indinavir ๐Ÿถ Veterinary Use | 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 ยตM/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 203.06 51.47 32 626 1597 50602869
Drug resistance 134.58 51.47 34 624 18955 50585511
Virologic failure 84.24 51.47 15 643 1549 50602917
Pathogen resistance 75.73 51.47 17 641 5672 50598794
Nephrolithiasis 52.79 51.47 19 639 34674 50569792
Pregnancy 51.85 51.47 18 640 29559 50574907
Exposure during pregnancy 51.82 51.47 27 631 120988 50483478

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 839.08 44.08 153 2161 2941 29569272
Mitochondrial toxicity 710.34 44.08 128 2186 2283 29569930
Eyelid ptosis 612.50 44.08 128 2186 5058 29567155
Diplopia 485.64 44.08 127 2187 13391 29558822
Progressive external ophthalmoplegia 394.20 44.08 71 2243 1246 29570967
Ophthalmoplegia 133.20 44.08 30 2284 1652 29570561
Blood lactic acid increased 105.04 44.08 32 2282 5734 29566479
Dysphagia 97.87 44.08 58 2256 54868 29517345
Virologic failure 88.66 44.08 24 2290 2823 29569390
Hypertriglyceridaemia 77.21 44.08 27 2287 7448 29564765
Lipoatrophy 74.66 44.08 15 2299 474 29571739
Pathogen resistance 67.59 44.08 25 2289 8091 29564122
Viral mutation identified 59.24 44.08 17 2297 2471 29569742
Multiple-drug resistance 55.77 44.08 18 2296 3882 29568331
Dyslipidaemia 51.67 44.08 19 2295 6042 29566171
Nephrolithiasis 48.27 44.08 28 2286 25306 29546907
Foetal exposure during pregnancy 48.07 44.08 31 2283 33836 29538377
Mitochondrial myopathy 48.05 44.08 9 2305 195 29572018

FDA Adverse Event Reporting System (Geriatric)

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 886.97 41.53 151 2429 3876 64492276
Mitochondrial toxicity 773.86 41.53 127 2453 2579 64493573
Eyelid ptosis 614.30 41.53 127 2453 9398 64486754
Diplopia 478.92 41.53 126 2454 26639 64469513
Progressive external ophthalmoplegia 441.14 41.53 71 2509 1256 64494896
Viral mutation identified 211.50 41.53 44 2536 3302 64492850
Drug resistance 141.36 41.53 53 2527 35049 64461103
Virologic failure 137.03 41.53 31 2549 3435 64492717
Ophthalmoplegia 133.44 41.53 29 2551 2673 64493479
Pathogen resistance 105.85 41.53 33 2547 12510 64483642
Dysphagia 98.11 41.53 58 2522 106754 64389398
Lipoatrophy 93.42 41.53 17 2563 628 64495524
Multiple-drug resistance 89.52 41.53 25 2555 6477 64489675
Nephrolithiasis 87.26 41.53 40 2540 43643 64452509
Dyslipidaemia 68.36 41.53 22 2558 9220 64486932
Immune reconstitution inflammatory syndrome 58.12 41.53 21 2559 12449 64483703
Blood lactic acid increased 57.94 41.53 20 2560 10381 64485771
Mitochondrial myopathy 50.94 41.53 9 2571 280 64495872
Osteonecrosis 50.59 41.53 24 2556 28205 64467947
Pinealoblastoma 47.49 41.53 7 2573 66 64496086
Foetal exposure during pregnancy 42.92 41.53 13 2567 4463 64491689

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Protease inhibitors
CHEBI has role CHEBI:35660 HIV 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

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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 1 Transporter IC50 5.77 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 5.11 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
Protease Unclassified Ki 9.06 CHEMBL
Protease Unclassified Ki 9.42 CHEMBL

External reference:

IDSource
4024026 VUID
N0000022031 NUI
D00897 KEGG_DRUG
157810-81-6 SECONDARY_CAS_RN
4020965 VANDF
4024026 VANDF
C0376637 UMLSCUI
CHEBI:44032 CHEBI
MK1 PDB_CHEM_ID
CHEMBL115 ChEMBL_ID
CHEMBL1735 ChEMBL_ID
D019469 MESH_DESCRIPTOR_UI
DB00224 DRUGBANK_ID
5W6YA9PKKH UNII
5362440 PUBCHEM_CID
114289 RXNORM
4875 MMSL
6513 MMSL
d03985 MMSL
005733 NDDF
005734 NDDF
108695003 SNOMEDCT_US
108696002 SNOMEDCT_US
372529006 SNOMEDCT_US
180683-37-8 SECONDARY_CAS_RN

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