DIHYDROURACIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H6N2O2
Molecular Weight	114.1026
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CCNC(=O)N1

InChI

InChIKey=OIVLITBTBDPEFK-UHFFFAOYSA-N

InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

HIDE SMILES / InChI

Molecular Formula	C4H6N2O2
Molecular Weight	114.1026
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase.	2002-07-18	12084458
Simple liquid chromatographic method for the determination of uracil and dihydrouracil plasma levels: a potential pretreatment predictor of 5-fluorouracil toxicity.	2002-07-15	12076692
A high-throughput denaturing high-performance liquid chromatography method for the identification of variant alleles associated with dihydropyrimidine dehydrogenase deficiency.	2002-07-01	12069415
Intratumoral dihydropyrimidine dehydrogenase messenger RNA level reflects tumor progression in human colorectal cancer.	2002-07	12095978
[Dihydropyrimidine dehydrogenase and thymidylate synthase in colon carcinoma].	2002-06	12090040
Allele and genotype frequencies of polymorphic cytochromes P450 (CYP2C9, CYP2C19, CYP2E1) and dihydropyrimidine dehydrogenase (DPYD) in the Egyptian population.	2002-06	12047484
Enhancement of the antitumour activity of 5-fluorouracil (5-FU) by inhibiting dihydropyrimidine dehydrogenase activity (DPD) using 5-chloro-2,4-dihydroxypyridine (CDHP) in human tumour cells.	2002-06	12044515
Association of time to recurrence with thymidylate synthase and dihydropyrimidine dehydrogenase mRNA expression in stage II and III colorectal cancer.	2002-05-23	12022983
Thymidine kinase in epithelial ovarian cancer: relationship with the other pyrimidine pathway enzymes.	2002-05-20	11992400
Roles of thymidylate synthase and dihydropyrimidine dehydrogenase in tumor progression and sensitivity to 5-fluorouracil in human gastric cancer.	2002-05-17	12014648
Novel disease-causing mutations in the dihydropyrimidine dehydrogenase gene interpreted by analysis of the three-dimensional protein structure.	2002-05-15	11988088
Porous graphitic carbon shows promise for the rapid screening partial DPD deficiency in lymphocyte dihydropyrimidine dehydrogenase in Chinese, Indian and Malay in Singapore by using semi-automated HPLC-radioassay.	2002-05	12074825
[The antitumor activity of DPD inhibitory-fluoropyrimidine (DIF) and non-DIF alone or in combination with paclitaxel against orthotopically implanted human breast cancer].	2002-05	12040690
Correspondence re: Raida, M. et al., prevalence of a common point mutation in the dihydropyrimidine dehydrogenase (DPD) gene within the 5'-splice donor site of intron 14 in patients with severe 5-fluorouracil (5-FU)-related toxicity compared with controls.	2002-05	12006555
Impact of two weekly schedules of oral eniluracil given with fluorouracil and leucovorin on the duration of dihydropyrimidine dehydrogenase inhibition.	2002-05	12006517
Estimation of the effect of food on the disposition of oral 5-fluorouracil in combination with eniluracil.	2002-05	11976834
Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase.	2002-05	11961132
How to calculate the dose of chemotherapy.	2002-04-22	11953888
Thymidine phosphorylase and dihydropyrimidine dehydrogenase levels in primary colorectal cancer show a relationship to clinical effects of 5'-deoxy-5-fluorouridine as adjuvant chemotherapy.	2002-04-17	11956613
Crystal structure of the productive ternary complex of dihydropyrimidine dehydrogenase with NADPH and 5-iodouracil. Implications for mechanism of inhibition and electron transfer.	2002-04-12	11796730
Reduced 5-FU clearance in a patient with low DPD activity due to heterozygosity for a mutant allele of the DPYD gene.	2002-04-08	11953843
Dihydropyrimidine dehydrogenase-related enzymes predict efficacy and adverse reactions of UFT1+cisplatin neoadjuvant chemotherapy for gastric cancer.	2002-04	11984087
Dihydropyrimidine dehydrogenase expression in preoperative biopsy and surgically resected specimens of gastric carcinoma.	2002-04	11914904
Measurement of endogenous uracil and dihydrouracil in plasma and urine of normal subjects by liquid chromatography-tandem mass spectrometry.	2002-03-25	11936689
Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors.	2002-03-15	11896120
[Detection of DPD-exon-14 skipping before 5-fluorouracil treatment?].	2002-03-01	11870563
A conserved family of Saccharomyces cerevisiae synthases effects dihydrouridine modification of tRNA.	2002-03	12003496
[Correlation between clinical pathophysiologic factors and expression of orotate phosphoribosyl transferase (OPRT), thymidylate synthase (TS), and dihydropyrimidine dehydrogenase (DPD) in colorectal cancer].	2002-03	11915731
Profound dihydropyrimidine dehydrogenase deficiency resulting from a novel compound heterozygote genotype.	2002-03	11895907
A comparative analysis of translated dihydropyrimidine dehydrogenase cDNA; conservation of functional domains and relevance to genetic polymorphisms.	2002-03	11875367
Mechanism(s) of antitumor action in protracted infusion of low dose 5-fluorouracil and cisplatin in gastric carcinoma.	2002-03	11836567
Prognostic significance of a combination of thymidylate synthase and dihydropyrimidine dehydrogenase activities in grades 1 and 2 superficial bladder cancer.	2002-02-12	11836594
Influence of liver dysfunction on dihydropyrimidine dehydrogenase activity in peripheral blood mononuclear cells.	2002-02	11890111
[Dihydropyrimidine dehydrogenase expression in gastric cancer using anti-human dihydropyrimidine dehydrogenase monoclonal antibody].	2002-02	11865631
Circadian variation of dihydropyrimidine dehydrogenase mRNA expression in leukocytes and serum cortisol levels in patients with advanced gastrointestinal carcinomas compared to healthy controls.	2002-02	11862480
Prognostic significance of dihydropyrimidine dehydrogenase expression in breast cancer.	2002-01-21	11870510
Alternative nucleotide incision repair pathway for oxidative DNA damage.	2002-01-10	11805838
Clinical pharmacokinetics of 5-fluorouracil with consideration of chronopharmacokinetics.	2002-01	11962674
[A complete response after neoadjuvant chemotherapy for advanced gastric cancer with esophageal invasion].	2002-01	11816467
Biopsy specimen microvessel density is a useful prognostic marker in patients with T(2-4)M(0) esophageal cancer treated with chemoradiotherapy.	2002-01	11801548
Dihydropyrimidine dehydrogenase enzyme deficiency: clinical and genetic assessment of prevalence in Turkish cancer patients.	2002	12025228
Thymidine phosphorylase and dihydropyrimidine dehydrogenase in bladder cancer.	2002	11834904
DNA polymerase beta is the major dRP lyase involved in repair of oxidative base lesions in DNA by mammalian cell extracts.	2001-12-03	11726527
Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level.	2001-12	11804209
[Activities of thymidylate synthase and dihydropyrimidine dehydrogenase in patients with colorectal cancer].	2001-12	11791381
Retroviral transduction of human dihydropyrimidine dehydrogenase cDNA confers resistance to 5-fluorouracil in murine hematopoietic progenitor cells and human CD34+-enriched peripheral blood progenitor cells.	2001-12	11781659
Thymidylate synthase and dihydropyrimidine dehydrogenase activities in non-small cell lung cancer tissues: relationship with in vitro sensitivity to 5-fluorouracil.	2001-12	11714538
Synthesis and evaluation of N-acyl-2-(5-fluorouracil-1-yl)-D,L-glycine as a colon-specific prodrug of 5-fluorouracil.	2001-11	11745736
[Dihydropyrimidine dehydrogenase activity in urothelial cancer--influence of UFT administration on DPD activity].	2001-11	11729480
Therapy of disseminated colorectal cancer: the emerging role of intratumoral molecular biology.	2001	11718526

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:37:23 GMT 2025` Edited by `admin` on `Mon Mar 31 21:37:23 GMT 2025`
Record UNII	016FR52RU5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-11867

Preferred Name

English

DIHYDROURACIL

Systematic Name

English

5,6-DIHYDROURACIL

Systematic Name

English

HYDROURACIL

Common Name

English

5,6-DIHYDRO-2,4(1H,3H)-PYRIMIDINEDIONE

Systematic Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, DIHYDRO-

Systematic Name

English

Classification Tree Code System Code

LOINC

79685-4