Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C44H69NO12 |
Molecular Weight | 804.0199 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 14 / 14 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CC[C@]1([H])/C(/[H])=C(\C)/C[C@]([H])(C)C[C@@]([H])([C@]2([H])[C@]([H])(C[C@@]([H])(C)[C@@](C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O[C@]([H])(/C(=C(\[H])/[C@]4([H])CC[C@]([H])([C@@]([H])(C4)OC)O)/C)[C@]([H])(C)[C@]([H])(CC1=O)O)(O)O2)OC)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
Molecular Formula | C44H69NO12 |
Molecular Weight | 804.0199 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 14 / 14 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|
Target ID: CHEMBL1902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16289353 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 Date7.6576319E11 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
---|---|---|
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: |
|
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: |
|
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: |
|
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 |
---|---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
yes | |||
Page: - |
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 |
---|---|---|
Neurotoxicity after orthotopic liver transplantation in cyclosporin A- and FK 506-treated patients. | 1994 |
|
Tacrolimus toxicity in rhesus monkey: model for clinical side effects. | 1999 Dec |
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Oscillopsia and pseudonystagmus in kidney transplant patients. | 1999 Dec |
|
Which calcineurin inhibitor is preferred in renal transplantation: tacrolimus or cyclosporine? | 1999 Nov |
|
Leg bone pain syndrome in a kidney transplant patient treated with tacrolimus (FK506). | 1999 Oct |
|
Successful use of cyclosporine in a lung transplant recipient with tacrolimus-associated hemolytic uremic syndrome. | 1999 Oct |
|
Tacrolimus (FK506)-induced severe and late encephalopathy in a renal transplant recipient. | 1999 Oct |
|
FK506 markedly enhances apoptosis of antigen-stimulated peripheral T cells by down-regulation of Bcl-xL. | 1999 Oct 15 |
|
Trimetazidine counteracts tacrolimus nephrotoxicity in a hypertensive liver transplant patient. | 1999 Oct 27 |
|
Hemolytic-uremic syndrome in association with both cyclosporine and tacrolimus. | 2000 |
|
Tacrolimus in acute renal failure: does L-arginine-infusion prevent changes in renal hemodynamics? | 2000 |
|
Arteriolopathy in non-episode biopsies of renal transplant allograft. | 2000 |
|
Treatment of tacrolimus-related adverse effects by conversion to cyclosporine in liver transplant recipients. | 2000 |
|
A case of bilateral optic neuropathy in a patient on tacrolimus (FK506) therapy after liver transplantation. | 2000 Apr |
|
Suppressive effects of cyclosporin A and FK-506 on superoxide generation in human polymorphonuclear leukocytes primed by tumor necrosis factor alpha. | 2000 Dec |
|
Sirolimus in pediatric gastrointestinal transplantation: the use of sirolimus for pediatric transplant patients with tacrolimus-related cardiomyopathy. | 2000 Feb |
|
FK506-induced intractable leukoencephalopathy following allogeneic bone marrow transplantation. | 2000 Feb |
|
Conversion to neoral for neurotoxicity after primary adult liver transplantation under tacrolimus. | 2000 Jan 15 |
|
Tacrolimus (FK506) and methotrexate as prophylaxis for acute graft-versus-host disease in pediatric allogeneic stem cell transplantation. | 2000 Jul |
|
Caspase-mediated proteolytic activation of calcineurin in thapsigargin-mediated apoptosis in SH-SY5Y neuroblastoma cells. | 2000 Jul 15 |
|
Effect of aminophylline on urine flow in children with tacrolimus-induced renal insufficiency. | 2000 Jun |
|
Tacrolimus-induced hemolytic uremic syndrome and end-stage renal failure after liver transplantation. | 2000 Jun |
|
Cortical laminar necrosis caused by immunosuppressive therapy and chemotherapy. | 2000 Mar |
|
FK506 inhibition of histamine release and cytokine production by mast cells and basophils. | 2000 Mar |
|
Immunosuppressive drugs: the first 50 years and a glance forward. | 2000 May |
|
Tacrolimus and myocardial hypertrophy. | 2000 May 15 |
|
Clinical outcome after conversion to FK 506 (tacrolimus) therapy for acute graft-versus-host disease resistant to cyclosporine or for cyclosporine-associated toxicities. | 2000 Nov |
|
Tacrolimus has less fibrogenic potential than cyclosporin A in a model of renal ischaemia-reperfusion injury. | 2000 Nov |
|
Fatal cerebral hemorrhage associated with cyclosporin-A/FK506-related encephalopathy after allogeneic bone marrow transplantation. | 2000 Oct |
|
Cyclosporine and tacrolimus-associated thrombotic microangiopathy. | 2000 Oct |
|
Delayed transient neurologic toxicity due to tacrolimus: CT and MRI. | 2000 Sep |
|
[Acute peripheral demyelinating polyneuropathy and acute renal failure after administration of FK506]. | 2001 |
|
Calcineurin-inhibitor induced pain syndrome (CIPS): a severe disabling complication after organ transplantation. | 2001 |
|
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients. | 2001 Aug 27 |
|
Mycophenolate mofetil monotherapy in liver transplantation. | 2001 Feb 24 |
|
Nonclinical and early clinical development of tacrolimus ointment for the treatment of atopic dermatitis. | 2001 Jan |
|
Reversible encephalopathy associated with tacrolimus in pediatric renal transplants. | 2001 Jul |
|
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis. | 2001 Nov |
|
Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus. | 2001 Oct |
|
Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients. | 2001 Oct |
|
Changes in lipid metabolism and effect of simvastatin in renal transplant recipients induced by cyclosporine or tacrolimus. | 2001 Oct |
|
Neurotoxicity induced by tacrolimus after liver transplantation: relation to genetic polymorphisms of the ABCB1 (MDR1) gene. | 2002 Aug 27 |
|
Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines. | 2002 Jul 19 |
|
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 |
|
Tacrolimus-induced pain syndrome in a pediatric orthotopic liver transplant patient. | 2002 Oct |
|
Asymmetric cardiac hypertrophy at autopsy in patients who received FK506 (tacrolimus) or cyclosporine A after liver transplant. | 2002 Sep 27 |
|
Speech disorder related to tacrolimus-induced pontine myelinolysis after orthotopic liver transplantation. | 2003 Aug |
|
Renin mRNA expression and renal dysfunction in tacrolimus-induced acute nephrotoxicity. | 2003 Jan |
|
Severe acute renal failure after exposure to sirolimus-tacrolimus in two living donor kidney recipients. | 2003 Jan 15 |
|
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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 04:58:58 UTC 2021
by
admin
on
Sat Jun 26 04:58:58 UTC 2021
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Record UNII |
Y5L2157C4J
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-ATC |
L04AD02
Created by
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NDF-RT |
N0000175458
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NCI_THESAURUS |
C146638
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NDF-RT |
N0000175457
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WHO-ATC |
D11AH01
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CFR |
21 CFR 862.1678
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DB00864
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SUB21717
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8195
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SUB10797MIG
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235991
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445643
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Y5L2157C4J
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104987-11-3
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C76066
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6878
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M10425
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PRIMARY | Merck Index |
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
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ACTIVE MOIETY |