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Chemistry

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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
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

Clevidipine

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 Weight 456.3 g/mol
Molecular Formula C21H23Cl2NO6
XLogP34.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count10
Exact Mass455.0902428 g/mol
Monoisotopic Mass455.0902428 g/mol
Topological Polar Surface Area90.9 Ų
Heavy Atom Count30
Formal Charge0
Complexity748
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCleviprex
PubMed HealthClevidipine (Injection)
Drug ClassesAntihypertensive
Drug LabelCleviprex 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 IngredientClevidipine
Dosage FormEmulsion
RouteIntravenous
Strength125mg/250ml (0.5mg/ml); 25mg/50ml (0.5mg/ml); 50mg/100ml (0.5mg/ml)
Market StatusPrescription
CompanyMedicines

2 of 2  
Drug NameCleviprex
PubMed HealthClevidipine (Injection)
Drug ClassesAntihypertensive
Drug LabelCleviprex 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 IngredientClevidipine
Dosage FormEmulsion
RouteIntravenous
Strength125mg/250ml (0.5mg/ml); 25mg/50ml (0.5mg/ml); 50mg/100ml (0.5mg/ml)
Market StatusPrescription
CompanyMedicines

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.


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04-Jun-2022
04-Jun-2022
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DOSAGE - EMULSION;INTRAVENOUS - 125MG/250ML (...DOSAGE - EMULSION;INTRAVENOUS - 125MG/250ML (0.5MG/ML)

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DOSAGE - EMULSION;INTRAVENOUS - 25MG/50ML (0....DOSAGE - EMULSION;INTRAVENOUS - 25MG/50ML (0.5MG/ML)

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US Patent Number : 11103490

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US Patent Number : 11103490

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Patent Expiration Date : 2031-10-10

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CLEVIDIPINE

US Patent Number : 8658676

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Application Number : 22156

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Patent Expiration Date : 2031-10-10

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