U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12FN5O4
Molecular Weight 285.2318
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUDARABINE

SMILES

NC1=NC(F)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

InChIKey=HBUBKKRHXORPQB-FJFJXFQQSA-N
InChI=1S/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-/m1/s1

HIDE SMILES / InChI
Fludarabine or fludarabine phosphate is a chemotherapy drug used in the treatment of hematological malignancies (cancers of blood cells such as leukemias and lymphomas). It is a purine analog, which interferes with DNA synthesis. Fludarabine phosphate is a fluorinated nucleotide analog of the antiviral agent vidarabine, 9-β-D-arabinofuranosyladenine (ara-A), that is relatively resistant to deamination by adenosine deaminase. Fludarabine (marketed as fludarabine phosphate under the trade name Fludara) is a chemotherapy drug used in the treatment of hematological malignancies. 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLUDARABINE PHOSPHATE

Approved Use

Fludarabine Phosphate Injection is indicated for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to or whose disease has progressed during treatment with at least one standard alkylating-agent containing regimen. The safety and effectiveness of Fludarabine Phosphate Injection in previously untreated or non-refractory patients with CLL have not been established. Important Limitations Fludarabine Phosphate Injection should not be used in patients with severe renal impairment (creatinine clearance less than 30 mL/min/1.73 m2).

Launch Date

1.19024635E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.28 μM
30 mg/m² single, intravenous
dose: 30 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUDARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
21.55 μM × h
30 mg/m² single, intravenous
dose: 30 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUDARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.9 h
30 mg/m² single, intravenous
dose: 30 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUDARABINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
20 h
25 mg/m² 1 times / day multiple, intravenous
dose: 25 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
FLUDARABINE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy, 32 years (range: 19-59 years)
n = 2
Health Status: unhealthy
Condition: Acute Leukemia
Age Group: 32 years (range: 19-59 years)
Sex: M+F
Population Size: 2
Sources:
Other AEs: Leukopenia...
Other AEs:
Leukopenia (2 patients)
Sources:
40 mg/m2 1 times / day steady, intravenous
MTD
Dose: 40 mg/m2, 1 times / day
Route: intravenous
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources:
unhealthy, 32 years (range: 19-59 years)
n = 11
Health Status: unhealthy
Condition: Acute Leukemia
Age Group: 32 years (range: 19-59 years)
Sex: M+F
Population Size: 11
Sources:
20 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 20 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 20 mg/m2, 1 times / day
Sources:
unhealthy, 55 years (range: 26-78 years)
Health Status: unhealthy
Age Group: 55 years (range: 26-78 years)
Sex: M+F
Sources:
45 mg/m2 1 times / day multiple, intravenous
Dose: 45 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 45 mg/m2, 1 times / day
Sources:
unhealthy, 55 years (range: 26-78 years)
n = 1
Health Status: unhealthy
Age Group: 55 years (range: 26-78 years)
Sex: M+F
Population Size: 1
Sources:
DLT: Myelosuppression...
Dose limiting toxicities:
Myelosuppression (1 patient)
Sources:
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Disc. AE: Thrombocytopenia, Anemia hemolytic autoimmune...
AEs leading to
discontinuation/dose reduction:
Thrombocytopenia (1 patient)
Anemia hemolytic autoimmune (3 patients)
Pneumonia (1 patient)
Anemia (1 patient)
Foot drop (1 patient)
Sepsis (1 patient)
Bronchitis (1 patient)
Rash (1 patient)
Face edema (1 patient)
Sources: Page: p. 61
25 mg/m2 1 times / day steady, intravenous
Recommended
Dose: 25 mg/m2, 1 times / day
Route: intravenous
Route: steady
Dose: 25 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Other AEs: CNS toxicity, Hemolytic anemia...
Other AEs:
CNS toxicity
Hemolytic anemia
Pulmonary toxicity
Sources:
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Other AEs: CNS toxicity, Hemolytic anemia...
Other AEs:
CNS toxicity
Hemolytic anemia
Pulmonary toxicity
Sources:
AEs

AEs

AESignificanceDosePopulation
Leukopenia 2 patients
100 mg/m2 1 times / day multiple, intravenous
Highest studied dose
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy, 32 years (range: 19-59 years)
n = 2
Health Status: unhealthy
Condition: Acute Leukemia
Age Group: 32 years (range: 19-59 years)
Sex: M+F
Population Size: 2
Sources:
Myelosuppression 1 patient
DLT, Disc. AE
45 mg/m2 1 times / day multiple, intravenous
Dose: 45 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 45 mg/m2, 1 times / day
Sources:
unhealthy, 55 years (range: 26-78 years)
n = 1
Health Status: unhealthy
Age Group: 55 years (range: 26-78 years)
Sex: M+F
Population Size: 1
Sources:
Anemia 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Bronchitis 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Face edema 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Foot drop 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Pneumonia 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Rash 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Sepsis 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Thrombocytopenia 1 patient
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
Anemia hemolytic autoimmune 3 patients
Disc. AE
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources: Page: p. 61
unhealthy, 64 years (range: 30-75 years)
n = 81
Health Status: unhealthy
Age Group: 64 years (range: 30-75 years)
Sex: M+F
Population Size: 81
Sources: Page: p. 61
CNS toxicity
25 mg/m2 1 times / day steady, intravenous
Recommended
Dose: 25 mg/m2, 1 times / day
Route: intravenous
Route: steady
Dose: 25 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Hemolytic anemia
25 mg/m2 1 times / day steady, intravenous
Recommended
Dose: 25 mg/m2, 1 times / day
Route: intravenous
Route: steady
Dose: 25 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Pulmonary toxicity
25 mg/m2 1 times / day steady, intravenous
Recommended
Dose: 25 mg/m2, 1 times / day
Route: intravenous
Route: steady
Dose: 25 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
CNS toxicity
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Hemolytic anemia
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Pulmonary toxicity
40 mg/m2 1 times / day steady, oral
Recommended
Dose: 40 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 40 mg/m2, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: B-cell chronic lymphocytic leukemia
Age Group: adult
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Fludarabine + Ara-C + G-CSF: cytotoxic effect and induction of apoptosis on fresh acute myeloid leukemia cells.
1994 Dec
Cellular and clinical pharmacology of fludarabine.
2002
The effects of cladribine and fludarabine on DNA methylation in K562 cells.
2003 Jan 15
The histone deacetylase inhibitor MS-275 interacts synergistically with fludarabine to induce apoptosis in human leukemia cells.
2004 Apr 1
Post-transcriptional regulation of inducible nitric oxide synthase in chronic lymphocytic leukemia B cells in pro- and antiapoptotic culture conditions.
2004 Jan
A phase I and pharmacodynamic study of fludarabine, carboplatin, and topotecan in patients with relapsed, refractory, or high-risk acute leukemia.
2004 Oct 15
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.
2005 Apr 22
Resistance to 9-beta-D-arabinofuranosyl-2-fluoroadenine due to reduced incorporation into DNA from competition by excess deoxyadenosine triphosphate: implications for different sensitivities to nucleoside analogues.
2005 Jun
Inhibition of the PI3K pathway sensitizes fludarabine-induced apoptosis in human leukemic cells through an inactivation of MAPK-dependent pathway.
2005 Jun 3
Alteration of DNA methylation status in K562 and MCF-7 cancer cell lines by nucleoside analogues.
2006
Characterization of the rat Na+/nucleoside cotransporter 2 and transport of nucleoside-derived drugs using electrophysiological methods.
2006 Dec
Chronic lymphocytic leukaemia, synchronous small cell carcinoma and squamous neoplasia of the urinary bladder in a paraplegic man following long-term phenoxybenzamine therapy.
2006 Mar
Functional integrity of the p53-mediated apoptotic pathway induced by the nongenotoxic agent nutlin-3 in B-cell chronic lymphocytic leukemia (B-CLL).
2006 May 15
Fatal leukoencephalopathy after reduced-intensity allogeneic stem cell transplantation.
2007 Feb
Myelopathy due to intrathecal chemotherapy: magnetic resonance imaging findings.
2007 Feb
Drug resistance in B-cell chronic lymphocytic leukemia: predictable by in vitro evaluation with a multiparameter flow cytometric cytotoxicity assay.
2007 May
Prodrug converting enzyme gene delivery by L. monocytogenes.
2008 Apr 10
Targeting lipid metabolism by the lipoprotein lipase inhibitor orlistat results in apoptosis of B-cell chronic lymphocytic leukemia cells.
2008 Mar
Hypomethylation and induction of retinoic acid receptor beta 2 by concurrent action of adenosine analogues and natural compounds in breast cancer cells.
2010 Jul 25
Incidence and susceptibility to therapy-related myeloid neoplasms.
2010 Mar 19
Inhibitory effect of leptin on rosiglitazone-induced differentiation of primary adipocytes prepared from TallyHO/Jng mice.
2011 Mar 25
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

Chronic Lymphocytic Leukemia (CLL): The recommended adult dose is 25 mg/m2 administered intravenously over a period of approximately 30 minutes daily for five consecutive days. Each 5-day course of treatment should commence every 28 days.
Route of Administration: Intravenous
The growth of RPMI8226 and KM3 cells was suppressed by fludarabine treatment in a dose and time-dependent manner. After treatment with fludarabine for 24 h, the IC(50) for RPMI8226 cells was 2.13 µg/ml, and 0.36 µg/ml for KM3 cells. Apoptotic cells of RPMI8226 and KM3 increased in a dose- dependent manner after exposure to fludarabine for 24 h. Western blot analysis showed the activation of caspase-3 and PARP in the MM cells treated with fludarabine.
Name Type Language
FLUDARABINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FLURADOSA
Brand Name English
FLUDARABINE PHOSPHATE IMPURITY, 2-FLUORO-ARA-ADENINE- [USP IMPURITY]
Common Name English
NSC-118218
Code English
9-.BETA.-D-ARABINOFURANOSYL-2-FLUOROADENINE
Common Name English
FLUDARABINE [HSDB]
Common Name English
2-F-ARAA
Common Name English
2-FLUORO-9-.BETA.-D-ARABINOFURANOSYLADENINE
Common Name English
FLUDARABINE [VANDF]
Common Name English
fludarabine [INN]
Common Name English
Fludarabine [WHO-DD]
Common Name English
2-FLUOROVIDARABINE
Common Name English
FLUDARABINE [MI]
Common Name English
9-.BETA.-D-ARABINOFURANOSYL-2-FLUORO-9H-PURIN-6-AMINE
Common Name English
FLUDARABINE PHOSPHATE IMPURITY E [EP IMPURITY]
Common Name English
2-FLUORO ARA-A
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2150
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
NDF-RT N0000000233
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
WHO-VATC QL01BB05
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
NDF-RT N0000175595
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
LIVERTOX NBK548845
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
WHO-ATC L01BB05
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C1094
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
DAILYMED
P2K93U8740
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
HSDB
6964
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
MERCK INDEX
m5427
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB01073
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
SMS_ID
100000081235
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
ECHA (EC/EINECS)
244-525-5
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
NSC
118218
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
EVMPD
SUB07678MIG
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
RXCUI
24698
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
FLUDARABINE
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL1096882
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID4039657
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
PUBCHEM
657237
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
INN
5214
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
MESH
C024352
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
CAS
21679-14-1
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
FDA UNII
P2K93U8740
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY
IUPHAR
4802
Created by admin on Fri Dec 15 16:20:07 UTC 2023 , Edited by admin on Fri Dec 15 16:20:07 UTC 2023
PRIMARY