Details
Stereochemistry | ACHIRAL |
Molecular Formula | CO5P.3Na |
Molecular Weight | 191.9508 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O
InChI
InChIKey=DFHAXXVZCFXGOQ-UHFFFAOYSA-K
InChI=1S/CH3O5P.3Na/c2-1(3)7(4,5)6;;;/h(H,2,3)(H2,4,5,6);;;/q;3*+1/p-3
Molecular Formula | CO5P |
Molecular Weight | 122.9815 |
Charge | -3 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Foscarnet is an antiviral agent. Foscarnet shows activity against human herpesviruses and HIV. Foscarnet is used for treating eye problems caused by CMV in people with AIDS. It is also used to treat a type of HSV that cannot be treated by another medicine in people with a weak immune system. FOSCAVIR is the brand name for foscarnet sodium. FOSCAVIR is an organic analogue of inorganic
pyrophosphate that inhibits replication of herpesviruses in
vitro including cytomegalovirus (CMV) and herpes simplex
virus types 1 and 2 (HSV-1 and HSV-2). FOSCAVIR exerts its antiviral activity by a selective
inhibition at the pyrophosphate binding site on virusspecific
DNA polymerases at concentrations that do not
affect cellular DNA polymerases. FOSCAVIR does not
require activation (phosphorylation) by thymidine kinase or
other kinases and therefore is active in vitro against HSV
TK deficient mutants and CMV UL97 mutants. Thus, HSV
strains resistant to acyclovir or CMV strains resistant to
ganciclovir may be sensitive to FOSCAVIR.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL247 |
2.03 µM [IC50] | ||
Target ID: CHEMBL3414 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16134946 |
2.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FOSCAVIR Approved UseINDICATIONS CMV Retinitis FOSCAVIR is indicated for the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS). Combination therapy with FOSCAVIR and ganciclovir is indicated for patients who have relapsed after monotherapy with either drug. SAFETY AND EFFICACY OF FOSCAVIR HAVE NOT BEEN ESTABLISHED FOR TREATMENT OF OTHER CMV INFECTIONS (e.g., PNEUMONITIS, GASTROENTERITIS); CONGENITAL OR NEONATAL CMV DISEASE; OR NONIMMUNOCOMPROMISED INDIVIDUALS. Mucocutaneous Acyclovir Resistant HSV Infections FOSCAVIR is indicated for the treatment of acyclovir-resistant mucocutaneous HSV infections in immunocompromised patients. SAFETY AND EFFICACY OF FOSCAVIR HAVE NOT BEEN ESTABLISHED FOR TREATMENT OF OTHER HSV INFECTIONS (e.g., RETINITIS, ENCEPHALITIS); CONGENITAL OR NEONATAL HSV DISEASE; OR HSV IN NONIMMUNOCOMPROMISED INDIVIDUALS. Launch Date1991 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
46.4 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, oral dose: 90 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
887.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
64.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw single, oral dose: 180 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
86.2 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 1 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
78.7 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 2 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
86.4 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw 1 times / day multiple, oral dose: 180 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
589 μM |
60 mg/kg bw 3 times / day steady-state, intravenous dose: 60 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
623 μM |
90 mg/kg bw 2 times / day steady-state, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
300 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, oral dose: 90 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3308 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
494 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw single, oral dose: 180 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
646 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 1 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
688 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 2 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
826 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw 1 times / day multiple, oral dose: 180 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, oral dose: 90 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw single, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw single, oral dose: 180 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 1 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
90 mg/kg bw 2 times / day multiple, oral dose: 90 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9527775/ |
180 mg/kg bw 1 times / day multiple, oral dose: 180 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4 h |
60 mg/kg bw 3 times / day steady-state, intravenous dose: 60 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.3 h |
90 mg/kg bw 2 times / day steady-state, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84.5% |
60 mg/kg bw 3 times / day steady-state, intravenous dose: 60 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
84.5% |
90 mg/kg bw 2 times / day steady-state, intravenous dose: 90 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
FOSCARNET plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2400 ug 2 times / week multiple, intravitreal Highest studied dose Dose: 2400 ug, 2 times / week Route: intravitreal Route: multiple Dose: 2400 ug, 2 times / week Sources: |
unhealthy, 36.6 n = 11 Health Status: unhealthy Condition: AIDS Age Group: 36.6 Sex: M+F Population Size: 11 Sources: |
|
5.45 g 2 times / day multiple, intravenous Overdose Dose: 5.45 g, 2 times / day Route: intravenous Route: multiple Dose: 5.45 g, 2 times / day Sources: |
unknown, adult n = 9 Health Status: unknown Age Group: adult Sex: unknown Population Size: 9 Sources: |
Other AEs: Impaired renal function... Other AEs: Impaired renal function (grade 5) Sources: |
6.25 g 2 times / day multiple, intravenous Overdose Dose: 6.25 g, 2 times / day Route: intravenous Route: multiple Dose: 6.25 g, 2 times / day Sources: |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: |
Other AEs: Cardio-respiratory arrest... Other AEs: Cardio-respiratory arrest (grade 5) Sources: |
60 mg/kg 2 times / day multiple, intravenous Recommended Dose: 60 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 2 times / day Sources: |
unhealthy, adult n = 20 Health Status: unhealthy Condition: allogeneic bone marrow transplantation Age Group: adult Population Size: 20 Sources: |
Disc. AE: Impaired renal function, Hematuria... AEs leading to discontinuation/dose reduction: Impaired renal function Sources: Hematuria Cerebral hemorrhage Physical impairment |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Impaired renal function | grade 5 | 5.45 g 2 times / day multiple, intravenous Overdose Dose: 5.45 g, 2 times / day Route: intravenous Route: multiple Dose: 5.45 g, 2 times / day Sources: |
unknown, adult n = 9 Health Status: unknown Age Group: adult Sex: unknown Population Size: 9 Sources: |
Cardio-respiratory arrest | grade 5 | 6.25 g 2 times / day multiple, intravenous Overdose Dose: 6.25 g, 2 times / day Route: intravenous Route: multiple Dose: 6.25 g, 2 times / day Sources: |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: unknown Population Size: 1 Sources: |
Cerebral hemorrhage | Disc. AE | 60 mg/kg 2 times / day multiple, intravenous Recommended Dose: 60 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 2 times / day Sources: |
unhealthy, adult n = 20 Health Status: unhealthy Condition: allogeneic bone marrow transplantation Age Group: adult Population Size: 20 Sources: |
Hematuria | Disc. AE | 60 mg/kg 2 times / day multiple, intravenous Recommended Dose: 60 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 2 times / day Sources: |
unhealthy, adult n = 20 Health Status: unhealthy Condition: allogeneic bone marrow transplantation Age Group: adult Population Size: 20 Sources: |
Impaired renal function | Disc. AE | 60 mg/kg 2 times / day multiple, intravenous Recommended Dose: 60 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 2 times / day Sources: |
unhealthy, adult n = 20 Health Status: unhealthy Condition: allogeneic bone marrow transplantation Age Group: adult Population Size: 20 Sources: |
Physical impairment | Disc. AE | 60 mg/kg 2 times / day multiple, intravenous Recommended Dose: 60 mg/kg, 2 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 2 times / day Sources: |
unhealthy, adult n = 20 Health Status: unhealthy Condition: allogeneic bone marrow transplantation Age Group: adult Population Size: 20 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Prevention and treatment studies for CMV open. | 1995 Mar-Apr |
|
International Congress on Chemotherapy. | 1995 Sep |
|
Susceptibility of human cytomegalovirus to two-drug combinations in vitro. | 1996 Dec |
|
CMV news. | 1996 Jan-Feb |
|
Current and potential therapies for the treatment of herpesvirus infections. | 2001 |
|
Treatment of gastrointestinal viruses. | 2001 |
|
Current and potential therapies for the treatment of herpesvirus infections. | 2001 |
|
Flow cytometric evaluation of antiviral agents against human herpesvirus 6. | 2001 |
|
Prophylaxis against herpesvirus infections in transplant recipients. | 2001 |
|
Intravitreal pharmacokinetics and retinal concentrations of ganciclovir and foscarnet after intravitreal administration in rabbits. | 2001 Apr |
|
Risk for cytomegalovirus disease in patients receiving polymerase chain reaction-based preemptive antiviral therapy after allogeneic stem cell transplantation depends on transplantation modality. | 2001 Apr 1 |
|
Progressive outer retinal necrosis syndrome: successful treatment with a new combination of antiviral drugs. | 2001 Apr-Jun |
|
Cytomegalovirus treatment options in immunocompromised patients. | 2001 Aug |
|
Valacyclovir for the prevention of cytomegalovirus infection after allogeneic stem cell transplantation: a single institution retrospective cohort analysis. | 2001 Aug |
|
Chemoselectivity in metal cation mediated hydrolysis of a phosphonoformate diester. | 2001 Aug 1 |
|
Expression dynamics of human cytomegalovirus immune evasion genes US3, US6, and US11 in the blood of lung transplant recipients. | 2001 Aug 1 |
|
[Anti-hepatitis B virus effects of lamivudine and other five drugs in vitro]. | 2001 Aug 25 |
|
[Cytomegalovirus sensitivity to anti-retroviral agents in patients infected with the human immunodeficiency virus with chorioretinitis in Spain]. | 2001 Dec |
|
Sequence analysis of UL54 and UL97 genes and evaluation of antiviral susceptibility of human cytomegalovirus isolates obtained from kidney allograft recipients before and after treatment. | 2001 Dec |
|
Risk factors for cytomegalovirus retinitis following bone marrow transplantation from unrelated donors in patients with severe aplastic anemia or myelodysplasia. | 2001 Dec |
|
Variations in the cytomegalovirus DNA polymerase and phosphotransferase genes in relation to foscarnet and ganciclovir sensitivity. | 2001 Dec |
|
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor. | 2001 Feb |
|
Fatal primary infection due to human herpesvirus 6 variant A in a renal transplant recipient. | 2001 Jan 27 |
|
Generation of hydroxyl radicals by the antiviral compound phosphonoformic acid (foscarnet). | 2001 Jul |
|
Progressive outer retinal necrosis syndrome in a lymphoma patient with good visual outcome. | 2001 Jul |
|
Differences between the quantitative antigenemia assay and the cobas amplicor monitor quantitative PCR assay for detecting CMV viraemia in bone marrow and solid organ transplant patients. | 2001 Jul |
|
Foscarnet therapy for ganciclovir-resistant cytomegalovirus retinitis after stem cell transplantation: effective monitoring of CMV infection by quantitative analysis of CMV mRNA. | 2001 Jun |
|
Progress in understanding cytomegalovirus drug resistance. | 2001 Jun |
|
Alkylglycerol prodrugs of phosphonoformate are potent in vitro inhibitors of nucleoside-resistant human immunodeficiency virus type 1 and select for resistance mutations that suppress zidovudine resistance. | 2001 Jun |
|
[Efficacy of cidofovir in an HIV infected patient with an acyclovir and foscarnet resistant herpes simplex virus infection]. | 2001 Jun-Jul |
|
Prevalence of cytomegalovirus infection in severe refractory ulcerative and Crohn's colitis. | 2001 Mar |
|
High-dose intravitreal ganciclovir and foscarnet for cytomegalovirus retinitis. | 2001 Mar |
|
Frosted branch angiitis in a child with HIV infection. | 2001 Mar |
|
Persistent herpes simplex virus infection. | 2001 May |
|
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections. | 2001 Nov |
|
Development of acyclovir-resistant herpes simplex virus early during the treatment of herpes neonatorum. | 2001 Nov |
|
Successful treatment of foscarnet-resistant herpes simplex stomatitis with intravenous cidofovir in a child. | 2001 Nov |
|
Selection of the same mutation in the U69 protein kinase gene of human herpesvirus-6 after prolonged exposure to ganciclovir in vitro and in vivo. | 2001 Nov |
|
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance. | 2001 Nov 1 |
|
The biological effects of structural variation at the meta position of the aromatic rings and at the end of the alkenyl chain in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors. | 2001 Nov 22 |
|
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient. | 2001 Oct |
|
Cytomegalovirus infection: the point in 2001. | 2001 Oct |
|
Strategies for management of cytomegalovirus (CMV) infection after allogeneic bone marrow transplantation: the "doubling of baseline CMV pp65 antigenemia" and the "cidofovir as rescue treatment approaches. | 2001 Sep 1 |
|
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients. | 2001 Sep 1 |
|
Antiviral treatment of Epstein-Barr virus-associated lymphoproliferations. | 2002 |
|
Development of drug-resistant herpes simplex virus infection after haploidentical hematopoietic progenitor cell transplantation. | 2002 Feb 1 |
|
Effect of antivirals on human herpesvirus 6 replication in hematopoietic stem cell transplant recipients. | 2002 Feb 1 |
|
Randomized multicenter trial of foscarnet versus ganciclovir for preemptive therapy of cytomegalovirus infection after allogeneic stem cell transplantation. | 2002 Feb 15 |
|
Drugs for non-HIV viral infections. | 2002 Feb 4 |
|
[Therapeutic effect of gefin, a new antiviral drug, in experimental genital herpes ]. | 2002 Jan-Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/foscarnet.html
Usual Adult Dose for CMV Retinitis
Induction therapy: 90 mg/kg IV (90- to 120-minute infusion) every 12 hours or 60 mg/kg IV (minimum 1-hour infusion) every 8 hours over 2 to 3 weeks depending on clinical response
Maintenance therapy: 90 to 120 mg/kg IV (2-hour infusion) once a day
Usual Adult Dose for Herpes Simplex - Mucocutaneous/Immunocompromised Host
Induction therapy: 40 mg/kg IV (minimum 1-hour infusion) every 8 or 12 hours
Duration of therapy: 2 to 3 weeks or until healed
Usual Adult Dose for CMV Gastroenteritis
US CDC, NIH, and IDSA recommendations for the treatment of CMV esophagitis or colitis in HIV-infected patients: 60 mg/kg IV every 8 hours or 90 mg/kg IV every 12 hours
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18611671
Foscarnet inhibits in vitro the replication of all herpes viruses, including human cytomegalovirus (HCMV) at concentrations of 100 to 300 umol/l and has a dose-related inhibitory effect on HIV-1 virus, influenza virus and hepatitis B virus.
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
8C5OQ81LWT
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