CARBAZERAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H24N4O4
Molecular Weight	360.4076
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC(=O)OC1CCN(CC1)C2=NN=CC3=CC(OC)=C(OC)C=C23

InChI

InChIKey=QJGVXJYGDBSPSJ-UHFFFAOYSA-N

InChI=1S/C18H24N4O4/c1-4-19-18(23)26-13-5-7-22(8-6-13)17-14-10-16(25-3)15(24-2)9-12(14)11-20-21-17/h9-11,13H,4-8H2,1-3H3,(H,19,23)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2478244 | https://www.ncbi.nlm.nih.gov/pubmed/6531941
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2825712

Carbazeran is a potent PDE-II and PDE-III inhibitor. Potently inhibits cAMP hydrolysis. Shows chronotropic and inotropic effect in vivo (EC50 = 100 μM, ionotropic effects, independent of adrenergic mechanisms). Carbazeran is a potent cardiac stimulant. Phosphodiesterase inhibition and elevation of intracellular cyclic AMP concentration may be involved, at least in part, in carbazeran`s cardiac effect.

Approval Year

Targets

Primary Target	Pharmacology	Potency
cAMP metabolic process 2 Target ID: GO:0046058 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2478244	Modulator 828	4.1 µM [IC50]
Phosphodiesterase 2A 7 Target ID: CHEMBL2652 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2478244 \| https://www.ncbi.nlm.nih.gov/pubmed/2825712	Inhibitor 8297	4.0 µM [IC50]
Phosphodiesterase 3 60 Target ID: CHEMBL2094125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2478244 \| https://www.ncbi.nlm.nih.gov/pubmed/2825712	Inhibitor 8297	6.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart diseases 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6531941	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

When administered orally to the dog at a dose level of 5mg/kg the compound elicits a marked inotropic response, causing a 60% increase in the maximum rate of pressure change during systole measured via an indwelling pressure transducer in the left ventricle. When administered by i.v. infusion to human subjects at dose levels up to 1.28 mg/kg a dose-related increase in myocardial contractility was observed, judged from changes in systolic time intervals. However, when human volunteers received single oral doses of up to 350mg (i.e. approximately 5 mg/kg) no effects on the heart or circulation were observed.

Route of Administration: Other

In Vitro Use Guide

Carbazeran (9.1 x 10(-6) M-1.2 x 10(-3) M) produced concentration-dependent positive inotropic responses of papillary muscle preparations from rabbit heart.

Name

Type

Language

CARBAZERAN

Official Name

English

UK-31557

Code

English

1-(6,7-Dimethoxy-1-phthalazinyl)-4-piperidyl ethylcarbamate

Systematic Name

English

UK-31,557

Code

English

CARBAMIC ACID, ETHYL-, 1-(6,7-DIMETHOXY-1-PHTHALAZINYL)-4-PIPERIDINYL ESTER

Common Name

English

carbazeran [INN]

Common Name

English

CARBAZERAN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744