42399-41-7

42399-41-7 structure

Name: Diltiazem
Chemical Name: diltiazem
CAS Number: 42399-41-7
Molecular Formula: C₂₂H₂₆N₂O₄S
Molecular Weight: 414.518
Catalog: API Circulatory system medication Prevention and treatment of angina pectoris
Create Date: 2018-06-13 21:38:16
Modify Date: 2024-01-02 18:40:27
Diltiazem is an orally active L-type Ca2+ channel blocker, with antihypertensive and antiarrhythmic effects. Diltiazem can be used for the research of cardiac arrhythmia, hypertension, and angina pectoris[1][2][3].

Name	diltiazem
Synonyms	(+)-cis-5-[2-(Dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one Acetate (Ester) Adizem EINECS 255-796-4 d-Diltiazem Citizem Diladel DILTIAZEN Deltazen Adizem XL 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)- (2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate TILDIEM300LP diltiazemum [INN_la] (2S-cis)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (+)-cis-Diltiazem (+)-Diltiazem 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)- Dilrene Diltiazem (2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-ylacetat 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)- (2S,3S)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one Cardizen LA MFCD00868239 Coras (2S,3S)-5-[2-(dimethylamino)ethyl]-2-[4-(methyloxy)phenyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate Zilden

Description	Diltiazem is an orally active L-type Ca2+ channel blocker, with antihypertensive and antiarrhythmic effects. Diltiazem can be used for the research of cardiac arrhythmia, hypertension, and angina pectoris[1][2][3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Research Areas >> Cardiovascular Disease
Target	L-type Ca2+ channel[1]
In Vitro	Diltiazem (200 µM) in the superfusate, multichannel currents shows a use-dependent decline in amplitude reflecting reductions in the numbers of superpositions of channel openings in isolated guinea pig ventricular myocytes[1]. Diltiazem reduces Ca2+ influx by accelerating inactivation during action potentials, and that the use-dependent blockade is due to increases in the number of channels in a sustained closed state[1].
In Vivo	Diltiazem (100 mg/kg; p.o.; for 4 weeks) prevents aortic aneurysm formation in a blood pressure-independent manner[3]. Diltiazem limits aortic aneurysm formation in mice by a blood pressure–independent anti-inflammatory effect on monocytic cells[3]. Diltiazem (2 mg/kg; i.v.) has t1/2 of 61.2 min, CLel of 3.2 mL/min[4]. Animal Model: Male ApoE−/− mice, angiotensin II induced aneurysms[3] Dosage: 100 mg/kg Administration: Oral administration, in drinking water, for 4 weeks Result: Srongly reduced the vascular remodeling but also lowered the blood pressure. Animal Model: Rat (200-250 g)[4] Dosage: 2 mg/kg (Pharmacokinetic Analysis) Administration: Intravenous injection Result: T1/2 (61.2 min), CLel (3.2 mL/min)
References	[1]. Yoshinari Niimi, et al. Diltiazem facilitates inactivation of single L-type calcium channels in guinea pig ventricular myocytes. Jpn Heart J. 2003 Nov;44(6):1005-14. [2]. S Lin Tang, et l. Structural Basis for Diltiazem Block of a Voltage-Gated Ca2+ Channel. Mol Pharmacol. 2019 Oct; 96(4): 485–492. [3]. Anja Mieth , et al. L-type calcium channel inhibitor diltiazem prevents aneurysm formation by blood pressure-independent anti-inflammatory effects. Hypertension. 2013 Dec;62(6):1098-104. [4]. S. J. Downing, et al. Diltiazem pharmacokinetics in the rat and relationship between its serum concentration and uterine and cardiovascular effects. Br J Pharmacol. 1987 Aug; 91(4): 735–745.

Density	1.3±0.1 g/cm3
Boiling Point	594.4±50.0 °C at 760 mmHg
Melting Point	104-106°C (lit.)
Molecular Formula	C₂₂H₂₆N₂O₄S
Molecular Weight	414.518
Flash Point	313.3±30.1 °C
Exact Mass	414.161316
PSA	84.38000
LogP	3.63
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.621
Storage condition	20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DL0280000

CHEMICAL NAME :: 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro- 2-(4- methoxyphenyl)-, (2S-cis)-

CAS REGISTRY NUMBER :: 42399-41-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H26-N2-O4-S

MOLECULAR WEIGHT :: 414.56

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 740 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 4,121,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 61 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 4,121,1991

Hazard Codes	Xi

Precursor 9
42399-40-6 108-24-7 4584-46-7 33286-22-5
99109-07-6 696-62-8 24393-56-4 137-07-5
182268-43-5
DownStream 2
42399-40-6 84903-82-2

42399-41-7	56209-45-1
2385-77-5	75472-92-3
1242184-41-3	38411-61-9
33286-22-5	84675-89-8
112259-41-3	142843-04-7