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Lacidipine

Product Name
Lacidipine
CAS No.
103890-78-4
Chemical Name
Lacidipine
Synonyms
β-GPA;MOTENS;SN-305;LACIPIL;LACIREX;GX-1048;CALDINE;Lacidipin;GR-43659X;LACIDIPINE
CBNumber
CB5296310
Molecular Formula
C26H33NO6
Formula Weight
455.54
MOL File
103890-78-4.mol
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Lacidipine Property

Melting point:
174-175°C
Boiling point:
558.4±50.0 °C(Predicted)
Density 
1.127±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble20mg/mL, clear
form 
powder
pka
3.00±0.70(Predicted)
color 
white to beige
Merck 
14,5331
InChI
InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+
InChIKey
GKQPCPXONLDCMU-CCEZHUSRSA-N
SMILES
C1(C)NC(C)=C(C(OCC)=O)C(C2=CC=CC=C2/C=C/C(OC(C)(C)C)=O)C=1C(OCC)=O
CAS DataBase Reference
103890-78-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
US7970200
Toxicity
mouse,LD50,intraperitoneal,80200ug/kg (80.2mg/kg),SKIN AND APPENDAGES (SKIN): HAIR: OTHERSENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYEBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22, Pg. 335, 1994.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0946
Product name
Lacidipine
Purity
≥98% (HPLC)
Packaging
10mg
Price
$77.6
Updated
2025/07/31
Sigma-Aldrich
Product number
SML0946
Product name
Lacidipine
Purity
≥98% (HPLC)
Packaging
50mg
Price
$250
Updated
2025/07/31
TCI Chemical
Product number
L0276
Product name
Lacidipine
Purity
>98.0%(HPLC)(N)
Packaging
1g
Price
$480
Updated
2023/01/07
TCI Chemical
Product number
L0276
Product name
Lacidipine
Purity
>98.0%(HPLC)(N)
Packaging
200mg
Price
$146
Updated
2021/12/16
Cayman Chemical
Product number
28270
Product name
Lacidipine
Packaging
100mg
Price
$97
Updated
2024/03/01
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Lacidipine Chemical Properties,Usage,Production

Description

Lacidipine is a new second-generation dihydropyridine calcium antagonist introduced as a once a day treatment for mild to moderate hypertension. It is reported to have high selectivity for vascular smooth muscle and also a long duration of action. The use of lacidipine as an antiatherosclerotic agent is currently under investigation.

Description

Lacidipine is a dihydropyridine L-type calcium channel blocker. It induces relaxation of isolated rat aorta and inhibits calcium-induced contraction of rabbit ear artery (pA2 = 9.4). It also induces relaxation of calcium-induced contractions in isolated rat colon and bladder and guinea pig trachea (IC50s = 6.7, 6, and 7.8 nM, respectively). Lacidipine induces negative inotropy in isolated guinea pig ventricular strips (IC50 = 110 nM). It reduces mean blood pressure in spontaneously hypertensive rats (ED25 = 0.35 mg/kg) and in renal hypertensive dogs (ED25 = 0.22 mg/kg) with a transient increase in heart rate. Lacidipine inhibits copper-induced oxidation of isolated human LDL when used at concentrations of 1 and 5 μM. It reduces the extension of aortic atheromatous lesions and decreases renal injury in ApoE-/- mice in a model of Western diet-induced atherosclerosis.

Chemical Properties

White-to-Off-White Crystalline Solid

Originator

Glaxo (United Kingdom)

Uses

A dihydropyridine calcium channel blocker. Antihypertensive.

Uses

antihypertensive;dihydropyridinr calcium channel blocker

Definition

ChEBI: Lacidipine is a cinnamate ester and a tert-butyl ester.

brand name

Lacipil; Lacirex; Viapres

Biochem/physiol Actions

Lacidipine is a long-acting calcium antagonist that is used in the management of hypertension. Lacidipine is a L-type Ca(2+) channel blocker belonging to 1,4-dihydropyridine class. Also, Lacidipine inhibits ryanodine receptors on the ER membrane that enhances folding, trafficking and lysosomal activity of ERAD (ER-associated degradation) misfolded lysosomal glucocerebrosidase (GS).

Synthesis

59159-39-6

626-34-6

643-79-8

103890-78-4

1. 18 liters of dichloromethane were added to the reactor, followed by 5 kg of tert-butoxycarbonylmethyltriphenylphosphonium bromide (prepared with reference to Example 1). 2. 2.05 kg of o-phthalaldehyde was added, followed by 1 liter of dichloromethane, and the mixture was stirred for about 15 minutes, then cooled to -5°C. 3. A solution of 2.65 kg of sodium hydroxide flakes in 5 liters of water (pre-prepared at 25°C) was added to the reaction mixture at -3°C and kept at -3°C for 2.5 hours. The reaction process was monitored by thin layer chromatography. 4. After completion of the reaction, the mixture was warmed up to 25°C and stirring was continued for 30 minutes. The organic layer was separated and the solvent was removed by atmospheric pressure distillation at 52°C. The residue was kept at 52°C for 15 minutes. 5. 35 liters of n-heptane were added and 4 liters of n-heptane were distilled under 500 mmHg vacuum and at 63 °C. The mixture was then cooled to 0°C and held at 35°C for 1.5 hours. 6. The insoluble material was removed by vacuum filtration and the filter cake was washed with 7.5 liters of n-heptane. The filtrate was transferred to another reactor and the solvent was removed by complete distillation under vacuum at 610 mmHg and 68°C. 7. Cooled to 33 °C, 11.5 liters of isopropanol was added and subsequently cooled to -7 °C. 8. At -7 °C, a solution of 4.25 kg ethyl 3-aminocrotonate in 12.5 liters of isopropanol was slowly added, followed by 2.8 liters of trifluoroacetic acid and 1 liter of isopropanol, and the reaction was kept at -7 °C for 2 hours and 45 minutes. The reaction process was monitored by thin layer chromatography. 9. A solution of 2.6 kg of sodium bicarbonate in 50 liters of water was added to the reaction mixture at 0 °C, followed by 25 liters of ethyl acetate. Increase the temperature to 25°C and stir for 20 minutes. Separate the aqueous layer and extract with 12.5 liters of ethyl acetate. The organic layers were combined and the solvent was removed by atmospheric pressure distillation at 81 °C. 10. Add 5 liters of isopropanol to the residue and distill completely to remove the solvent. This operation is repeated once. Finally, the residue was dissolved in 63 liters of isopropanol and heated to 85°C to obtain a clarified solution. 11. Cool to 2 °C, keep for 1.5 h. Separate the solid by filtration and wash with 2.5 liters of isopropanol. The wet product was dried at 50°C for 30 minutes. 12. The dried substance was added to 23 liters of isopropanol, heated to 65°C and held for 30 minutes, cooled to 2°C and held for 1 hour, filtered and washed with 1.5 liters of isopropanol. 13. The wet solid was dried at 60 °C and 630 mmHg under vacuum for 5 h to give 2.04 kg of ethyl (E)-diethyl 4-(2-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in 40.9% yield. The content of triphenylphosphine oxide was less than 0.0011 area%.

References

[1] Patent: US2007/43088, 2007, A1. Location in patent: Page/Page column 6

Lacidipine Preparation Products And Raw materials

Raw materials

tert-Butyl acetate Ethyl crotonate o-Phthalaldehyde trans-Cinnamic acid Triphenylphosphine tert-Butyl acrylate

Preparation Products

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Lacidipine Suppliers

Americas 1 Belgium 1 Brazil 1 Canada 6 China 275 Europe 3 France 1 Germany 2 India 34 Italy 1 Japan 1 Nepal 1 South Korea 4 Spain 2 Turkey 1 United Arab Emirates 1 United Kingdom 13 United States 43 Global 391
Hubei Yuanmeng Biotechnology Co., Ltd
Tel
027-68897569 18120462897
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027-68897569
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fiona@yuanmengbio.com
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China
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Hubei Hongfuda Biotechnology Co., Ltd.
Tel
19107255884
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2013537414@qq.com
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China
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J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
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China
ProdList
96815
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3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
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China
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
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Sales-CN@TCIchemicals.com
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China
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24529
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Beijing HwrkChemical Technology Co., Ltd
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18515581800 18501085097
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010-89508210
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sales.bj@hwrkchemical.com
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China
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Energy Chemical
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021-021-58432009 400-005-6266
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021-58436166
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Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
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001-617-206-9595
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sales@chemreagents.com
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United States
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Adamas Reagent, Ltd.
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400-6009262 16621234537
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021-64823266
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chenyj@titansci.com
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LGM Pharma
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1-(800)-881-8210
Fax
615-250-9817
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inquiries@lgmpharma.com
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United States
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View Lastest Price from Lacidipine manufacturers

Sichuan Zhuoyu Yantang Technology Co., Ltd.
Product
Lacidipine 103890-78-4
Price
US $100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000kg/week
Release date
2025-09-25
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Lacidipine 103890-78-4
Price
US $0.00/G
Min. Order
10G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-08
Moxin Chemicals
Product
Lacidipine 103890-78-4
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
95%+
Supply Ability
10000000
Release date
2025-02-24

103890-78-4, LacidipineRelated Search:

Phenyl salicylate Ethoxyquin DIETHOXYMETHANE Diphenyl ether PHENYL VALERATE Fentin hydroxide Ethoxyamine hydrochloride PHENYL RESIN Phenylacetic acid Oxygen cis Lacidipine trans Lacidipine-d10,LACIDIPINE-D10 Dehydro Lacidipine 2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID Lacidipine LACIDIPINE INTERMEDIATE:4-(2-BROMOPHENYL)-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER 4-(2-bromophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester (intermediate of lacidipine) LACIDIPINE IMPURITY STANDARD

  • 3,5-pyridinedicarboxylicacid,1,4-dihydro-2,6-dimethyl-4-(2-(3-(1,1-dimethylet
  • diethylester,(e)-hoxy)-3-oxo-1-propenyl)phenyl)
  • MOTENS
  • 3,5-Diethyl 4-{2-[(1E)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  • CID 5311217
  • Lacidipine，Lacipil
  • Lacidipine Solution, 100ppm
  • 4-[2-[(1E)-3-(1,1-dimethylethoxy)-3-oxo-1-propen-1-yl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid 3,5-diethyl ester
  • GX-1048,GR-43659X,SN-305
  • Lacidipine Solution, 1000ppm
  • LACIPIL;MOTENS
  • LACIPIL
  • LACIREX
  • LACIDIPINE
  • LACIDIPINE-D9
  • Lacidipin
  • LACIDIPINE, IMPURITY STANDARD BP STANDARD
  • LACIDIPINE, BP STANDARD
  • LACIDIPINE ASSAY STANDARD BP(CRM STANDARD)
  • LACIDIPINE BP STANDARD(CRM STANDARD)
  • LACIDIPINE IMPURITY STANDARD BP STANDARD(CRM STANDARD)
  • LACIDIPINE IMPURITY STANDARD BP(CRM STANDARD)
  • LacidipineC26H33N06
  • GX-1048
  • GR-43659X
  • CALDINE
  • (E)-4-[2-[3-(1,1-DIMETHYLETHOXY)-3-OXO-1-PROPENYL]PHENYL]-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER
  • (E)-4-[2-[3-(1,1-Dimethylethoxy)-3-oxo-1-propenyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Diethyl Ester, GR-43659X, GX-1048, Caldine, Lacipil, Lacirex, Motens
  • trans Lacidipine
  • Lacidipine (Lacipil, Motens)
  • 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-(3-(1,1-dimethylethoxy)-3-oxo-1- propenyl)phenyl)-, diethyl ester, (E)-
  • Diethyl 2,6-dimethyl-4-[2-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
  • 4-[2-[(1E)-3-(1,1-Dimethylethoxy)-3-oxo-1-propenyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester
  • 4-[2-[(E)-3-(1,1-Dimethylethoxy)-3-oxo-1-propenyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester
  • SN-305
  • 2,6-dimethyl-4-[2-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
  • 3,5-Pyridinedicarboxylic acid, 4-[2-[(1E)-3-(1,1-dimethylethoxy)-3-oxo-1-propen-1-yl]phenyl]-1,4-dihydro-2,6-dimethyl-, 3,5-diethyl ester
  • Lacidipine USP/EP/BP
  • (E)-Diethyl 4-(2-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  • Lacidipine (GX-1048, GR-43659X, SN-305, Lacipil, Motens)
  • LacidipineQ: What is Lacidipine Q: What is the CAS Number of Lacidipine Q: What is the storage condition of Lacidipine Q: What are the applications of Lacidipine
  • β-GPA
  • Lacidipine flat
  • Lacipil, Motens, Lacidipine
  • iethyl2,6-dimethyl-4-[2-[(E)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
  • Lacidipine Diethyl 4-{o-[(E)-2-tert-butoxycarbonylethenyl]phenyl}-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  • Lacidipine in methanol
  • Racidipine
  • Lacidipine Impurity
  • Lacidipine, 10 mM in DMSO
  • 103890-78-4
  • Lacidipine - Bio-X ?
  • 2,7,12-tris(dimesitylboryl)-5,5',10,10',15,15'-hexaethyltruxene
  • 103890-78-4
  • 118505-88-8
  • C26H33NO6
  • C26H24NO6D9
  • Calcium channel