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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H17N3O.ClH
Molecular Weight 315.797
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VERUBULIN HYDROCHLORIDE

SMILES

Cl.COC1=CC=C(C=C1)N(C)C2=NC(C)=NC3=CC=CC=C23

InChI

InChIKey=VYUWDIKZJLOZJL-UHFFFAOYSA-N
InChI=1S/C17H17N3O.ClH/c1-12-18-16-7-5-4-6-15(16)17(19-12)20(2)13-8-10-14(21-3)11-9-13;/h4-11H,1-3H3;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C17H17N3O
Molecular Weight 279.3364
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://adisinsight.springer.com/drugs/800022153 | http://www.prnewswire.com/news-releases/new-data-suggests-improved-tumor-response-for-the-combination-of-azixa-and-immune-checkpoint-inhibitors-in-the-treatment-of-cancer-300291030.html

Veribulin is a novel microtubule destabilizer that both functions as a potent cytotoxin and acts as a vascular disrupting agent (VDA). It binds to the same (or nearby) sites on β-tubulin as colchicine. It is capable of evading multidrug resistance pumps and, thus, achieves high CNS concentrations. It is efficacious in multiple xenograft models without CNS toxicity. Veribulin had previously demonstrated pre-clinical and clinical activity in multiple tumor types. Veribulin is in phase II clinical trial for the treatment of Glioblastoma and Malignant melanoma.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21.3 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.3 mg/m² 1 times / week multiple, intravenous
dose: 3.3 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
62 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
4.5 mg/m² 1 times / week multiple, intravenous
dose: 4.5 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
30.7 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.9 mg/m² 1 times / week multiple, intravenous
dose: 3.9 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
116.8 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.3 mg/m² 1 times / week multiple, intravenous
dose: 3.3 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
183.6 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
4.5 mg/m² 1 times / week multiple, intravenous
dose: 4.5 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
139.3 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.9 mg/m² 1 times / week multiple, intravenous
dose: 3.9 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.3 mg/m² 1 times / week multiple, intravenous
dose: 3.3 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
4.5 mg/m² 1 times / week multiple, intravenous
dose: 4.5 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21159616
3.9 mg/m² 1 times / week multiple, intravenous
dose: 3.9 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
VERUBULIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4.5 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 4.5 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 4.5 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
DLT: Myocardial infarction...
Dose limiting toxicities:
Myocardial infarction (grade 3, 14.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
3.3 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 3.3 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 3.3 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
3.3 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 3.3 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 3.3 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/24740196
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/24740196
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction (grade 4, 3.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24740196
3.9 mg/m2 1 times / week multiple, intravenous
Studied dose
Dose: 3.9 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 3.9 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
DLT: Myocardial infarction...
Dose limiting toxicities:
Myocardial infarction (grade 3, 16.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
AEs

AEs

AESignificanceDosePopulation
Myocardial infarction grade 3, 14.3%
DLT
4.5 mg/m2 1 times / week multiple, intravenous
Highest studied dose
Dose: 4.5 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 4.5 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
Myocardial infarction grade 4, 3.2%
Disc. AE
3.3 mg/m2 1 times / week multiple, intravenous
MTD
Dose: 3.3 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 3.3 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/24740196
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/24740196
Myocardial infarction grade 3, 16.7%
DLT
3.9 mg/m2 1 times / week multiple, intravenous
Studied dose
Dose: 3.9 mg/m2, 1 times / week
Route: intravenous
Route: multiple
Dose: 3.9 mg/m2, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/21159616
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MRP1
113

P-gp
2052

BCRP
697

CYP2C19
1119

CYP1A2
1197
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
697
 no
MRP1
113
 no
P-gp
2052
 no
CYP1A2
1197
 yes
CYP2C19
1119
 yes
CYP3A4
1946
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Discovery of N-methyl-4-(4-methoxyanilino)quinazolines as potent apoptosis inducers. Structure-activity relationship of the quinazoline ring.
2010-04-01
Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration.
2009-04-23
Patents

Patents

20050137213
2

Sample Use Guides

In Vivo Use Guide
Verubulin was administered at 3.3 mg/m(2) as a 2-h intravenous infusion once weekly for 3 consecutive weeks in a 4-week cycle.
Route of Administration: Intravenous
In Vitro Use Guide
Verubulin was highly active in HCT116 and SNU-398 cells with EC50 values of 3 nM and 2 nM, respectively, similar to its high activity in T47D cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:10:51 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:51 GMT 2025
Record UNII
33380QZ0QW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZIXA
Preferred Name English
VERUBULIN HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
VERUBULIN HYDROCHLORIDE [USAN]
Common Name English
4-QUINAZOLINAMINE, N-(4-METHOXYPHENYL)-N,2-DIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
VERUBULIN HCL
Common Name English
N-(4-Methoxyphenyl)-N,2-dimethylquinazolin-4-amine hydrochloride
Systematic Name English
Verubulin hydrochloride [WHO-DD]
Common Name English
MPC-6827
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 290809
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
NCI_THESAURUS C25974
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
Code System Code Type Description
PUBCHEM
11638255
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
USAN
UU-21
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID80238682
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
CAS
917369-31-4
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
NCI_THESAURUS
C64782
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL492399
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
MESH
C522974
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
FDA UNII
33380QZ0QW
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
SMS_ID
300000044542
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
DRUG BANK
DBSALT002603
Created by admin on Mon Mar 31 18:10:51 GMT 2025 , Edited by admin on Mon Mar 31 18:10:51 GMT 2025
PRIMARY
Related Record Type Details
Structure of VERUBULIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of VERUBULIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
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