Indinavir

Identification

Summary

Indinavir is a protease inhibitor used to treat HIV infection.

Brand Names
Crixivan
Generic Name
Indinavir
DrugBank Accession Number
DB00224
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 613.7895
Monoisotopic: 613.362805017
Chemical Formula
C36H47N5O4
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
  • Indinavir anhydrous

Pharmacology

Indication

Indinavir is an antiretroviral drug for the treatment of HIV infection.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatHiv-1 infection••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Indinavir 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 action

Indinavir inhibits the HIV viral protease enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.

TargetActionsOrganism
AHuman immunodeficiency virus type 1 protease
inhibitor
Human immunodeficiency virus 1
Absorption

Rapidly absorbed

Volume of distribution

Not Available

Protein binding

60%

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.

Hover over products below to view reaction partners

Route of elimination

Less than 20% of indinavir is excreted unchanged in the urine.

Half-life

1.8 (± 0.4) hours

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include myocardial infarction and angina pectoris.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Indinavir.
AbacavirThe metabolism of Abacavir can be decreased when combined with Indinavir.
AbametapirThe serum concentration of Indinavir can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Indinavir can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Indinavir.
Food Interactions
  • Avoid excessive or chronic alcohol consumption.
  • Avoid grapefruit products.
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.
  • Take with a full glass of water.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Indinavir monohydrate5W6YA9PKKH180683-37-8XTYSXGHMTNTKFH-BDEHJDMKSA-N
Indinavir sulfate771H53976Q157810-81-6NUBQKPWHXMGDLP-BDEHJDMKSA-N
Indinavir sulfate ethanolate34OB95C8AENot AvailableQDNVAYDEAGXHTB-NOYQBWMBSA-N
International/Other Brands
Crixivan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CrixivanCapsule400 mgOralMerck Sharp & Dohme B.V.2016-09-082022-07-12EU flag
CrixivanCapsule333 mg/1OralMerck & Co., Inc2006-08-072006-08-07US flag
CrixivanCapsule200 mgOralMerck Sharp & Dohme B.V.2016-09-082022-07-12EU flag
CrixivanCapsule400 mg/1OralRebel Distributors1996-03-13Not applicableUS flag
CrixivanCapsule200 mgOralMerck Ltd.1996-09-262014-09-19Canada flag

Categories

ATC Codes
J05AE02 — Indinavir
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Indanes / Piperazine carboxamides / Aralkylamines / N-alkylpiperazines / Benzene and substituted derivatives / N-acyl amines / Pyridines and derivatives / Heteroaromatic compounds / Secondary alcohols / Trialkylamines
show 7 more
Substituents
1,2-aminoalcohol / 1,4-diazinane / Alcohol / Alpha-amino acid amide / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid diamide, N-(2-hydroxyethyl)piperazine, piperazinecarboxamide (CHEBI:44032)
Affected organisms
  • Human Immunodeficiency Virus

Chemical Identifiers

UNII
9MG78X43ZT
CAS number
150378-17-9
InChI Key
CBVCZFGXHXORBI-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-yl)methyl]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[C@H](O)CC2=CC=CC=C12

References

Synthesis Reference
US5413999
General References
Not Available
Human Metabolome Database
HMDB0014369
KEGG Compound
C07051
PubChem Compound
5362440
PubChem Substance
46506442
ChemSpider
4515036
BindingDB
517
RxNav
114289
ChEBI
44032
ChEMBL
CHEMBL115
ZINC
ZINC000022448696
Therapeutic Targets Database
DAP000168
PharmGKB
PA449977
PDBe Ligand
MK1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Indinavir
PDB Entries
1c6y / 1hsg / 1hsh / 1k6c / 1sdt / 1sdu / 1sdv / 1sgu / 2avo / 2avs
show 5 more
FDA label
Download (671 KB)
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Merck sharp and dohme corp
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Dispensing Solutions
  • H.J. Harkins Co. Inc.
  • Merck & Co.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Remedy Repack
  • Stat Rx Usa
Dosage Forms
FormRouteStrength
CapsuleOral100 mg/1
CapsuleOral200 mg/1
CapsuleOral300 mg
CapsuleOral333 mg/1
CapsuleOral400 mg
CapsuleOral400 mg/1
CapsuleOral200 mg
Capsule, coatedOral400 mg
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)Region
US5413999No1995-05-092012-05-09US flag
CA2081970No1997-07-082012-11-02Canada flag
US6689761No2004-02-102021-02-10US flag
US6645961No2003-11-112018-03-04US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)167.5-168 °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)13.01Chemaxon
pKa (Strongest Basic)6.76Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area118.03 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity175.89 m3·mol-1Chemaxon
Polarizability68.94 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03di-1211090000-aee08bb3c9ef87a0acf4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-0300459000-65558be6f01e2b125548
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0111439000-1757a396009b677d77df
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-1914556000-9c3292cce7b2b7e93ad6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xu-4329625000-69eeafc0178dcee0031e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pa-2715593000-379ca4edb2773fc89e61
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-009i-0509411000-5eeb27cdc2da77631b9b
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-265.3368174
predicted
DarkChem Lite v0.1.0
[M-H]-235.94691
predicted
DeepCCS 1.0 (2019)
[M+H]+265.3314174
predicted
DarkChem Lite v0.1.0
[M+H]+237.80699
predicted
DeepCCS 1.0 (2019)
[M+Na]+265.4859174
predicted
DarkChem Lite v0.1.0
[M+Na]+243.49065
predicted
DeepCCS 1.0 (2019)

Targets

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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
Uniprot Name
Pol polyprotein
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Details
1. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. von Moltke LL, Greenblatt DJ, Duan SX, Daily JP, Harmatz JS, Shader RI: Inhibition of desipramine hydroxylation (Cytochrome P450-2D6) in vitro by quinidine and by viral protease inhibitors: relation to drug interactions in vivo. J Pharm Sci. 1998 Oct;87(10):1184-9. doi: 10.1021/js980197h. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Yong WP, Ramirez J, Innocenti F, Ratain MJ: Effects of ketoconazole on glucuronidation by UDP-glucuronosyltransferase enzymes. Clin Cancer Res. 2005 Sep 15;11(18):6699-704. doi: 10.1158/1078-0432.CCR-05-0703. [Article]
Details
3. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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. [Article]
  2. Inaba T, Fischer NE, Riddick DS, Stewart DJ, Hidaka T: HIV protease inhibitors, saquinavir, indinavir and ritonavir: inhibition of CYP3A4-mediated metabolism of testosterone and benzoxazinorifamycin, KRM-1648, in human liver microsomes. Toxicol Lett. 1997 Dec;93(2-3):215-9. doi: 10.1016/s0378-4274(97)00098-2. [Article]
  3. Mouly S, Rizzo-Padoin N, Simoneau G, Verstuyft C, Aymard G, Salvat C, Mahe I, Bergmann JF: Effect of widely used combinations of antiretroviral therapy on liver CYP3A4 activity in HIV-infected patients. Br J Clin Pharmacol. 2006 Aug;62(2):200-9. doi: 10.1111/j.1365-2125.2006.02637.x. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Granfors MT, Wang JS, Kajosaari LI, Laitila J, Neuvonen PJ, Backman JT: Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):79-85. doi: 10.1111/j.1742-7843.2006.pto_249.x. [Article]
  2. Koudriakova T, Iatsimirskaia E, Utkin I, Gangl E, Vouros P, Storozhuk E, Orza D, Marinina J, Gerber N: Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug Metab Dispos. 1998 Jun;26(6):552-61. [Article]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Granfors MT, Wang JS, Kajosaari LI, Laitila J, Neuvonen PJ, Backman JT: Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):79-85. doi: 10.1111/j.1742-7843.2006.pto_249.x. [Article]
  2. Flockhart Table of Drug Interactions [Link]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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
Uniprot Name
Multidrug resistance protein 1
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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. [Article]
Kind
Protein
Organism
Humans
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, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
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. [Article]
Kind
Protein
Organism
Humans
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 inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
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. [Article]
Kind
Protein
Organism
Humans
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, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Canalicular multispecific organic anion transporter 1
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. [Article]
Kind
Protein
Organism
Humans
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 taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Annaert P, Ye ZW, Stieger B, Augustijns P: Interaction of HIV protease inhibitors with OATP1B1, 1B3, and 2B1. Xenobiotica. 2010 Mar;40(3):163-76. doi: 10.3109/00498250903509375. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48