Identification

Name
Tofacitinib
Accession Number
DB08895
Description

Tofacitinib is an inhibitor of Janus kinases, a group of intracellular enzymes involved in signalling pathways that affect hematopoiesis and immune cell function. It is approved by the FDA for treatment of moderate to severe rheumatoid arthritis that responds inadequately to methotrexate or in those who are intolerant to methotrexate. Besides rheumatoid arthritis, tofacitinib has also been studied in clinical trials for the prevention of organ transplant rejection, and is currently under investigation for the treatment of psoriasis. Known adverse effects include nausea and headache as well as more serious immunologic and hematological adverse effects. Tofacitinib is marketed under the brand name Xeljanz by Pfizer.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 312.3696
Monoisotopic: 312.169859292
Chemical Formula
C16H20N6O
Synonyms
  • Tasocitinib
  • Tofacitinib
  • Tofacitinibum
External IDs
  • CP 690550
  • CP- 690 550
  • CP-690 free base
  • CP-690-550
  • CP-690,550
  • CP-690,550 free base
  • CP-690550
  • CP-690550 free base
  • CP690,550
  • CP690550

Pharmacology

Indication

For the treatment of moderate to severe rheumatoid arthritis which is resistant or intolerant to methotrexate therapy. It may also be used as an adjunct to methotrexate therapy, or other non-biologic disease-modifying antirheumatic drugs (DMARDS), when methotrexate alone is not sufficient.

Tofacitinib has also been investigated as a preventative therapy for kidney transplant rejections, and as a treatment for psoriasis, ulcerative colitis, and ankylosing spondylitis.

It is not to be initiated in patients with a history of chronic or recurrent infections, or in the presence of active infection, even if localized, due to reports of serious and sometimes fatal infections (commonly pneumonia, herpes zoster and urinary tract infections). Use of tofacitinib is also discouraged in those who have been, or are likely to be, exposed to TB. An increased likelihood of exposure may be encountered by traveling to certain areas. In addition, tofacitinib is not to be used in patients with severe hepatic impairment, or low hemoglobin (less than 9g/dL). Cautioned is advised when using tofacitinib in patients at risk of gastrointestinal perforation, and in the elderly who are more susceptible to infection.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tofacitinib targets inflammation present in rheumatoid arthritis by inhibiting the janus kinases involved in the inflammatory response pathway.

In placebo controlled trials of rheumatoid arthritis patients receiving 5mg or 10mg of tofacitinib twice daily, higher ACR20 responses were observed within 2 weeks in some patients (with ACR20 being defined as a minimum 20% reduction in joint pain or tenderness and 20% reduction in arthritis pain, patient disability, inflammatory markers, or global assessments of arthritis by patients or by doctors, according to the American College of Rheumatology (ACR) response criteria list), and improvements in physical functioning greater than placebo were also noted.

Common known adverse effects of tofacitinib include headaches, diarrhea, nausea, nasopharyngitis and upper respiratory tract infection. More serious immunologic and hematological adverse effects have also been noted resulting in lymphopenia, neutropenia, anemia, and increased risk of cancer and infection.

Before initiations of tofacitinib patients should be tested for latent infections of tuberculosis, and should be closely monitored for signs and symptoms of infection (fungal, viral, bacterial, or mycobacterial) during therapy. Therapy is not to be started in the presence of active infection, systemic or localized, and is to be interrupted if a serious infection occurs.

Tofacitinib has been associated with an increased risk of lymphomas, such as Epstein-Barr virus associated lymphomas, and other malignancies (including lung, breast, gastric, and colorectal cancers). It is recommended to monitor lymphocytes, neutrophils, hemoglobin, liver enzymes, and lipids.

Tofacitinib use is associated with a rapid decrease in C-reactive protein (CRP), dose dependent decreases in natural killer cells, and dose dependent increases in B cells. Depression in C-reactive protein levels continue after 2 weeks of tofacitinib discontinuation and suggest that pharmacodynamic activity last longer than pharmacokinetic half life.

Mechanism of action

Rheumatoid arthritis is an autoimmune disease characterized by a dysregulation of pro-inflammatory cytokines including IL7, IL15, IL21, IL6, IFN-alpha, and IFN-beta. (3) Cytokines signalling results in tissue inflammation and joint damage by stimulating the recruitment and activation of immune cells via the janus kinase signalling pathway.

Tofacitinib is a partial and reversible janus kinase (JAK) inihibitor that will prevent the body from responding to cytokine signals. By inhibiting JAKs, tofacitinib prevents the phosphorylation and activation of STATs. The JAK-STAT signalling pathway is involved in the transcription of cells involved in hematopoiesis, and immune cell function. Tofacitinib works therapeutically by inhibiting the JAK-STAT pathway to decrease the inflammatory response. However, there is evidence to suggest that it may also achieve efficacy via other pathways as well.

TargetActionsOrganism
ATyrosine-protein kinase JAK1
inhibitor
Humans
ATyrosine-protein kinase JAK2
antagonist
inhibitor
Humans
ATyrosine-protein kinase JAK3
inhibitor
Humans
UNon-receptor tyrosine-protein kinase TYK2Not AvailableHumans
Absorption

74% oral absorption (absolute bioavailability), with peak plasma concentrations (T max) achieved in 0.5-1 hour.

Administration with fatty meals does not alter AUC but reduces Cmax by 32%.

Volume of distribution

Vd= 87L after intravenous administration. Distribution is equal between red blood cells and plasma.

Protein binding

40%, mostly bound to albumin.

Metabolism

Metabolized in the liver by CYP3A4 and CYP2C19. Metabolites produced are inactive.

Route of elimination

70% metabolized in the liver by CYP3A4 (major) and CYP2C19 (minor). Metabolites produced are inactive. 30% renally eliminated as unchanged drug.

Half-life

~3 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Minimum lethal dose in rat: 500 mg/kg. Maximum asymptomatic dose in non human primate: 40 mg/kg.

Lymphatic, immune system, bone marrow and erythroid cell toxicity was seen in animal studies involving rate and monkeys. Doses used in these studies ranged from 1mg/kg/day to 10mg/kg/day, over a duration of 6 weeks to 6 months. Lymphopenia, neutropenia, and anemia is seen in human subjects and may call for an interruption or discontinuation of therapy if severe.

Reduced female fertility in rats was seen at exposures 17 times the maximum recommended human dose. Fertility may be impaired in human females and harm may be caused to unborn child. Carcinogenic potential is seen, however evidence for dose dependency is lacking.

Because the janus kinase pathway plays a role in stimulating the production of red blood cells and is involved in immune cell function, inhibition of this pathway leads to increased risk of anemia, neutropenia, lymphopenia, cancer and infection.

Lymphopenia, neutropenia, and anemia in human subjects may call for an interruption or discontinuation of therapy if severe.

Role of JAK inhibition in the development of gastrointestinal perforation is not known.

Affected organisms
  • Humans and other mammals
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
AbametapirThe serum concentration of Tofacitinib can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Tofacitinib.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Tofacitinib.
AcalabrutinibThe metabolism of Tofacitinib can be decreased when combined with Acalabrutinib.
AcebutololAcebutolol may increase the bradycardic activities of Tofacitinib.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Tofacitinib.
AcetaminophenThe metabolism of Tofacitinib can be decreased when combined with Acetaminophen.
AcetazolamideThe metabolism of Tofacitinib can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Tofacitinib.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Tofacitinib.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid grapefruit products. Dose adjustments are required when administering CYP3A4 inhibitors (grapefruit) and CYP2C19 inhibitors with tofacitinib.
  • Avoid St. John's Wort. This herb induces the CYP3A4 metabolism of tofacitinib and may reduce its serum concentration.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tofacitinib citrateO1FF4DIV0D540737-29-9SYIKUFDOYJFGBQ-YLAFAASESA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
XeljanzTablet, film coated10 mg/1OralPfizer Laboratories Div Pfizer Inc2018-07-02Not applicableUS flag
XeljanzTablet10 mgOralPfizer Canada Ulc2019-01-30Not applicableCanada flag
XeljanzTablet, film coated5 mg/1OralU.S. Pharmaceuticals2012-11-08Not applicableUS flag
XeljanzSolution1 mg/1mLOralPfizer Laboratories Div Pfizer Inc2020-09-252020-09-25US flag
XeljanzTablet, film coated10 mg/1OralU.S. Pharmaceuticals2018-07-02Not applicableUS flag
XeljanzTablet, film coated5 mg/1OralPfizer Laboratories Div Pfizer Inc2012-11-09Not applicableUS flag
XeljanzTablet5 mgOralPfizer Canada Ulc2014-06-03Not applicableCanada flag
Xeljanz XRTablet, extended release22 mg/1OralU.S. Pharmaceuticals2020-01-21Not applicableUS flag
Xeljanz XRTablet, film coated, extended release11 mg/1OralPfizer Laboratories Div Pfizer Inc2016-03-07Not applicableUS flag
Xeljanz XRTablet, extended release11 mgOralPfizer Canada Ulc2018-03-29Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
L04AA29 — Tofacitinib
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acylpiperidines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of a piperidine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
N-acylpiperidines
Direct Parent
N-acylpiperidines
Alternative Parents
Pyrrolo[2,3-d]pyrimidines / Dialkylarylamines / Aminopyrimidines and derivatives / Aminopiperidines / Imidolactams / Tertiary carboxylic acid amides / Pyrroles / Heteroaromatic compounds / Nitriles / Azacyclic compounds
show 4 more
Substituents
3-aminopiperidine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkylarylamine / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, N-acylpiperidine, nitrile, pyrrolopyrimidine (CHEBI:71200)

Chemical Identifiers

UNII
87LA6FU830
CAS number
477600-75-2
InChI Key
UJLAWZDWDVHWOW-YPMHNXCESA-N
InChI
InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1
IUPAC Name
3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile
SMILES
C[[email protected]@H]1CCN(C[[email protected]@H]1N(C)C1=NC=NC2=C1C=CN2)C(=O)CC#N

References

General References
  1. Papp KA, Krueger JG, Feldman SR, Langley RG, Thaci D, Torii H, Tyring S, Wolk R, Gardner A, Mebus C, Tan H, Luo Y, Gupta P, Mallbris L, Tatulych S: Tofacitinib, an oral Janus kinase inhibitor, for the treatment of chronic plaque psoriasis: Long-term efficacy and safety results from 2 randomized phase-III studies and 1 open-label long-term extension study. J Am Acad Dermatol. 2016 May;74(5):841-850. doi: 10.1016/j.jaad.2016.01.013. Epub 2016 Feb 19. [PubMed:26899199]
  2. Link [Link]
  3. BusinessWire: U.S. FDA Approves Pfizer’s XELJANZ® (tofacitinib) for the Treatment of Active Polyarticular Course Juvenile Idiopathic Arthritis [Link]
KEGG Drug
D09970
PubChem Compound
9926791
PubChem Substance
347827811
ChemSpider
8102425
BindingDB
50193995
RxNav
1357536
ChEBI
71200
ChEMBL
CHEMBL221959
ZINC
ZINC000003818808
PDBe Ligand
MI1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tofacitinib
AHFS Codes
  • 92:36.00 — Disease-modifying Antirheumatic Agents
PDB Entries
3eyg / 3fup / 3lxk / 3lxn / 4oti
FDA label
Download (722 KB)
MSDS
Download (44.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAlopecia Areata (AA)1
4Active Not RecruitingTreatmentRheumatoid Arthritis1
4Active Not RecruitingTreatmentUlcerative Colitis1
4CompletedTreatmentRheumatoid Arthritis4
4Not Yet RecruitingTreatmentInterstitial Lung Disease Due to Systemic Disease (Disorder) / Interstitial Lung Diseases (ILD) / Rheumatoid Arthritis1
4RecruitingTreatmentInhibitions / Methotrexate / Takayasu's Disease / Treatments1
4RecruitingTreatmentRheumatoid Arthritis3
4Unknown StatusPreventionSpondyloarthritis1
3CompletedTreatmentAnkylosing Spondylitis (AS)1
3CompletedTreatmentJuvenile Idiopathic Arthritis (JIA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral1 mg/1mL
TabletOral10 mg
TabletOral11 MG
Tablet, film coatedOral10 MG
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 MG
Tablet, film coatedOral5 mg/1
TabletOral5 mg
Tablet, extended releaseOral11 mg/1
Tablet, extended releaseOral11 mg
Tablet, extended releaseOral22 mg/1
Tablet, film coated, extended releaseOral11 mg/1
Tablet, film coated, extended releaseOral22 mg/1
Tablet, delayed releaseOral11 mg
Tablet, coatedOral5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7091208No2006-08-152020-12-08US flag
US6965027No2005-11-152023-03-25US flag
USRE41783No2010-09-282020-12-08US flag
US7265221No2007-09-042020-12-08US flag
US6956041No2005-10-182020-12-08US flag
US7301023No2007-11-272022-05-23US flag
US6956027No2005-10-182023-03-25US flag
US9937181No2018-04-102034-03-14US flag
US7842699No2010-11-302020-12-08US flag
US10639309No2014-03-142034-03-14US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.808 MSDS, Tofacitinib Citrate
Predicted Properties
PropertyValueSource
Water Solubility0.299 mg/mLALOGPS
logP1.58ALOGPS
logP1.24ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)6.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.8 m3·mol-1ChemAxon
Polarizability32.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9897
Blood Brain Barrier+0.9568
Caco-2 permeable+0.5154
P-glycoprotein substrateSubstrate0.6524
P-glycoprotein inhibitor IInhibitor0.7609
P-glycoprotein inhibitor IIInhibitor0.8898
Renal organic cation transporterInhibitor0.6368
CYP450 2C9 substrateNon-substrate0.8246
CYP450 2D6 substrateNon-substrate0.723
CYP450 3A4 substrateSubstrate0.7649
CYP450 1A2 substrateNon-inhibitor0.734
CYP450 2C9 inhibitorNon-inhibitor0.8014
CYP450 2D6 inhibitorNon-inhibitor0.9537
CYP450 2C19 inhibitorNon-inhibitor0.8036
CYP450 3A4 inhibitorNon-inhibitor0.9307
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7937
Ames testNon AMES toxic0.5492
CarcinogenicityNon-carcinogens0.9032
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.7249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5995
hERG inhibition (predictor II)Inhibitor0.7324
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ubiquitin protein ligase binding
Specific Function
Tyrosine kinase of the non-receptor type, involved in the IFN-alpha/beta/gamma signal pathway. Kinase partner for the interleukin (IL)-2 receptor.
Gene Name
JAK1
Uniprot ID
P23458
Uniprot Name
Tyrosine-protein kinase JAK1
Molecular Weight
133275.995 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Sh2 domain binding
Specific Function
Non-receptor tyrosine kinase involved in various processes such as cell growth, development, differentiation or histone modifications. Mediates essential signaling events in both innate and adaptiv...
Gene Name
JAK2
Uniprot ID
O60674
Uniprot Name
Tyrosine-protein kinase JAK2
Molecular Weight
130672.475 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Protein tyrosine kinase activity
Specific Function
Non-receptor tyrosine kinase involved in various processes such as cell growth, development, or differentiation. Mediates essential signaling events in both innate and adaptive immunity and plays a...
Gene Name
JAK3
Uniprot ID
P52333
Uniprot Name
Tyrosine-protein kinase JAK3
Molecular Weight
125097.565 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein tyrosine kinase activity
Specific Function
Probably involved in intracellular signal transduction by being involved in the initiation of type I IFN signaling. Phosphorylates the interferon-alpha/beta receptor alpha chain.
Gene Name
TYK2
Uniprot ID
P29597
Uniprot Name
Non-receptor tyrosine-protein kinase TYK2
Molecular Weight
133648.77 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Details
1. Cytochrome P450 3A4
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
Details
2. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Drug created on June 03, 2013 14:44 / Updated on November 23, 2020 09:08

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