AZARIBINE

US Previously Marketed

First approved in 1975

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2469090 | https://www.ncbi.nlm.nih.gov/pubmed/14023746 | https://www.ncbi.nlm.nih.gov/pubmed/946586

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 The drug was withdrawn because it may cause life-threatening or fatal blood clots in the veins and arteries.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

Targets

Primary Target	Pharmacology	Condition	Potency
Orotidine phosphate decarboxylase 1 Target ID: CHEMBL4858 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2469090 \| https://www.ncbi.nlm.nih.gov/pubmed/14234861 \| https://www.ncbi.nlm.nih.gov/pubmed/14023746	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1243822 https://www.ncbi.nlm.nih.gov/pubmed/946586	Primary		Withdrawn	TRIAZURE Approved Use oral treatment of extensive severe recalcitrant psoriasis that had not adequately responded to topical forms of therapy.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
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14023746	Primary		Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
The treatment of psoriasis with azaribine.	1975	1243822
Treatment of psoriatic arthritis with azaribine.	1976 Jan-Feb	766762
Systemic chemotherapy for psoriasis: a national survey.	1976 Jul	947151
Chemotherapy of psoriasis: ten years of experience.	1976 Jun	946966

Patents

Sample Use Guides

In Vivo Use Guide

125 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

AZARIBINE

Official Name

English

Azaribine [WHO-DD]

Common Name

English

azaribine [INN]

Common Name

English

6-AZAURIDINE 2',3',5'-TRIACETATE

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