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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11FN2O5
Molecular Weight 246.1928
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLOXURIDINE

SMILES

C1[C@@]([H])([C@@]([H])(CO)O[C@@]1([H])n2cc(c(nc2=O)O)F)O

InChI

InChIKey=ODKNJVUHOIMIIZ-RRKCRQDMSA-N
InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/floxuridine.html

Floxuridine is a pyrimidine analog that acts as an inhibitor of the S-phase of cell division. This selectively kills rapidly dividing cells. Floxuridine is an anti-metabolite. Anti-metabolites masquerade as pyramidine-like molecules which prevents normal pyrimidines from being incorporated into DNA during the S phase of the cell cycle. Flurouracil (the end-product of catabolism of floxuridine) blocks an enzyme which converts cytosine nucleosides into the deoxy derivative. In addition, DNA synthesis is further inhibited because fluoruracil blocks the incorporation of the thymdine nucleotide into the DNA strand. Floxuridine is used for palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. Also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion).Floxuridine first gained FDA approval in December 1970 under the brand name FUDR. The drug was initially marketed by Roche, which also did a lot of the initial work on 5-fluorouracil. The National Cancer Institute was an early developer of the drug. Roche sold its FUDR product line in 2001 to F H Faulding, which became Mayne Pharma.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.4 nM [IC50]
Target ID: CHEMBL614353
5.02 µM [IC50]
12.45 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FLOXURIDINE

Approved Use

Floxuridine for Injection, USP is effective in the palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means.

Launch Date

9.5489281E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5547 ng/mL
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
79304 ng × h/mL
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.5 h
10.8 mg/m² 1 times / 2 weeks multiple, intravenous
dose: 10.8 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered: Irinotecan | 7-Ethyl-10-hydroxycamptothecin | 5-Fluorouracil
FLOXURIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1750 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 1750 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1750 mg/m2, 1 times / week
Co-administed with::
leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6)
Sources: Page: p.263
unhealthy, 30-79
n = 3
Health Status: unhealthy
Condition: Carcinoma
Age Group: 30-79
Sex: M+F
Population Size: 3
Sources: Page: p.263
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 4, 50%)
Sources: Page: p.263
1650 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 1650 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1650 mg/m2, 1 times / week
Co-administed with::
leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6)
Sources: Page: p.263
unhealthy, 30-79
n = 6
Health Status: unhealthy
Condition: Carcinoma
Age Group: 30-79
Sex: M+F
Population Size: 6
Sources: Page: p.263
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 3, 33.3%)
Sources: Page: p.263
544 mg/m2 5 times / day multiple, intraarterial (mean)
MTD
Dose: 544 mg/m2, 5 times / day
Route: intraarterial
Route: multiple
Dose: 544 mg/m2, 5 times / day
Co-administed with::
5-FU, i.v(6025 mg/m2/cycle (5 days))
Sources: Page: p.390
unhealthy, 44-75
n = 29
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Age Group: 44-75
Sex: M+F
Population Size: 29
Sources: Page: p.390
DLT: Mucositis...
Dose limiting toxicities:
Mucositis (grade 3-4, 72%)
Sources: Page: p.390
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Disc. AE: Fetal damage, Myocardial ischemia...
AEs leading to
discontinuation/dose reduction:
Fetal damage
Myocardial ischemia
Stomatitis
Esophagitis
Leukopenia
Vomiting
Diarrhea
Gastrointestinal ulcer
Gastrointestinal bleeding
Thrombocytopenia
Hemorrhage
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea grade 4, 50%
DLT, Disc. AE
1750 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 1750 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1750 mg/m2, 1 times / week
Co-administed with::
leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6)
Sources: Page: p.263
unhealthy, 30-79
n = 3
Health Status: unhealthy
Condition: Carcinoma
Age Group: 30-79
Sex: M+F
Population Size: 3
Sources: Page: p.263
Diarrhea grade 3, 33.3%
DLT, Disc. AE
1650 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 1650 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 1650 mg/m2, 1 times / week
Co-administed with::
leucovorin, i.v(500 mg/m2 by 2-h infusion; weekly x 6)
Sources: Page: p.263
unhealthy, 30-79
n = 6
Health Status: unhealthy
Condition: Carcinoma
Age Group: 30-79
Sex: M+F
Population Size: 6
Sources: Page: p.263
Mucositis grade 3-4, 72%
DLT
544 mg/m2 5 times / day multiple, intraarterial (mean)
MTD
Dose: 544 mg/m2, 5 times / day
Route: intraarterial
Route: multiple
Dose: 544 mg/m2, 5 times / day
Co-administed with::
5-FU, i.v(6025 mg/m2/cycle (5 days))
Sources: Page: p.390
unhealthy, 44-75
n = 29
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Age Group: 44-75
Sex: M+F
Population Size: 29
Sources: Page: p.390
Diarrhea Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Esophagitis Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Fetal damage Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Gastrointestinal bleeding Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Gastrointestinal ulcer Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Hemorrhage Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Leukopenia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Myocardial ischemia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Stomatitis Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Thrombocytopenia Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
Vomiting Disc. AE
0.6 mg/kg 1 times / day multiple, intraarterial (max)
Recommended
Dose: 0.6 mg/kg, 1 times / day
Route: intraarterial
Route: multiple
Dose: 0.6 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal adenocarcinoma metastatic to the liver
Sources:
PubMed

PubMed

TitleDatePubMed
gamma-Hydroxybutyric acid and 5-fluorouracil, metabolites of UFT, inhibit the angiogenesis induced by vascular endothelial growth factor.
2001
Randomised trial of SIR-Spheres plus chemotherapy vs. chemotherapy alone for treating patients with liver metastases from primary large bowel cancer.
2001 Dec
Surgical debulking and intraperitoneal chemotherapy for established peritoneal metastases from colon and appendix cancer.
2001 Dec
Surgery as adjuvant therapy? The treatment of peritoneal metastases from gastrointestinal malignancy.
2001 Dec
Antisense-induced down-regulation of thymidylate synthase and enhanced cytotoxicity of 5-FUdR in 5-FUdR-resistant HeLa cells.
2001 Dec
Regional chemotherapy of nonresectable colorectal liver metastases with mitoxantrone, 5-fluorouracil, folinic acid, and mitomycin C may prolong survival.
2001 Dec 1
Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs.
2001 Dec 6
Malnutrition and cachexia in ovarian cancer patients: pathophysiology and management.
2001 Jul-Aug
Survival benefits of adjuvant chemotherapy with oral doxifluridine (5'-DFUR) following radiotherapy in patients with unresectable pancreatic cancer.
2001 Nov
[A case of lung metastasis from colon cancer treated successfully with combined chemotherapy of CPT-11 and 5'-DFUR].
2001 Nov
[Hepatic infusion of docetaxel using PEIT for a patient with stage IV breast cancer].
2001 Nov
Plasma, intestine and tumor levels of 5-fluorouracil in mice bearing L1210 ascites tumor following oral administration of 5-fluorouracil, UFT (mixed compound of tegafur and uracil), carmofur and 5'-deoxy-5-fluorouridine.
2001 Nov
P53 mutation and response to hepatic arterial floxuridine in patients with colorectal liver metastases.
2001 Nov
Fluorodeoxyuridine improves imaging of human glioblastoma xenografts with radiolabeled iododeoxyuridine.
2001 Nov 1
Interaction of thymidylate synthase with the 5'-thiophosphates, 5'-dithiophosphates, 5'-H-phosphonates and 5'-S-thiosulfates of 2'-deoxyuridine, thymidine and 5-fluoro-2'-deoxyuridine.
2001 Oct
Combined effects of docetaxel and fluoropyrimidines on tumor growth and expression of interleukin-6 and thymidine phosphorylase in breast cancer xenografts.
2001 Oct
[Effect of peroral doxifluridine plus hepatic arterial infusion for synchronous liver metastasis of colorectal cancer--correlation with the expression of thymidine phosphorylase and dihydropyrimidine dehydrogenase in primary colorectal cancer lesions].
2001 Oct
[A patient with recurrent breast cancer whose liver metastasis regressed following combined use of weekly docetaxel and MPA.5'-DFUR].
2001 Oct
[A case report of effective chemoradiation with 5'-DFUR and concomitant preoperative radiotherapy of the lower rectum].
2002 Apr
Intrahepatic arterial infusion of chemotherapy: clinical results.
2002 Apr
Intrahepatic arterial infusion of chemotherapy: pharmacologic principles.
2002 Apr
Downstaging of hepatocellular carcinoma and liver metastases from colorectal cancer by selective intra-arterial chemotherapy.
2002 Apr
Impact of the oxaliplatin-5 fluorouracil-folinic acid combination on respective intracellular determinants of drug activity.
2002 Apr 8
[A case of long surviving advanced recurrent breast cancer with multiple bone metastases responding to treatment with 5'-DFUR combined with MPA].
2002 Feb
[Evidence for and practical use of arterial infusion chemotherapy for liver metastases].
2002 Feb
A controlled "before-after" study: impact of a clinical guidelines programme and regional cancer network organization on medical practice.
2002 Feb 1
CT-guided intratumoural administration of cisplatin/epinephrine gel for treatment of malignant liver tumours.
2002 Feb 12
Circadian chemotherapy for gynecological and genitourinary cancers.
2002 Jan
[Antimetastatic and antitumor effects of fluoropyrimidines alone and combined with taxanes in a murine model of breast cancer metastatic to the lung].
2002 Jan
[Adjuvant chemotherapy after curative resection for gastric cancer-5'-DFUR + cisplatin vs 5'-DFUR].
2002 Jan
[A 5'-DFUR + CPA + THP therapy that was effective for paclitaxel-refractory pulmonary metastasis of breast cancer--a case report].
2002 Jan
Use of 5-[(76)Br]bromo-2'-fluoro-2'-deoxyuridine as a ligand for tumour proliferation: validation in an animal tumour model.
2002 Jan
Immunohistochemical variation of human equilibrative nucleoside transporter 1 protein in primary breast cancers.
2002 Jan
Biochemical and molecular effects of UCN-01 in combination with 5-fluorodeoxyuridine in A431 human epidermoid cancer cells.
2002 Mar
A phase II study of doxifluridine in elderly patients with advanced gastric cancer: the Japan Clinical Oncology Group Study (JCOG 9410).
2002 Mar
Overexpression of pyrimidine nucleoside phosphorylase enhances the sensitivity to 5'-deoxy-5-fluorouridine in tumour cells in vitro and in vivo.
2002 Mar
[Successful treatment of advanced recurent breast cancer using DMpC therapy as maintenance therapy].
2002 Mar
Systemic irinotecan and regional floxuridine after hepatic cytoreduction in 185 patients with unresectable colorectal cancer metastases.
2002 Mar
Fighting wars, winning battles.
2002 Mar
The effect of adjuvant 5'-deoxy-5-fluorouridine in early stage breast cancer patients: results from a multicenter randomized controlled trial.
2002 Mar
Echogenicity of liver metastases from colorectal carcinoma is an independent prognostic factor in patients treated with regional chemotherapy.
2002 Mar 15
Combined-modality treatment for resectable metastatic colorectal carcinoma to the liver: surgical resection of hepatic metastases in combination with continuous infusion of chemotherapy--an intergroup study.
2002 Mar 15
Isolation perfusion of the liver.
2002 Mar-Apr
Percutaneous vs. surgical placement of hepatic artery indwelling catheters for regional chemotherapy.
2002 Mar-Apr
Neoadjuvant chemotherapy with CPT-11 and cisplatin downstages locally advanced gastric cancer.
2002 Mar-Apr
Treatment of patients with superficial bladder cancer by intravesical instillation of anticancer drugs plus oral chemotherapy following TUR-Bt: a randomized controlled trial.
2002 Mar-Apr
Probable metabolic interaction of doxifluridine with phenytoin.
2002 May
Conjugates of nucleoside analogs with lactosaminated human albumin to selectively increase the drug levels in liver blood: requirements for a regional chemotherapy.
2002 May
Schedule-selective biochemical modulation of 5-fluorouracil in advanced colorectal cancer--a phase II study.
2002 May 2
Thymidine phosphorylase and dihydropyrimidine dehydrogenase levels in primary colorectal cancer show a relationship to clinical effects of 5'-deoxy-5-fluorouridine as adjuvant chemotherapy.
2002 May-Jun
Patents

Sample Use Guides

Usual Adult Dose for Liver Metastasis in Adenocarcinoma Recommended dose: 0.1 to 0.6 mg/kg/day by continuous arterial infusion; the higher dosage ranges (0.4 mg to 0.6 mg) are usually used for hepatic artery infusion
Route of Administration: Intra-arterial
Coincubation of [3H]-FAU in vitro with 50 nmol/L Floxuridine decreased FAU incorporation into DNA by 70% in HT29 and 84% in LS174T cells
Name Type Language
FLOXURIDINE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
5-FLUORO-2'-DEOXYURIDINE
Systematic Name English
5-FUDR
Common Name English
FLOXURIDINE [USP MONOGRAPH]
Common Name English
FLOXURIDINE [ORANGE BOOK]
Common Name English
FUDR
Code English
NSC-27640
Code English
FLOXURIDINE [USP-RS]
Common Name English
FLOXURIDINE [MART.]
Common Name English
FLOXURIDINE [MI]
Common Name English
FLOXURIDINE [INN]
Common Name English
FLOXURIDINE [VANDF]
Common Name English
FLOXURIDINE [HSDB]
Common Name English
FLOXURIDINE [USAN]
Common Name English
URIDINE, 2'-DEOXY-5-FLUORO-
Systematic Name English
FLOXURIDINE [USP]
Common Name English
FLUORODEOXYURIDINE
Systematic Name English
2'-DEOXY-5-FLUOROURIDINE
Systematic Name English
Classification Tree Code System Code
WHO-ATC L01BC09
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
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NDF-RT N0000007770
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NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
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LIVERTOX 417
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NCI_THESAURUS C1557
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NDF-RT N0000180853
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NDF-RT N0000007770
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FDA ORPHAN DRUG 195104
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
NDF-RT N0000007770
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
Code System Code Type Description
MERCK INDEX
M5414
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PRIMARY Merck Index
FDA UNII
039LU44I5M
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PRIMARY
CAS
50-91-9
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PRIMARY
MESH
D005467
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PRIMARY
PUBCHEM
5790
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PRIMARY
WIKIPEDIA
FLOXURIDINE
Created by admin on Fri Jun 25 20:56:14 UTC 2021 , Edited by admin on Fri Jun 25 20:56:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-072-5
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PRIMARY
IUPHAR
4801
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PRIMARY
DRUG CENTRAL
1184
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PRIMARY
DRUG BANK
DB00322
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PRIMARY
INN
2010
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PRIMARY
EPA CompTox
50-91-9
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PRIMARY
NCI_THESAURUS
C504
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PRIMARY
HSDB
3227
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PRIMARY
ChEMBL
CHEMBL917
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PRIMARY
RXCUI
4488
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PRIMARY RxNorm
USP_CATALOG
1271008
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PRIMARY USP-RS
EVMPD
SUB07659MIG
Created by admin on Fri Jun 25 20:56:13 UTC 2021 , Edited by admin on Fri Jun 25 20:56:13 UTC 2021
PRIMARY