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CAS

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91599-74-5

Benidipine hydrochloride, also known as Coniel, is a long-acting dihydropyridine calcium antagonist that serves as an orally bioavailable blocker of L-, T-, and N-type calcium channels. It is a yellow crystalline powder with potent hypotensive effects and neuroprotective properties, making it useful in the treatment of hypertension and angina pectoris.
Used in Pharmaceutical Industry:
Benidipine hydrochloride is used as an antihypertensive agent for its ability to induce hypotension with a potency 6 and 12 times more than nifedipine and nicardipine, respectively. Its slow onset of action and neuroprotective properties for neural stem cells after oxidative stress-induced injury make it a valuable treatment option for hypertension and angina pectoris.
Additionally, Benidipine hydrochloride is used as a calcium channel blocker for its IC50 of 2.7 nM for calcium currents in guinea pig ventricular cells, as determined using whole cell voltage clamp electrophysiology. This property allows it to prevent oxidative stress dose-dependently in vitro and decrease blood pressure in spontaneously hypertensive rats.
Furthermore, Benidipine hydrochloride is used as a competitive antagonist at mineralocorticoid receptors, which can contribute to its therapeutic effects in treating hypertension and related conditions.

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  • 91599-74-5 Structure

  • Basic information

    1. Product Name: Benidipine hydrochloride
    2. Synonyms: (R,R)-(+/-)-2,6-DIMETHYL-4-(3-NITROPHENYL)-1,4-DIHYDRO-3,5-PYRIDINE,DICARBOXYLIC ACID METHYL-1-BENZYL-3-PIPERIDYL-ESTER,MONOHYDROCHLORIDE SALT;monohydrochloride,(r*,r*)-(+-)-hyl1-(phenylmethyl)-3-piperidinyleste;1-(BENZYLMETHYL)-3-PIPERIDINYL 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3,5-PYRIDINEDICARBOLATE;2,6-Dimethyl-4-(3-Nitrophenyl)-1,4-Dihydropyridine-3,5-DimethoxyCarboxylate;(R,R)-(+/)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicacidmethyl-1-(phenylmethyl)-3-piperidiny;Coniel, Capadipine, KW-3049, Nacadipine;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3R)-1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (4R)-rel-;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (R*,R*)-(+-)-
    3. CAS NO:91599-74-5
    4. Molecular Formula: C28H31N3O6*ClH
    5. Molecular Weight: 505.56
    6. EINECS: 1592732-453-0
    7. Product Categories: Antihypertensive;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chiral Reagents;Heterocycles;Inhibitors
    8. Mol File: 91599-74-5.mol

  • Chemical Properties

    1. Melting Point: 199-201°C
    2. Boiling Point: 625.2 °C at 760 mmHg
    3. Flash Point: 331.9 °C
    4. Appearance: yellow/
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: Desiccate at RT
    8. Solubility: DMSO: ≥20mg/mL
    9. PKA: 7.34(at 25℃)
    10. CAS DataBase Reference: Benidipine hydrochloride(CAS DataBase Reference)
    11. NIST Chemistry Reference: Benidipine hydrochloride(91599-74-5)
    12. EPA Substance Registry System: Benidipine hydrochloride(91599-74-5)

  • Safety Data

    1. Hazard Codes: T
    2. Statements: 25
    3. Safety Statements: 45
    4. RIDADR: UN 2811 6.1 / PGIII
    5. WGK Germany: 3
    6. RTECS: US7975657
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 91599-74-5(Hazardous Substances Data)

91599-74-5 Usage

Biological Activity

Orally active antihypertensive agent which displays a wide range of activities in vitro and in vivo . Inhibits L-, N- and T-type Ca 2+ channels. Also inhibits aldosterone-induced mineralocorticoid receptor activation. Exhibits cardioprotective and antiartherosclerotic effects.

Safety Profile

A poison by ingestion,intraperitoneal, and intravenous routes. When heated todecomposition it emits toxic vapors of NOx and HCl.

Check Digit Verification of cas no

The CAS Registry Mumber 91599-74-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,5,9 and 9 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 91599-74:
(7*9)+(6*1)+(5*5)+(4*9)+(3*9)+(2*7)+(1*4)=175
175 % 10 = 5
So 91599-74-5 is a valid CAS Registry Number.

91599-74-5 Well-known Company Product Price

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  • Sigma

  • (B6813)  Benidipine hydrochloride  ≥98% (HPLC)

  • 91599-74-5

  • B6813-10MG

  • 724.23CNY

  • Detail

  • Sigma

  • (B6813)  Benidipine hydrochloride  ≥98% (HPLC)

  • 91599-74-5

  • B6813-50MG

  • 2,925.00CNY

  • Detail

91599-74-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-O-[(3R)-1-benzylpiperidin-3-yl] 3-O-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate,hydrochloride

1.2 Other means of identification

Product number -
Other names (+-)-Benidipine hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:91599-74-5 SDS

91599-74-5Downstream Products

91599-74-5Relevant articles and documents

BENIDIPINE HYDROCHLORIDE

-

Page/Page column 5; 6, (2012/11/07)

Disclosed is a method for preparing benidipine hydrochloride, which comprising: 1) during the pre-treatment stage including acylchloridizing the main ring of dihydropyridine and then linking the side chain to synthesize directly benidipine hydrochloride, ultrasound technology is introduced, and the reactant material is dispersed and dissolved by untrasound to increase reaction rate; and/or 2) during the post-treatment stage, ultrasound technology is introduced and crude crystals or product obtained by heating to dryness of benidipine hydrochloride obtained via the method described above or any other synthetic routes is dissolved once more and then highly purified benidipine hydrochloride is obtained by untrasound.

Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester

Muto,Kuroda,Kawato,Karasawa,Kubo,Nakamizo

, p. 1662 - 1665 (2007/10/02)

1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester 1, a highly potent calcium antagonist, was separated into stereo- and optical isomers to investigate the differences of antihypertensive activities between them. Fractional crystallization of the hydrochlorides of 1 gave α- and β-diasterioisomers. The α-isomer (benidipine hydrochloride, KW-3049) showed very strong hypotensive effect, but little activity was observed in the β-isomer. From optically resolved 1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridi necarboxylic acids 2, and 1-benzyl-3-piperidinols 3, four optical isomers of 1 were synthesized, and their absolute configurations were deduced. The hypotensive activity of (+)-α, namely (S)-(S)-1, was 30 to 100 times stronger than that of (-)-α in intravenously administered spontaneously hypertensive rats.

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