Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H11ClFN5O3 |
Molecular Weight | 303.677 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(Cl)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3F
InChI
InChIKey=WDDPHFBMKLOVOX-AYQXTPAHSA-N
InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1
Molecular Formula | C10H11ClFN5O3 |
Molecular Weight | 303.677 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22840768Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021673s024lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22840768
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021673s024lbl.pdf
Clofarabine is a anti-cancer drug which was approved by FDA for the treatment of pediatric patients with relapsed or refractory acute lymphoblastic leukemia. After crossing the cell membrane the drug is rapidly metabolized by deoxycytidine kinase to diphosphate and triphosphate metabolites and these metabolites reversibly inhibit hRNR by binding to alpha subunit. Also the triphosphate is incorporated to DNA where it acts as a chain terminator.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16115942
Curator's Comment: Only a small amount of the drug was shown to cross the blood brain barrier in non-human primates.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
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Target ID: CHEMBL2095215 |
17.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLOLAR Approved UseClolar® (clofarabine) Injection is indicated for the treatment of pediatric patients 1 to 21 years old with relapsed or refractory acute lymphoblastic leukemia after at least two prior regimens. Launch Date1.10419195E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
308 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28509593 |
40 mg/m² 1 times / day multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: CYTARABINE |
CLOFARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1793 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28509593 |
40 mg/m² 1 times / day multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: CYTARABINE |
CLOFARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
28 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29773602 |
40 mg/m² 1 times / day multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CLOFARABINE blood | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28509593 |
40 mg/m² 1 times / day multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: CYTARABINE |
CLOFARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29773602 |
40 mg/m² 1 times / day multiple, intravenous dose: 40 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CLOFARABINE blood | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
55 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 55 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 55 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 4 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 4 Sources: |
Other AEs: Nausea, Diarrhea... Other AEs: Nausea (grade 1-2, 2 patients) Sources: Diarrhea (grade 1, 3 patients) Hepatotoxicity (grade 3, 2 patients) |
40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Other AEs: Nausea, Fatigue... Other AEs: Nausea (grade 1-2, 3 patients) Sources: Fatigue (grade 3, 1 patient) Diarrhea (grade 1, 2 patients) Cramp (grade 1, 1 patient) Anorexia (grade 1, 1 patient) Mucositis (grade 1, 1 patient) Edema (grade 1, 1 patient) Hepatotoxicity (grade 3-4, 4 patients) |
2 mg/m2 1 times / day multiple, intravenous MTD Dose: 2 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / day Sources: |
unhealthy, 51 years n = 6 Health Status: unhealthy Condition: solid tumors Age Group: 51 years Sex: M+F Population Size: 6 Sources: |
DLT: Myelosuppression... Dose limiting toxicities: Myelosuppression (grade 3, 2 patients) Sources: |
6 mg 1 times / day multiple, oral Highest studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 60-76 years n = 1 Health Status: unhealthy Condition: Acute Myeloid Leukemia Age Group: 60-76 years Population Size: 1 Sources: |
Other AEs: Nausea, Hypoalbuminemia... Other AEs: Nausea (grade 1-2, 1 patient) Sources: Hypoalbuminemia (grade 1-2, 1 patient) Blood bilirubin decreased (grade 1-2, 1 patient) Lymphopenia (grade 3-4) |
70 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 70 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 70 mg/m2, 1 times / day Sources: |
unhealthy, child n = 2 Health Status: unhealthy Condition: ALL Age Group: child Population Size: 2 Sources: |
Other AEs: Hyperbilirubinemia, Vomiting... Other AEs: Hyperbilirubinemia (grade 4, 2 patients) Sources: Vomiting (grade 2-3, 2 patients) Maculopapular rash (grade 3, 2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | grade 1, 3 patients | 55 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 55 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 55 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 4 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 4 Sources: |
Nausea | grade 1-2, 2 patients | 55 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 55 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 55 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 4 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 4 Sources: |
Hepatotoxicity | grade 3, 2 patients | 55 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 55 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 55 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 4 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 4 Sources: |
Anorexia | grade 1, 1 patient | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Cramp | grade 1, 1 patient | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Edema | grade 1, 1 patient | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Mucositis | grade 1, 1 patient | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Diarrhea | grade 1, 2 patients | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Nausea | grade 1-2, 3 patients | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Fatigue | grade 3, 1 patient | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Hepatotoxicity | grade 3-4, 4 patients | 40 mg/m2 1 times / day multiple, intravenous MTD Dose: 40 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 1 times / day Sources: |
unhealthy, 42 years n = 31 Health Status: unhealthy Condition: acute leukemia Age Group: 42 years Sex: M+F Population Size: 31 Sources: |
Myelosuppression | grade 3, 2 patients DLT |
2 mg/m2 1 times / day multiple, intravenous MTD Dose: 2 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / day Sources: |
unhealthy, 51 years n = 6 Health Status: unhealthy Condition: solid tumors Age Group: 51 years Sex: M+F Population Size: 6 Sources: |
Blood bilirubin decreased | grade 1-2, 1 patient | 6 mg 1 times / day multiple, oral Highest studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 60-76 years n = 1 Health Status: unhealthy Condition: Acute Myeloid Leukemia Age Group: 60-76 years Population Size: 1 Sources: |
Hypoalbuminemia | grade 1-2, 1 patient | 6 mg 1 times / day multiple, oral Highest studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 60-76 years n = 1 Health Status: unhealthy Condition: Acute Myeloid Leukemia Age Group: 60-76 years Population Size: 1 Sources: |
Nausea | grade 1-2, 1 patient | 6 mg 1 times / day multiple, oral Highest studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 60-76 years n = 1 Health Status: unhealthy Condition: Acute Myeloid Leukemia Age Group: 60-76 years Population Size: 1 Sources: |
Lymphopenia | grade 3-4 | 6 mg 1 times / day multiple, oral Highest studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy, 60-76 years n = 1 Health Status: unhealthy Condition: Acute Myeloid Leukemia Age Group: 60-76 years Population Size: 1 Sources: |
Vomiting | grade 2-3, 2 patients | 70 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 70 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 70 mg/m2, 1 times / day Sources: |
unhealthy, child n = 2 Health Status: unhealthy Condition: ALL Age Group: child Population Size: 2 Sources: |
Maculopapular rash | grade 3, 2 patients | 70 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 70 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 70 mg/m2, 1 times / day Sources: |
unhealthy, child n = 2 Health Status: unhealthy Condition: ALL Age Group: child Population Size: 2 Sources: |
Hyperbilirubinemia | grade 4, 2 patients | 70 mg/m2 1 times / day multiple, intravenous Highest studied dose Dose: 70 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 70 mg/m2, 1 times / day Sources: |
unhealthy, child n = 2 Health Status: unhealthy Condition: ALL Age Group: child Population Size: 2 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-673_Clolar_biopharmr.PDF#page=18 Page: 18.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 30.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Nucleoside analogues in the treatment of haematological malignancies. | 2001 Jun |
|
Gateways to Clinical Trials. | 2002 Apr |
|
New drugs in acute myeloid leukemia. | 2002 Sep |
|
Clofarabine-induced acral erythema during the treatment of patients with myelodysplasia and acute leukemia: report of two cases. | 2003 Aug |
|
Pharmacokinetics and pharmacodynamics of plasma clofarabine and cellular clofarabine triphosphate in patients with acute leukemias. | 2003 Dec 15 |
|
Advanced-phase chronic myeloid leukemia. | 2003 Jan |
|
New designs for phase 2 clinical trials. | 2003 Jul 15 |
|
Phase I clinical and pharmacology study of clofarabine in patients with solid and hematologic cancers. | 2003 Mar 15 |
|
Clofarabine. | 2004 |
|
In vitro assessment of nucleoside analogs in multiple myeloma. | 2004 Aug |
|
Purine nucleoside antimetabolites in development for the treatment of cancer. | 2004 Jun |
|
Bibliography. Current world literature. Therapeutic modalities. | 2004 Nov |
|
Pediatric drug trials facing some obstacles. | 2005 Dec 7 |
|
Gateways to clinical trials. | 2005 Jun |
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The role of clofarabine in hematologic and solid malignancies--development of a next-generation nucleoside analog. | 2005 May 15 |
|
Gateways to clinical trials. | 2005 Sep |
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Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. | 2006 |
|
Efficacy of low dose clofarabine in refractory precursor T- acute lymphoblastic leukemia. | 2006 Dec |
|
Gateways to clinical trials. | 2006 Oct |
|
Discovery and development of clofarabine: a nucleoside analogue for treating cancer. | 2006 Oct |
|
Clofarabine for the treatment of acute lymphoblastic leukemia. | 2007 Feb |
|
The combination of clofarabine and cytarabine in pediatric relapsed acute lymphoblastic leukemia: a case report. | 2008 |
|
Novel purine nucleoside analogues for hematological malignancies. | 2008 Jun |
|
Clofarabine in refractory Langerhans cell histiocytosis. | 2008 Nov |
|
Clofarabine: in search of combinations for the treatment of patients with high-risk acute myeloid leukemia. | 2008 Oct 15 |
|
Enhancement of the in vivo antitumor activity of clofarabine by 1-beta-D-[4-thio-arabinofuranosyl]-cytosine. | 2009 Jul |
Patents
Sample Use Guides
The recommended pediatric dose is 52 mg/m2 given as an intravenous infusion over 2 hours daily for 5 consecutive days of a 28-day cycle. Repeat cycles every 2-6 week.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24692694
HL-60 cells or HL/ara-C20 cells were incubated with different concentrations of clofarabine for 72 h. The 50%-growth-inhibitory concentration IC50 was 50 nM for HL60 and 320 nM for HL/ara-C20 cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:34:47 UTC 2023
by
admin
on
Fri Dec 15 15:34:47 UTC 2023
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Record UNII |
762RDY0Y2H
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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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FDA ORPHAN DRUG |
668118
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NDF-RT |
N0000000233
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FDA ORPHAN DRUG |
153201
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NCI_THESAURUS |
C1556
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WHO-VATC |
QL01BB06
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EMA ASSESSMENT REPORTS |
EVOLTRA (AUTHORIZED: PRECURSOR CELL LYMPHOBLASTIC LEUKEMIA-LYMPHOMA)
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NDF-RT |
N0000175595
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FDA ORPHAN DRUG |
154802
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LIVERTOX |
NBK548185
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WHO-ATC |
L01BB06
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NCI_THESAURUS |
C2150
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Code System | Code | Type | Description | ||
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44151
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PRIMARY | RxNorm | ||
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762RDY0Y2H
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PRIMARY | |||
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759857
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DTXSID5046437
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DB00631
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CHEMBL1750
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PRIMARY | |||
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EU/3/01/082(EXPIRED)
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PRIMARY | Please note that this product was withdrawn from the Community Register of designated orphan medicinal products in May 2016 at the end of the period of market exclusivity. On 5 February 2002, orphan designation (EU/3/01/082) was granted by the European Commission to ILEX Services Limited, United Kingdom, for 2-chloro-9-[2-deoxy-2-fluoro-ß-D-arabinofuranosyl]adenine for the treatment of acute lymphoblastic leukaemia (ALL). The sponsorship was transferred to Bioenvision, United Kingdom, in December 2002 and subsequently to Genzyme Europe BV, The Netherlands, in May 2008. Update: 2-chloro-9-[2-deoxy-2-fluoro-ß-D-arabinofuranosyl]adenine has been authorised in the European Union as Evoltra since 29 May 2006. | ||
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8422
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CLOFARABINE
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691
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PRIMARY | |||
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SUB21902
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100000089587
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C068329
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m3636
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PRIMARY | Merck Index | ||
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6802
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119182
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681569
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123318-82-1
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EU/3/03/141(WITHDRAWN)
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PRIMARY | Please note that this product was withdrawn from the Community Register of designated Orphan Medicinal Products in July 2014 on request of the Sponsor. On 8 May 2003, orphan designation (EU/3/03/141) was granted by the European Commission to Bioenvision Limited, United Kingdom, for 2-chloro-9-[2-deoxy-2’-fluoro-ß-D-arabinofuranosyl]adenine for the treatment of acute myeloid leukaemia. The sponsorship was transferred to Genzyme Europe BV, The Netherlands, in May 2008. | ||
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C26638
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OO-77
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762RDY0Y2H
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ACTIVE MOIETY |
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Biological Half-life | PHARMACOKINETIC |
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