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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H17N3O9
Molecular Weight 371.2995
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZARIBINE

SMILES

CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H]1OC(C)=O)N2N=CC(=O)NC2=O

InChI

InChIKey=QQOBRRFOVWGIMD-OJAKKHQRSA-N
InChI=1S/C14H17N3O9/c1-6(18)23-5-9-11(24-7(2)19)12(25-8(3)20)13(26-9)17-14(22)16-10(21)4-15-17/h4,9,11-13H,5H2,1-3H3,(H,16,21,22)/t9-,11-,12-,13-/m1/s1

HIDE SMILES / InChI
Molecular Formula C14H17N3O9
Molecular Weight 371.2995
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Azaribine (2′, 3′, 5′-triacetyl-6-azauridine) is the orally absorbable triacetylated derivative of the pyrimidine analog 6-azauridine. Ribonucleoside of 6-azauracil, which can be derived in the tissues by the deacetylation of azaribine, has been shown, after its intracellular conversion to 6-azauridine-5'-monophosphate, to serve as an inhibitor of the activity of a key enzyme, orotidine-5'-monophosphate (OMP) decarboxylase, critically concerned with the biosynthesis de novo of pyrimidines essential for the formation of nucleic acids. Azaribine exerts antineoplastic action. In 1975 azaribine was approved for the treatment of psoriasis. The drug was withdrawn because it may cause life-threatening or fatal blood clots in the veins and arteries.

Originator

Approval Year

1975
63
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
TRIAZURE

Approved Use

oral treatment of extensive severe recalcitrant psoriasis that had not adequately responded to topical forms of therapy.

Launch Date

1975
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
270 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 270 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 270 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14234861
unhealthy, 30-80 years
n = 10
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 30-80 years
Sex: M+F
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/14234861
Disc. AE: Anemia...
AEs leading to
discontinuation/dose reduction:
Anemia
Sources:
https://pubmed.ncbi.nlm.nih.gov/14234861
125 mg/kg 1 times / day multiple, oral
Dose: 125 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 125 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Disc. AE: Anemia, Cutaneous hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Anemia (severe, 2 patients)
Cutaneous hypersensitivity (3 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
150 mg/kg 1 times / day multiple, oral
Dose: 150 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Other AEs: Arterial thromboembolism...
Other AEs:
Arterial thromboembolism
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
163 mg/kg 1 times / day multiple, oral
Dose: 163 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 163 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Disc. AE: Myoclonic seizure NOS...
AEs leading to
discontinuation/dose reduction:
Myoclonic seizure NOS (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
AEs

AEs

AESignificanceDosePopulation
Anemia Disc. AE
270 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 270 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 270 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14234861
unhealthy, 30-80 years
n = 10
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 30-80 years
Sex: M+F
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/14234861
Cutaneous hypersensitivity 3 patients
Disc. AE
125 mg/kg 1 times / day multiple, oral
Dose: 125 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 125 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Anemia severe, 2 patients
Disc. AE
125 mg/kg 1 times / day multiple, oral
Dose: 125 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 125 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Arterial thromboembolism
150 mg/kg 1 times / day multiple, oral
Dose: 150 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Myoclonic seizure NOS 1 patient
Disc. AE
163 mg/kg 1 times / day multiple, oral
Dose: 163 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 163 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
unhealthy, 47 years (range: 16-73 years)
n = 25
Health Status: unhealthy
Condition: PSORIASIS
Age Group: 47 years (range: 16-73 years)
Sex: M+F
Population Size: 25
Sources:
https://pubmed.ncbi.nlm.nih.gov/1243822
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:88272
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:88272
MolPort
MolPort-003-925-981
https://www.molport.com/shop/molecule-link/MolPort-003-925-981
ZINC
ZINC000004214908
http://zinc15.docking.org/substances/ZINC000004214908
eMolecules
478405
https://www.emolecules.com/cgi-bin/more?vid=478405
PubMed

PubMed

TitleDatePubMed
The treatment of psoriasis with azaribine.
1975
Double-blind controlled crossover high-dose study of Azaribine in psoriasis.
1975 Feb
Anemia of azaribine in the treatment of psoriasis.
1976 Dec
Systemic chemotherapy for psoriasis: a national survey.
1976 Jul
Chemotherapy of psoriasis: ten years of experience.
1976 Jun
Patents

Patents

US5023083A
1

Sample Use Guides

In Vivo Use Guide
125 mg/kg/day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:05:09 GMT 2023
Edited
by admin
on Sat Dec 16 16:05:09 GMT 2023
Record UNII
K1U80DO9EB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZARIBINE
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
Azaribine [WHO-DD]
Common Name English
azaribine [INN]
Common Name English
6-AZAURIDINE 2',3',5'-TRIACETATE
MI  
Systematic Name English
TRIAZURE
Brand Name English
AZARIBINE [USAN]
Common Name English
1,2,4-TRIAZINE-3,5(2H,4H)-DIONE, 2-(2,3,5-TRI-O-ACETYL-.BETA.-D-RIBOFURANOSYL)-
Common Name English
CB 304
Code English
2-.BETA.-D-RIBOFURANOSYL-AS-TRIAZINE-3,5(2H,4H)-DIONE 2',3',5'-TRIACETATE
Common Name English
AZARIBINE [MART.]
Common Name English
CB-304
Code English
NSC-67239
Code English
6-AZAURIDINE 2',3',5'-TRIACETATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2170
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
NCI_THESAURUS C1557
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
Code System Code Type Description
INN
2502
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
FDA UNII
K1U80DO9EB
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
DRUG CENTRAL
27
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
MERCK INDEX
m2167
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID1022635
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
NCI_THESAURUS
C1008
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
CHEBI
88272
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
NSC
67239
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
WIKIPEDIA
Azaribine
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-515-6
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL515914
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
EVMPD
SUB05640MIG
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
CAS
2169-64-4
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
MESH
C100231
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
SMS_ID
100000086077
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
PUBCHEM
16574
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
Related Record Type Details
Structure of AZARIBINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966