3D Mol Similar

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+

Request For Quotation

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; View all

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. ?

View all

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

View all

6. Synthesis Route

87333-19-5Total: 9 Synthesis Route

87269-88-3

87333-19-5 339 Suppliers

Literatures:
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
Yield: ~95%

87269-99-6 1 Suppliers

87333-19-5 339 Suppliers

Literatures:
Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401
Yield: null

87269-98-5 1 Suppliers

87333-19-5 339 Suppliers

Literatures:
Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401
Yield: null

View all

7. Precursor and Product

precursor:

15121-89-8

87269-86-1

124492-03-1

114192-42-6

82717-96-2

87269-87-2

87269-88-3

87269-98-5

84793-24-8

87269-99-6

109428-53-7

product :

87269-97-4

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

What is Ramipril and its main applications? Oct 27 2022
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..
What body problems can Ramipril improve? Nov 12 2021
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..
What is Ramipril and how is it prepared? Oct 18 2020
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..
What is the function of Ramipril tablets? Apr 15 2018
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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11. Realated Product Infomation

108731-95-9 Ramipril Diketopiperazine

295328-72-2 RAMIPRIL RELATED COMPOUND B (20 MG) (RAMIPRIL ISOPROPYLESTER)

104195-90-6 (1R)-epi-RaMipril

Ramipril Related Compound A (30 mg) ((2S,3aS,6aS)-1-[(S)2-[[(S)-1-(methoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid)

108313-11-7 Ramipril Related Compound A (30 mg) ((2S,3aS,6aS)-1-[(S)2-[[(S)-1-(methoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid)

RAMIPRIL RELATED COMPOUND A (20 MG) ((2S,3AS,6AS)-1 -[(S)2-[[(S)1 -(METHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-1-OXOPROPYL]-OCTAHYDRO-CYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID)

91224-69-0 RAMIPRIL RELATED COMPOUND A (20 MG) ((2S,3AS,6AS)-1 -[(S)2-[[(S)1 -(METHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-1-OXOPROPYL]-OCTAHYDRO-CYCLOPENTA[B]PYRROLE-2-CARBOXYLIC ACID)

Recently Updated : 1932530-95-4 1379444-92-4 186893-71-0 1933714-75-0 98291-26-0 310456-63-4 355824-69-0 1932187-58-0 664975-71-7 508184-49-4