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Identification
NameIndinavir
Accession NumberDB00224  (APRD00069)
TypeSmall Molecule
GroupsApproved
Description

A potent and specific HIV protease inhibitor that appears to have good oral bioavailability. [PubChem]

Structure
Thumb
Synonyms
(1(1S,2R),5(S))-2,3,5-Trideoxy-N-(2,3-dihydro-2-hydroxy-1H-inden-1-yl)-5-(2-(((1,1-dimethylethyl)amino)carbonyl)-4-(3-pyridinylmethyl)-1-piperazinyl)-2-(phenylmethyl)-D-erythro-pentonamide
Indinavir anhydrous
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Crixivancapsule300 mgoralMerck Canada IncNot applicableNot applicableCanada
Crixivancapsule200 mg/1oralMerck Sharp & Dohme Corp.1996-03-13Not applicableUs
Crixivancapsule200 mgoralMerck Canada Inc1996-09-262014-09-19Canada
Crixivancapsule400 mgoralMerck Canada Inc1996-09-30Not applicableCanada
Crixivancapsule400 mg/1oralAvera Mc Kennan Hospital2015-03-01Not applicableUs
Crixivancapsule400 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Crixivancapsule400 mg/1oralRebel Distributors Corp1996-03-13Not applicableUs
Crixivancapsule400 mg/1oralSTAT Rx USA LLC1996-03-13Not applicableUs
Crixivancapsule400 mg/1oralMerck Sharp & Dohme Corp.1996-03-13Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Indinavir monohydrate
180683-37-8
Thumb
  • InChI Key: XTYSXGHMTNTKFH-BDEHJDMKSA-N
  • Monoisotopic Mass: 631.373369698
  • Average Mass: 631.818
DBSALT001802
Indinavir sulfate
157810-81-6
Thumb
  • InChI Key: NUBQKPWHXMGDLP-BDEHJDMKSA-N
  • Monoisotopic Mass: 711.330184259
  • Average Mass: 711.868
DBSALT000338
Categories
UNII9MG78X43ZT
CAS number150378-17-9
WeightAverage: 613.7895
Monoisotopic: 613.362805017
Chemical FormulaC36H47N5O4
InChI KeyCBVCZFGXHXORBI-PXQQMZJSSA-N
InChI
InChI=1S/C36H47N5O4/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/t28-,29+,31+,32-,33+/m1/s1
IUPAC Name
(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
SMILES
CC(C)(C)NC(=O)[C@@H]1CN(CC2=CN=CC=C2)CCN1C[C@@H](O)C[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]1[[email protected]](O)CC2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Piperazine-2-carboxamide
  • Indane
  • Aralkylamine
  • N-alkylpiperazine
  • Fatty acyl
  • Benzenoid
  • Pyridine
  • Piperazine
  • N-acyl-amine
  • Fatty amide
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-aminoalcohol
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationIndinavir is an antiretroviral drug for the treatment of HIV infection.
PharmacodynamicsIndinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Indinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
Mechanism of actionIndinavir inhibits the HIV viral protease enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Related Articles
AbsorptionRapidly absorbed
Volume of distributionNot Available
Protein binding60%
Metabolism

Hepatic. Seven metabolites have been identified, one glucuronide conjugate and six oxidative metabolites. In vitro studies indicate that cytochrome P-450 3A4 (CYP3A4) is the major enzyme responsible for formation of the oxidative metabolites.

SubstrateEnzymesProduct
Indinavir
Metabolite M6Details
Route of eliminationLess than 20% of indinavir is excreted unchanged in the urine.
Half life1.8 (± 0.4) hours
ClearanceNot Available
ToxicitySymptoms of overdose include myocardial infarction and angina pectoris.
Affected organisms
  • Human Immunodeficiency Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.821
Blood Brain Barrier-0.9923
Caco-2 permeable-0.8183
P-glycoprotein substrateSubstrate0.8899
P-glycoprotein inhibitor IInhibitor0.7987
P-glycoprotein inhibitor IINon-inhibitor0.5819
Renal organic cation transporterNon-inhibitor0.8501
CYP450 2C9 substrateNon-substrate0.7816
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7831
CYP450 1A2 substrateNon-inhibitor0.9057
CYP450 2C9 inhibitorNon-inhibitor0.6278
CYP450 2D6 inhibitorNon-inhibitor0.7476
CYP450 2C19 inhibitorNon-inhibitor0.6264
CYP450 3A4 inhibitorInhibitor0.6525
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7808
Ames testNon AMES toxic0.8629
CarcinogenicityNon-carcinogens0.887
BiodegradationNot ready biodegradable0.9951
Rat acute toxicity2.1844 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9557
hERG inhibition (predictor II)Inhibitor0.7265
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Merck sharp and dohme corp
Packagers
Dosage forms
FormRouteStrength
Capsuleoral200 mg/1
Capsuleoral200 mg
Capsuleoral300 mg
Capsuleoral400 mg
Capsuleoral400 mg/1
Prices
Unit descriptionCostUnit
Crixivan 360 200 mg capsule Bottle570.02USD bottle
Crixivan 400 mg capsule2.86USD each
Crixivan 333 mg capsule2.54USD each
Crixivan 200 mg capsule1.52USD each
Crixivan 100 mg capsule0.76USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2081970 No1997-07-082012-11-02Canada
US5413999 No1995-05-092012-05-09Us
US6645961 No1998-03-042018-03-04Us
US6689761 No2001-02-102021-02-10Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point167.5-168 °CNot Available
water solubility0.015 mg/mlNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0482 mg/mLALOGPS
logP3.26ALOGPS
logP2.81ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.19ChemAxon
pKa (Strongest Basic)7.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.03 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity175.89 m3·mol-1ChemAxon
Polarizability68.63 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5413999
General ReferencesNot Available
External Links
ATC CodesJ05AE02
AHFS Codes
  • 08:18.08.08
PDB Entries
FDA labelDownload (671 KB)
MSDSDownload (57 KB)
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Indinavir.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Indinavir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Indinavir.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Indinavir.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Indinavir.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Indinavir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Indinavir.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Indinavir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Indinavir.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Indinavir.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Indinavir.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Indinavir.
AtazanavirThe risk or severity of adverse effects can be increased when Atazanavir is combined with Indinavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Indinavir.
AtovaquoneThe serum concentration of Indinavir can be decreased when it is combined with Atovaquone.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Indinavir.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Indinavir.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Indinavir.
BatimastatThe serum concentration of Indinavir can be increased when it is combined with Batimastat.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Indinavir.
BepridilThe metabolism of Bepridil can be decreased when combined with Indinavir.
BexaroteneThe serum concentration of Indinavir can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Indinavir can be decreased when it is combined with Boceprevir.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Indinavir.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Indinavir.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Indinavir.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Indinavir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Indinavir.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Indinavir.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Indinavir.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Indinavir.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Indinavir.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Indinavir.
CarbamazepineThe metabolism of Indinavir can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Indinavir.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Indinavir.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Indinavir.
CimetidineThe serum concentration of Indinavir can be decreased when it is combined with Cimetidine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Indinavir.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Indinavir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Indinavir.
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Indinavir.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Indinavir.
CyclophosphamideThe risk or severity of adverse effects can be increased when Indinavir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Indinavir.
DabrafenibThe serum concentration of Indinavir can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Indinavir.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Indinavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Indinavir.
DeferasiroxThe serum concentration of Indinavir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Indinavir.
DidanosineThe serum concentration of Indinavir can be decreased when it is combined with Didanosine.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Indinavir.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Indinavir.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Indinavir.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Indinavir.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Indinavir.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Indinavir.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Indinavir.
DrospirenoneThe serum concentration of Drospirenone can be increased when it is combined with Indinavir.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Indinavir.
EfavirenzThe serum concentration of Indinavir can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Indinavir.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Indinavir.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Indinavir.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Indinavir.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Indinavir.
EsomeprazoleThe serum concentration of Indinavir can be decreased when it is combined with Esomeprazole.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Indinavir.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Indinavir.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Indinavir.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Indinavir.
FamotidineThe serum concentration of Indinavir can be decreased when it is combined with Famotidine.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Indinavir.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Indinavir.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Indinavir.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Indinavir.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Indinavir.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Indinavir.
GarlicThe serum concentration of Indinavir can be decreased when it is combined with Garlic.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Indinavir.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Indinavir.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Indinavir.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Indinavir.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Indinavir.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Indinavir.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Indinavir.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Indinavir.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Indinavir.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Indinavir resulting in a loss in efficacy.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Indinavir.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Indinavir.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Indinavir.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Indinavir.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Indinavir.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Indinavir.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Indinavir.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Indinavir.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Indinavir.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Indinavir.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Indinavir.
IsoflurophateThe serum concentration of Indinavir can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Indinavir can be increased when it is combined with Itraconazole.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Indinavir.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Indinavir.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Indinavir.
KetoconazoleThe serum concentration of Indinavir can be increased when it is combined with Ketoconazole.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Indinavir.
LansoprazoleThe serum concentration of Indinavir can be decreased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Indinavir.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Indinavir.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Indinavir.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Indinavir.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Indinavir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Indinavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Indinavir.
LumefantrineThe serum concentration of Lumefantrine can be increased when it is combined with Indinavir.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Indinavir.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Indinavir.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Indinavir.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Indinavir.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Indinavir.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Indinavir.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Indinavir.
MifepristoneThe serum concentration of Mifepristone can be increased when it is combined with Indinavir.
MitotaneThe serum concentration of Indinavir can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Indinavir.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Indinavir.
NevirapineThe serum concentration of Indinavir can be decreased when it is combined with Nevirapine.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Indinavir.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Indinavir.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Indinavir.
NizatidineThe serum concentration of Indinavir can be decreased when it is combined with Nizatidine.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Indinavir.
OmeprazoleThe serum concentration of Indinavir can be decreased when it is combined with Omeprazole.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Indinavir.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Indinavir.
OxycodoneThe risk or severity of adverse effects can be increased when Indinavir is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Indinavir.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Indinavir.
PantoprazoleThe serum concentration of Indinavir can be decreased when it is combined with Pantoprazole.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Indinavir.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Indinavir.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Indinavir.
PethidineThe risk or severity of adverse effects can be increased when Indinavir is combined with Pethidine.
PhenytoinThe metabolism of Indinavir can be increased when combined with Phenytoin.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Indinavir.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Indinavir.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Indinavir.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Indinavir.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Indinavir resulting in a loss in efficacy.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Indinavir.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Indinavir.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Indinavir.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Indinavir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Indinavir.
RabeprazoleThe serum concentration of Indinavir can be decreased when it is combined with Rabeprazole.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Indinavir.
RanitidineThe serum concentration of Indinavir can be decreased when it is combined with Ranitidine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Indinavir.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Indinavir.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Indinavir.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Indinavir.
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Indinavir.
RifampicinThe serum concentration of Indinavir can be decreased when it is combined with Rifampicin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Indinavir.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Indinavir.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Indinavir.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Indinavir.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Indinavir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Indinavir.
SaquinavirThe serum concentration of Indinavir can be increased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Indinavir.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Indinavir.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Indinavir.
SiltuximabThe serum concentration of Indinavir can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Indinavir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Indinavir.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Indinavir.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Indinavir.
St. John's WortThe metabolism of Indinavir can be increased when combined with St. John's Wort.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Indinavir.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Indinavir.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Indinavir.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Indinavir.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Indinavir.
TemsirolimusThe risk or severity of adverse effects can be increased when Indinavir is combined with Temsirolimus.
TerfenadineThe serum concentration of Terfenadine can be increased when it is combined with Indinavir.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Indinavir resulting in a loss in efficacy.
TipranavirThe serum concentration of Indinavir can be decreased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Indinavir can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Indinavir.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Indinavir.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Indinavir.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Indinavir.
ToremifeneThe risk or severity of adverse effects can be increased when Indinavir is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Indinavir.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Indinavir.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Indinavir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Indinavir.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Indinavir.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Indinavir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Indinavir.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Indinavir.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Indinavir.
VenlafaxineThe serum concentration of Indinavir can be decreased when it is combined with Venlafaxine.
VerapamilThe serum concentration of Indinavir can be increased when it is combined with Verapamil.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Indinavir.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Indinavir.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Indinavir.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Indinavir.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Indinavir.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Indinavir.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Indinavir.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Indinavir.
Food Interactions
  • Avoid excessive or chronic alcohol use.
  • Avoid taking with grapefruit juice
  • Take on empty stomach: 1 hour before or 2 hours after meals.
  • Take with a full glass of water.

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
yes
Actions
inhibitor
General Function:
Aspartic-type endopeptidase activity
Specific Function:
Not Available
Gene Name:
pol
Uniprot ID:
Q72874
Molecular Weight:
10778.7 Da
References
  1. Wittayanarakul K, Hannongbua S, Feig M: Accurate prediction of protonation state as a prerequisite for reliable MM-PB(GB)SA binding free energy calculations of HIV-1 protease inhibitors. J Comput Chem. 2008 Apr 15;29(5):673-85. [PubMed:17849388 ]
  2. Dandache S, Sevigny G, Yelle J, Stranix BR, Parkin N, Schapiro JM, Wainberg MA, Wu JJ: In vitro antiviral activity and cross-resistance profile of PL-100, a novel protease inhibitor of human immunodeficiency virus type 1. Antimicrob Agents Chemother. 2007 Nov;51(11):4036-43. Epub 2007 Jul 16. [PubMed:17638694 ]
  3. Hoetelmans RM, Meenhorst PL, Mulder JW, Burger DM, Koks CH, Beijnen JH: Clinical pharmacology of HIV protease inhibitors: focus on saquinavir, indinavir, and ritonavir. Pharm World Sci. 1997 Aug;19(4):159-75. [PubMed:9297727 ]
  4. Stein DS, Fish DG, Bilello JA, Preston SL, Martineau GL, Drusano GL: A 24-week open-label phase I/II evaluation of the HIV protease inhibitor MK-639 (indinavir). AIDS. 1996 May;10(5):485-92. [PubMed:8724039 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Perloff MD, von Moltke LL, Fahey JM, Daily JP, Greenblatt DJ: Induction of P-glycoprotein expression by HIV protease inhibitors in cell culture. AIDS. 2000 Jun 16;14(9):1287-9. [PubMed:10894301 ]
  2. Choo EF, Leake B, Wandel C, Imamura H, Wood AJ, Wilkinson GR, Kim RB: Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug Metab Dispos. 2000 Jun;28(6):655-60. [PubMed:10820137 ]
  3. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
  4. Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [PubMed:11181899 ]
  5. Kim RB, Fromm MF, Wandel C, Leake B, Wood AJ, Roden DM, Wilkinson GR: The drug transporter P-glycoprotein limits oral absorption and brain entry of HIV-1 protease inhibitors. J Clin Invest. 1998 Jan 15;101(2):289-94. [PubMed:9435299 ]
  6. Hochman JH, Chiba M, Nishime J, Yamazaki M, Lin JH: Influence of P-glycoprotein on the transport and metabolism of indinavir in Caco-2 cells expressing cytochrome P-450 3A4. J Pharmacol Exp Ther. 2000 Jan;292(1):310-8. [PubMed:10604964 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Zhang L, Gorset W, Washington CB, Blaschke TF, Kroetz DL, Giacomini KM: Interactions of HIV protease inhibitors with a human organic cation transporter in a mammalian expression system. Drug Metab Dispos. 2000 Mar;28(3):329-34. [PubMed:10681378 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular Weight:
74144.105 Da
References
  1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Tirona RG, Leake BF, Wolkoff AW, Kim RB: Human organic anion transporting polypeptide-C (SLC21A6) is a major determinant of rifampin-mediated pregnane X receptor activation. J Pharmacol Exp Ther. 2003 Jan;304(1):223-8. [PubMed:12490595 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Huisman MT, Smit JW, Crommentuyn KM, Zelcer N, Wiltshire HR, Beijnen JH, Schinkel AH: Multidrug resistance protein 2 (MRP2) transports HIV protease inhibitors, and transport can be enhanced by other drugs. AIDS. 2002 Nov 22;16(17):2295-301. [PubMed:12441801 ]
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Drug created on June 13, 2005 07:24 / Updated on June 30, 2016 01:49