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CI928

Names

[ CAS No. ]:
82768-85-2

[ Name ]:
CI928

[Synonym ]:
(3S)-2-[(S)-2-[[(S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
quinapril diacid
ci928
(3s-(2(r*(r*)),3r*))-yl)amino)-1-oxopropyl)
(3S)-2-[(S)-2-[[(S)-1-Carboxy-3-phenylpropyl]amino]propionyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
[3S-[2[R*(R*)],3R*]]-2[2-[[1-(carboxy)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
CI-92
3-Isoquinolinecarboxylic acid,2-(2S)-2-(1S)-1-carboxy-3-phenylpropylamino-1-oxopropyl-1,2,3,4-tetrahydro-,(3S)
3-isoquinolinecarboxylicacid,1,2,3,4-tetrahydro-2-(2-((1-carboxy-3-phenylprop
quinaprilate
(3S)-2-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid

Biological Activity

[Description]:

Quinaprilat is an orally active non-mercapto Angiotensin Converting Enzyme (ACE) inhibitor, the active metabolite of Quinapril. Quinaprilat specifically blocks the conversion of angiotensin I to the vasoconstrictor angiotensin II and inhibits the degradation of bradykinin. Quinaprilat acts as anti-hypertensive agent and vasodilator[1][2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease
Signaling Pathways >> Metabolic Enzyme/Protease >> Angiotensin-converting Enzyme (ACE)

[In Vitro]

Quinaprilat (5 μM) mediates the interaction of organic anion transporter 3 (hOAT3) which can promote renal active secretion of quinapril that increases uptake of quinaprilat to 25-fold in HEK293 cells and hOAT3 affinity Km for quinaprilat is 13.4 μM[1]. Quinaprilat (100 nM, 20 min) can inhibit the activity of protein kinase C (PKC) by activing the B1 receptor resulting in the release of NO in human lung microvascular endothelial (HLMVE) cells[2].

[References]

[1]. Haodan Yuan, et al. Renal organic anion transporter-mediated drug-drug interaction between gemcabene and quinapril. J Pharmacol Exp Ther. 2009 Jul;330(1):191-7. doi: 10.1124/jpet.108.149476. Epub 2009 Apr 6.

[2]. Sinisa Stanisavljevic, et al. Angiotensin I-converting enzyme inhibitors block protein kinase C epsilon by activating bradykinin B1 receptors in human endothelial cells. J Pharmacol Exp Ther. 2006 Mar;316(3):1153-8.

Chemical & Physical Properties

[ Density]:
1.289 g/cm3

[ Boiling Point ]:
674.5ºC at 760 mmHg

[ Melting Point ]:
166-168ºC

[ Molecular Formula ]:
C23H26N2O5

[ Molecular Weight ]:
410.46300

[ Flash Point ]:
361.7ºC

[ Exact Mass ]:
410.18400

[ PSA ]:
106.94000

[ LogP ]:
2.41740

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NW7160900
CHEMICAL NAME :
3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-2-(2-((1-carboxy-3-phenylpropyl)am ino)-1- oxopropyl)-, (3S-(2(R*(R*)),3R*))-
CAS REGISTRY NUMBER :
82768-85-2
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C23-H26-N2-O5
MOLECULAR WEIGHT :
410.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream