Ramipril

Modify Date: 2024-01-02 22:37:05

Ramipril Structure
Ramipril structure
 Common Name Ramipril
CAS Number 87333-19-5 Molecular Weight 416.511
Density 1.2±0.1 g/cm3 Boiling Point 616.2±55.0 °C at 760 mmHg
Molecular Formula C23H32N2O5 Melting Point 106-108°C
MSDS Chinese USA Flash Point 326.4±31.5 °C

 Use of Ramipril


Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM.Target: ACERamipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM [1]. Ramipril enhances the activity of ACE-associated CK2 and the phosphorylation of ACE Ser1270 in cultured endothelial cells, but is unable to activate JNK or stimulate the nuclear accumulation of c-Jun in endothelial cells expressing a S1270A ACE mutant or in ACE-deficient cells. Prolonged Ramipril treatment increases ACE expression in primary cultures of human endothelial cells and in vivo (mouse lung), which can be prevented by pretreatment with the JNK inhibitor SP600125 [2].Chronic in vivo administration of Ramipril to rats at a dosage that has similar hypotensive effects in vitro HUVECs significantly reduces the rate of LPS-induced apoptosis compared to the other ACE inhibitors, which contrasts with the apoptosis effect in vitro [3]. Ramipril inhibits systolic blood pressure (SBP) with IC50 of 1.97 mg/kg in spontaneously hypertensive rats (SHR). When in combination with AT1-receptor blockade by candesartan-cilexetil increases SBP reduction synergistically rather than additively [4].

 Names

Name ramipril
Synonym More Synonyms

 Ramipril Biological Activity

Description Ramipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM.Target: ACERamipril is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 5 nM [1]. Ramipril enhances the activity of ACE-associated CK2 and the phosphorylation of ACE Ser1270 in cultured endothelial cells, but is unable to activate JNK or stimulate the nuclear accumulation of c-Jun in endothelial cells expressing a S1270A ACE mutant or in ACE-deficient cells. Prolonged Ramipril treatment increases ACE expression in primary cultures of human endothelial cells and in vivo (mouse lung), which can be prevented by pretreatment with the JNK inhibitor SP600125 [2].Chronic in vivo administration of Ramipril to rats at a dosage that has similar hypotensive effects in vitro HUVECs significantly reduces the rate of LPS-induced apoptosis compared to the other ACE inhibitors, which contrasts with the apoptosis effect in vitro [3]. Ramipril inhibits systolic blood pressure (SBP) with IC50 of 1.97 mg/kg in spontaneously hypertensive rats (SHR). When in combination with AT1-receptor blockade by candesartan-cilexetil increases SBP reduction synergistically rather than additively [4].
Related Catalog
References

[1]. Raasch, W., et al., Combined blockade of AT1-receptors and ACE synergistically potentiates antihypertensive effects in SHR. J Hypertens, 2004. 22(3): p. 611-8.

[2]. Stevens, B.R., M.I. Phillips, and A. Fernandez, Ramipril inhibition of rabbit (Oryctolagus cuniculus) small intestinal brush border membrane angiotensin converting enzyme. Comp Biochem Physiol C, 1988. 91(2): p. 493-7.

[3]. Kohlstedt, K., et al., Angiotensin-converting enzyme is involved in outside-in signaling in endothelial cells. Circ Res, 2004. 94(1): p. 60-7.

[4]. Ceconi, C., et al., Differences in the effect of angiotensin-converting enzyme inhibitors on the rate of endothelial cell apoptosis: in vitro and in vivo studies. Cardiovasc Drugs Ther, 2007. 21(6): p. 423-9.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 616.2±55.0 °C at 760 mmHg
Melting Point 106-108°C
Molecular Formula C23H32N2O5
Molecular Weight 416.511
Flash Point 326.4±31.5 °C
Exact Mass 416.231110
PSA 95.94000
LogP 3.41
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.556
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GY5879600
CHEMICAL NAME :
Cyclopenta(b)pyrrole-2-carboxylic acid, octahydro-1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl) amino)-1-oxopropyl), (2S-(1(R*(R*)),2-alpha,3a-beta,6a-beta))-
CAS REGISTRY NUMBER :
87333-19-5
LAST UPDATED :
199610
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C23-H32-N2-O5
MOLECULAR WEIGHT :
416.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 38,14,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCDREP New Cardiovascular Drugs. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) 1985- Volume(issue)/page/year: 5,57,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10048 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 38,14,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCDREP New Cardiovascular Drugs. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) 1985- Volume(issue)/page/year: 5,57,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 38,14,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCDREP New Cardiovascular Drugs. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) 1985- Volume(issue)/page/year: 5,57,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 gm/kg/90D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in erythrocyte (RBC) count
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 38,14,1988
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
91 gm/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
NCDREP New Cardiovascular Drugs. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) 1985- Volume(issue)/page/year: 5,57,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
58240 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
NCDREP New Cardiovascular Drugs. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) 1985- Volume(issue)/page/year: 5,57,1987

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/38
Safety Phrases S26-S37/39
RIDADR NONH for all modes of transport
RTECS GY5879600
HS Code 3004909090

 Synthetic Route

2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER structure

2-[N-[(S)-1-ETH...

CAS#:87269-88-3

~95%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Malakondaiah, Golla China; Gurav; Reddy, Lekkala Amarnath; Babu, Karrothu Srihari; Bhaskar, Bolugoddu Vijaya; Reddy, Padi Pratap; Bhattacharya, Apurba; Anand, Ramasamy Vijaya Synthetic Communications, 2008 , vol. 38, # 11 p. 1737 - 1744
N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride structure

N-[(S)-1-carbet...

CAS#:114192-42-6
3-Azabicyclo[3.3.0]octane-2-carboxylic acid structure

3-Azabicyclo[3....

CAS#:109428-53-7

~89%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: DSM IP ASSETS B.V. Patent: WO2009/62999 A1, 2009 ; Location in patent: Page/Page column 8 ;
(E)-(-)-octahydrocyclopenta(b)pyrrole-2-carboxylic acid hydrochloride structure

(E)-(-)-octahyd...

CAS#:87269-86-1
Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate structure

Ethyl (S)-2-[(S...

CAS#:84793-24-8

~%

(2R,3aR,6aR)-Ramipril structure

(2R,3aR,6aR)-Ra...

CAS#:129939-63-5
Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: WO2005/108366 A1, ; Page/Page column 12 ;
N-[(S)-1-Ethoxycarbonyl-3-phenylpropyl]-L-alanine structure

N-[(S)-1-Ethoxy...

CAS#:82717-96-2

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Synthetic Communications, , vol. 35, # 2 p. 243 - 248
N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester structure

N-[1(S)-ethoxyc...

CAS#:124492-03-1

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Synthetic Communications, , vol. 35, # 2 p. 243 - 248
Ethyl trans-3-Benzoylacrylate structure

Ethyl trans-3-B...

CAS#:15121-89-8

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401
(1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride structure

(1S,3S,5S)-2-Az...

CAS#:87269-87-2

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401
(1'S,2S)-2-(1'-Methyl-2'-oxo-2'-phenylmethoxy-ethylamino)-4-oxo-4-phenyl-buttersaeure-ethylester structure

(1'S,2S)-2-(1'-...

CAS#:87269-98-5

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401
N-(1-(S)-Ethoxycarbonyl-3-Phenylpropyl)-L-Alaninyl-N-Carboxyanhydride structure

N-(1-(S)-Ethoxy...

CAS#:87269-99-6

~%

Ramipril Structure

Ramipril

CAS#:87333-19-5
Literature: Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401

 Customs

HS Code 3004909090

 Articles69

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 Synonyms

RAMACE
UNIPRIL
PRAMACE
vesdil
DELIX
(2S,3aS,6aS)-1-{2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
N-(1S-Carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3S-carboxylic Acid
Ramipril
Trimce
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
[2S-[1[R*(R*)],2a,3ab,6ab]]-1-[2-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid
HOE-498
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
(2S,3aS,6aS)-1-[(S)-N-[(S)-1-Carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid 1-Ethyl Ester
MFCD00865775
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
ALTACE
CARDACE
TRITACE
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Related Compounds: More...
Ramipril-d3
2673269-81-1
Ramipril-d5
1132661-86-9
Ramipril,(-)
1246253-05-3
Ramiprilat-d3
1356933-70-4
2-epi-Ramipril
129939-65-7
1-epi-Ramipril
104195-90-6
Hexahydroramipril
99742-35-5
Ramipril Impurity 2
108736-10-3
Ramipril impurity D
108731-95-9
Chemsrc provides Ramipril(CAS#:87333-19-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Ramipril are included as well.>> amp version: Ramipril

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