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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H27N5O4.ClH
Molecular Weight 473.953
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLAZOSIN HYDROCHLORIDE

SMILES

Cl.[H][C@]12CCCC[C@@]1([H])N(CCN2C(=O)C3=CC=CO3)C4=NC(N)=C5C=C(OC)C(OC)=CC5=N4

InChI

InChIKey=SKDIDWRQDBIQBS-MCJVGQIASA-N
InChI=1S/C23H27N5O4.ClH/c1-30-19-12-14-15(13-20(19)31-2)25-23(26-21(14)24)28-10-9-27(16-6-3-4-7-17(16)28)22(29)18-8-5-11-32-18;/h5,8,11-13,16-17H,3-4,6-7,9-10H2,1-2H3,(H2,24,25,26);1H/t16-,17+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C23H27N5O4
Molecular Weight 437.4916
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18037913 | https://www.ncbi.nlm.nih.gov/pubmed/15598431

CYCLAZOSIN HYDROCHLORIDE is a quinazoline derivative pharmacologically characterized as putative a1B-adrenoceptor antagonist.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.24 nM [Ki]
12.3 nM [Ki]
0.135 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis and biological profile of the enantiomers of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin- 1-yl]furan-2-ylmethanone (cyclazosin), a potent competitive alpha 1B- adrenoceptor antagonist.
1996 Nov 8
Synthesis and alpha(1)-adrenoceptor antagonist activity of derivatives and isosters of the furan portion of (+)-cyclazosin.
2007 Mar 15
Patents

Sample Use Guides

Male C-57 WT mice (22–35 g) were injected s.c. with the putative a1B-adrenoceptor antagonist cyclazosin (1.0mg/kg). Cyclazosin was administered 30 min prior to the injection of vehicle (1 ml/kg) or MDMA (20mg/kg). The putative a1B-adrenoceptor antagonist cyclazosin (1mg/kg) in vehicle experiments did not significantly alter the body temperature when compared to vehicle group. The pretreatment of mice with cyclazosin significantly altered the effect of MDMA on core body temperature
Route of Administration: Topical
Sections of the abdominal aorta, obtained from adult female New Zealand rabbits, were treated with agonists and antagonists of adrenergic receptors. Administration of cyclazosin at a dose of 0.002 μM caused a decrease in the muscle tonus of -0.49 ± 0.10 mN. After blockade of the α1B-adrenergic receptor by 0.02 mkM cyclazosin, the administration of 0.05 μM phenylephrine resulted in an increase of the aortic muscle tonus of 1.49 ± 0.14 mN.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:03:54 GMT 2023
Edited
by admin
on Sat Dec 16 09:03:54 GMT 2023
Record UNII
RLN802138L
Record Status Validated (UNII)
Record Version
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Name Type Language
CYCLAZOSIN HYDROCHLORIDE
Common Name English
METHANONE, ((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)OCTAHYDRO-1(2H)-QUINOXALINYL)-2-FURANYL-, HYDROCHLORIDE (1:1), REL-
Systematic Name English
QUINOXALINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-(2-FURANYLCARBONYL)DECAHYDRO-, MONOHYDROCHLORIDE, CIS-
Common Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-2,3,4A,5,6,7,8,8A-OCTAHYDROQUINOXALIN-1-YL)-(FURAN-2-YL)METHANONE HYDROCHLORIDE
Systematic Name English
QUINOXALINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-(2-FURANYLCARBONYL)DECAHYDRO-, MONOHYDROCHLORIDE, (4AR,8AS)-REL-
Systematic Name English
(+)-CYCLAZOSIN HYDROCHLORIDE
Common Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)OCTAHYDRO-1(2H)-QUINOXALINYL)(2-FURYL)METHANONE HYDROCHLORIDE (1:1)
Systematic Name English
CYCLAZOSIN HCL
Common Name English
((4AR,8AS)-4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)OCTAHYDROQUINOXALIN-1(2H)-YL)(2-FURYL)METHANONE HYDROCHLORIDE
Systematic Name English
(4-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-CIS-OCTAHYDROQUINOXALIN-L-YL)FURAN-2-YLMETHANONE HYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
9869475
Created by admin on Sat Dec 16 09:03:54 GMT 2023 , Edited by admin on Sat Dec 16 09:03:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID1040453
Created by admin on Sat Dec 16 09:03:54 GMT 2023 , Edited by admin on Sat Dec 16 09:03:54 GMT 2023
PRIMARY
CAS
146929-33-1
Created by admin on Sat Dec 16 09:03:54 GMT 2023 , Edited by admin on Sat Dec 16 09:03:54 GMT 2023
PRIMARY
FDA UNII
RLN802138L
Created by admin on Sat Dec 16 09:03:54 GMT 2023 , Edited by admin on Sat Dec 16 09:03:54 GMT 2023
PRIMARY
CAS
184033-31-6
Created by admin on Sat Dec 16 09:03:54 GMT 2023 , Edited by admin on Sat Dec 16 09:03:54 GMT 2023
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE