indinavir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
HIV protease inhibitors 1437 150378-17-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • indinavir
  • indinavir sulphate
  • crixivan
  • indinavir sulfate
A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.
  • Molecular weight: 613.80
  • Formula: C36H47N5O4
  • CLOGP: 3.68
  • LIPINSKI: 1
  • HAC: 9
  • HDO: 4
  • TPSA: 118.03
  • ALOGS: -4.11
  • ROTB: 12

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.02 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 27.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 65 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.82 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 18 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.36 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 13, 1996 FDA MERCK SHARP DOHME

FDA Adverse Event Reporting System (Female)

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
Viral mutation identified 194.38 50.56 33 810 1866 46683353
Drug resistance 131.06 50.56 35 808 17333 46667886
Virologic failure 75.20 50.56 15 828 2040 46683179
Pathogen resistance 69.06 50.56 17 826 6043 46679176
Pregnancy 54.90 50.56 20 823 27117 46658102
Nephrolithiasis 54.62 50.56 21 822 33030 46652189
Exposure during pregnancy 54.37 50.56 30 813 108182 46577037

FDA Adverse Event Reporting System (Male)

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
Lipodystrophy acquired 831.84 40.00 157 2356 3403 29946562
Mitochondrial toxicity 663.58 40.00 123 2390 2391 29947574
Eyelid ptosis 563.31 40.00 121 2392 5067 29944898
Diplopia 436.48 40.00 119 2394 13653 29936312
Progressive external ophthalmoplegia 353.03 40.00 65 2448 1201 29948764
Ophthalmoplegia 127.52 40.00 28 2485 1276 29948689
Lipoatrophy 99.92 40.00 20 2493 577 29949388
Extraocular muscle paresis 92.60 40.00 18 2495 445 29949520
Blood lactic acid increased 81.93 40.00 27 2486 5803 29944162
Hypertriglyceridaemia 80.70 40.00 29 2484 8069 29941896
Dysphagia 75.17 40.00 51 2462 56647 29893318
Virologic failure 70.78 40.00 21 2492 3198 29946767
Viral mutation identified 61.54 40.00 18 2495 2608 29947357
Osteonecrosis 55.30 40.00 27 2486 16108 29933857
Nephrolithiasis 54.98 40.00 31 2482 24779 29925186
Pathogen resistance 54.47 40.00 22 2491 8388 29941577
Foetal exposure during pregnancy 46.03 40.00 32 2481 36839 29913126
Drug resistance 44.16 40.00 25 2488 20108 29929857
Multiple-drug resistance 42.82 40.00 14 2499 2927 29947038
Pinealoblastoma 42.30 40.00 8 2505 170 29949795

Pharmacologic Action:

SourceCodeDescription
ATC J05AE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease 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 D004791 Enzyme Inhibitors
MeSH PA D017320 HIV Protease Inhibitors
MeSH PA D011480 Protease Inhibitors
MeSH PA D000084762 Viral Protease Inhibitors
CHEBI has role CHEBI:35660 hiv protease inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Prevention of HIV Infection after Exposure off-label use
Pyuria contraindication 4800001 DOID:1439
Hypercholesterolemia contraindication 13644009
Hyperbilirubinemia contraindication 14783006 DOID:2741
Cirrhosis of liver contraindication 19943007 DOID:5082
Blood in urine contraindication 34436003
Hemolytic anemia contraindication 61261009 DOID:583
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Hemophilia contraindication 90935002
Kidney stone contraindication 95570007
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Hypertriglyceridemia contraindication 302870006
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.82 acidic
pKa2 12.01 acidic
pKa3 6.96 Basic
pKa4 3.56 Basic
pKa5 2.83 Basic

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
Thromboxane-A synthase Enzyme IC50 5.73 DRUG MATRIX
Substance-K receptor GPCR Ki 5.77 DRUG MATRIX
Multidrug and toxin extrusion protein 2 Transporter IC50 5.11 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.77 CHEMBL
Cytochrome P450 3A4 Enzyme IC50 6.40 DRUG MATRIX
Pol polyprotein Enzyme INHIBITOR Ki 10.15 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein IC50 9.22 WOMBAT-PK
Protease Enzyme Ki 8.48 CHEMBL
Protease Enzyme Ki 9.27 CHEMBL

External reference:

IDSource
4024026 VUID
N0000022031 NUI
D00897 KEGG_DRUG
180683-37-8 SECONDARY_CAS_RN
4020965 VANDF
4024026 VANDF
C0701105 UMLSCUI
CHEBI:44032 CHEBI
MK1 PDB_CHEM_ID
CHEMBL115 ChEMBL_ID
CHEMBL1735 ChEMBL_ID
DB00224 DRUGBANK_ID
D019469 MESH_DESCRIPTOR_UI
5362440 PUBCHEM_CID
5W6YA9PKKH UNII
114289 RXNORM
4875 MMSL
6513 MMSL
d03985 MMSL
005733 NDDF
005734 NDDF
108695003 SNOMEDCT_US
108696002 SNOMEDCT_US
372529006 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 0006-0570 CAPSULE 100 mg ORAL NDA 28 sections
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 0006-0571 CAPSULE 200 mg ORAL NDA 28 sections
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 0006-0573 CAPSULE 400 mg ORAL NDA 28 sections
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 16590-064 CAPSULE 400 mg ORAL NDA 28 sections
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 21695-366 CAPSULE 400 mg ORAL NDA 27 sections
CRIXIVAN HUMAN PRESCRIPTION DRUG LABEL 1 53808-0661 CAPSULE 400 mg ORAL NDA 27 sections