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Ramipril structure
Ramipril structure

Ramipril

Iupac Name:(2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
CAS No.: 87333-19-5
Molecular Weight:416.518
Modify Date.: 2022-10-31 01:22
Introduction: Ramipril (brand name: Altace) is a kind of prodrug which is capable of inhibiting the angiotensin-converting enzyme (ACE) which converting angiotensin I to angiotensin II. It is metabolized to ramiprilat in the liver which exerts the effect of ACE inhibition. It is used for the treatment of hypertension, congestive heart failure and nephropathy. It can also be used for the prevention of heart attack, stroke and cardiovascular death. It can also be used for the treatment of kidney damage due to diabetes with protein-containing urine. Ramiprilat, is the competitive inhibitor of ATI for binding to ACE, further inhibiting the enzymatic proteolysis of ATI to ATII, alleviating the effect of ATII on blood pressure. View more+
1. Names and Identifiers
1.1 Name
Ramipril
1.2 Synonyms

(2s-(1(r*(r*)),2-alpha,3a-beta,6a-beta))-henylpropyl)amino)-1-oxopropyl (2S,3aS,6aS)- (2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]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 2-[[1-(2-ethoxycarbonyl-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrol-1-yl)-1-oxopropan-2-yl]amino]-4-phenylbutanoic acid Altace Cardace Corpril Cyclopenta[b]pyrrole-2-carboxylic acid, 1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydro-, (2S,3aS,6aS)- Cyclopenta[b]pyrrole-2-carboxylic acid, 1-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydro-, [2S-[1[R*(R*)],2α,3aβ,6aβ]]- Delix Ecator HOE 498 Hopace Pramace Ramace Ramipres RaMipril API RaMipril(Altace) Rampicardin Ranipril Triatec Tritace Unipril Vesdil

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1.3 CAS No.
87333-19-5
1.4 CID
5362129
1.5 EINECS(EC#)
642-904-3
1.6 Molecular Formula
C23H32N2O5 (isomer)
1.7 Inchi
InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
1.8 InChIkey
HDACQVRGBOVJII-JBDAPHQKSA-N
1.9 Canonical Smiles
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCC3CC2C(=O)O
1.10 Isomers Smiles
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@H]3CCC[C@H]3C[C@H]2C(=O)O
2. Properties
2.1 Density
1.2
2.1 Melting point
106-108°C
2.1 Boiling point
616.2 °C at 760 mmHg
2.1 Refractive index
1.556
2.1 Flash Point
616.2 °C at 760 mmHg
2.1 Precise Quality
416.23100
2.1 PSA
95.94000
2.1 logP
2.71200
2.1 Solubility
DMSO: ~18mg/mL
2.2 Appearance
White solid
2.3 Storage
2-8°C
2.4 Chemical Properties
White Solid
2.5 Color/Form
white
2.6 Physical
Solid
2.7 pKa
pKa 3.30±0.01(H2Ot = 25.0I = 0.15 (KCl)) (Uncertain);5.75±0.00(H2Ot = 25.0I = 0.15 (KCl)) (Uncertain)
2.8 Water Solubility
Insoluble
2.9 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.
3.2 General Description
Ramipril, (2S, 3aS, 6aS)-1-[(S)-N-[(S)-1-carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]-pyrrole-2-carboxylic acid 1-ethyl ester (Altace), ishydrolyzed to ramiprilat, its active diacid form, faster thanenalapril is hydrolyzed to its active diacid form. Peak serumconcentrations from a single oral dose are achieved between1.5 and 3 hours. The ramiprilate formed completely suppresses ACE activity for up to 12 hours, with 80% inhibitionof the enzyme still observed after 24 hours.
3.3 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 51 companies from 10 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria by 1 of 51 companies. For more detailed information, please visit ECHA C&L website

Of the 9 notification(s) provided by 50 of 51 companies with hazard statement code(s):

H360 (94%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501
View all
3.4 Usage
cardiotonic
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/38
4.1 Safety Statements
S26;S37/39
4.1 WGK Germany
2
4.1 RTECS
GY5879600
4.1 Specification

The IUPAC name of?Ramipril is?(2S,3aS,6aS)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid.?With the?CAS registry number 87333-19-5, it is also named as?Cyclopenta(b)pyrrole-2-carboxylic acid, 1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2S-(1(R*(R*)),2alpha,3abeta,6abeta))-;?Lostapres.?The product's categories are?active pharmaceutical ingredients, ramipril, aromatics, heterocycles, intermediates & fine chemicals, pharmaceuticals and angiotensin.?It is white solid.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 3.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.24; (4)ACD/BCF (pH 5.5): 1.57; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 11.66; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 7; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 10; (11)Index of Refraction: 1.555; (12)Molar Refractivity: 111.41 cm3; (13)Molar Volume: 346.8 cm3; (14)Polarizability: 44.16×10-24 cm3; (15)Surface Tension: 50.1 dyne/cm; (16)Enthalpy of Vaporization: 96.09 kJ/mol; (17)Vapour Pressure: 4.86E-16 mmHg at 25°C; (18)Rotatable Bond Count: 10; (19)Exact Mass: 416.231122; (20)MonoIsotopic Mass: 416.231122; (21)Topological Polar Surface Area: 95.9; (22)Heavy Atom Count: 30.

Uses of Ramipril:?It is an angiotensin-converting enzyme (ACE) inhibitor which is used to treat hypertension and congestive heart failure. ACE inhibitors lower the production of angiotensin II, therefore relaxing arterial muscles while at the same time enlarging the arteries, allowing the heart to pump blood more easily, and increasing blood flow due to more blood being pumped into and through larger passageways.

When you are using this chemical, please be cautious about it as the following:?
It is irritating to eyes and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1.?SMILES: O=C(OCC)[C@@H](N[C@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@H]12)C)CCc3ccccc3;
2.?InChI: InChI=1/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1.

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 250mg/kg (250mg/kg) ? New Cardiovascular Drugs. Vol. 5, Pg. 57, 1987.
dog LD50 oral > 1gm/kg (1000mg/kg) ? Arzneimittel-Forschung. Drug Research. Vol. 38, Pg. 14, 1988.
mouse LD50 intravenous 1100mg/kg (1100mg/kg) ? New Cardiovascular Drugs. Vol. 5, Pg. 57, 1987.
mouse LD50 oral 10048mg/kg (10048mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 38, Pg. 14, 1988.
?
rat LD50 intravenous 600mg/kg (600mg/kg) ? New Cardiovascular Drugs. Vol. 5, Pg. 57, 1987.
rat LD50 oral > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 38, Pg. 14, 1988.
?

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4.2 Toxicity

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
View all
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H360 May damage fertility or the unborn child

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Computational chemical data
  • Molecular Weight: 416.518g/mol
  • Molecular Formula: C23H32N2O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 416.23112213
  • Monoisotopic Mass: 416.23112213
  • Complexity: 619
  • Rotatable Bond Count: 10
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 95.9
  • Heavy Atom Count: 30
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB7OAAAAAAAAAAAAAAAAAAAAeIAAAAwAAAAAAAWAAABAAAAHgAQCAAADSjhmAYyCIPABgCIAiHSGAACAAAgAAAIiIGIAIgKYDKAkTCXYAAklgCYiAeY2bOeAAAAAAAAAAAAAAAAAAAAAAAAAQAAAA==
9. Question & Answer
  • The product known as Ramipril is not widely known by many people. It is commonly used in the pharmaceutical and chemical industries, particularly in the pharmaceutical industry, where it can be used a..
  • When it comes to different body problems, the type of medication used naturally varies. Ramipril serves as both a main component and a name of a medication. Choosing this medication to treat body prob..
  • Ramipril (Ramipril) is a long-acting and potent angiotensin-converting enzyme inhibitor (ACEI), which is the preferred drug for the treatment of mild to moderate essential hypertension, renal hyperten..
  • The issue of aging population is becoming increasingly serious, and along with it comes the problem of medical treatment for elderly patients. Since most elderly patients have chronic diseases, the us..
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