Paritaprevir

Identification

Summary

Paritaprevir is a direct acting antiviral agent used in combination with other antiviral agents for the treatment of Hepatitis C Virus (HCV) infections.

Brand Names
Viekira Pak
Generic Name
Paritaprevir
DrugBank Accession Number
DB09297
Background

Paritaprevir is a direct acting antiviral medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients 8. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as paritaprevir. As a newer generation and directly acting HCV antiviral, paritaprevir products have better Sustained Virological Response (SVR) rates, higher barriers to resistance, fewer side effects, and a reduced pill burden compared to older agents such as Boceprevir, Telaprevir, Peginterferon alfa-2a, Peginterferon alfa-2b, and Ribavirin. By combining multiple antiretroviral medications into fixed dose products, the viral lifecycle can be targeted at multiple stages while simultaneously reducing the risk of developing resistant viral strains 7. Within Canada and the United States, paritaprevir is currently available in three fixed dose products: Viekira Pak (FDA), Technivie (FDA and Health Canada), and Holkira Pak (Health Canada).

More specifically, paritaprevir prevents viral replication by inhibiting the NS3/4A serine protease of Hepatitis C Virus (HCV) Label. Following viral replication of HCV genetic material and translation into a single polypeptide, Nonstructural Protein 3 (NS3) and its activating cofactor Nonstructural Protein 4A (NS4A) are responsible for cleaving genetic material into the following structural and nonstructural proteins required for assembly into mature virus: NS3, NS4A, NS4B, NS5A, and NS5B 6. By inhibiting viral protease NS3/4A, paritaprevir therefore prevents viral replication and function.

In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend Paritaprevir as a first line therapy option when used in combination with other antivirals for genotypes 1a, 1b, and 48. Depending on the genotype, Paritaprevir is often used in combination with other antivirals such as Ombitasvir, Dasabuvir, Ritonavir, and Ribavirin, with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality 4. Treatment with direct acting antivirals such as paritaprevir is associated with very minimal side effects, with the most common being headache and fatigue Label. Lack of significant side effects and short duration of therapy is a considerable advantage over older interferon-based regimens, which were limited by infusion site reactions, reduced blood count, and neuropsychiatric effects 5.

Paritaprevir first came on the market as a fixed-dose combination product with Ombitasvir, Dasabuvir, and Ritonavir as the FDA-approved product Viekira Pak. First approved in December 2014, Viekira Pak is indicated for the treatment of HCV genotype 1b without cirrhosis or with compensated cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a without cirrhosis or with compensated cirrhosis.

Paritaprevir is also available as a fixed-dose combination product with Ombitasvir and Ritonavir as the FDA- and Health Canada-approved product Technivie. First approved in July 2015, Technivie is indicated in combination with Ribavirin for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis or with compensated cirrhosis.

In Canada, paritaprevir is also available as a fixed-dose combination product with Ombitasvir, Dasabuvir, and Ritonavir as the Health Canada-approved, commercially available product Holkira Pak. First approved in January 2015, Holkira Pak is indicated for the treatment of HCV genotype 1b with or without cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a with or without cirrhosis.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 765.89
Monoisotopic: 765.294467927
Chemical Formula
C40H43N7O7S
Synonyms
  • (2R,6S,12Z,13aR,14aR,16aS)-N-(cyclopropanesulfonyl)-6-[(5-methylpyrazine-2-carbonyl)amino]-5,16-dioxo-2-[(phenanthridin-6-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide
  • Paritaprevir
  • Veruprevir
External IDs
  • ABT 450
  • ABT-450
  • ABT450

Pharmacology

Indication

When used within the fixed-dose combination product with Ombitasvir, Dasabuvir, and Ritonavir as the FDA-approved product Viekira Pak, paritaprevir is indicated for the treatment of HCV genotype 1b without cirrhosis or with compensated cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a without cirrhosis or with compensated cirrhosis.

When used within the fixed-dose combination product with Ombitasvir and Ritonavir as the FDA- and Health Canada-approved product Technivie, paritaprevir is indicated in combination with Ribavirin for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis or with compensated cirrhosis.

When used within the fixed-dose combination product with Ombitasvir, Dasabuvir, and Ritonavir as the Health Canada-approved, commercially available product Holkira Pak, paritaprevir is indicated for the treatment of HCV genotype 1b with or without cirrhosis, and when combined with Ribavirin for the treatment of HCV genotype 1a with or without cirrhosis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatWith compensated cirrhosis chronic hepatitis c genotype 1aRegimen in combination with: Ombitasvir (DB09296), Dasabuvir (DB09183), Ritonavir (DB00503), Ribavirin (DB00811)••••••••••••
Used in combination to treatWith compensated cirrhosis chronic hepatitis c genotype 1bCombination Product in combination with: Ombitasvir (DB09296), Ritonavir (DB00503), Dasabuvir (DB09183)••••••••••••
Used in combination to treatWithout cirrhosis chronic hepatitis c genotype 1aRegimen in combination with: Ritonavir (DB00503), Dasabuvir (DB09183), Ribavirin (DB00811), Ombitasvir (DB09296)••••••••••••
Used in combination to treatWithout cirrhosis chronic hepatitis c genotype 1bCombination Product in combination with: Dasabuvir (DB09183), Ritonavir (DB00503), Ombitasvir (DB09296)••••••••••••
Used in combination to treatWithout cirrhosis chronic hepatitis c genotype 4Regimen in combination with: Ribavirin (DB00811), Ombitasvir (DB09296), Ritonavir (DB00503)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

At concentrations approximately 6 and 1.8 times the therapeutic concentrations of paritaprevir and ombitasvir, the combination did not prolong QTc to any clinically relevant extent Label.

Mechanism of action

Paritaprevir is a potent inhibitor of the NS3/4A serine protease of Hepatitis C Virus (HCV) Label. Following viral replication of HCV genetic material and translation into a single polypeptide, Nonstructural Protein 3 (NS3) and its activating cofactor Nonstructural Protein 4A (NS4A) are responsible for cleaving it into the following structural and nonstructural proteins required for assembly into mature virus: NS3, NS4A, NS4B, NS5A, and NS5B. By inhibiting viral protease NS3/4A, paritaprevir therefore prevents viral replication and function.

TargetActionsOrganism
ANS3/4A protein
inhibitor
Hepatitis C Virus
Absorption

Tmax of approximately 4 to 5 hours with a maximum concentration (Cmax) of 194 ng/mL Label.

Volume of distribution

Volume of distribution at steady state is approximately 103 L Label.

Protein binding

97 to 98.6% bound to human plasma proteins Label.

Metabolism

Paritaprevir is predominantly metabolized by CYP3A4 and to a lesser extent by CYP3A5 Label.

Route of elimination

Following a single dose administration of 14C-paritaprevir co-dosed with 100 mg of ritonavir, approximately 88% of the radioactivity was recovered in feces with limited radioactivity (8.8%) in urine; unchanged paritaprevir accounted for 1.1% of the radioactivity in the feces and 0.05% in the urine Label.

Half-life

5.5 hr Label

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
AbacavirThe metabolism of Abacavir can be decreased when combined with Paritaprevir.
AbametapirThe serum concentration of Paritaprevir can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Paritaprevir can be increased when combined with Abatacept.
AbemaciclibParitaprevir may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbrocitinibThe serum concentration of Paritaprevir can be increased when it is combined with Abrocitinib.
Food Interactions
  • Avoid St. John's Wort.
  • Take with food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Paritaprevir dihydrateHRQ5901O781456607-71-8AWGQIDLXYMGEEH-RHSIAEQTSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Holkira PakParitaprevir (75 mg) + Dasabuvir sodium monohydrate (250 mg) + Ombitasvir (12.5 mg) + Ritonavir (50 mg)Kit; TabletOralAbbvie2015-01-062018-08-15Canada flag
TechnivieParitaprevir dihydrate (75 mg/1) + Ombitasvir heminonahydrate (12.5 mg/1) + Ritonavir (50 mg/1)TabletOralAbbVie Inc.2015-07-242019-03-14US flag
TechnivieParitaprevir (75 mg) + Ombitasvir (12.5 mg) + Ritonavir (50 mg)TabletOralAbbvie2015-11-242018-07-30Canada flag
Viekira PakParitaprevir dihydrate (75 mg/1) + Dasabuvir sodium monohydrate (250 mg/1) + Ombitasvir heminonahydrate (12.5 mg/1) + Ritonavir (50 mg/1)Kit; Tablet, film coatedOralAbbVie Inc.2014-12-19Not applicableUS flag
VIEKIRA PAK TABLETParitaprevir (75 mg) + Dasabuvir (250 mg) + Ombitasvir (12.5 mg) + Ritonavir (50 mg)Tablet, film coatedOralABBVIE PTE. LTD.2015-11-02Not applicableSingapore flag

Categories

ATC Codes
J05AP53 — Ombitasvir, paritaprevir and ritonavirJ05AP52 — Dasabuvir, ombitasvir, paritaprevir and ritonavir
Drug Categories
Classification
Not classified
Affected organisms
  • Hepatitis C Virus

Chemical Identifiers

UNII
OU2YM37K86
CAS number
1216941-48-8
InChI Key
UAUIUKWPKRJZJV-QPLHLKROSA-N
InChI
InChI=1S/C40H43N7O7S/c1-24-21-42-33(22-41-24)35(48)43-32-16-6-4-2-3-5-11-25-20-40(25,39(51)46-55(52,53)27-17-18-27)45-36(49)34-19-26(23-47(34)38(32)50)54-37-30-14-8-7-12-28(30)29-13-9-10-15-31(29)44-37/h5,7-15,21-22,25-27,32,34H,2-4,6,16-20,23H2,1H3,(H,43,48)(H,45,49)(H,46,51)/b11-5-/t25-,26-,32+,34+,40-/m1/s1
IUPAC Name
(1S,4R,6S,7Z,14S,18R)-N-(cyclopropanesulfonyl)-14-(5-methylpyrazine-2-amido)-2,15-dioxo-18-(phenanthridin-6-yloxy)-3,16-diazatricyclo[14.3.0.0^{4,6}]nonadec-7-ene-4-carboxamide
SMILES
[H][C@@]12C[C@]1(NC(=O)[C@]1([H])C[C@H](CN1C(=O)[C@H](CCCCC\C=C/2)NC(=O)C1=CN=C(C)C=N1)OC1=NC2=C(C=CC=C2)C2=C1C=CC=C2)C(=O)NS(=O)(=O)C1CC1

References

General References
  1. Klibanov OM, Gale SE, Santevecchi B: Ombitasvir/paritaprevir/ritonavir and dasabuvir tablets for hepatitis C virus genotype 1 infection. Ann Pharmacother. 2015 May;49(5):566-81. doi: 10.1177/1060028015570729. Epub 2015 Feb 13. [Article]
  2. Hull MW, Yoshida EM, Montaner JS: Update on Current Evidence for Hepatitis C Therapeutic Options in HCV Mono-infected Patients. Curr Infect Dis Rep. 2016 Jul;18(7):22. doi: 10.1007/s11908-016-0527-8. [Article]
  3. Lam JT, Salazar L: New combination antiviral for the treatment of hepatitis C. Am J Health Syst Pharm. 2016 Jul 15;73(14):1042-50. doi: 10.2146/ajhp150163. Epub 2016 May 23. [Article]
  4. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [Article]
  5. Dusheiko G: Side effects of alpha interferon in chronic hepatitis C. Hepatology. 1997 Sep;26(3 Suppl 1):112S-121S. [Article]
  6. Moradpour D, Penin F: Hepatitis C virus proteins: from structure to function. Curr Top Microbiol Immunol. 2013;369:113-42. doi: 10.1007/978-3-642-27340-7_5. [Article]
  7. Bagaglio S, Uberti-Foppa C, Morsica G: Resistance Mechanisms in Hepatitis C Virus: implications for Direct-Acting Antiviral Use. Drugs. 2017 May 12. doi: 10.1007/s40265-017-0753-x. [Article]
  8. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
KEGG Drug
D10580
PubChem Compound
68498031
PubChem Substance
310265189
ChemSpider
32700634
RxNav
1597373
ChEBI
85188
ChEMBL
CHEMBL3391662
ZINC
ZINC000197964623
PharmGKB
PA166163410
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Paritaprevir
FDA label
Download (6.48 MB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Kit; tablet, film coatedOral
Tablet, film coatedOral250 mg
Kit; tabletOral
Tablet, film coatedOral
Tablet, coatedOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6703403Yes2004-03-092016-12-26US flag
US6037157Yes2000-03-142016-12-26US flag
US7364752Yes2008-04-292021-05-10US flag
US7148359Yes2006-12-122020-01-19US flag
US8268349Yes2012-09-182025-02-25US flag
US8399015Yes2013-03-192025-02-25US flag
US9139536No2015-09-222028-11-09US flag
US8685984No2014-04-012032-09-04US flag
US8466159No2013-06-182032-09-04US flag
US8642538No2014-02-042029-09-10US flag
US8501238No2013-08-062028-09-17US flag
US8680106No2014-03-252032-09-04US flag
US8492386No2013-07-232032-09-04US flag
US8188104No2012-05-292029-05-17US flag
US9006387No2015-04-142030-06-10US flag
US9044480No2015-06-022031-04-10US flag
US8686026No2014-04-012031-06-09US flag
US8420596Yes2013-04-162031-10-10US flag
US8691938No2014-04-082032-04-13US flag
US9629841No2017-04-252033-10-18US flag
US9333204No2016-05-102035-01-02US flag
US9744170No2017-08-292035-01-02US flag
US10105365No2018-10-232035-01-02US flag
US10201584No2019-02-122032-05-17US flag
US10201542No2019-02-122033-10-18US flag
US10201541No2019-02-122032-05-17US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00778 mg/mLALOGPS
logP3.5ALOGPS
logP2.49Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)3.8Chemaxon
pKa (Strongest Basic)2.64Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area189.65 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity200.98 m3·mol-1Chemaxon
Polarizability78.72 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-0300017900-b1a92eab4059067fbc19
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dm-0200025900-cb8882e798484ad1edcb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0500409200-29ce3b473d055fe6580f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-4100219600-f02b7823e0f0cea1d0e3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-9700104500-41a5211885facadc4979
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006w-9500042200-8412e4abeaed255b6c97
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Hepatitis C Virus
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type peptidase activity
Specific Function
Not Available
Gene Name
NS3/4A
Uniprot ID
B0B3C9
Uniprot Name
Genome polyprotein
Molecular Weight
72789.28 Da
References
  1. Lam JT, Salazar L: New combination antiviral for the treatment of hepatitis C. Am J Health Syst Pharm. 2016 Jul 15;73(14):1042-50. doi: 10.2146/ajhp150163. Epub 2016 May 23. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Shen J, Serby M, Reed A, Lee AJ, Zhang X, Marsh K, Khatri A, Menon R, Kavetskaia O, Fischer V: Metabolism and Disposition of the Hepatitis C Protease Inhibitor Paritaprevir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1164-73. doi: 10.1124/dmd.115.067488. Epub 2016 May 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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. Shen J, Serby M, Reed A, Lee AJ, Zhang X, Marsh K, Khatri A, Menon R, Kavetskaia O, Fischer V: Metabolism and Disposition of the Hepatitis C Protease Inhibitor Paritaprevir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1164-73. doi: 10.1124/dmd.115.067488. Epub 2016 May 13. [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. Alam N, Angeli MG, Greenblatt DJ: Mechanism of in-vitro inhibition of UGT1A1 by paritaprevir. J Pharm Pharmacol. 2017 Dec;69(12):1794-1801. doi: 10.1111/jphp.12821. Epub 2017 Oct 9. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da

Drug created at October 30, 2015 16:02 / Updated at February 21, 2021 18:52