Basic information
- Standard SMILES
Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O- InChIKey
HBUBKKRHXORPQB-FJFJXFQQSA-N- Molecular formula
- C10H12FN5O4
- Average molar mass
- 285.23 g/mol
- Monoisotopic mass
- 285.08733208
Overview
(2R,3S,4S,5R)-2-(6-amino-2-fluoro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol is a purine nucleoside.
Names & identifiers
- Preferred name
- Fludarabine
- IUPAC
- (2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- English name
- Fludarabine
- Molecular formula
- C10H12FN5O4
- Molecular weight
- 285.23
Names & synonyms
Show more names
Database identifiers
- CAS
21679-14-1- PubChem CID
- 657237
- DTXSID
DTXSID4039657- ChEMBL
CHEMBL1568- ChEBI
CHEBI:94701- UNII
- P2K93U8740
- EC Number
- 244-525-5
- Nikkaji
- J33.087F
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 367
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents
Cytotoxic medicines
Physicochemical properties
- Melting point
- 265 · 265-268°C
- alpha
- 25 · D25 +17 ±2.5° (c = 0.1 in ethanol)
- Boiling point
- 747.3 · 747.3±70.0 °C(Predicted)
- Density
- 2.17 · 2.17±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 20 mg/mL, · DMF: 20 mg/mL, clear, faintly yellow
- form
- Powder
- pka
- 13.05 · 13.05±0.70(Predicted)
- color
- White to Pale Yellow
- Water Solubility
- Soluble in DMF, DMSO, methanol or ethanol. Sparingly soluble in water
- Merck
- 13 · 13,4152
- BRN
- 1225932 · 1225932
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChI
- InChI=1/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/s3
- InChIKey
- HBUBKKRHXORPQB-VOSPVXAENA-N
- SMILES
- C12N=C(N=C(N)C=1N=CN2[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1)F |&1:10,11,13,15,r|
- CAS DataBase Reference
- 21679 · 21679-14-1(CAS DataBase Reference)
- FDA UNII
- 2 K93U8740 · P2K93U8740
- ATC code
- 1 BB05 · L01BB05
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 341 · H341-H361d
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 23 · 23/24/25-36/37/38-39/23/24/25-39-22
- Safety Statements
- 26 · 26-36/37-45-36
- WGK Germany
- 3 · 3
- RTECS
- 6207000 · AU6207000
- F
- 10 · 10
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Repr · Muta. 2Repr. 2
- Hazardous Substances Data
- 21679 · 21679-14-1(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (95.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory.
Hazard information
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions
Fludarabine may raise the concentration of blood uric acid as part of a tumor lysis syndrome; dosage adjustment of antigout agents /allopurinol, colchicine, probenecid, sulfinpyrazone/ may be necessary to control hyperuricemia and gout; allopurinol may be preferred to prevent or reverse fludarabine-induced hyperuricemia because of risk of uric acid nephropathy with uricosuric antigout agents.
Leukopenic and/or thrombocytopenic effects of fludarabine may be increased with concurrent or recent therapy if these medications /blood dyscrasia causing medications/ cause the same effects; dosage adjustment of fludarabine, if necessary, should be based on blood counts.
Additive bone marrow depression may occur; dosage reduction may be required when two or more bone marrow depressants, including radiation, are used concurrently or consecutively.
Concurrent use with fludarabine is not recommended because of a possible increased risk of fatal pulmonary toxicity. /Pentostatin/
For more Interactions (Complete) data for FLUDARABINE (10 total), please visit the HSDB record page.
Hepatotoxicity
In clinical trials, serum enzymes elevations occurred in only a small proportion of patients treated with fludarabine for leukemia. The role of fludarabine as opposed to other antineoplastics used in antileukemic regimens was not always clear from these studies. Cases of clinically apparent liver injury due to fludarabine have been reported to occur, but few details were available and most patients were receiving other cancer chemotherapeutic agents.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
fludarabine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts
Dose-related adverse effects on the male reproductive system have been demonstrated in mice, rats, and dogs; effects consisted of a decrease in mean testicular weights in mice and rats with a trend toward decreased testicular weights in dogs, and degeneration and necrosis of spermatogenic epithelium of the testes in mice, rats, and dogs.
Studies in rats at intravenous doses of 0, 1, 10, or 30 mg per kg of body weight (mg/kg) per day on days 6 to 15 of gestation found an increased incidence of skeletal malformations. Studies in rabbits at doses of 5 and 8 mg/kg per day found dose-related teratogenic effects (external deformities and skeletal malformations).
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- AU6207000
- hs_code
- 29349990
- risk_code
- 23/24/25-36/37/38-39/23/24/25-39-22
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 26-36/37-45-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H341-H361d
- Hazard Classifications
- Muta. 2Repr. 2
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
- Hazardous Substances Data
- 21679-14-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
L01BB05
L - Antineoplastic and immunomodulating agents
L01BB05
Mechanism of Action
Fludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite appears to act by inhibiting DNA polymerase alpha, ribonucleotide reductase and DNA primase, thus inhibiting DNA synthesis. The mechanism of action of this antimetabolite is not completely characterized and may be multi-faceted.
Fluorinated adenine analog causes inhibition of DNA synthesis by inhibiting ribonucleotide reductase & DNA polymerase.
Fludarabine is a purine antimetabolite. Activity occurs as the result of activation to 2-fluoro-ara-ATP and includes inhibition of DNA synthesis (primarily in the S-phase of cell division by inhibition of ribonucleotide reductase and the DNA polymerases. It is also postulated that fludarabine interferes with RNA by decreased incorporation of uridine and leucine into RNA and protein, respectively. Fludarabine is also active against non-proliferating cells.
This review establishes the pharmacokinetic characteristics of the major nucleoside analogs with cytotoxic activity. Cytarabine, pentostatin, fludarabine, cladribine & gemcitabine are all prodrugs whose plasma pharmacokinetics do not fully reflect their therapeutic activity; after cellular uptake, these compounds undergo phosphorylation by deoxycytidine kinase before their incorporation into DNA results in cell death. Cytarabine is principally active in the S phase of the cell cycle & is most toxic to replicating cells, whereas pentostatin, fludarabine & cladribine are incorporated into DNA during the process in which strand breaks are repaired & are therefore cytotoxic to slowly replicating cells (although the action of pentostatin results from its inhibition of adenosine deaminase). Gemcitabine is unusual in being highly metabolized in solid tumor cells. The cytotoxic activity of pentostatin, fludarabine and cladribine against the clonal cells of lymphoproliferative disorders is accompanied by damage to normal lymphoid cells, which results in significant & long-lasting immunosuppression. Useful interactions between nucleoside analogs have been defined. Cells that are primed by exposure to fludarabine or cladribine exhibit enhanced accumulation of cytarabine triphosphate (the cytotoxic nucleotide of cytarabine) & an improved therapeutic effect against acute myeloid leukemia & chronic lymphocytic leukemia can be achieved by clinical schedules that exploit this effect. Combinations of alkylating agents & fludarabine or cladribine are also synergistic in producing significantly enhanced activity against refractory lymphoid malignancies, but at the cost of increased hematological toxicity. Developments in the clinical admin of gemcitabine are concentrating on efforts to extend the duration of exposure to the drug as a means of counteracting its rapid catabolism in the circulation. Future developments with this group of agents will further explore the use of fludarabine-based combination therapies to produce a transient period of myelosuppression & immunosuppression that is sufficient to permit the engraftment of allogeneic hemopoietic stem cells & also exploit the immunological benefits of graft-versus-tumor reactions. In addition, the clinical spectrum of activity of gemcitabine is also being extended by combining the drug with other active chemotherapeutic agents, such as cisplatin, & by early studies of its role as a radiosensitiser.
FDA Pharmacological Classification
P2K93U8740
FLUDARABINE
Mechanisms of Action [MoA] - Nucleic Acid Synthesis Inhibitors
Established Pharmacologic Class [EPC] - Nucleoside Metabolic Inhibitor
Fludarabine is a Nucleoside Metabolic Inhibitor. The mechanism of action of fludarabine is as a Nucleic Acid Synthesis Inhibitor.
Absorption, Distribution and Excretion
Bioavailability is 55% following oral administration.
117-145 mL/min [patients with B-cell CLL receiving IV administration of a single dose of 40 mg/m^2.
... To compare the pharmacokinetics of sc & iv fludarabine in patients with lupus nephritis. ... Open-label, randomized, crossover trial conducted with a phase I-II trial. ... Government research hospital. ... Five patients with lupus nephritis. ... Fludarabine 30 mg/m2/day was administered either sc or as a 0.5-hr iv infusion for 3 consecutive days. All patients received oral cyclophosphamide 0.5 g/m2 on the first day of each cycle. ... Plasma samples were collected before & 0.5, 1, 1.5, 2, 4, 8, & 24 hrs after the first dose. Urine was collected at 6-hr intervals for 24 hrs. Plasma & urine were analyzed for fluoro-arabinofuranosyladenine (F-ara-A), fludarabine's main metabolite, using high-performance liquid chromatography. Compartmental techniques were used to determine the pharmacokinetics of F-ara-A; a linear two-compartment model best described them. Comparison of the pharmacokinetics between sc & iv admin was done by using a Wilcoxon signed rank test. No significant differences were found between sc & iv admin in median (interquartile range) maximum concns of 0.51 (0.38-0.56) & 0.75 (0.52-0.91) mg/L, respectively, or in fitted area under the concn-time curves from 0-24 hrs of 4.65 (4.17-4.98) & 4.55 (3.5-4.94) mg x hr/L, respectively. Bioavailability of F-ara-A after sc dosing was approx 105% of the bioavailability after iv admin. Differences in renal clearance & % of dose excreted in urine for sc & iv admin were nonsignificant. No injection site reactions were seen with subcutaneous dosing. ... Sc & iv admin of fludarabine appear to have similar pharmacokinetics in patients with lupus nephritis. Sc injection may offer a convenient alternative to iv admin.
Uses & manufacturing
Applications
DescriptionFludarabine (21679-14-1) is a synthetic adenosine analog that inhibits DNA biosynthesis and is a clinically useful antineoplastic agent.1 In cells fludarabine accumulates as its 5’-triphosphate (F-ara-ATP) for which the rate-limiting step in formation is the conversion of fludarabine to its monophosphate.2 F-ara-ATP has multiple mechanisms of action including inhibition of ribonucleotide reductase, DNA polymerase, ligase and primase.2 A frequently used agent in myeloablative conditioning regimens for allogeneic hematopoietic cell transplantation.3 Immunosuppressive effects are mediated via inhibition of TNFa-stimulated production of IL-2 and IFN-g through inactivation of NFkB.4 Antagonist at adenosine A1 receptors.5
UsesFludarabine is not one of the most used drugs in pediatric oncology area. It is used in combination with other drugs to treat AML in children, mostly those who are receiving second-line therapy. It is commonly sold as 10 mg film-coated tablets and IV vial containing 50mg.
UsesFludarabine is used in the treatment of chroniclymphocytic leukaemia. It is a DNA synthesis and methylation inhibitor;A cell permeable agent that interferes with DNA synthesis and repair; also inhibits RNA transcription.
General DescriptionThe drug is available as the phosphate salt in a 50-mg vialfor IV use. Fludarabine is used to treat chronic lymphocyticleukemia and non-Hodgkin’s lymphoma. The mechanism ofaction involves the triphosphate metabolite and its inhibitionof DNA chain elongation. The 2-fluoro group on the adeninering renders fludarabine resistant to breakdown byadenosine deaminase. The drug is rapidly dephosphorylatedto 2-fluoro-ara-adenosine (F-ara-A) after administration. Fara-A is taken into the cell and subsequently re-phosphorylatedto yield the triphosphate (F-ara-ATP), the active drugspecies. Resistance can occur via decreased expression ofthe activating enzymes and decreased drug transport.Fludarabine is orally bioavailable and is distributed throughoutthe body reaching high levels in liver, kidney, andspleen. The drug is metabolized to F-ara-A, which enterscells via the nucleoside transport system and is rephosphorylatedby deoxycytidine kinase to fludarabine monophosphateand finally fludarabine triphosphate, the activespecies. About 25% of F-ara-A is excreted unchanged inurine. Drug interactions include an increased incidence offatal pulmonary toxicity when fludarabine is used in combinationwith pentostatin. Additionally, fludarabine may potentiate the effects of several other anticancer drugs includingcytarabine, cyclophosphamide, and cisplatin.Toxicities include myelosuppression, immunosuppression,fever, nausea, and vomiting.
Preparation methods
PreparationSynthesis of fludarabine 1: 2-Fluoroadenine is reacted with 9-β-D-arabinosyl-uracile, taking water as a solvent. The reaction will take place in the presence of Enterobacter aerogenes. Fludarabine so formed is then treated with acetic anhydride to form the acetylderivative.The acetyl derivative is then crystallize to get back the pure Fludarabine.Synthesis of fludarabine 2: 2,4,5,6-tetraaminopyrimidine and formamide were cyclized together by heating to give 2,6-diaminopurine. acylation with acetic anhydride-pyridine complex gave 2,6-diacetamidopurine. then reacted with 2,3,5-tri-o-benzyl-d-arabinofuranosyl chloride to give compound (i). (i) was deacetylated to give compound (ii). (ii) in fluoroboronic acid-tetrahydrofuran, first nitrosated and then substituted to give compound (ili). in the presence of boron trichloride, the benzyl group was removed to give fludarabine. the yield was 17.5% in terms of 2,3,5-tri-o-benzyl-d-arabinofuranosyl chloride.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: (2R,3S,4S,5R)-2-(6-amino-2-fluoro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol is a purine nucleoside.
Related reactions
Linked notes
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