Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C44H69NO12 |
Molecular Weight | 804.0182 |
Optical Activity | ( - ) |
Defined Stereocenters | 14 / 14 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CC[C@@H](O)[C@@H](C1)OC)\C=C(/C)[C@@]2([H])OC(=O)[C@]3([H])CCCCN3C(=O)C(=O)[C@]4(O)O[C@@]([H])([C@H](C[C@H]4C)OC)[C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)OC
InChI
InChIKey=QJJXYPPXXYFBGM-LFZNUXCKSA-N
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
Tacrolimus, previously known as FK506, is the active ingredient in Prograf. Tacrolimus is a macrolide immunosuppressant produced by Streptomyces tsukubaensis. It reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP-12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex interacts with and inhibits calcineurin thus inhibiting both T-lymphocyte signal transduction and IL-2 transcription. Tacrolimus inhibits T-lymphocyte activation, although the exact mechanism of action is not known. Experimental evidence suggests that tacrolimus binds to an intracellular protein, FKBP-12. A complex of tacrolimus-FKBP-12, calcium, calmodulin, and calcineurin is then formed and the phosphatase activity of calcineurin inhibited. This effect may prevent the dephosphorylation and translocation of nuclear factor of activated T-cells (NF-AT), a nuclear component thought to initiate gene transcription for the formation of lymphokines (such as interleukin-2, gamma interferon). The net result is the inhibition of T-lymphocyte activation (i.e., immunosuppression). Prograf is indicated for the prophylaxis of organ rejection in patients receiving allogeneic liver transplants, kidney transplants, heart transplants. It has also been used in a topical preparation in the treatment of severe atopic dermatitis.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16289353 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | PROGRAF Approved UsePrograf is a calcineurin-inhibitor immunosuppressant indicated for: Prophylaxis of organ rejection in patients receiving allogeneic liver, kidney or heart transplants. Use concomitantly with adrenal corticosteroids; in kidney and heart transplant, use in conjunction with azathioprine or mycophenolate mofetil (MMF) Launch Date1994 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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26 ng/mL |
0.2 mg/kg 1 times / day multiple, oral dose: 0.2 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
TACROLIMUS unknown | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
6.2 ng/mL |
4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TACROLIMUS unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
372 ng × h/mL |
0.2 mg/kg 1 times / day multiple, oral dose: 0.2 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
TACROLIMUS unknown | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
74 ng × h/mL |
4 mg 1 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TACROLIMUS unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
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0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Disc. AE: Anemia, Edema lung... AEs leading to discontinuation/dose reduction: Anemia Sources: Page: p. 79Edema lung Allergic reaction Abnormal liver function tests Bilirubinemia Lymphoma like reaction Diarrhea Intestinal obstruction |
5.2 mg 1 times / day multiple, oral Highest studied dose Dose: 5.2 mg, 1 times / day Route: oral Route: multiple Dose: 5.2 mg, 1 times / day Sources: |
unhealthy, adult n = 60 Health Status: unhealthy Condition: kidney transplantation Age Group: adult Population Size: 60 Sources: |
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8 mg single, oral Highest studied dose Dose: 8 mg Route: oral Route: single Dose: 8 mg Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
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0.1 mg/kg 2 times / day multiple, oral Recommended Dose: 0.1 mg/kg, 2 times / day Route: oral Route: multiple Dose: 0.1 mg/kg, 2 times / day Co-administed with:: Azathioprine Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Infection... Other AEs: Infection (serious) Sources: |
0.02 mg/kg single, intravenous Dose: 0.02 mg/kg Route: intravenous Route: single Dose: 0.02 mg/kg Sources: |
unhealthy, adult n = 12 Health Status: unhealthy Condition: Renal Impairment Age Group: adult Population Size: 12 Sources: |
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0.03 % 1 times / day multiple, topical Dose: 0.03 %, 1 times / day Route: topical Route: multiple Dose: 0.03 %, 1 times / day Sources: |
unhealthy n = 31 Health Status: unhealthy Condition: non-segmental vitiligo Population Size: 31 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abnormal liver function tests | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Allergic reaction | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Anemia | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Bilirubinemia | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Diarrhea | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Edema lung | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Intestinal obstruction | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Lymphoma like reaction | Disc. AE | 0.15 mg/kg 2 times / day steady, oral Dose: 0.15 mg/kg, 2 times / day Route: oral Route: steady Dose: 0.15 mg/kg, 2 times / day Sources: Page: p. 79 |
unhealthy, 1.9 years (range: 3-15 years) n = 91 Health Status: unhealthy Condition: Primary Liver Transplantation Age Group: 1.9 years (range: 3-15 years) Sex: M+F Population Size: 91 Sources: Page: p. 79 |
Infection | serious | 0.1 mg/kg 2 times / day multiple, oral Recommended Dose: 0.1 mg/kg, 2 times / day Route: oral Route: multiple Dose: 0.1 mg/kg, 2 times / day Co-administed with:: Azathioprine Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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Page: - |
no | |||
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no | |||
Page: - |
no | |||
Page: - |
no | |||
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no | |||
Page: - |
no | |||
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no | |||
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yes | |||
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yes | |||
Page: - |
yes | yes (co-administration study) Comment: Tacrolimus was metabolized by the cytochrome P450 (CYP) 3A subfamily. Metabolic drug-drug interaction studies were conducted to provide information regarding the optimal usage of tacrolimus, and its metabolism was inhibited by known CYP3A inhibitors such as ketoconazole, cyclosporine A, and nifedipine. Recent reports on clinical pharmacokinetics indicate that dose levels of tacrolimus need to be adjusted in transplant patients with CYP3A5 polymorphism. Page: - |
||
Page: - |
yes | yes (pharmacogenomic study) Comment: Tacrolimus was metabolized by the cytochrome P450 (CYP) 3A subfamily. Metabolic drug-drug interaction studies were conducted to provide information regarding the optimal usage of tacrolimus, and its metabolism was inhibited by known CYP3A inhibitors such as ketoconazole, cyclosporine A, and nifedipine. Recent reports on clinical pharmacokinetics indicate that dose levels of tacrolimus need to be adjusted in transplant patients with CYP3A5 polymorphism. Page: - |
PubMed
Title | Date | PubMed |
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Nephrotoxicity after orthotopic liver transplantation in cyclosporin A and FK 506-treated patients. | 1994 |
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Neurotoxicity after orthotopic liver transplantation in cyclosporin A- and FK 506-treated patients. | 1994 |
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[Acute peripheral demyelinating polyneuropathy and acute renal failure after administration of FK506]. | 2001 |
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Renal cholesterol accumulation: a durable response after acute and subacute renal insults. | 2001 Aug |
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Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients. | 2001 Aug 27 |
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Calcineurin inhibitor attenuates cardiac hypertrophy due to energy metabolic disorder. | 2001 Dec |
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Severe axonal polyneuropathy after a FK506 overdosage in a lung transplant recipient. | 2001 Dec 15 |
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End-stage renal disease (ESRD) after orthotopic liver transplantation (OLTX) using calcineurin-based immunotherapy: risk of development and treatment. | 2001 Dec 27 |
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Mycophenolate mofetil monotherapy in liver transplantation. | 2001 Feb 24 |
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Reversible encephalopathy associated with tacrolimus in pediatric renal transplants. | 2001 Jul |
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Beneficial effects of converting liver transplant recipients from cyclosporine to tacrolimus on blood pressure, serum lipids, and weight. | 2001 Jun |
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Echocardiographic findings of hypertrophic cardiomyopathy in children after orthotopic liver transplantation. | 2001 Jun |
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Tacrolimus suppressed the production of cytokines involved in atopic dermatitis by direct stimulation of human PBMC system. (Comparison with steroids). | 2001 Jun |
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[Blood concentrations and side effects of tacrolimus in a living renal transplantation]. | 2001 Mar |
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Clinical utility of monitoring tacrolimus blood concentrations in liver transplant patients. | 2001 May |
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Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis. | 2001 Nov |
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Posttransplantation diabetes mellitus in FK-506-treated renal transplant recipients: analysis of incidence and risk factors. | 2001 Nov 27 |
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Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports. | 2001 Nov-Dec |
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Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus. | 2001 Oct |
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Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients. | 2001 Oct |
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Changes in lipid metabolism and effect of simvastatin in renal transplant recipients induced by cyclosporine or tacrolimus. | 2001 Oct |
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Neurotoxicity induced by tacrolimus after liver transplantation: relation to genetic polymorphisms of the ABCB1 (MDR1) gene. | 2002 Aug 27 |
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Expression of TGF-beta and fibrogenic genes in transplant recipients with tacrolimus and cyclosporine nephrotoxicity. | 2002 Dec |
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[A case of FK 506-induced leukoencephalopathy]. | 2002 Jan |
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Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines. | 2002 Jul 19 |
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Recurrent reversible cerebral edema after long term immunosuppression with tacrolimus. | 2002 Jun |
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FK 506-induced fulminant leukoencephalopathy after kidney transplantation: case report. | 2002 Jun |
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Tacrolimus is a class II low-solubility high-permeability drug: the effect of P-glycoprotein efflux on regional permeability of tacrolimus in rats. | 2002 Mar |
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Downregulation of both interleukin-12 and interleukin-2 in heart allografts by pretransplant host treatment with granulocyte colony-stimulating factor and tacrolimus. | 2002 May 7 |
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Tacrolimus-induced life-threatening arrhythmia in a pediatric liver-transplant patient. | 2002 Nov |
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Tacrolimus-induced pain syndrome in a pediatric orthotopic liver transplant patient. | 2002 Oct |
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Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril. | 2002 Oct |
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Long-term comparison of tacrolimus- and cyclosporine-induced nephrotoxicity in pediatric heart-transplant recipients. | 2002 Sep |
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Asymmetric cardiac hypertrophy at autopsy in patients who received FK506 (tacrolimus) or cyclosporine A after liver transplant. | 2002 Sep 27 |
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Neuropsychologic side-effects of tacrolimus in pediatric renal transplantation. | 2003 Apr |
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Delayed graft function and cast nephropathy associated with tacrolimus plus rapamycin use. | 2003 Apr |
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Speech disorder related to tacrolimus-induced pontine myelinolysis after orthotopic liver transplantation. | 2003 Aug |
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Tacrolimus (FK506)-induced mutism after liver transplant. | 2003 Feb |
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Treatment of human T cells with bisperoxovanadium phosphotyrosyl phosphatase inhibitors leads to activation of cyclooxygenase-2 gene. | 2003 Feb 28 |
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Tacrolimus. | 2003 Jan |
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Inhibition of nuclear factor-kappaB activation by pyrrolidine dithiocarbamate prevents chronic FK506 nephropathy. | 2003 Jan |
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Renin mRNA expression and renal dysfunction in tacrolimus-induced acute nephrotoxicity. | 2003 Jan |
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Severe acute renal failure after exposure to sirolimus-tacrolimus in two living donor kidney recipients. | 2003 Jan 15 |
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Steroid-free immunosuppression during and after liver transplantation--a 3-yr follow-up report. | 2003 Jun |
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Microangiopathic haemolytic anaemia and thrombocytopenia following lung volume reduction surgery in a single lung transplant recipient on maintenance tacrolimus (FK506) therapy. | 2003 Jun |
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Tacrolimus-induced hemolytic uremic syndrome case presentation in a lung transplant recipient. | 2003 Mar |
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The immunophilin-ligands FK506 and V-10,367 mediate neuroprotection by the heat shock response. | 2003 Mar |
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Kidney function and morphology after short-term combination therapy with cyclosporine A, tacrolimus and sirolimus in the rat. | 2003 Mar |
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Enhanced interleukin-4 production in CD4+ T cells and elevated immunoglobulin E levels in antigen-primed mice by bisphenol A and nonylphenol, endocrine disruptors: involvement of nuclear factor-AT and Ca2+. | 2003 May |
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MR imaging with quantitative diffusion mapping of tacrolimus-induced neurotoxicity in organ transplant patients. | 2003 May |
Patents
Sample Use Guides
Dosage in Adult Kidney, Liver, or Heart Transplant Patients:
Adult kidney transplant patients (Oral Dosage: daily doses should be administered as two divided doses, every 12 hours): in combination with azathioprine: 0.2 mg/kg/day; in combination with MMF/IL-2 receptor antagonist: 0.1 mg/kg/day. Adult liver transplant patients: 0.10-0.15 mg/kg/day. Adult heart transplant patients: 0.075 mg/kg/day.
Prograf (TACROLIMUS) injection should be used only as a continuous IV infusion and when the patient cannot tolerate oral administration of Prograf capsules. Prograf injection should be discontinued as soon as the patient can tolerate oral administration of Prograf capsules, usually within 2-3 days. In a patient receiving an IV infusion, the first dose of oral therapy should be given 8-12 hours after discontinuing the IV infusion. The recommended starting dose of Prograf injection is 0.03-0.05 mg/kg/day in kidney and liver transplant and 0.01 mg/kg/day in heart transplant given as a continuous IV infusion. Adult patients should receive doses at the lower end of the dosing range. Concomitant adrenal corticosteroid therapy is recommended early post-transplantation.
Dosage in Pediatric Liver Transplant Patients: (Oral Dosage): Pediatric liver transplant patients 0.15-0.20 mg/kg/day (daily doses should be administered as two divided doses, every 12 hours)
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25339327
Tacrolimus at concentration of 0.06 μmol/L could promote collagen induced platelet aggregation, inhibit thrombin induced platelet aggregation, have no effect on ristocetin and vWF induced platelet aggregation function. Tacrolimus at concentration of 120 μmol/L and 240 μmol/L could reduce the platelet mitochondrial membrane potential and induce the expression of apoptosis protein caspase-3. In vitro experimental results showed that high concentration of tacrolimus could lead to platelet apoptosis. But the current therapeutic dose of tacrolimus at 0.06 μmol/L (which is equivalent to 50 ng/ml blood concentration) could have different effects on platelet aggregation function according to different stimulating agents.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
L04AD02
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N0000175458
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C146638
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D11AH01
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CFR |
21 CFR 862.1678
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)