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DSSTox_CID_31450

DSSTox_CID_31450

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

EMULSION;INTRAVENOUS - 125MG/250ML (0.5MG/ML), EMULSION;INTRAVENOUS - 25MG/50ML (0.5MG/ML), EMULSION;INTRAVENOUS - 50MG/100ML (0.5MG/ML)

EMULSION;INTRAVENOUS - 125MG/250ML (0.5MG/ML)
EMULSION;INTRAVENOUS - 25MG/50ML (0.5MG/ML)
EMULSION;INTRAVENOUS - 50MG/100ML (0.5MG/ML)

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Suppliers, 3 Nanjing Well Pharmaceutical, 2 Actylis, 2 Kewpie Corporation, 1 Kerry

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5 Parenteral, 4 Emulsifying Agents, 2 Solubilizers, 1 Controlled & Modified Release, 1 Film Formers & Plasticizers, 1 Coating Systems & Additives

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Also known as: 167221-71-8, Clevidipine butyrate, Cleviprex, Clevelox, Clevidepine, Clevidepine butyrate

Molecular Formula

C₂₁H₂₃Cl₂NO₆

Molecular Weight

456.3 g/mol

InChI Key

KPBZROQVTHLCDU-UHFFFAOYSA-N

FDA UNII

19O2GP3B7Q

Clevidipine is a dihydropyridine L-type calcium channel blocker that is selective for vascular smooth muscle and is indicated for blood pressure reduction when oral therapy is not an option.

Clevidipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of clevidipine is as a Calcium Channel Antagonist.

1 2D Structure

DSSTox_CID_31450

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-O-(butanoyloxymethyl) 3-O-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

2.1.2 InChI

InChI=1S/C21H23Cl2NO6/c1-5-7-15(25)29-10-30-21(27)17-12(3)24-11(2)16(20(26)28-4)18(17)13-8-6-9-14(22)19(13)23/h6,8-9,18,24H,5,7,10H2,1-4H3

2.1.3 InChI Key

KPBZROQVTHLCDU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCC(=O)OCOC(=O)C1=C(NC(=C(C1C2=C(C(=CC=C2)Cl)Cl)C(=O)OC)C)C

2.2 Other Identifiers

2.2.1 UNII

19O2GP3B7Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Butyroxymethyl Methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

2. Cleviprex

2.3.2 Depositor-Supplied Synonyms

1. 167221-71-8

2. Clevidipine Butyrate

3. Cleviprex

4. Clevelox

5. Clevidepine

6. Clevidepine Butyrate

7. 166432-28-6

8. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-[(1-oxobutoxy)methyl] Ester

9. Methyl (1-oxobutoxy)methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dime Thyl-3,5-pyridinedicarboxylate

10. 19o2gp3b7q

11. 3-((butyryloxy)methyl) 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

12. 5-o-(butanoyloxymethyl) 3-o-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

13. Methyl (1-oxobutoxy)methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

14. Rac-clevidipine

15. H324/38

16. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, Methyl (1-oxobutoxy)methyl Ester

17. Methyl 5-{[(butanoyloxy)methoxy]carbonyl}-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

18. H-324/38

19. (butanoyloxy)methyl Methyl (4rs)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

20. Sr-01000945183

21. Clevidipine [usan:inn]

22. Unii-19o2gp3b7q

23. Cleviprex (tn)

24. 3,5-pyridinedicarboxylic Acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl 5-((1-oxobutoxy)methyl) Ester

25. 3-[(butyryloxy)methyl] 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

26. Clevidipine [inn]

27. H 324/38

28. Cleviprex (clevidipine)

29. Clevidipine [mi]

30. Clevidipine (usan/inn)

31. Clevidipine [usan]

32. Clevidepine [vandf]

33. Clevidipine [vandf]

34. Clevidipine [mart.]

35. Dsstox_cid_31450

36. Dsstox_rid_97336

37. Dsstox_gsid_57661

38. Clevidipine [who-dd]

39. Schembl115522

40. Gtpl7468

41. Clevidipine Butyrate;clevidipine

42. Chembl1237132

43. Dtxsid6057661

44. Clevidipine [orange Book]

45. Chebi:135738

46. Hms3604h21

47. Hms3651g10

48. Hms3884l03

49. Amy22141

50. Bcp22676

51. Bcp22687

52. Ex-a2898

53. Clevidepine Butyrate [vandf]

54. Clevidipine Butyrate [vandf]

55. Tox21_113923

56. Bdbm50088387

57. Mfcd00940070

58. S2080

59. Akos015896325

60. Ccg-269294

61. Cs-1427

62. Db04920

63. Ncgc00262928-01

64. 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid 3-methyl 5-[(1-oxobutoxy)methyl] Ester

65. Ac-24370

66. As-19935

67. Butyroxymethyl Methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

68. Clevidipine Butyrate [orange Book]

69. Hy-17436

70. Db-064636

71. C3503

72. Cas-167221-71-8

73. Ft-0659562

74. Ft-0688416

75. Sw220087-1

76. D08892

77. Ab01566888_01

78. 221c718

79. A810832

80. J-520103

81. Q5132338

82. Sr-01000945183-1

83. Sr-01000945183-2

84. Z1691545244

85. 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic Aicd 3-[(butyryloxy)methyl] 5-methyl Ester

86. Butyroxymethyl Methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylat

87. O3-(butanoyloxymethyl) O5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₃Cl₂NO₆
Molecular Weight	456.3 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	10
Exact Mass	455.0902428 g/mol
Monoisotopic Mass	455.0902428 g/mol
Topological Polar Surface Area	90.9 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	748
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Cleviprex
PubMed Health	Clevidipine (Injection)
Drug Classes	Antihypertensive
Drug Label	Cleviprex is a sterile, milky-white emulsion containing 0.5 mg/mL of clevidipine suitable for intravenous administration. Clevidipine is a dihydropyridine calcium channel blocker. Chemically, the active substance, clevidipine, is butyroxymethyl methy...
Active Ingredient	Clevidipine
Dosage Form	Emulsion
Route	Intravenous
Strength	125mg/250ml (0.5mg/ml); 25mg/50ml (0.5mg/ml); 50mg/100ml (0.5mg/ml)
Market Status	Prescription
Company	Medicines

2 of 2
Drug Name	Cleviprex
PubMed Health	Clevidipine (Injection)
Drug Classes	Antihypertensive
Drug Label	Cleviprex is a sterile, milky-white emulsion containing 0.5 mg/mL of clevidipine suitable for intravenous administration. Clevidipine is a dihydropyridine calcium channel blocker. Chemically, the active substance, clevidipine, is butyroxymethyl methy...
Active Ingredient	Clevidipine
Dosage Form	Emulsion
Route	Intravenous
Strength	125mg/250ml (0.5mg/ml); 25mg/50ml (0.5mg/ml); 50mg/100ml (0.5mg/ml)
Market Status	Prescription
Company	Medicines

4.2 Drug Indication

For the reduction of blood pressure when when oral antihypertensive therapy is not feasible or not desirable.

FDA Label

Treatment of hypertensive disease

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clevidipine belongs to a well-known class of drugs called dihydropyridine calcium channel antagonists. Clevidpine is the first third generation intravenous dihydropyridine calcium channel blocker. In vitro studies demonstrated that clevidipine acts by selectively relaxing the smooth muscle cells that line small arteries, resulting in arterial dilation, widening of the artery opening, and without reducing central venous pressure or reducing cardiac output.

5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CLEVIDIPINE

5.3.2 FDA UNII

19O2GP3B7Q

5.3.3 Pharmacological Classes

Dihydropyridine Calcium Channel Blocker [EPC]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]

5.4 ATC Code

C08CA16

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA16 - Clevidipine

5.5 Absorption, Distribution and Excretion

Route of Elimination

urine 63-74%, feces 7-22%

5.6 Metabolism/Metabolites

Clevidipine is rapidly hydrolyzed to inactive metabolites by esterases in arterial blood.

5.7 Biological Half-Life

1 minute

5.8 Mechanism of Action

Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, clevidipine inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.