Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H15N5O5 |
Molecular Weight | 297.2677 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1c2c([nH]c(=N)n1)n(cn2)[C@@]3([H])[C@]([H])([C@@]([H])([C@@]([H])(CO)O3)O)O
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
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18318562
Curator's Comment:: Nelarabine is widely distributed throughout the body and lower levels detected in the CNS
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18318562 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ARRANON Approved UseARRANON 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 Date1.1304576E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16953392 |
35 mg/kg single, intravenous dose: 35 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NELARABINE blood | Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2820 μM × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16953392 |
35 mg/kg single, intravenous dose: 35 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NELARABINE blood | Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16953392 |
35 mg/kg single, intravenous dose: 35 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NELARABINE blood | Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.5 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10694549 |
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
Dose | Population | Adverse 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 n = 2 Health Status: unhealthy Age Group: adult Population Size: 2 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) Sources: Convulsions (severe) Numbness (severe) Paresthesia (severe) Weakness (severe) Paralysis (severe) |
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 n = 31 Health Status: unhealthy Age Group: adult Population Size: 31 Sources: |
DLT: Weakness, Ataxia... Dose limiting toxicities: Weakness (2 patients) Sources: Ataxia (2 patients) Confusion (2 patients) Coma (2 patients) |
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 n = 4 Health Status: unhealthy Age Group: adult Population Size: 4 Sources: |
DLT: Weakness, Ataxia... Dose limiting toxicities: Weakness (3 patients) Sources: Ataxia (3 patients) Confusion (3 patients) Coma (3 patients) |
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 n = 1 Health Status: unhealthy Age Group: child Population Size: 1 Sources: |
Other AEs: Somnolence... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 n = 31 Health Status: unhealthy Age Group: adult Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: adult Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: adult Population Size: 31 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 n = 31 Health Status: unhealthy Age Group: adult Population Size: 31 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 n = 4 Health Status: unhealthy Age Group: adult Population Size: 4 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 n = 4 Health Status: unhealthy Age Group: adult Population Size: 4 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 n = 4 Health Status: unhealthy Age Group: adult Population Size: 4 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 n = 4 Health Status: unhealthy Age Group: adult Population Size: 4 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 n = 1 Health Status: unhealthy Age Group: child Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021877_s000_Arranon_BioPharmr.pdf Page: 46.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021877_s000_Arranon_BioPharmr.pdf Page: 47.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
6-Methoxypurine arabinoside as a selective and potent inhibitor of varicella-zoster virus. | 1991 May |
|
Nelarabine: a nucleoside analog with efficacy in T-cell and other leukemias. | 2005 Jun |
|
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 analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. | 2006 |
|
Novel purine nucleoside analogues for T-cell-lineage acute lymphoblastic leukaemia and lymphoma. | 2006 Dec |
|
Nelarabine. | 2006 Jan |
|
New drug to treat rare leukemia and lymphoma. | 2006 Jan-Feb |
|
Nelarabine use in leukemias. | 2006 Jul |
|
Multifocal necrotizing leukoencephalopathy: An unusual complication of acute leukemia. | 2006 Jul |
|
Gateways to clinical trials. | 2006 Jun |
|
New drugs: abatacept, sorafenib, and nelarabine. | 2006 Mar-Apr |
|
Pharmacological and clinical studies on purine nucleoside analogs--new anticancer agents. | 2006 May |
|
Nelarabine: a new purine analog in the treatment of hematologic malignancies. | 2006 Sep |
|
Approval summary: nelarabine for the treatment of T-cell lymphoblastic leukemia/lymphoma. | 2006 Sep 15 |
|
Treatment of acute lymphoblastic leukaemia : a new era. | 2007 |
|
In vitro cytotoxicity of nelarabine, clofarabine and flavopiridol in paediatric acute lymphoblastic leukaemia. | 2007 Apr |
|
Role of nelarabine in the treatment of T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. | 2007 Dec |
|
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 |
|
The long and winding road of the clinical development of Nelarabine. | 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 |
|
Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy. | 2008 |
|
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 |
|
Gateways to clinical trials. | 2008 Jan-Feb |
|
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 |
|
T-cell acute lymphoblastic leukemia in adults: clinical features, immunophenotype, cytogenetics, and outcome from the large randomized prospective trial (UKALL XII/ECOG 2993). | 2009 Dec 10 |
|
Development of fludarabine formulations in the treatment of chronic lymphocytic leukemia. | 2009 Dec 29 |
|
Nelarabine: new drug. T-lymphoblastic leukaemia/lymphoma: more evaluation needed. | 2009 Feb |
|
Profile of nelarabine: use in the treatment of T-cell acute lymphoblastic leukemia. | 2009 Feb 18 |
|
[Severe liver injury following nelarabine chemotherapy for T-cell lymphoblastic lymphoma]. | 2009 Jan |
|
Novel therapies for relapsed acute lymphoblastic leukemia. | 2009 Jul |
|
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 |
|
Hydronephrosis Resulting from Bilateral Ureteral Stenosis: A Late Complication of Polyoma BK Virus Cystitis? | 2010 |
|
Complete paraplegia after nelarabine treatment in a T-cell acute lymphoblastic leukemia adult patient. | 2010 Aug |
|
Salvage therapy with nelarabine, etoposide, and cyclophosphamide in relapsed/refractory paediatric T-cell lymphoblastic leukaemia and lymphoma. | 2010 Aug |
|
A new high-performance liquid chromatography method determines low production of 9-beta-D-arabinofuranosylguanine triphosphate, an active metabolite of nelarabine, in adult T-cell leukemia cells. | 2010 Feb |
|
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 |
|
Towards the development of a rapid, portable, surface enhanced Raman spectroscopy based cleaning verification system for the drug nelarabine. | 2010 Sep |
|
Nelarabine neurotoxicity with concurrent intrathecal chemotherapy: Case report and review of literature. | 2015 Aug |
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/17391490
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.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
L01BB07
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EU-Orphan Drug |
EU/3/05/293
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NDF-RT |
N0000175595
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NCI_THESAURUS |
C1556
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EMA ASSESSMENT REPORTS |
ATTRIANCE (AUTHORIZED: PRECURSOR T-CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA)
Created by
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FDA ORPHAN DRUG |
125999
Created by
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LIVERTOX |
674
Created by
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WHO-VATC |
QL01BB07
Created by
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NDF-RT |
N0000000233
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FDA ORPHAN DRUG |
184404
Created by
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C104457
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NELARABINE
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3011155
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DB01280
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M7797
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PRIMARY | Merck Index | ||
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7704
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PRIMARY | |||
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60158CV180
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SUB09188MIG
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274771
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121032-29-9
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7090
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121032-29-9
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CHEMBL1201112
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1892
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C1704
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)