Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H28N4O4.3H2O |
Molecular Weight | 382.4531 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[H][C@@]1([C@@H](NC(C)=O)C(CC)CC)[C@H](O)[C@H](C[C@H]1NC(N)=N)C(O)=O
InChI
InChIKey=RFUCJKFZFXNIGB-ZBBHRWOZSA-N
InChI=1S/C15H28N4O4.3H2O/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23;;;/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19);3*1H2/t9-,10+,11+,12-,13+;;;/m0.../s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H28N4O4 |
Molecular Weight | 328.4072 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fdedaec-9e53-4a37-a4e4-a301c8a251b8; http://www.rxlist.com/script/main/art.asp?articlekey=185939
Curator's Comment: description was created based on several sources, including
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7fdedaec-9e53-4a37-a4e4-a301c8a251b8; http://www.rxlist.com/script/main/art.asp?articlekey=185939
Peramivir is a transition-state analogue and a potent, specific influenza viral neuraminidase inhibitor. Rapivab (peramivir injection) is indicated for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than 2 days. Efficacy of Rapivab is based on clinical trials in which the predominant influenza virus type was influenza A and a limited number of subjects infected with influenza B virus were enrolled. Since influenza viruses change over time emergence of resistance substitutions could decrease drug effectiveness. Other factors such as changes in viral virulence might also diminish clinical benefit of antiviral drug. Efficacy could not be established in patients with serious influenza requiring hospitalization.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: UNIPROT: O91745 (Neuraminidase) Sources: http://www.ncbi.nlm.nih.gov/pubmed/24080660 |
0.08 nM [IC50] | ||
Target ID: WP3430 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=14715540 |
0.22 nM [EC50] | ||
Target ID: WP3214 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23759505 |
0.045 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | RAPIVAB Approved UseRAPIVAB is indicated for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than 2 days. Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
46800 ng/mL |
600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERAMIVIR ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
102700 ng × h/mL |
600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERAMIVIR ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20 h |
600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERAMIVIR ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% |
600 mg single, intravenous dose: 600 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PERAMIVIR ANHYDROUS serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Other AEs: Leukopenia, Neutropenia... Other AEs: Leukopenia (42.9%) Sources: Page: 500Neutropenia (14.3%) Hyperglycemia (42.9%) Hypertension (28.6%) AST increased (14.3%) ALT increased (14.3%) Diarrhea (14.3%) |
400 mg 2 times / day multiple, intravenous Highest studied dose Dose: 400 mg, 2 times / day Route: intravenous Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, adult |
|
400 mg 2 times / day multiple, intravenous Highest studied dose Dose: 400 mg, 2 times / day Route: intravenous Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, adult |
|
600 mg 1 times / day multiple, intramuscular Highest studied dose Dose: 600 mg, 1 times / day Route: intramuscular Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 60 |
healthy, adult Health Status: healthy Age Group: adult Sex: unknown Sources: Page: 60 |
|
800 mg 1 times / day multiple, intravenous Highest studied dose Dose: 800 mg, 1 times / day Route: intravenous Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, adult |
|
800 mg 1 times / day multiple, intravenous Highest studied dose Dose: 800 mg, 1 times / day Route: intravenous Route: multiple Dose: 800 mg, 1 times / day Sources: |
healthy, adult |
|
300 mg 1 times / day multiple, intravenous Minumum effective dose Dose: 300 mg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 363 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 363 Sources: Page: 98 |
Disc. AE: Lymphadenopathy, Gingival pain... AEs leading to discontinuation/dose reduction: Lymphadenopathy (<1%) Sources: Page: 98Gingival pain (<1%) Salivary gland pain (<1%) Rash (<1%) |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 654 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 654 Sources: Page: 4 |
Other AEs: Alanine aminotransferase, Creatine phosphokinase... Other AEs: Alanine aminotransferase (grade 2-4, 3%) Sources: Page: 4Creatine phosphokinase (grade 2-4, 4%) Neutrophils (grade 2-4, 8%) |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 660 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 660 Sources: Page: 4 |
Other AEs: Serum glucose... Other AEs: Serum glucose (grade 2-4, 5%) Sources: Page: 4 |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
Disc. AE: Abdominal pain upper, Arthralgia... AEs leading to discontinuation/dose reduction: Abdominal pain upper (<1%) Sources: Page: 98Arthralgia (<1%) Drug eruption (<1%) Eczema (<1%) Rash (<1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
ALT increased | 14.3% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
AST increased | 14.3% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Diarrhea | 14.3% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Neutropenia | 14.3% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Hypertension | 28.6% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Hyperglycemia | 42.9% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Leukopenia | 42.9% | 11.4 mg/kg 1 times / day steady, intravenous (median) Dose: 11.4 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 11.4 mg/kg, 1 times / day Sources: Page: 500 |
unhealthy, 2.4-9.8 years n = 7 Health Status: unhealthy Condition: H1N1 Age Group: 2.4-9.8 years Sex: M+F Population Size: 7 Sources: Page: 500 |
Gingival pain | <1% Disc. AE |
300 mg 1 times / day multiple, intravenous Minumum effective dose Dose: 300 mg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 363 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 363 Sources: Page: 98 |
Lymphadenopathy | <1% Disc. AE |
300 mg 1 times / day multiple, intravenous Minumum effective dose Dose: 300 mg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 363 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 363 Sources: Page: 98 |
Rash | <1% Disc. AE |
300 mg 1 times / day multiple, intravenous Minumum effective dose Dose: 300 mg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 363 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 363 Sources: Page: 98 |
Salivary gland pain | <1% Disc. AE |
300 mg 1 times / day multiple, intravenous Minumum effective dose Dose: 300 mg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 363 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 363 Sources: Page: 98 |
Alanine aminotransferase | grade 2-4, 3% | 600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 654 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 654 Sources: Page: 4 |
Creatine phosphokinase | grade 2-4, 4% | 600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 654 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 654 Sources: Page: 4 |
Neutrophils | grade 2-4, 8% | 600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 654 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 654 Sources: Page: 4 |
Serum glucose | grade 2-4, 5% | 600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 4 |
unhealthy, adult n = 660 Health Status: unhealthy Condition: H1N1 Age Group: adult Sex: unknown Population Size: 660 Sources: Page: 4 |
Abdominal pain upper | <1% Disc. AE |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
Arthralgia | <1% Disc. AE |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
Drug eruption | <1% Disc. AE |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
Eczema | <1% Disc. AE |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
Rash | <1% Disc. AE |
600 mg 1 times / day multiple, intravenous Recommended Dose: 600 mg, 1 times / day Route: intravenous Route: multiple Dose: 600 mg, 1 times / day Sources: Page: 98 |
unhealthy, adult n = 365 Health Status: unhealthy Condition: acute uncomplicated influenza Age Group: adult Sex: unknown Population Size: 365 Sources: Page: 98 |
PubMed
Title | Date | PubMed |
---|---|---|
Primary immune system effects of the orally administered cyclopentane neuraminidase inhibitor RWJ-270201 in influenza virus-infected mice. | 2001 Jun |
|
Comparison of efficacies of RWJ-270201, zanamivir, and oseltamivir against H5N1, H9N2, and other avian influenza viruses. | 2001 Oct |
|
Peramivir (BCX-1812, RWJ-270201): potential new therapy for influenza. | 2002 Jun |
Patents
Sample Use Guides
The recommended dose of RAPIVAB in adult patients 18 years of age or older with acute uncomplicated influenza is a single 600 mg dose, administered via intravenous infusion for 15 to 30 minutes. The dose should be reduced for patients with baseline creatinine clearance below 50 mL/min to 200 mg dose (at 30-49 mL/min creatinine clearance), and 100 mg dose (at 10-29 mL/min creatinine clearance).
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=14715540
The concentrations of peramivir required for inhibition of influenza virus in cell culture varied with the virus strain tested. The effect of antiviral compounds on the replication of influenza viruses in MDCK cells was determined by flow cytometric analysis of virus-infected cells. The mean 50% effective concentrations (EC50 values) of peramivir were in the range of 0.045-0.071 nM), 0.065-0.07 nM and 0.215-33.58 nM for influenza A/H1N1 virus, A/H3N2 virus, and B virus strains, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:30:36 GMT 2023
by
admin
on
Fri Dec 15 15:30:36 GMT 2023
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Record UNII |
QW7Y7ZR15U
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Record Status |
Validated (UNII)
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WHO-ATC |
J05AH03
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175524
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RAPIACTA
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PRIMARY | APPROVED JANUARY 2010 | ||
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C81611
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m8534
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TARGET ORGANISM->INHIBITOR |
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ANHYDROUS->SOLVATE | |||
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TARGET ORGANISM->INHIBITOR |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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