Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H12ClN5O3 |
Molecular Weight | 285.687 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(Cl)=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3
InChI
InChIKey=PTOAARAWEBMLNO-KVQBGUIXSA-N
InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
Molecular Formula | C10H12ClN5O3 |
Molecular Weight | 285.687 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created using several sources including:
https://www.scripps.edu/newsandviews/e_20090601/MS.html; http://comtecmed.com/CONY/2008/Uploads/assets/speakers%20abstracts/stelmasiak.pdf
Curator's Comment: Description was created using several sources including:
https://www.scripps.edu/newsandviews/e_20090601/MS.html; http://comtecmed.com/CONY/2008/Uploads/assets/speakers%20abstracts/stelmasiak.pdf
Cladribine is used for the treatment of hairy cell leukemia and multiple sclerosis (MS). As a purine analog, it is a synthetic anti-cancer agent that also suppresses the immune system. Chemically, it mimics the nucleoside adenosine and thus inhibits the enzyme adenosine deaminase, which interferes with the cell's ability to process DNA. It can be distinguished from other chemotherapeutic agents affecting purine metabolism in that it is cytotoxic to both actively dividing and quiescent lymphocytes and monocytes, inhibiting both DNA synthesis and repair. Cladribine injection is a potent antineoplastic agent with potentially significant toxic side effects. In MS, the novel mechanism of action of cladribine is expected to reduce inflammation, autoimmune effects and autoreactive cell damage, thereby improving the integrity of the blood–brain barrier. Thus, the effects of cladribine may target some of the key events that are central to the pathophysiology of MS.
CNS Activity
Sources: http://multiple-sclerosis-research.blogspot.com/2016/01/the-special-one-cladribine-acting-in-cns.html
Curator's Comment: As cladribine can cross the blood brain barrier and can kill dividing and non-dividing T and B cells and can apparently kill plasma cells. It could target plasma cells in the brain, unlike any other MS drug.
Originator
Curator's Comment: The drug, cladribine, which is currently marketed under the name LEUSTATIN® by Ortho Biotech, Inc. (an affiliate of Johnson & Johnson) for the treatment of hairy cell leukemia, was initially identified and developed using a single treatment of the new compound to target abnormal white blood cells in patients suffering from hairy cell leukemia by Dennis Carson in collaboration with Ernest Beutler a Scripps Research scientists who licensed caldribine as an orphan drug in 1994. Merck Serono's CLARITY study, involving 1326 Multiple Sclerosis patients, began in 2004 and was completed in December 2008.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P06746 Gene ID: 5423.0 Gene Symbol: POLB Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=20634380 |
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Target ID: CHEMBL2311221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=20634380 |
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Target ID: P23526 Gene ID: 191.0 Gene Symbol: AHCY Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=20634380 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLADRIBINE Approved Usethe treatment of active Hairy Cell Leukemia as defined by clinically significant anemia, neutropenia, thrombocytopenia or disease-related symptoms. Launch Date7.9185602E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.57 ng/mL |
3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
29.05 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
69.4 ng × h/mL |
3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
99.17 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.4 h |
3 mg single, intravenous dose: 3 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
19.7 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLADRIBINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5.25 mg/kg multiple, oral (total) Highest studied dose Dose: 5.25 mg/kg Route: oral Route: multiple Dose: 5.25 mg/kg Sources: Page: p.262 |
unhealthy, ADULT n = 204 Health Status: unhealthy Condition: multiple sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 204 Sources: Page: p.262 |
Disc. AE: Lymphopenia... AEs leading to discontinuation/dose reduction: Lymphopenia (grade 3-4) Sources: Page: p.262 |
8 mg/m2 1 times / day multiple, intravenous MTD Dose: 8 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 8 mg/m2, 1 times / day Sources: Page: p.170 |
unhealthy, ADULT n = 4 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: Page: p.170 |
DLT: Neutropenia, Leukopenia... Dose limiting toxicities: Neutropenia (grade 4, 50%) Sources: Page: p.170Leukopenia (grade 4, 50%) |
0.07 mg/kg 1 times / day multiple, subcutaneous Studied dose Dose: 0.07 mg/kg, 1 times / day Route: subcutaneous Route: multiple Dose: 0.07 mg/kg, 1 times / day Sources: Page: p.1152 |
unhealthy, ADULT n = 52 Health Status: unhealthy Condition: multiple sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 52 Sources: Page: p.1152 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Lymphopenia | grade 3-4 Disc. AE |
5.25 mg/kg multiple, oral (total) Highest studied dose Dose: 5.25 mg/kg Route: oral Route: multiple Dose: 5.25 mg/kg Sources: Page: p.262 |
unhealthy, ADULT n = 204 Health Status: unhealthy Condition: multiple sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 204 Sources: Page: p.262 |
Leukopenia | grade 4, 50% DLT |
8 mg/m2 1 times / day multiple, intravenous MTD Dose: 8 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 8 mg/m2, 1 times / day Sources: Page: p.170 |
unhealthy, ADULT n = 4 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: Page: p.170 |
Neutropenia | grade 4, 50% DLT |
8 mg/m2 1 times / day multiple, intravenous MTD Dose: 8 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 8 mg/m2, 1 times / day Sources: Page: p.170 |
unhealthy, ADULT n = 4 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 4 Sources: Page: p.170 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29987837/ |
no | |||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29987837/ |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29987837/ |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Severe skin rash in two consecutive patients treated with 2-chlorodeoxyadenosine for hairy cell leukaemia at a single institution. | 2000 Apr |
|
Guillain-Barre syndrome following 2-chlorodeoxyadenosine treatment for Hairy Cell Leukemia. | 2000 Nov |
|
[Nucleoside analogues--new drugs for the treatment of lymphatic cancers]. | 2001 |
|
[Lupus nephritis: treatments for today and tomorrow]. | 2001 |
|
Immunomodulatory drugs for multiple sclerosis: a systematic review of clinical and cost effectiveness. | 2001 Apr |
|
Langerhans cell histiocytosis: central nervous system involvement treated successfully with 2-chlorodeoxyadenosine. | 2001 Apr-May |
|
A phase II study of sequential combination chemotherapy with cyclophosphamide, prednisone, and 2-chlorodeoxyadenosine in previously untreated patients with chronic lymphocytic leukemia. | 2001 Aug |
|
Cladribine. Ortho Biotech Inc. | 2001 Dec |
|
Hematological effects of intermittent 2-hour infusions of cladribine in multiple sclerosis patients: a comparison of 2 dosage patterns. | 2001 Dec |
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Second primary tumors and immune phenomena after fludarabine or 2-chloro-2'-deoxyadenosine treatment. | 2001 Feb |
|
Melphalan and purine analog-containing preparative regimens: reduced-intensity conditioning for patients with hematologic malignancies undergoing allogeneic progenitor cell transplantation. | 2001 Feb 1 |
|
Hairy cell leukemia. | 2001 Jun |
|
Nucleoside analogues: mechanisms of drug resistance and reversal strategies. | 2001 Jun |
|
Experience with 2-chlorodeoxyadenosine in previously untreated children with newly diagnosed acute myeloid leukemia and myelodysplastic diseases. | 2001 Jun 1 |
|
Cladribine in combination with mitoxantrone and cyclophosphamide(CMC) in the treatment of heavily pre-treated patients with advanced indolent lymphoid malignancies. | 2001 Mar |
|
Effective treatment with rituximab in a patient with refractory prolymphocytoid transformed B-chronic lymphocytic leukemia and Evans syndrome. | 2001 Mar |
|
Immunosuppressive and cytotoxic drugs in the treatment of rheumatic skin disorders. | 2001 Mar |
|
Immunologic therapy for secondary and primary progressive multiple sclerosis. | 2001 May |
|
Plasmablastic lymphoma in a patient with chronic lymphocytic leukemia heavily pretreated with cladribine (2-CdA): an unusual variant of Richter's syndrome. | 2001 Nov-Dec |
|
Efficacy of anti-CD20 monoclonal antibodies (Mabthera) in patients with progressed hairy cell leukemia. | 2001 Oct |
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Cladribine combined with cyclophosphamide and mitoxantrone as front-line therapy in chronic lymphocytic leukemia. | 2001 Oct |
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In vitro release of cytotoxic nucleoside analogs from lactide-caprolactone and lactide-glycolide copolymers. | 2002 |
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5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents. | 2002 |
|
Therapeutic approaches in multiple sclerosis: lessons from failed and interrupted treatment trials. | 2002 |
|
Immunosuppression with limited toxicity: the characteristics of nucleoside analogs and anti-lymphocyte antibodies used in non-myeloablative hematopoietic cell transplantation. | 2002 |
|
Gateways to Clinical Trials. | 2002 Apr |
|
Simultaneous diagnosis of hairy cell leukemia and chronic lymphocytic leukemia/small lymphocytic lymphoma: a frequent association? | 2002 Aug |
|
Use of 2-chlorodeoxyadenosine to treat infantile myofibromatosis. | 2002 Jan |
|
Bax expression correlates with cellular drug sensitivity to doxorubicin, cyclophosphamide and chlorambucil but not fludarabine, cladribine or corticosteroids in B cell chronic lymphocytic leukemia. | 2002 Jun |
|
Alkylating agents and nucleoside analogues in the treatment of B cell chronic lymphocytic leukemia. | 2002 Jun |
|
Oral cladribine for B-cell chronic lymphocytic leukaemia: report of a phase II trial with a 3-d, 3-weekly schedule in untreated and pretreated patients, and a long-term follow-up of 126 previously untreated patients. | 2002 Mar |
|
[Therapeutic effectiveness of cladribine and cellular immunodeficiency--related effects in hairy-cell leukemia?]. | 2002 May |
|
Aggressive growth of epithelial carcinomas following treatment with nucleoside analogues. | 2002 May |
|
Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1. | 2002 Sep |
Sample Use Guides
0.09 mg/kg/day
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24972933
Curator's Comment: The lethal dose of cytarabine for CTRL cells (Mantle cell lymphoma cell line ) ranged from 0.05 to 0.4 μM determined in In vitro cytotoxicity assay that was used to analyze cells relative responsiveness to araC (cladribine).
0.05 - 0.4 uM
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 15:57:02 UTC 2022
by
admin
on
Fri Dec 16 15:57:02 UTC 2022
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Record UNII |
47M74X9YT5
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2157
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FDA ORPHAN DRUG |
54190
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FDA ORPHAN DRUG |
51690
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WHO-VATC |
QL01BB04
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EU-Orphan Drug |
EU/3/01/055
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EMA ASSESSMENT REPORTS |
LITAK (AUTHORIZED: LEUKEMIA, HAIRY CELL)
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FDA ORPHAN DRUG |
467214
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LIVERTOX |
NBK548555
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FDA ORPHAN DRUG |
68092
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NCI_THESAURUS |
C1556
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FDA ORPHAN DRUG |
77793
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WHO-ATC |
L04AA40
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NCI_THESAURUS |
C798
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FDA ORPHAN DRUG |
47990
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NDF-RT |
N0000175712
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WHO-ATC |
L01BB04
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667
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Cladribine
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47M74X9YT5
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CHEMBL1619
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567361
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CLADRIBINE
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47M74X9YT5
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D017338
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44157
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DB00242
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4291-63-8
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DTXSID8022828
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DD-79
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SUB06635MIG
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20279
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4799
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1134200
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105014
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M3606
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6997
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C1336
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7564
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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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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