lopinavir Indications/Contra | FAERs | Orange Book | BioActivity |

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

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 2683.40 41.98 707 4951 32264 4601070
Foetal exposure during pregnancy 2535.14 41.98 630 5028 22539 4610795
Premature baby 1149.65 41.98 285 5373 9766 4623568
Lipodystrophy acquired 899.63 41.98 152 5506 648 4632686
Virologic failure 827.47 41.98 166 5492 2063 4631271
Abortion spontaneous 821.57 41.98 235 5423 13957 4619377
Immune reconstitution inflammatory syndrome 663.00 41.98 146 5512 2908 4630426
Stillbirth 640.77 41.98 132 5526 1882 4631452
Drug resistance 637.23 41.98 171 5487 7965 4625369
Abortion induced 547.42 41.98 132 5526 3965 4629369
Mitochondrial toxicity 479.34 41.98 78 5580 247 4633087
Maternal exposure during pregnancy 476.27 41.98 162 5496 16931 4616403
Drug interaction 448.23 41.98 226 5432 64282 4569052
Premature delivery 389.62 41.98 101 5557 4083 4629251
Diarrhoea 374.24 41.98 272 5386 149913 4483421
Foetal death 339.48 41.98 82 5576 2470 4630864
Anaemia 334.82 41.98 193 5465 71367 4561967
Eyelid ptosis 326.64 41.98 76 5582 1941 4631393
Kaposi's sarcoma 306.68 41.98 67 5591 1275 4632059
Progressive external ophthalmoplegia 300.86 41.98 42 5616 21 4633313
Viral mutation identified 260.00 41.98 57 5601 1102 4632232
Vomiting 253.13 41.98 197 5461 119502 4513832
Congenital anomaly 248.04 41.98 62 5596 2154 4631180
Trisomy 21 245.93 41.98 48 5610 507 4632827
Pyrexia 241.00 41.98 183 5475 106961 4526373
Viral load increased 236.60 41.98 52 5606 1017 4632317
Diplopia 222.68 41.98 72 5586 6379 4626955
Live birth 208.59 41.98 50 5608 1453 4631881
Spina bifida 208.10 41.98 41 5617 456 4632878
Gastrointestinal disorder 204.48 41.98 86 5572 15975 4617359
Premature labour 196.28 41.98 52 5606 2280 4631054
Nausea 195.39 41.98 202 5456 177131 4456203
Hyperlipidaemia 192.22 41.98 61 5597 5084 4628250
Foetal growth restriction 191.35 41.98 52 5606 2514 4630820
HIV infection 188.42 41.98 39 5619 565 4632769
Caesarean section 184.51 41.98 59 5599 5039 4628295
Hyperlactacidaemia 184.02 41.98 41 5617 855 4632479
Acute kidney injury 182.03 41.98 131 5527 70300 4563034
Cushing's syndrome 180.73 41.98 45 5613 1536 4631798
Abdominal pain 179.23 41.98 122 5536 59902 4573432
Portal hypertension 177.21 41.98 43 5615 1316 4632018
Polydactyly 175.66 41.98 36 5622 495 4632839
Pregnancy 174.40 41.98 65 5593 8779 4624555
Ventricular septal defect 171.83 41.98 47 5611 2328 4631006
Treatment noncompliance 168.56 41.98 69 5589 11958 4621376
Weight decreased 165.64 41.98 112 5546 54352 4578982
Premature rupture of membranes 163.10 41.98 38 5620 973 4632361
Small for dates baby 160.15 41.98 43 5615 1984 4631350
Pancytopenia 159.90 41.98 83 5575 24770 4608564
Blood triglycerides increased 157.87 41.98 53 5605 5272 4628062
Hepatitis 157.45 41.98 66 5592 12139 4621195
Fanconi syndrome 157.11 41.98 34 5624 616 4632718
Treatment failure 144.87 41.98 65 5593 14082 4619252
Maternal drugs affecting foetus 143.91 41.98 46 5612 3919 4629415
Skull malformation 143.21 41.98 28 5630 298 4633036
Liver disorder 143.17 41.98 63 5595 13035 4620299
Hypertriglyceridaemia 140.20 41.98 40 5618 2313 4631021
Depression 139.93 41.98 96 5562 47637 4585697
General physical health deterioration 132.32 41.98 77 5581 28701 4604633
Lactic acidosis 132.26 41.98 58 5600 11898 4621436
Dysmorphism 131.70 41.98 32 5626 984 4632350
Cerebral toxoplasmosis 130.74 41.98 26 5632 304 4633030
Cerebral ventricle dilatation 130.39 41.98 28 5630 488 4632846
Renal failure 127.87 41.98 86 5572 41283 4592051
Aspartate aminotransferase increased 123.37 41.98 70 5588 24868 4608466
Renal tubular disorder 123.04 41.98 33 5625 1515 4631819
Cardiac murmur 121.46 41.98 38 5620 3017 4630317
Abdominal distension 112.55 41.98 59 5599 17930 4615404
Asthenia 112.53 41.98 108 5550 86055 4547279
Cryptorchism 111.45 41.98 24 5634 424 4632910
Blood alkaline phosphatase increased 110.87 41.98 52 5606 12455 4620879
Alanine aminotransferase increased 107.34 41.98 67 5591 28306 4605028
Gamma-glutamyltransferase increased 106.62 41.98 49 5609 11205 4622129
Hydrocephalus 104.94 41.98 31 5627 2026 4631308
Jaundice 104.85 41.98 50 5608 12424 4620910
Atrial septal defect 104.47 41.98 35 5623 3454 4629880
Hypokalaemia 101.86 41.98 56 5602 18704 4614630
Hepatic cirrhosis 99.57 41.98 38 5620 5464 4627870
Renal impairment 98.78 41.98 61 5597 25277 4608057
Mitochondrial cytopathy 97.35 41.98 18 5640 138 4633196
Low birth weight baby 96.52 41.98 31 5627 2679 4630655
Normal newborn 95.93 41.98 28 5630 1754 4631580
Blood bilirubin increased 95.15 41.98 47 5611 12605 4620729
Pneumocystis jirovecii pneumonia 93.23 41.98 36 5622 5342 4627992
Patent ductus arteriosus 93.20 41.98 27 5631 1647 4631687
Osteonecrosis 92.84 41.98 46 5612 12418 4620916
Dysphagia 90.82 41.98 58 5600 25473 4607861
Ascites 90.70 41.98 45 5613 12180 4621154
Cardiac malposition 89.90 41.98 14 5644 30 4633304
Exomphalos 88.25 41.98 18 5640 241 4633093
Nervous system disorder 86.99 41.98 36 5622 6395 4626939
Thrombocytopenia 86.44 41.98 72 5586 47601 4585733
Pre-eclampsia 85.09 41.98 25 5633 1602 4631732
Acquired immunodeficiency syndrome 84.65 41.98 16 5642 140 4633194
Talipes 84.64 41.98 23 5635 1109 4632225
Fanconi syndrome acquired 83.98 41.98 21 5637 728 4632606
Lipoatrophy 83.79 41.98 18 5640 314 4633020
Osteoporosis 83.29 41.98 35 5623 6460 4626874
HIV-associated neurocognitive disorder 82.57 41.98 15 5643 103 4633231
Mycobacterium avium complex infection 81.44 41.98 21 5637 825 4632509
Death neonatal 81.31 41.98 19 5639 492 4632842
Hepatic displacement 79.81 41.98 11 5647 4 4633330
Low set ears 79.61 41.98 16 5642 198 4633136
Death 78.12 41.98 137 5521 198026 4435308
Liver function test abnormal 77.38 41.98 43 5615 14649 4618685
Myocardial infarction 76.16 41.98 68 5590 49308 4584026
Cachexia 76.09 41.98 24 5634 1955 4631379
Rash 75.72 41.98 98 5560 108290 4525044
CD4 lymphocytes decreased 75.52 41.98 20 5638 873 4632461
Unevaluable event 75.42 41.98 44 5614 16432 4616902
Cytomegalovirus chorioretinitis 75.18 41.98 19 5639 688 4632646
Encephalitis 73.51 41.98 25 5633 2580 4630754
Atypical mycobacterial infection 72.87 41.98 17 5641 437 4632897
Progressive multifocal leukoencephalopathy 72.66 41.98 28 5630 4129 4629205
Decreased appetite 72.18 41.98 70 5588 56327 4577007
Hepatotoxicity 71.96 41.98 34 5624 8265 4625069
Pneumonia 71.86 41.98 93 5565 102722 4530612
Hypophosphataemia 71.15 41.98 25 5633 2844 4630490
Oesophageal candidiasis 70.43 41.98 21 5637 1416 4631918
Diabetes mellitus 69.90 41.98 41 5617 15460 4617874
Pulmonary tuberculosis 69.85 41.98 23 5635 2149 4631185
Vertigo 68.61 41.98 40 5618 14916 4618418
Coarctation of the aorta 68.56 41.98 16 5642 412 4632922
Blood lactic acid increased 68.27 41.98 22 5636 1920 4631414
Abdominal hernia 67.77 41.98 19 5639 1029 4632305
Brain herniation 67.32 41.98 20 5638 1332 4632002
Spinocerebellar disorder 66.91 41.98 10 5648 14 4633320
Hyperbilirubinaemia 66.74 41.98 27 5631 4524 4628810
Oral candidiasis 66.32 41.98 25 5633 3472 4629862
Burkitt's lymphoma 66.07 41.98 14 5644 228 4633106
Sepsis 66.05 41.98 59 5599 42780 4590554
Hepatic failure 65.20 41.98 37 5621 13112 4620222
Dehydration 64.72 41.98 58 5600 42232 4591102
Metabolic acidosis 64.38 41.98 36 5622 12404 4620930
Headache 62.16 41.98 95 5563 122278 4511056
Lymphadenopathy 61.88 41.98 33 5625 10359 4622975
Placental insufficiency 61.79 41.98 14 5644 315 4633019
Microcephaly 61.50 41.98 15 5643 468 4632866
Drug level increased 61.49 41.98 28 5630 6258 4627076
Cholestasis 61.25 41.98 30 5628 7890 4625444
Neuropathy peripheral 60.84 41.98 44 5614 23625 4609709
Oligohydramnios 60.36 41.98 18 5640 1214 4632120
Hepatic function abnormal 59.40 41.98 36 5622 14400 4618934
Placenta praevia 59.17 41.98 13 5645 253 4633081
Placental disorder 58.76 41.98 14 5644 395 4632939
Nephropathy toxic 58.72 41.98 24 5634 4128 4629206
Volvulus 58.20 41.98 15 5643 588 4632746
C-reactive protein increased 58.05 41.98 34 5624 12778 4620556
Gastritis 57.36 41.98 29 5629 8157 4625177
Nodular regenerative hyperplasia 57.19 41.98 13 5645 297 4633037
Varices oesophageal 57.12 41.98 17 5641 1139 4632195
Diaphragmatic aplasia 56.64 41.98 8 5650 5 4633329
Human immunodeficiency virus transmission 56.50 41.98 10 5648 58 4633276
Transaminases increased 55.78 41.98 30 5628 9576 4623758
Cerebellar hypoplasia 55.39 41.98 10 5648 66 4633268
Tachypnoea 54.83 41.98 24 5634 4887 4628447
Arnold-Chiari malformation 54.79 41.98 12 5646 230 4633104
Neural tube defect 54.73 41.98 11 5647 136 4633198
Hyponatraemia 54.68 41.98 42 5616 24688 4608646
Developmental delay 53.42 41.98 16 5642 1095 4632239
Myalgia 53.40 41.98 52 5606 41996 4591338
Neutropenia 53.01 41.98 55 5603 47895 4585439
Blood cholesterol increased 52.83 41.98 28 5630 8678 4624656
Hepatosplenomegaly 52.10 41.98 16 5642 1192 4632142
Congenital hearing disorder 51.81 41.98 9 5649 46 4633288
Hypercholesterolaemia 51.67 41.98 20 5638 2983 4630351
Proteinuria 50.90 41.98 25 5633 6611 4626723
Ophthalmoplegia 50.80 41.98 13 5645 495 4632839
Blood creatine phosphokinase increased 50.44 41.98 33 5625 15066 4618268
Cholestasis of pregnancy 49.66 41.98 10 5648 125 4633209
Renal tubular necrosis 49.33 41.98 21 5637 3997 4629337
Pancreatitis 48.91 41.98 34 5624 17144 4616190
Congenital choroid plexus cyst 48.67 41.98 10 5648 139 4633195
Malaise 48.58 41.98 72 5586 90085 4543249
Gestational diabetes 48.40 41.98 16 5642 1512 4631822
Foetal distress syndrome 48.25 41.98 14 5644 858 4632476
Leukopenia 48.23 41.98 37 5621 21699 4611635
Hepatitis C 48.17 41.98 22 5636 4948 4628386
Adrenal insufficiency 47.91 41.98 19 5639 3021 4630313
Kidney malformation 47.90 41.98 10 5648 151 4633183
Syphilis 47.84 41.98 10 5648 152 4633182
Ergot poisoning 47.79 41.98 9 5649 77 4633257
Polyhydramnios 47.52 41.98 12 5646 433 4632901
Pancreatitis acute 47.42 41.98 26 5632 8617 4624717
Osteomalacia 47.39 41.98 13 5645 649 4632685
Opportunistic infection 47.37 41.98 14 5644 915 4632419
Adverse drug reaction 46.30 41.98 31 5627 14708 4618626
Gastroschisis 46.20 41.98 10 5648 181 4633153
Coronary artery disease 45.88 41.98 32 5626 16220 4617114
Seizure 45.70 41.98 52 5606 50185 4583149
Pyelocaliectasis 45.20 41.98 11 5647 340 4632994
Anaemia neonatal 44.70 41.98 10 5648 212 4633122
HIV associated nephropathy 44.34 41.98 7 5651 17 4633317
Herpes zoster 44.23 41.98 31 5627 15832 4617502
Hepatomegaly 44.23 41.98 19 5639 3696 4629638
Dyslipidaemia 42.85 41.98 15 5643 1686 4631648
Congenital central nervous system anomaly 42.83 41.98 11 5647 425 4632909
Multiple-drug resistance 42.68 41.98 12 5646 656 4632678
Meningomyelocele 42.50 41.98 10 5648 267 4633067

Pharmacologic Action:

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)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Coronavirus infection off-label use 186747009
Prevention of HIV Infection after Exposure off-label use
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

Acid dissociation constants calculated using MoKa v3.0.0

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

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-0522 TABLET, FILM COATED 100 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-1575 TABLET, FILM COATED 100 mg ORAL NDA 18 sections
Kaletra HUMAN PRESCRIPTION DRUG LABEL 2 0074-2605 TABLET, FILM COATED 200 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 55289-947 TABLET, FILM COATED 200 mg ORAL NDA 18 sections
Lopinavir and Ritonavir HUMAN PRESCRIPTION DRUG LABEL 2 65015-299 GRANULE 40 mg ORAL Export only 1 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