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ChemSpider ID: |
4514937
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Empirical Formula: |
C23H32N2O5
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Molecular Weight: |
416.5106
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Nominal Mass: |
416
Da
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Average Mass: |
416.5106
Da
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Monoisotopic Mass: |
416.231122
Da
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Systematic Name: |
(2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[d]pyrrole-2-carboxylic acid
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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
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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
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InChIKey: |
HDACQVRGBOVJII-JBDAPHQKBG
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Std. 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
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Std. InChIKey: |
HDACQVRGBOVJII-JBDAPHQKSA-N
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Ramipril (marketed as Ramipro by Westfield Pharma in the Philippines, marketed by Sanofi-Aventis as Tritace and by King Pharmaceuticals as Altace in the United States) is an angiotensin-converting enzyme (ACE) inhibitor, 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.
Ramipril is a prodrug and is converted to the active metabolite ramiprilat by liver esterase enzymes. Ramiprilat is mostly excreted by the kidneys. The half-life of ramiprilat is variable (3-16 hours), and is prolonged by heart and liver failure, as well as kidney failure.
It is marketed by King Pharmaceuticals under the brand name Altace. The compound was protected by the (was scheduled to expire on 29 th Oct, 2008) assigned to Aventis. On September 11, 2007 in an appeal by Lupin Pharmaceuticals the United States Court of Appeals for the Federal Circuit reversed a district court trial verdict, finding that Aventis's patent on Altace was invalid for obviousness - opening the gate of this medicine to generic manufacturers.
Ramipril is marketed in India under the brand names of Cardace, Zigpril and Zorem.
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(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrol-2-carbonsäure
(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-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)
(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,3aS,6aS)-1-[(S)-N-[(S)-1-Carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid 1-Ethyl Ester
(2S,3aS,6aS)-1-{2-[(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
acide (2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(éthoxycarbonyl)-3-phénylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylique
N-(1S-Carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3S-carboxylic Acid
More...
ramipril usp
(2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)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
(2S,3aS,6aS)-1-((S)-N-((S)-1-Ethoxycarbonyl-3-phenylpropyl)alanyl)octahydrocyclopenta(b)pyrrol-2-carbonsaeure
(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-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
1-[2-(1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid(Ramipril)
337376-15-5
[RN]
4214464
[Beilstein]
87333-19-5
[RN]
Acovil
ALTACE
[Wiki]
Altace (TN)
Carasel
Cardace
Cyclopenta(b)pyrrole-2-carboxylic acid, 1-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2S-(1(R*(R*)),2alpha,3abeta,6abeta))-
Delix
[Wiki]
Hytren
Lostapres
Pramace
Quark
[Wiki]
Ramace
Ramipril
[Wiki]
Ramipril (USP)
Ramipril [USAN:BAN:INN]
Ramiprilum
[Latin]
Ramiprilum [Latin]
Triatec
Tritace
[Wiki]
Unipril
Vesdil
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users,
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ACD/LogP: |
3.41
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
1.24
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ACD/LogD (pH 7.4): |
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ACD/BCF (pH 5.5): |
1.57
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ACD/BCF (pH 7.4): |
1
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ACD/KOC (pH 5.5): |
11.66
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ACD/KOC (pH 7.4): |
1
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#H bond acceptors: |
7
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#H bond donors: |
2
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#Freely Rotating Bonds: |
10
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Polar Surface Area: |
76.15
Å2
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Index of Refraction: |
1.555
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Molar Refractivity: |
111.41
cm3
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Molar Volume: |
346.8
cm3
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Polarizability: |
44.16
10-24cm3
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Surface Tension: |
50.1
dyne/cm
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Density: |
1.2
g/cm3
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Flash Point: |
326.4
°C
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Enthalpy of Vaporization: |
96.09
kJ/mol
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Boiling Point: |
616.2
°C at 760 mmHg
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Vapour Pressure: |
4.86E-16
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 3.32
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 579.38 (Adapted Stein & Brown method)
Melting Pt (deg C): 318.54 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 3.8E-011 (Modified Grain method)
MP (exp database): 109 deg C
Subcooled liquid VP: 2.54E-010 mm Hg (25 deg C, Mod-Grain method)
Water Solubility Estimate from Log Kow (WSKOW v1.41):
Water Solubility at 25 deg C (mg/L): 3.551
log Kow used: 3.32 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 1106.5 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Aliphatic Amines-acid
Esters-acid
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 3.44E-016 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 5.865E-012 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 3.32 (KowWin est)
Log Kaw used: -13.852 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 17.172
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : 1.3429
Biowin2 (Non-Linear Model) : 0.9997
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 2.7009 (weeks-months)
Biowin4 (Primary Survey Model) : 4.0464 (days )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : 0.2577
Biowin6 (MITI Non-Linear Model): 0.0270
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): -0.3772
Ready Biodegradability Prediction: NO
Hydrocarbon Biodegradation (BioHCwin v1.01):
Structure incompatible with current estimation method!
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 3.39E-008 Pa (2.54E-010 mm Hg)
Log Koa (Koawin est ): 17.172
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 88.6
Octanol/air (Koa) model: 3.65E+004
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 1
Mackay model : 1
Octanol/air (Koa) model: 1
Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
Hydroxyl Radicals Reaction:
OVERALL OH Rate Constant = 123.2510 E-12 cm3/molecule-sec
Half-Life = 0.087 Days (12-hr day; 1.5E6 OH/cm3)
Half-Life = 1.041 Hrs
Ozone Reaction:
No Ozone Reaction Estimation
Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
Note: the sorbed fraction may be resistant to atmospheric oxidation
Soil Adsorption Coefficient (PCKOCWIN v1.66):
Koc : 1674
Log Koc: 3.224
Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
Total Kb for pH > 8 at 25 deg C : 1.747E-003 L/mol-sec
Kb Half-Life at pH 8: 12.575 years
Kb Half-Life at pH 7: 125.745 years
Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
Log BCF from regression-based method = 0.500 (BCF = 3.162)
log Kow used: 3.32 (estimated)
Volatilization from Water:
Henry LC: 3.44E-016 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 3.474E+012 hours (1.447E+011 days)
Half-Life from Model Lake : 3.789E+013 hours (1.579E+012 days)
Removal In Wastewater Treatment:
Total removal: 9.54 percent
Total biodegradation: 0.16 percent
Total sludge adsorption: 9.39 percent
Total to Air: 0.00 percent
(using 10000 hr Bio P,A,S)
Level III Fugacity Model:
Mass Amount Half-Life Emissions
(percent) (hr) (kg/hr)
Air 7.88e-008 2.08 1000
Water 11.9 900 1000
Soil 87.5 1.8e+003 1000
Sediment 0.566 8.1e+003 0
Persistence Time: 1.82e+003 hr
Descriptors:
0, 0, 0, 2, 0, 0, 0, 7, 1, 0, 0, 0, 21, 5, 4, 0, 6, 6, 3, 1, 0, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Metalloenzymes | ACE, angiotensin-converting enzyme | 1o86 | 0.03 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor | 1fm9 | 0.03 |
| Other Enzymes | AChE, acetylcholinesterase | 1eve | 0.01 |
| Kinases | SRC, tyrosine kinase SRC | 2src | 0.01 |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase | 1hw8 | 0.01 |
| Other Enzymes | HIVPR, HIV protease | 1hpx | 0.01 |
| Metalloenzymes | PDE5, phosphodiesterase 5 | 1xp0 | 0.01 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor | 2aa2 | 0.01 |
| Serine Proteases | Thrombin | 1ba8 | 0.01 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase | 1efy | 0.01 |
| Other Enzymes | PNP, purine nucleoside phosphorylase | 1b8o | 0.00 |
| Other Enzymes | AmpC, AmpC beta-lactamase | 1xgj | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Folate Enzymes | DHFR, dihydrofolate reductase | 3dfr | 0.00 |
| Other Enzymes | HIVRT, HIV reverse transcriptase | 1rt1 | 0.00 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor | 1vr2 | 0.00 |
| Other Enzymes | GPB, glycogen phosphorylase | 1a8i | 0.00 |
| Other Enzymes | NA, neuraminidase | 1a4g | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase | 1a7a | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase | 1agw | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R | 1mvc | 0.00 |
| Other Enzymes | InhA, enoyl ACP reductase | 1p44 | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase | 1h1d | 0.00 |
| Other Enzymes | ALR2, aldose reductase | 1ah3 | 0.00 |
| Kinases | CDK2, cyclindependent kinase 2 | 1ckp | 0.00 |
| Other Enzymes | COX-1, cyclooxygenase-1 | 1p4g | 0.00 |
| Kinases | P38 MAP, P38 mitogen activated protein | 1kv2 | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor | 1xq2 | 0.00 |
| Nuclear Hormone Receptors | GR, glucocorticoid receptor | 1m2z | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; antagonist | 3ert | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase | 1c2t | 0.00 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase | N/A | 0.00 |
| Kinases | HSP90, human heat shock protein 90 | 1uy6 | 0.00 |
| Serine Proteases | Trypsin | 1bju | 0.00 |
| Kinases | TK, thymidine kinase | 1kim | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor | 1m17 | 0.00 |
| Serine Proteases | FXa, factor Xa | 1f0r | 0.00 |
| Metalloenzymes | ADA, adenosine deaminase | 1stw | 0.00 |
| Other Enzymes | COX-2, cyclooxygenase-2 | 1cx2 | 0.00 |
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