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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
Structure of TACROLIMUS ANHYDROUS

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PROGRAF

Approved Use

Prograf 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 Date

7.6576319E11
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Edema lung
Allergic reaction
Abnormal liver function tests
Bilirubinemia
Lymphoma like reaction
Diarrhea
Intestinal obstruction
Sources: Page: p. 79
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
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
Other AEs: Infection...
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

AEs

AESignificanceDosePopulation
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
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
yes
yes
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: -
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

PubMed

TitleDatePubMed
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
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
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 Sat Jun 26 04:58:58 UTC 2021
Edited
by admin
on Sat Jun 26 04:58:58 UTC 2021
Record UNII
Y5L2157C4J
Record Status Validated (UNII)
Record Version
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Name Type Language
TACROLIMUS ANHYDROUS
Common Name English
TACROLIMUS [INN]
Common Name English
TSUKUBAENOLIDE
Common Name English
PROGRAPH
Common Name English
FUJIMYCIN
Common Name English
TACROLIMUS [MART.]
Common Name English
TACROLIMUS, ANHYDROUS
Common Name English
TACROLIMUS [WHO-DD]
Common Name English
TACRO
Common Name English
ENVARSUS-XR
Common Name English
15,19-EPOXY-3H-PYRIDO(2,1-C)(1,4)OXAAZACYCLOTRICOSINE-1,7,20,21(4H,23H)-TETRONE, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26A-HEXADECAHYDRO-5,19-DIHYDROXY-3-((1E)-2-((1R,3R,4R)-4-HYDROXY-3-METHOXYCYCLOHEXYL)-1-METHYLETHENYL)-14,16-DIMETHOXY-4,10,12,18-T
Systematic Name English
TACROLIMUS [MI]
Common Name English
ANHYDROUS TACROLIMUS
Common Name English
Classification Tree Code System Code
WHO-ATC L04AD02
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
NDF-RT N0000175458
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
NCI_THESAURUS C146638
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
NDF-RT N0000175457
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
WHO-ATC D11AH01
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
CFR 21 CFR 862.1678
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
Code System Code Type Description
DRUG BANK
DB00864
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
EVMPD
SUB21717
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
HSDB
8195
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
EVMPD
SUB10797MIG
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
RXCUI
235991
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY RxNorm
PUBCHEM
445643
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
FDA UNII
Y5L2157C4J
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
CAS
104987-11-3
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
NCI_THESAURUS
C76066
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
INN
6878
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
EPA CompTox
104987-11-3
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY
MERCK INDEX
M10425
Created by admin on Sat Jun 26 04:58:58 UTC 2021 , Edited by admin on Sat Jun 26 04:58:58 UTC 2021
PRIMARY Merck Index
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