Manidipine hydrochloride

Modify Date: 2024-01-02 20:33:17

Manidipine hydrochloride Structure
Manidipine hydrochloride structure
 Common Name Manidipine hydrochloride
CAS Number 89226-75-5 Molecular Weight 683.62
Density N/A Boiling Point 722ºC at 760 mmHg
Molecular Formula C35H40Cl2N4O6 Melting Point 211 °C(dec.)
MSDS N/A Flash Point N/A

 Use of Manidipine hydrochloride


Manidipine 2Hcl (CV-4093) is a dihydropyridine compound and a calcium channel blocker for Ca2+ current with IC50 of 2.6 nM. IC50 value: 2.6 nMTarget: calcium channelManidipine is described to block T-type Ca2+ channels specifically and is also described to have a high selectivity for the vasculature, presenting negligible cardiodepression as compared to other Ca2+ channel antagonists. Manidipine is also described to not significantly affect norepinephrine levels, suggesting a lack of sympathetic activation with this compound. Manidipine reduces pro-inflammatory cytokines secretion in human endothelial cells and macrophages. Manidipine, unlike other third-generation dihydropyridine derived drugs, blocks T-type calcium channels present in the efferent glomerular arterioles, reducing intraglomerular pressure and microalbuminuria.

 Names

Name Manidipine Dihydrochloride
Synonym More Synonyms

 Manidipine hydrochloride Biological Activity

Description Manidipine 2Hcl (CV-4093) is a dihydropyridine compound and a calcium channel blocker for Ca2+ current with IC50 of 2.6 nM. IC50 value: 2.6 nMTarget: calcium channelManidipine is described to block T-type Ca2+ channels specifically and is also described to have a high selectivity for the vasculature, presenting negligible cardiodepression as compared to other Ca2+ channel antagonists. Manidipine is also described to not significantly affect norepinephrine levels, suggesting a lack of sympathetic activation with this compound. Manidipine reduces pro-inflammatory cytokines secretion in human endothelial cells and macrophages. Manidipine, unlike other third-generation dihydropyridine derived drugs, blocks T-type calcium channels present in the efferent glomerular arterioles, reducing intraglomerular pressure and microalbuminuria.
Related Catalog
References

[1]. Buset Ríos N, Rodríguez Esparragón F, Fernández-Andrade Rodríguez C, et al. Vascular and metabolic properties of manidipine . Nefrologia. 2011;31(3):268-74.

[2]. Costa S, Zimetti F, Pedrelli M, et al. Manidipine reduces pro-inflammatory cytokines secretion in human endothelial cells and macrophages. Pharmacol Res. 2010 Sep;62(3):265-70.

[3]. Cavalieri L, Cremonesi G. Metabolic effects of manidipine. Am J Cardiovasc Drugs. 2009;9(3):163-76. doi: 10.2165/00129784-200909030-00004.

[4]. Roca-Cusachs A, Triposkiadis F. Antihypertensive effect of manidipine. Drugs. 2005;65 Suppl 2:11-9.

[5]. Nagaoka A. Pharmacologic characteristics of a new calcium antagonist, manidipine: beneficial effects on renal circulation and vascular changes. Am Heart J. 1993 Feb;125(2 Pt 2):560-5.

 Chemical & Physical Properties

Boiling Point 722ºC at 760 mmHg
Melting Point 211 °C(dec.)
Molecular Formula C35H40Cl2N4O6
Molecular Weight 683.62
PSA 116.93000
LogP 6.48280

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
US7975300
CHEMICAL NAME :
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-(4-(diphenylmethyl)-1-piperazinyl)ethyl methyl ester, dihydrochloride
CAS REGISTRY NUMBER :
89226-75-5
LAST UPDATED :
199210
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C35-H38-N4-O6.2Cl-H
MOLECULAR WEIGHT :
683.69

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 :
156 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
49 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
199 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
171 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
62 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
340 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),961,1989 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2880 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),1101,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
136 mg/kg
SEX/DURATION :
female 15-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - stillbirth
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),1151,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
136 mg/kg
SEX/DURATION :
multigeneration
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),1151,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1300 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 17(Suppl 4),1141,1989

 Safety Information

Hazard Codes Xi
HS Code 2942000000

 Synthetic Route

Manidipine structure

Manidipine

CAS#:89226-50-6

~%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: WO2011/23954 A2, ; Page/Page column 18 ;
N-Benzhydrylpiperazine structure

N-Benzhydrylpip...

CAS#:841-77-0

~%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: WO2011/23954 A2, ;
2-(4-benzhydrylpiperazin-1-yl)ethanol structure

2-(4-benzhydryl...

CAS#:10527-64-7

~%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: Chemical and Pharmaceutical Bulletin, , vol. 33, # 9 p. 3787 - 3797
2-(4-benzhydrylpiperazin-1-yl)ethyl 3-oxobutanoate structure

2-(4-benzhydryl...

CAS#:89226-49-3

~%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: Chemical and Pharmaceutical Bulletin, , vol. 33, # 9 p. 3787 - 3797
Methyl 2-(3-nitrobenzylidene)-3-oxobutyrate structure

Methyl 2-(3-nit...

CAS#:39562-17-9
2-(4-diphenylmethyl-1-piperazinyl)ethyl 3-aminocrotonate structure

2-(4-diphenylme...

CAS#:90096-33-6

~14%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: Meguro; Aizawa; Sohda; Kawamatsu; Nagaoka Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 9 p. 3787 - 3797
3-Nitrobenzaldehyde structure

3-Nitrobenzaldehyde

CAS#:99-61-6
Methyl acetoacetate structure

Methyl acetoacetate

CAS#:105-45-3
2-(4-diphenylmethyl-1-piperazinyl)ethyl 3-aminocrotonate structure

2-(4-diphenylme...

CAS#:90096-33-6

~17%

Manidipine hydrochloride Structure

Manidipine hydr...

CAS#:89226-75-5
Literature: Meguro; Aizawa; Sohda; Kawamatsu; Nagaoka Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 9 p. 3787 - 3797

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl methyl ester, hydrochloride (1:1)
Manidipine hydrochloride
2-[4-(Diphenylmethyl)piperazin-1-yl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride (1:1)
MFCD00896434
2-[4-(Diphenylmethyl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate hydrochloride (1:1)
Manidipine 2HCl
Manidipine (dihydrochloride)
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