Entry

D00584                      Drug

Name

Fluorouracil (JP18/USP/INN);
5-FU (TN);
Adrucil (TN);
Carac (TN);
Fluoroplex (TN)

Product

FLUOROPLEX (Almirall), EFUDEX (Bausch Health US), CARAC (Bausch Health US), TOLAK (HILL DERMACEUTICALS)

Generic

FLUOROURACIL (A-S Medication Solutions), FLUOROURACIL (Accord Healthcare), FLUOROURACIL (Accord Healthcare), FLUOROURACIL (Accord Healthcare), FLUOROURACIL (BluePoint Laboratories), FLUOROURACIL (BluePoint Laboratories), FLUOROURACIL (BluePoint Laboratories), FLUOROURACIL (BluePoint Laboratories), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Fresenius Kabi USA), FLUOROURACIL (Gland Pharma Limited), FLUOROURACIL (Gland Pharma Limited), FLUOROURACIL (Mayne Pharma), FLUOROURACIL CREAM (Mylan Pharmaceuticals), FLUOROURACIL (Mylan Pharmaceuticals), FLUOROURACIL (NORTHSTAR RX LLC), FLUOROURACIL (Sagent Pharmaceuticals), FLUOROURACIL (Taro Pharmaceuticals U.S.A.), FLUOROURACIL (Taro Pharmaceuticals U.S.A.), FLUOROURACIL (Xiromed LLC), FLUOROURACIL (Xiromed LLC)

Formula

C4H3FN2O2

Exact mass

130.0179

Mol weight

130.0772

Structure

Simcomp

Class

Antineoplastic
DG02018  Antimetabolite
  DG01958  Nucleic acid derivative, antineoplastic
   DG01935  Fluoropyrimidine antineoplastic
Metabolizing enzyme substrate
DG02984  DPYD substrate

Remark

Same as:

C07649

Therapeutic category:

4223

ATC code:

L01BC02

Chemical structure group:

DG00687

Product (DG00687):

D00584<JP/US>

Efficacy

Antineoplastic, Antimetabolite

Disease

Superficial basal cell carcinomas [DS:H00039]

Comment

Fluorouracil exerts its anticancer effects through inhibition of thymidylate synthase (TYMS) and misincorporation of its metabolites into RNA and DNA in place of uracil or thymine.

Target

TYMS [HSA:7298] [KO:K00560]

Pathway

hsa00240

Pyrimidine metabolism

hsa00670

One carbon pool by folate

Metabolism

Enzyme: DPYD [HSA:1806]

Interaction

Structure map

map07041

Antineoplastics - antimetabolic agents

Other map

map00983

Drug metabolism - other enzymes

Brite

Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01B ANTIMETABOLITES
    L01BC Pyrimidine analogues
     L01BC02 Fluorouracil
      D00584  Fluorouracil (JP18/USP/INN) <JP/US>
USP drug classification [BR:br08302]
Dermatological Agents
  Dermatological Agents, Other
   Warts and Actinic Keratosis Agents
    Fluorouracil
     D00584  Fluorouracil (JP18/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
4  Agents affecting cellular function
  42  Antineoplastics
   422  Antimetabolites
    4223  Fluorouracils
     D00584  Fluorouracil (JP18/USP/INN)
Drug groups [BR:br08330]
Antineoplastic
  DG02018  Antimetabolite
   DG01958  Nucleic acid derivative, antineoplastic
    DG01935  Fluoropyrimidine antineoplastic
     DG00687  Fluorouracil
      D00584  Fluorouracil
Metabolizing enzyme substrate
  DG02984  DPYD substrate
   DG00687  Fluorouracil
    D00584  Fluorouracil
Drug classes [BR:br08332]
Antineoplastic
  DG02018  Antimetabolite
   D00584  Fluorouracil
Target-based classification of drugs [BR:br08310]
Enzymes
  Transferases (EC2)
   Methyltransferases
    TYMS
     D00584  Fluorouracil (JP18/USP/INN) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
Chemicals
  D00584  Fluorouracil
Drug metabolizing enzymes and transporters [br08309.html]
Drug metabolizing enzymes
  D00584
Pharmacogenomic biomarkers [br08341.html]
Polymorphisms and mutations affecting drug response
  D00584
Prodrugs [br08324.html]
D00584
Drug groups [BR:br08330]
Antineoplastic
  DG02018  Antimetabolite
   DG01958  Nucleic acid derivative, antineoplastic
    DG01935  Fluoropyrimidine antineoplastic
     DG00687  Fluorouracil
Metabolizing enzyme substrate
  DG02984  DPYD substrate
   DG00687  Fluorouracil

Other DBs

CAS:

51-21-8

PubChem:

7847650

ChEBI:

46345

PDB-CCD:

URF[PDBj]

LigandBox:

D00584

NIKKAJI:

J4.489J

KCF data

ATOM        9
            1   C8y C    20.7957  -18.3013
            2   C8y C    19.5791  -19.0057
            3   N4x N    22.0068  -19.0057
            4   O5x O    20.7843  -16.8981
            5   C8x C    19.5791  -20.4030
            6   X   F    18.3622  -18.3013
            7   C8y C    22.0068  -20.4030
            8   N4x N    20.7957  -21.1017
            9   O5x O    23.2061  -21.1017
BOND        9
            1     1   2 1
            2     1   3 1
            3     1   4 2
            4     2   5 2
            5     2   6 1
            6     3   7 1
            7     5   8 1
            8     7   9 2
            9     7   8 1