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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H28N4O4
Molecular Weight 328.4078
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAMIVIR ANHYDROUS

SMILES

CCC(CC)[C@@]([H])([C@@]1([H])[C@@]([H])(C[C@@]([H])([C@@]1([H])O)C(=O)O)NC(=N)N)N=C(C)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

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

1.4189472E12
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 activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates of influenza virus and neuraminidase inhibitor-resistant variants.
2001 Dec
Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201.
2001 Dec
Primary immune system effects of the orally administered cyclopentane neuraminidase inhibitor RWJ-270201 in influenza virus-infected mice.
2001 Jun
Inhibition of influenza virus infections in immunosuppressed mice with orally administered peramivir (BCX-1812).
2003 Sep
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.
Name Type Language
PERAMIVIR ANHYDROUS
Common Name English
RWJ-270201
Code English
(1S,2S,3R,4R)-3-((1S)-1-ACETYLAMINO-2-ETHYLBUTYL)-4-((AMINOIMINOMETHYL)AMINO)-2-HYDROXYCYCLOPENTANECARBOXYLIC ACID
Systematic Name English
PERAMIVIR [INN]
Common Name English
PERAMIVIR [MI]
Common Name English
Code System Code Type Description
EVMPD
SUB32136
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
PUBCHEM
154234
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
CAS
330600-85-6
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
MERCK INDEX
M8534
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY Merck Index
INN
8184
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
WIKIPEDIA
PERAMIVIR
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
FDA UNII
9ZS94HQO3B
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
NCI_THESAURUS
C175841
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY
RXCUI
1598096
Created by admin on Fri Jun 25 23:58:14 UTC 2021 , Edited by admin on Fri Jun 25 23:58:14 UTC 2021
PRIMARY RxNorm