Zofenopril-d5
- Iupac Name：(2S,
4S)-1-[(2S)-3-benzoylsulfanyl-2-methylpropanoyl]-4-
phenylsulfanylpyrrolidine-2-carboxylic acid
- CAS No.: 81872-10-8
- Molecular Weight：429.55232
- Modify Date.: 2022-11-29 05:19
- Introduction: Zofenopril-d5 is intended for use as an internal standard for the quantification of Zofenopril by GC- or LC-mass spectrometry.
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1. Names and Identifiers
- 1.1 Name
- Zofenopril-d5
- 1.2 Synonyms
(1(R*),2a,4a)-1-(3-(Benzoylthio)-2-methyl-1-oxopropyl)-4-(phenylthio)-L-proline (2S,4S)-1-[(2S)-3-benzoylsulfanyl-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid (4S)-1-[(2S)-3-(Benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)-L-proline (4S)-N-((S)-3-Mercapto-2-methylpropionyl)-4-(phenylthio)-L-proline Benzoate (Ester) (4S)-N-[3-(Benzoylsulfanyl)-2(S)-methylpropionyl]-4-(phenylsulfanyl)-L-proline 1-[(S)-3-(Benzoylthio)-2-methyl-1-oxopropyl]-4α-(phenylthio)-L-proline 1-NAPHTHYLACETICACIDα-NAPHTHYLACETICACID EINECS 201-705-8 L-Proline, 1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-, (4S)- MFCD00004046 NAA NAA(R) NAA(TM) S-Benzoyl-4-phenylthiocaptopril UNII-290ZY759PI Zofenopril Zofenoprilum Zoprace
- View all
- 1.3 CAS No.
- 81872-10-8
- 1.4 CID
- 92400
- 1.5 EINECS(EC#)
- 201-705-8
- 1.6 Molecular Formula
- C22H23NO4S2 (isomer)
- 1.7 Inchi
- InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
- 1.8 InChIkey
- IAIDUHCBNLFXEF-MNEFBYGVSA-N
- 1.9 Canonical Smiles
- CC(CSC(=O)C1=CC=CC=C1)C(=O)N2CC(CC2C(=O)O)SC3=CC=CC=C3
- 1.10 Isomers Smiles
- C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)O)SC3=CC=CC=C3
2. Properties
- 2.1 Density
- 1.34
- 2.1 Melting point
- 129-131.5 °C(lit.)
- 2.1 Boiling point
- 646.3 °C at 760 mmHg
- 2.1 Refractive index
- 1.658
- 2.1 Flash Point
- 344.7 °C
- 2.1 Precise Quality
- 429.10700
- 2.1 PSA
- 125.28000
- 2.1 logP
- 3.98040
- 2.1 Appearance
- light yellow crystalline
- 2.2 Storage
- 2-8°C
- 2.3 Color/Form
- light yellow
- 2.4 pKa
- pK1:4.236 (25°C)
- 2.5 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.
- 3.2 Usage
- Zofenopril-d5 is intended for use as an internal standard for the quantification of Zofenopril by GC- or LC-mass spectrometry.
4. Safety and Handling
- 4.1 Hazard Codes
- Xn; Xi
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- 23-24/25
- 4.1 Hazard Class
- IRRITANT
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- QJ0875000
- 4.1 Safety
-
Safety Information of L-Proline,1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-, (4S)- (CAS No. 81872-10-8):
Hazard Codes: Xn,Xi 
Risk Statements: 22-37/38-41
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin.
R41:Risk of serious damage to the eyes.
Safety Statements: 23-24/25
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: QJ0875000
HazardClass: IRRITANT
- 4.2 Specification
-
L-Proline,1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-, (4S)- with cas registry number of 81872-10-8 is also called Zofenopril ; Zofenopril [INN:BAN] ; UNII-290ZY759PI ; Zofenoprilum ; Zofenoprilum [Latin] ; L-Proline, 1-(3-(benzoylthio)-2-methyl-1-oxopropyl)-4-(phenylthio)-, (1(R*),2alpha,4alpha)- ; (4S)-N-[3-(Benzoylsulfanyl)-2(S)-methylpropionyl]-4-(phenylsulfanyl)-L-proline .
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
no data available
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | no data available |
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
2.3 Other hazards which do not result in classification
no data available
6. Synthesis Route
81872-10-8Total: 4 Synthesis Route
8. Other Information
- 8.0 靶点
-
- 8.1 体外研究
-
Kinetic analyses demonstrate that enalapril inhibits the uptake of GlySar in a competitive manner (K i approximately 6 mM). Fosinopril and Zofenopril have the greatest inhibitory potency (IC 50 values of 55 and 81μM, respectively) while the other ACE inhibitors exhibit low-affinity interactions with the renal peptide transporter.
- 8.2 体内研究
-
Zofenopril, a sulphydrylic compound, at doses higher than 70 mg/kg i.p. produces significant protection (i.e. at 70 mg/kg, P=0.044, F=2.17, d.f.=18; at higher concentration P<0.05) against the tonic phase of the audiogenic seizure response. Pretreatment with Zofenopril (15 mg/kg, i.p.) is able to produce a consistent shift to the left of the dose-response curves and a significant reduction of ED 50 values against clonus of some AEDs with the exceptions of diazepam, felbamate, phenobarbital and phenytoin compare with concurrent groups, suggesting an increase in anticonvulsant activity.
- 8.3 Originator
- Zofenopril Calcium,ZYF Pharm Chemical
- 8.4 Uses
- Zofenopril-d5 is intended for use as an internal standard for the quantification of Zofenopril by GC- or LC-mass spectrometry.
- 8.5 Definition
- ChEBI: A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.
- 8.6 Manufacturing Process
- 9.9 g (0.031 mole) of cis-4-phenylthio-L-proline is suspended in 100 ml of water (pH 5.6) and the pH is adjusted to 10.2 by the addition of about 20 ml of 10% sodium bicarbonate to provide a clear solution. The pH is then adjusted to 9.5 by the addition of about 4.5 ml of concentrated HCl. The solution is kept at 30°C while 8.1 g (0.033 mole) of (D)-3-(benzoylthio)-2- methylpropanoic acid chloride in 30 ml of toluene is added simultaneously with 100 ml of 10% sodium bicarbonate to keep the pH at 9.3. After about 1/4 of the acid chloride is added, a slimy precipitate begins to form which persists throughout the reaction. After stirring the reaction mixture at pH 9.3 for 2.5 h, it is made strongly acidic by adding 20% HCl in the presence of ethyl acetate. The aqueous layer is extracted twice with 350 ml portions of ethyl acetate and the combined organic layers are washed with 300 ml of saturated brine and dried (MgSO 4 ). The solvent is removed to yield 11.8 g of foamy solid cis-1-[D-3-(benzoylthyo)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline hydrochloride.
To a solution of this cis-1-[D-3-(benzoylthyo)-2-methyl-1-oxopropyl]-4- (phenylthio)-L-proline hydrochloride 11.8 g (0.027 mole) in 70 ml of acetonitrile there is added about 6.0 g of dicyclohexylamine in 25 ml of ether. A white crystalline precipitate forms immediately. After standing overnight in the cold room, the solid is filtered and washed with ether to yield (cis)-1-[D- 3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline, dicyclohexylamine salt (1:1).
he slightly moist (cis)-1-[D-3-(benzoylthio)-2-methyl-1-oxopropyl]-4- (phenylthio)-L-proline dicyclohexylamine salt is stirred for 2.5 h in a mixture of 300 ml of ethyl acetate and 200 ml of 10% potassium bisulfate. Two clear layers form. The aqueous layer is extracted with two 200 ml portions of ethyl acetate and the combined organic layers are dried (MgSO 4 ). The solvent is removed to yield 10.1 g of foamy solid (cis)-1-[D-3-(benzoylthio)-2-methyl-1- oxopropyl]-4-(phenylthio)-L-proline; melting point 42-44°C.
In practice it is usually used as calcium salt (2:1). - View all
- 8.7 Brand name
- Zoprace (Bristol-Myers Squibb).
- 8.8 Therapeutic Function
- Antihypertensive
- 8.9 Synthesis Reference(s)
- The Journal of Organic Chemistry, 33, p. 1675, 1968 DOI: 10.1021/jo01268a091
- 8.10 Mesh
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)|A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)
- 8.11 Mesh Entry Terms
- SQ 26900
- 8.12 Use Classification
- Human Drugs -> EU pediatric investigation plans
9. Computational chemical data
- Molecular Weight: 429.55232g/mol
- Molecular Formula: C22H23NO4S2
- Compound Is Canonicalized: True
- XLogP3-AA: 4.4
- Exact Mass: 429.10685056
- Monoisotopic Mass: 429.10685056
- Complexity: 587
- Rotatable Bond Count: 8
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 6
- Topological Polar Surface Area: 125
- Heavy Atom Count: 29
- Defined Atom Stereocenter Count: 3
- 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: AAADceB6OABgAAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAAABQAAAHgQACAAADSjF2ASyCYMAAgiIAiHSGAACAAAkCBAIiBmIAMgKIDKglTCEYQAkhgC4iYeYmQKOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
1-Naphthaleneacetic acid (NAA) is a synthetic plant growth stimulator that belongs to the naphthalene derivative family. It is commonly used in combination with naturally occurring auxins like indole..
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