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Details

Stereochemistry ACHIRAL
Molecular Formula C4H3N3O4
Molecular Weight 157.0843
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTERACIL

SMILES

OC(=O)C1=NC(=O)NC(=O)N1

InChI

InChIKey=RYYCJUAHISIHTL-UHFFFAOYSA-N
InChI=1S/C4H3N3O4/c8-2(9)1-5-3(10)7-4(11)6-1/h(H,8,9)(H2,5,6,7,10,11)

HIDE SMILES / InChI
Molecular Formula C4H3N3O4
Molecular Weight 157.0843
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://ec.europa.eu/health/documents/community-register/2011/2011031497328/anx_97328_en.pdf | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001242/WC500104417.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22162925

Oteracil is an adjunct to antineoplastic therapy, used in combination with Gimeracil and Tegafur. Gimeracil/oteracil/tegafur combination is approved for the gastric cancer treatment. Oteracil is an orotate phosphoribosyltransferase (OPRT) inhibitor that decreases the activity of 5-fluorocil (tegafur is a prodrug of 5-fluorocil) in normal gastrointestinal mucosa.

CNS Activity

Originator

Biltz, H.|Giesler, E.
2
Sources: DOI: 10.1002/cber.191304603122
Curator's Comment: Taiho Pharmaceutical http://adisinsight.springer.com/drugs/800004477

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
urate oxidase
2
Target ID: 114768.0
Gene Symbol: Uox
Inhibitor
8504
Inhibitor
8504
 3.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8583
S-1

Approved Use

Gimeracil/oteracil/tegafur combination is indicated in adults for the treatment of advanced gastric cancer when given in combination with cisplatin.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.21 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21143703/
11.8 mg/m² 2 times / day multiple, oral
dose: 11.8 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.93 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21143703/
11.8 mg/m² 2 times / day multiple, oral
dose: 11.8 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
55 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
210 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7.81 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21143703/
11.8 mg/m² 2 times / day multiple, oral
dose: 11.8 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.8 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21143703/
11.8 mg/m² 2 times / day multiple, oral
dose: 11.8 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
276 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1004 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17683513/
15.7 mg/m² single, oral
dose: 15.7 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered: TEGAFUR
TEGAFUR
 OTERACIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087

inhibitor
2252
inhibitor
2438
inhibitor
2507
inducer
24

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP1A1
132

CYP2A6
879

CYP2C8
1057

CYP2E1
1060

MATE1
415

CYP2C19
2057
CYP2C8
198

CYP2B6
669
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
1160
 likely
CYP2C8
1117
 likely
CYP3A4
2633
 likely
CYP1A1
272
 no
CYP1A2
2333
 no
CYP2A6
911
 no
CYP2C19
2141
 no
CYP2C8
1117
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP2E1
1146
 no
CYP3A4
2633
 no
MATE1
416
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Phase I study with pharmacokinetics of S-1 on an oral daily schedule for 28 days in patients with solid tumors.
2003-01
[Effectiveness of chemotherapy for outpatients with gastric or colorectal cancer].
2002-12
[Three cases of advanced and recurrent gastric cancer treated with paclitaxel after TS-1 administration].
2002-12
[A case of stage IV gastric carcinoma with lymph nodes metastases of the paraaorta responding markedly to TS-1].
2002-12
[A case of stomach cancer in which TS-1 neoadjuvant therapy was effective against multiple hepatic metastasis, allowing a radical cure A surgery].
2002-12
A role for uric acid in the progression of renal disease.
2002-12
[Adverse reactions to TS-1 for outpatients with recurrent head and neck cancer].
2002-11
[A case of recurrent advanced gastric cancer suggesting the efficacy of TS-1 and CDDP combination chemotherapy].
2002-11
Mild hyperuricemia induces glomerular hypertension in normal rats.
2002-11
High response rates in patients with pancreatic cancer using the novel oral fluoropyrimidine S-1.
2002-10-11
Hyperuricemia causes glomerular hypertrophy in the rat.
2002-10-10
Increased intestinal permeability correlates with gastrointestinal toxicity among formulations of the fluorouracil analogue tegafur in rats.
2002-10-05
[Effective use of TS-1 in a case of advanced gastric cancer, both in treating the tumor and in maintaining the patient's quality of life].
2002-10
[TS-1/CDDP therapy for advanced gastric cancer as neoadjuvant chemotherapy].
2002-10
[Complete response in a case of advanced scirrhous type 3 gastric cancer of with bulky N2 para-aorta lymph node metastases treated by combined chemotherapy of TS-1 and CDDP].
2002-10
Advanced gastric cancer with liver metastases successfully treated with S-1.
2002-10
Potassium oxonate modulation of 5-fluorouracil-induced myelotoxicity in murine and human colony forming assays of hematopoietic precursor cells.
2002-09-05
Peroxidase properties of extracellular superoxide dismutase: role of uric acid in modulating in vivo activity.
2002-09-01
[Every-other-day TS-1 administration for recurrent or non-curative advanced gastric carcinoma].
2002-09
[A case of advanced gastric cancer with invasion of pancreas effectively treated by combined chemotherapy of TS-1 and paclitaxel (TXL)].
2002-09
[Gastric cancer with multiple liver metastases, which responded significantly to oral administration of TS-1 following intravenous FMP therapy under hospitalization].
2002-09
[A pilot study of TS-1 combined with cisplatin in patients with advanced gastric cancer].
2002-09
[Long-term complete response to treatment with TS-1 in a patient with oropharyngeal squamous cell carcinoma].
2002-08
[Complete response in a case of recurrent gastric cancer treated with TS-1].
2002-08
[Two cases of stage IV type 4 gastric cancer with good response to TS-1].
2002-08
[A case of gastric cancer with paraaortic lymph node metastasis responding to TS-1/CDDP as neoadjuvant chemotherapy].
2002-08
[A case of gastric carcinoma with metastasis in a paraaortic lymph node that responded to TS-1/CDDP combination therapy, in which the patient was able to undergo extirpation with grade B curability].
2002-08
[A case of residual gastric cancer accompanied by esophageal invasion in which residual lesions were eradicated by half-dose administration of TS-1].
2002-08
[A new regimen for TS-1 therapy designed to minimize adverse reactions by introducing a one-week interval after each two-week dosing session].
2002-08
[The principles of cancer treatment--changes in chemotherapy].
2002-07
[Concentration of FT and CDHP and 5-FU in the ascites fluid of patient with peritoneal carcinomatosis after new anti-cancer drug TS-1 oral administration].
2002-07
[A novel combined chemotherapy using TS-1 and low-dose cisplatin against liver metastasis of gastric cancer].
2002-07
[Complete response in an elderly patient with advanced gastric scirrhous cancer treated with combined chemotherapy of TS-1 and CDDP].
2002-07
[Clinical study of individual TS-1 therapy for inoperable gastric cancer].
2002-07
Phase I and pharmacokinetic study of once daily oral administration of S-1 in patients with advanced cancer.
2002-07
Pharmacokinetic study of S-1, a novel oral fluorouracil antitumor agent in animal model and in patients with impaired renal function.
2002-07
Functional analysis and molecular model of the human urate transporter/channel, hUAT.
2002-07
Oral fluoropyrimidine anticancer drug TS-1 for gastric cancer patients with peritoneal dissemination.
2002-06-18
[Successful treatment of gastric cancer accompanied by multiple liver metastases with TS-1 followed by curative gastrectomy affiliation].
2002-06
[A case of unresectable gastric cancer complicated by a serious hepatic disorder and Virchow lymph node metastasis in which FP therapy and TS-1 administration were effective].
2002-06
[A case report of advanced gastric cancer responding to TS-1, a novel oral fluorouracil derivative].
2002-06
A novel mutant allele of the CYP2A6 gene (CYP2A6*11 ) found in a cancer patient who showed poor metabolic phenotype towards tegafur.
2002-06
[Evaluation of the efficacy of TS-1 for peritoneal dissemination of gastric cancer using a newly-developed animal model].
2002-05
[A case of gastric cancer with multiple liver metastases responding to TS-1].
2002-05
[Three cases of recurrent gastric cancer responding to TS-1 therapy following combination therapy with 5-fluorouracil, mitomycin C and cisplatin].
2002-05
[A case in which TS-1, an orally-administered 5-FU chemotherapeutic agent, showed marked effectiveness against scirrhous type gastric cancer with multiple organ metastases].
2002-05
Clinical studies of three oral prodrugs of 5-fluorouracil (capecitabine, UFT, S-1): a review.
2002
An oral anticancer drug, TS-1, enabled a patient with advanced gastric cancer with Virchow's metastasis to receive curative resection.
2002
Unusual survival for more than 2 years with peritoneal metastases of gastric cancer.
2002
Oral fluoropyrimidine treatment of colorectal cancer.
2001-08
Patents

Patents

CA2761243A1
2
CN104610180A
2
US9345767
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Each Teysuno capsule contains 15 mg tegafur, 4.35 mg gimeracil and 11.8 mg oteracil.
25 mg/m2 (expressed as tegafur content) twice daily, morning and evening, for 21 consecutive days followed by 7 days rest (1 treatment cycle). This treatment cycle is repeated every 4 weeks.
Route of Administration: Oral
In Vitro Use Guide
In vitro evaluation using primary cultures of human hepatocytes indicated that tegafur (0.7-70 uM), gimeracil (0.2-25 uM) and oteracil (0.04-4 uM) had little or no inductive effect on CYP1A2, CYP2B6 or CYP3A4/5 metabolic activities.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:46 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:46 GMT 2025
Record UNII
5VT6420TIG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXONIC ACID
MI  
Preferred Name English
OTERACIL
EMA EPAR   INN   WHO-DD  
INN  
Official Name English
OTERACIL [EMA EPAR]
Common Name English
oteracil [INN]
Common Name English
Oteracil [WHO-DD]
Common Name English
S-TRIAZINE-2,4-DIONE-6-CARBOXYLIC ACID
Common Name English
5-AZAOROTIC ACID
Common Name English
ALLANTOXANIC ACID
Common Name English
OXONIC ACID [MI]
Common Name English
1,4,5,6-TETRAHYDRO-4,6-DIOXO-S-TRIAZINE-2-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS TEYSUNI (AUTHORIZED: STOMACH NEOPLASMS)
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
NCI_THESAURUS C471
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
FDA ORPHAN DRUG 225006
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
Code System Code Type Description
FDA UNII
5VT6420TIG
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
PUBCHEM
4604
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
CAS
937-13-3
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
SMS_ID
100000115465
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
DRUG BANK
DB03209
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
MESH
D010094
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
CHEBI
30863
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
EVMPD
SUB30899
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
MERCK INDEX
m8316
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID9048358
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
INN
7729
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
NCI_THESAURUS
C76917
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
DRUG CENTRAL
2002
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
ChEMBL
CHEMBL181932
Created by admin on Mon Mar 31 18:24:46 GMT 2025 , Edited by admin on Mon Mar 31 18:24:46 GMT 2025
PRIMARY
Related Record Type Details
Structure of OTERACIL POTASSIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of OTERACIL
ACTIVE MOIETY
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