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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
Nephrotoxicity after orthotopic liver transplantation in cyclosporin A and FK 506-treated patients.
1994
Neurotoxicity after orthotopic liver transplantation in cyclosporin A- and FK 506-treated patients.
1994
Neurological complications in the European multicentre study of FK 506 and cyclosporin in primary liver transplantation.
1994
Hemolytic-uremic syndrome in association with both cyclosporine and tacrolimus.
2000
[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
Renal cholesterol accumulation: a durable response after acute and subacute renal insults.
2001 Aug
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients.
2001 Aug 27
Calcineurin inhibitor attenuates cardiac hypertrophy due to energy metabolic disorder.
2001 Dec
Severe axonal polyneuropathy after a FK506 overdosage in a lung transplant recipient.
2001 Dec 15
End-stage renal disease (ESRD) after orthotopic liver transplantation (OLTX) using calcineurin-based immunotherapy: risk of development and treatment.
2001 Dec 27
Sirolimus interferes with the innate response to bacterial products in human whole blood by attenuation of IL-10 production.
2001 Feb
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
Beneficial effects of converting liver transplant recipients from cyclosporine to tacrolimus on blood pressure, serum lipids, and weight.
2001 Jun
Echocardiographic findings of hypertrophic cardiomyopathy in children after orthotopic liver transplantation.
2001 Jun
Tacrolimus suppressed the production of cytokines involved in atopic dermatitis by direct stimulation of human PBMC system. (Comparison with steroids).
2001 Jun
Clinical utility of monitoring tacrolimus blood concentrations in liver transplant patients.
2001 May
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis.
2001 Nov
Posttransplantation diabetes mellitus in FK-506-treated renal transplant recipients: analysis of incidence and risk factors.
2001 Nov 27
Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports.
2001 Nov-Dec
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
[A case of FK 506-induced leukoencephalopathy].
2002 Jan
Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines.
2002 Jul 19
Recurrent reversible cerebral edema after long term immunosuppression with tacrolimus.
2002 Jun
FK 506-induced fulminant leukoencephalopathy after kidney transplantation: case report.
2002 Jun
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
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
Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril.
2002 Oct
Long-term comparison of tacrolimus- and cyclosporine-induced nephrotoxicity in pediatric heart-transplant recipients.
2002 Sep
Asymmetric cardiac hypertrophy at autopsy in patients who received FK506 (tacrolimus) or cyclosporine A after liver transplant.
2002 Sep 27
Neuropsychologic side-effects of tacrolimus in pediatric renal transplantation.
2003 Apr
Delayed graft function and cast nephropathy associated with tacrolimus plus rapamycin use.
2003 Apr
Speech disorder related to tacrolimus-induced pontine myelinolysis after orthotopic liver transplantation.
2003 Aug
Tacrolimus (FK506)-induced mutism after liver transplant.
2003 Feb
Treatment of human T cells with bisperoxovanadium phosphotyrosyl phosphatase inhibitors leads to activation of cyclooxygenase-2 gene.
2003 Feb 28
Inhibition of nuclear factor-kappaB activation by pyrrolidine dithiocarbamate prevents chronic FK506 nephropathy.
2003 Jan
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
Steroid-free immunosuppression during and after liver transplantation--a 3-yr follow-up report.
2003 Jun
Microangiopathic haemolytic anaemia and thrombocytopenia following lung volume reduction surgery in a single lung transplant recipient on maintenance tacrolimus (FK506) therapy.
2003 Jun
Tacrolimus-induced hemolytic uremic syndrome case presentation in a lung transplant recipient.
2003 Mar
The immunophilin-ligands FK506 and V-10,367 mediate neuroprotection by the heat shock response.
2003 Mar
Kidney function and morphology after short-term combination therapy with cyclosporine A, tacrolimus and sirolimus in the rat.
2003 Mar
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
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
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
  • Download
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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