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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15N5O5
Molecular Weight 297.2673
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NELARABINE

SMILES

COC1=NC(N)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

InChIKey=IXOXBSCIXZEQEQ-UHTZMRCNSA-N
InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C11H15N5O5
Molecular Weight 297.2673
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Arranon is a nucleoside metabolic inhibitor indicated for the treatment of patients with T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. It is a purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity. Administration of nelarabine in combination with adenosine deaminase inhibitors, such 195 as pentostatin, is not recommended. The most common (≥20%) adverse reactions were: anemia, thrombocytopenia, neutropenia, nausea, diarrhea, vomiting, constipation, fatigue, pyrexia, cough, and dyspnea

CNS Activity

Curator's Comment: Nelarabine is widely distributed throughout the body and lower levels detected in the CNS

Originator

Curator's Comment: Nelarabine was transfered from GlaxoSmithKline to Novartis http://www.pharmaceutical-journal.com/news-and-analysis/notice-board/transfer-of-products-from-glaxosmithkline-to-novartis/20068469.article

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARRANON

Approved Use

ARRANON is indicated for the treatment of patients with T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma whose disease has not responded to or has relapsed following treatment with at least two chemotherapy regimens. This use is based on the induction of complete responses. Randomized trials demonstrating increased survival or other clinical benefit have not been conducted. ARRANON is a nucleoside metabolic inhibitor indicated for the treatment of patients with T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma whose disease has not responded to or has relapsed following treatment with at least two chemotherapy regimens. This use is based on the induction of complete responses. Randomized trials demonstrating increased survival or other clinical benefit have not been conducted. (1)

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5 μg/mL
1500 mg/m² single, intravenous
dose: 1500 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NELARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.4 μg × h/mL
1500 mg/m² single, intravenous
dose: 1500 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NELARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.5 h
1500 mg/m² single, intravenous
dose: 1500 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NELARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.5 min
75 mg/kg 2 times / hour multiple, intravenous
dose: 75 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
NELARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2900 mg/m2 3 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 2900 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 2900 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Other AEs: Somnolence, Convulsions...
Other AEs:
Somnolence (severe)
Convulsions (severe)
Numbness (severe)
Paresthesia (severe)
Weakness (severe)
Paralysis (severe)
Sources:
1200 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1200 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
DLT: Weakness, Ataxia...
Dose limiting toxicities:
Weakness (2 patients)
Ataxia (2 patients)
Confusion (2 patients)
Coma (2 patients)
Sources:
1800 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1800 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1800 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
DLT: Weakness, Ataxia...
Dose limiting toxicities:
Weakness (3 patients)
Ataxia (3 patients)
Confusion (3 patients)
Coma (3 patients)
Sources:
2250 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 2250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2250 mg/m2, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Other AEs: Somnolence...
Other AEs:
Somnolence (severe, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Convulsions severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Numbness severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Paralysis severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Paresthesia severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Somnolence severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Weakness severe
1500 mg/m2 3 times / 3 weeks multiple, intravenous
Recommended
Dose: 1500 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1500 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Ataxia 2 patients
DLT
1200 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1200 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Coma 2 patients
DLT
1200 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1200 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Confusion 2 patients
DLT
1200 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1200 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Weakness 2 patients
DLT
1200 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1200 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1200 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Ataxia 3 patients
DLT
1800 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1800 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1800 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Coma 3 patients
DLT
1800 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1800 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1800 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Confusion 3 patients
DLT
1800 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1800 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1800 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Weakness 3 patients
DLT
1800 mg/m2 3 times / 3 weeks multiple, intravenous
Dose: 1800 mg/m2, 3 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 1800 mg/m2, 3 times / 3 weeks
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
Somnolence severe, 1 patient
2250 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 2250 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2250 mg/m2, 1 times / day
Sources:
unhealthy, child
Health Status: unhealthy
Age Group: child
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Nitric oxide enhancement of fludarabine cytotoxicity for B-CLL lymphocytes.
2001 Dec
Nucleoside analogues in the treatment of haematological malignancies.
2001 Jun
CD4-CD8-"Double-negative" cutaneous T-cell lymphomas share common histologic features and an aggressive clinical course.
2002 Feb
Arabinosylguanine is phosphorylated by both cytoplasmic deoxycytidine kinase and mitochondrial deoxyguanosine kinase.
2002 Jun 1
Gateways to clinical trials.
2003 Nov
Purine nucleoside antimetabolites in development for the treatment of cancer.
2004 Jun
New nucleoside analogs in the treatment of hematological disorders.
2004 May-Jun
Nelarabine: a nucleoside analog with efficacy in T-cell and other leukemias.
2005 Jun
Phase I study of 506U78 administered on a consecutive 5-day schedule in children and adults with refractory hematologic malignancies.
2005 May 20
Phase II study of nelarabine (compound 506U78) in children and young adults with refractory T-cell malignancies: a report from the Children's Oncology Group.
2005 May 20
Purine nucleoside analogues for the treatment of hematological malignancies: pharmacology and clinical applications.
2005 Sep
Novel purine nucleoside analogues for T-cell-lineage acute lymphoblastic leukaemia and lymphoma.
2006 Dec
Nelarabine (Arranon) for T-cell acute lymphoblastic leukemia.
2006 Feb 13
New drug to treat rare leukemia and lymphoma.
2006 Jan-Feb
Nelarabine use in leukemias.
2006 Jul
Gateways to clinical trials.
2006 Jun
Pharmacological and clinical studies on purine nucleoside analogs--new anticancer agents.
2006 May
Clofarabine and nelarabine: two new purine nucleoside analogs.
2006 Nov
The legacy of great science: the work of Nobel Laureate Gertrude Elion lives on.
2006 Oct
Milestones in oncology: introducing a new section.
2006 Oct
Nelarabine in the treatment of refractory T-cell malignant diseases.
2006 Sep
Approval summary: nelarabine for the treatment of T-cell lymphoblastic leukemia/lymphoma.
2006 Sep 15
Clinical management of T-cell malignancies: current perspectives, key issues, and emerging therapies.
2007 Dec
Three new drugs for acute lymphoblastic leukemia: nelarabine, clofarabine, and forodesine.
2007 Dec
Results of a phase II study of 506U78 in cutaneous T-cell lymphoma and peripheral T-cell lymphoma: CALGB 59901.
2007 Jan
Nelarabine induces complete remissions in adults with relapsed or refractory T-lineage acute lymphoblastic leukemia or lymphoblastic lymphoma: Cancer and Leukemia Group B study 19801.
2007 Jun 15
Nelarabine.
2008
Treating refractory leukemias in childhood, role of clofarabine.
2008 Apr
Beyond the guidelines in the treatment of peripheral T-cell lymphoma: new drug development.
2008 Apr
FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma.
2008 Jun
Novel purine nucleoside analogues for hematological malignancies.
2008 Jun
Phase I trial of nelarabine in indolent leukemias.
2008 Mar 1
Gateways to clinical trials.
2008 May
[Severe liver injury following nelarabine chemotherapy for T-cell lymphoblastic lymphoma].
2009 Jan
Nelarabine induced complete remission in an adult with refractory T-lineage acute lymphoblastic leukemia: A case report and review of the literature.
2009 Jul
Current status of older and new purine nucleoside analogues in the treatment of lymphoproliferative diseases.
2009 Mar 23
New trends in nucleoside biotechnology.
2010 Jul
Use of clofarabine for acute childhood leukemia.
2010 Jun 24
Application of new drugs in chronic lymphocytic leukemia.
2010 May 10
Influence of wild-type MLL on glucocorticoid sensitivity and response to DNA-damage in pediatric acute lymphoblastic leukemia.
2010 Oct 28
Rare tumors research in emerging countries.
2010 Sep 30
Nelarabine neurotoxicity with concurrent intrathecal chemotherapy: Case report and review of literature.
2015 Aug
Patents

Sample Use Guides

Adult: 1,500 mg/m² over 2 hours on Days 1, 3, and 5 repeated every 21 days Pediatric: 650 mg/m² over 1 hour daily for 5 consecutive days repeated every 21 days
Route of Administration: Intravenous
In Vitro Use Guide
The in vitro efficacy of nelarabine was assessed in a panel of acute lymphoblastic leukaemia (ALL) cell lines. IC50 values were 0.067-2.15 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:47 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:47 GMT 2025
Record UNII
60158CV180
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARRANON
Preferred Name English
NELARABINE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
506U78
Code English
NELARABINE [ORANGE BOOK]
Common Name English
NELARABINE [EMA EPAR]
Common Name English
506U
Code English
ATTRIANCE
Brand Name English
nelarabine [INN]
Common Name English
NELZARABINE
Common Name English
NELARABINE [MART.]
Common Name English
MAY
Code English
9H-PURIN-2-AMINE, 9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-
Systematic Name English
NELARABINE [MI]
Common Name English
NELARABINE [VANDF]
Common Name English
9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-9H-PURIN-2-AMINE
Common Name English
NSC-755985
Code English
Nelarabine [WHO-DD]
Common Name English
NSC-686673
Code English
NSC-759876
Code English
NELARABINE [JAN]
Common Name English
NELARABINE [USAN]
Common Name English
GW-506U78
Code English
2-AMINO-9-.BETA.-D-ARABINOFURANOSYL-6-METHOXY-9H-PURINE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 125999
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
WHO-ATC L01BB07
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
EU-Orphan Drug EU/3/05/293
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
NDF-RT N0000175595
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
EMA ASSESSMENT REPORTS ATTRIANCE (AUTHORIZED: PRECURSOR T-CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA)
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
LIVERTOX NBK548515
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
WHO-VATC QL01BB07
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
NDF-RT N0000000233
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
FDA ORPHAN DRUG 184404
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
Code System Code Type Description
MESH
C104457
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
SMS_ID
100000085469
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
WIKIPEDIA
NELARABINE
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
PUBCHEM
3011155
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
DRUG BANK
DB01280
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
DAILYMED
60158CV180
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
MERCK INDEX
m7797
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY Merck Index
INN
7704
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
FDA UNII
60158CV180
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
CHEBI
63612
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
EVMPD
SUB09188MIG
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
RXCUI
274771
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID6046842
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
IUPHAR
7090
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
NSC
686673
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
CAS
121032-29-9
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
NSC
755985
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201112
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
DRUG CENTRAL
1892
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
NCI_THESAURUS
C1704
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
NSC
759876
Created by admin on Mon Mar 31 18:13:47 GMT 2025 , Edited by admin on Mon Mar 31 18:13:47 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
Plasma protein binding is independent on nelarabine concentrations.
BINDING
EXCRETED UNCHANGED
URINE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
MINOR
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PRODRUG
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE ADMINISTRATION