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Details

Stereochemistry RACEMIC
Molecular Formula C15H28N4O4
Molecular Weight 328.4072
Optical Activity ( + / - )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAMIVIR, (±)-

SMILES

[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=XRQDFNLINLXZLB-CKIKVBCHSA-N
InChI=1S/C15H28N4O4/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)/t9-,10+,11+,12-,13+/m0/s1

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: UNIPROT: O91745 (Neuraminidase)
0.08 nM [IC50]
0.22 nM [EC50]
0.045 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RAPIVAB

Approved Use

RAPIVAB 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 Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Neutropenia (14.3%)
Hyperglycemia (42.9%)
Hypertension (28.6%)
AST increased (14.3%)
ALT increased (14.3%)
Diarrhea (14.3%)
Sources: Page: 500
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
Health Status: healthy
Age Group: adult
Sex: M
Sources:
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
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
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
Health Status: healthy
Age Group: adult
Sex: M
Sources:
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
Health Status: healthy
Age Group: adult
Sex: M+F
Sources:
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%)
Gingival pain (<1%)
Salivary gland pain (<1%)
Rash (<1%)
Sources: Page: 98
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%)
Creatine phosphokinase (grade 2-4, 4%)
Neutrophils (grade 2-4, 8%)
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: 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%)
Arthralgia (<1%)
Drug eruption (<1%)
Eczema (<1%)
Rash (<1%)
Sources: Page: 98
AEs

AEs

AESignificanceDosePopulation
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
BCX-1812 (RWJ-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design.
2000 Sep 21
Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir.
2001 Apr
Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201.
2001 Dec
Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity.
2001 Dec 6
Primary immune system effects of the orally administered cyclopentane neuraminidase inhibitor RWJ-270201 in influenza virus-infected mice.
2001 Jun
In vivo influenza virus-inhibitory effects of the cyclopentane neuraminidase inhibitor RJW-270201.
2001 Mar
Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities.
2001 Mar
Comparison of efficacies of RWJ-270201, zanamivir, and oseltamivir against H5N1, H9N2, and other avian influenza viruses.
2001 Oct
In vitro characterization of A-315675, a highly potent inhibitor of A and B strain influenza virus neuraminidases and influenza virus replication.
2002 Apr
Peramivir (BCX-1812, RWJ-270201): potential new therapy for influenza.
2002 Jun
Combination treatment of influenza A virus infections in cell culture and in mice with the cyclopentane neuraminidase inhibitor RWJ-270201 and ribavirin.
2002 May
Structural studies of the resistance of influenza virus neuramindase to inhibitors.
2002 May 23
Comparison of colorimetric, fluorometric, and visual methods for determining anti-influenza (H1N1 and H3N2) virus activities and toxicities of compounds.
2002 Oct
Inhibition of influenza virus infections in immunosuppressed mice with orally administered peramivir (BCX-1812).
2003 Sep
A QSAR study on influenza neuraminidase inhibitors.
2006 Feb 15
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
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 Sat Dec 16 10:00:29 GMT 2023
Edited
by admin
on Sat Dec 16 10:00:29 GMT 2023
Record UNII
IDL9Q29886
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERAMIVIR, (±)-
Common Name English
CYCLOPENTANECARBOXYLIC ACID, 3-((1S)-1-(ACETYLAMINO)-2-ETHYLBUTYL)-4-((AMINOIMINOMETHYL)AMINO)-2-HYDROXY-, (1R,2R,3S,4S)-REL-
Systematic Name English
PERAMIVIR (±)-FORM [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m8534
Created by admin on Sat Dec 16 10:00:30 GMT 2023 , Edited by admin on Sat Dec 16 10:00:30 GMT 2023
PRIMARY Merck Index
PUBCHEM
154234
Created by admin on Sat Dec 16 10:00:30 GMT 2023 , Edited by admin on Sat Dec 16 10:00:30 GMT 2023
PRIMARY
CAS
229614-56-6
Created by admin on Sat Dec 16 10:00:30 GMT 2023 , Edited by admin on Sat Dec 16 10:00:30 GMT 2023
PRIMARY
FDA UNII
IDL9Q29886
Created by admin on Sat Dec 16 10:00:30 GMT 2023 , Edited by admin on Sat Dec 16 10:00:30 GMT 2023
PRIMARY