022 1736 3379041
Trisomy 21 224.22 41.43 44 5038 402 3380375
Viral load increased 203.23 41.43 45 5037 771 3380006
Gastrointestinal disorder 194.16 41.43 77 5005 10492 3370285
Foetal growth restriction 189.88 41.43 50 5032 1819 3378958
Nausea 189.29 41.43 185 4897 129460 3251317
Progressive external ophthalmoplegia 187.22 41.43 26 5056 6 3380771
Polydactyly 186.52 41.43 37 5045 359 3380418
Ventricular septal defect 185.88 41.43 49 5033 1790 3378987
Acute kidney injury 182.66 41.43 122 4960 49561 3331216

Pharmacologic Action:

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SourceCodeDescription
ATC J05AR10 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
FDA EPC N0000175889 Protease Inhibitor
FDA MoA N0000185503 P-Glycoprotein Inhibitors
FDA MoA N0000190114 Cytochrome P450 3A Inhibitors
FDA MoA N0000190107 Organic Anion Transporting Polypeptide 1B1 Inhibitors
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D065692 Cytochrome P-450 CYP3A Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D017320 HIV Protease Inhibitors
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D011480 Protease Inhibitors
CHEBI has role CHEBI:36044 antiviral drug

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Hyperbilirubinemia contraindication 14783006 DOID:2741
Cirrhosis of liver contraindication 19943007 DOID:5082
Complete atrioventricular block contraindication 27885002
Hereditary factor VIII deficiency disease contraindication 28293008 DOID:12134
Torsades de pointes contraindication 31722008
Hereditary factor IX deficiency disease contraindication 41788008 DOID:12259
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Chronic type B viral hepatitis contraindication 61977001
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Cardiomyopathy contraindication 85898001 DOID:0050700
Prolonged QT interval contraindication 111975006
Chronic hepatitis C contraindication 128302006
Structural disorder of heart contraindication 128599005
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Second degree atrioventricular block contraindication 195042002
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Mixed hyperlipidemia contraindication 267434003
Hypertriglyceridemia contraindication 302870006
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Congenital long QT syndrome contraindication 442917000
First Degree Atrioventricular Heart Block contraindication
Prevention of HIV Infection after Exposure off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.03 acidic
pKa2 12.72 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG KALETRA ABBVIE N021906 Nov. 9, 2007 RX TABLET ORAL 7364752 Nov. 10, 2020 TREATMENT OF HIV-INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
200MG KALETRA ABBVIE N021906 Oct. 28, 2005 RX TABLET ORAL 7364752 Nov. 10, 2020 TREATMENT OF HIV-INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
80MG/ML KALETRA ABBVIE N021251 Sept. 15, 2000 RX SOLUTION ORAL 6911214 Nov. 28, 2021 TREATMENT OF HIV INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
100MG KALETRA ABBVIE N021906 Nov. 9, 2007 RX TABLET ORAL 8691878 Aug. 25, 2024 TREATMENT OF HIV-1 INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
200MG KALETRA ABBVIE N021906 Oct. 28, 2005 RX TABLET ORAL 8691878 Aug. 25, 2024 TREATMENT OF HIV-1 INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
100MG KALETRA ABBVIE N021906 Nov. 9, 2007 RX TABLET ORAL 8309613 Dec. 24, 2024 TREATMENT OF HIV-INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
200MG KALETRA ABBVIE N021906 Oct. 28, 2005 RX TABLET ORAL 8309613 Dec. 24, 2024 TREATMENT OF HIV-INFECTION IN COMBINATION WITH OTHER ANTIRETROVIRAL AGENTS
100MG KALETRA ABBVIE N021906 Nov. 9, 2007 RX TABLET ORAL 8377952 Oct. 22, 2027 ADMINISTRATION WITHOUT FOOD FOR TREATMENT OF HIV-1 INFECTION
200MG KALETRA ABBVIE N021906 Oct. 28, 2005 RX TABLET ORAL 8377952 Oct. 22, 2027 ADMINISTRATION WITHOUT FOOD FOR TREATMENT OF HIV-1 INFECTION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Multidrug resistance protein 1 Transporter IC50 4.99 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.07 CHEMBL
Pol polyprotein Enzyme INHIBITOR Ki 10.40 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein WOMBAT-PK
CAAX prenyl protease 1 homolog Enzyme IC50 4.74 CHEMBL
Protease Enzyme IC50 7.60 CHEMBL

External reference:

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IDSource
4021228 VUID
N0000179581 NUI
C0674432 UMLSCUI
D01425 KEGG_DRUG
2494G1JF75 UNII
7798 INN_ID
CHEMBL729 ChEMBL_ID
d04716 MMSL
15774 MMSL
195088 RXNORM
4021228 VANDF
129475001 SNOMEDCT_US
387067003 SNOMEDCT_US
N0000148672 NDFRT
N0000179581 NDFRT
008874 NDDF
DB01601 DRUGBANK_ID
92727 PUBCHEM_CID
D061466 MESH_DESCRIPTOR_UI
CHEBI:31781 CHEBI
AB1 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-0522 TABLET, FILM COATED 100 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-3956 SOLUTION 80 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-6799 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Lopinavir-Ritonavir HUMAN PRESCRIPTION DRUG LABEL 2 0527-1947 SOLUTION 80 mg ORAL ANDA 19 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 11819-342 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 21695-362 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 53808-0276 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 54868-5566 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 55154-6955 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 55289-947 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 66336-624 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 68258-1972 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 70518-0091 TABLET, FILM COATED 200 mg ORAL NDA 18 sections