Identification
- Summary
Clevidipine is a dihydropyridine L-type calcium channel blocker used to lower blood pressure when oral antihypertensive therapy is not feasible or not desirable.
- Brand Names
- Cleviprex
- Generic Name
- Clevidipine
- DrugBank Accession Number
- DB04920
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Clevidipine (DB04920)
- Weight
- Average: 456.316
Monoisotopic: 455.090242887 - Chemical Formula
- C21H23Cl2NO6
- Synonyms
- Clevidipine
- Clevidipine butyrate
- Clevidipino
- External IDs
- H-324/38
Pharmacology
- Indication
For the reduction of blood pressure when when oral antihypertensive therapy is not feasible or not desirable.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Hypertension •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- 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.
Target Actions Organism UVoltage-dependent L-type calcium channel subunit alpha-1F Not Available Humans UVoltage-dependent L-type calcium channel subunit alpha-1S Not Available Humans UVoltage-dependent L-type calcium channel subunit alpha-1D Not Available Humans UVoltage-dependent L-type calcium channel subunit alpha-1C Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
>99.5%
- Metabolism
Clevidipine is rapidly hydrolyzed to inactive metabolites by esterases in arterial blood.
- Route of elimination
urine 63-74%, feces 7-22%
- Half-life
1 minute
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Clevidipine which could result in a higher serum level. Abaloparatide The risk or severity of adverse effects can be increased when Clevidipine is combined with Abaloparatide. Abametapir The serum concentration of Clevidipine can be increased when it is combined with Abametapir. Abatacept The metabolism of Clevidipine can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Clevidipine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cleviprex Emulsion 0.5 mg/1mL Intravenous Chiesi USA, Inc. 2008-09-15 Not applicable US 
Cleviprex Emulsion 0.5 mg/1mL Intravenous Fresenius Kabi Austria GmbH 2008-09-15 Not applicable US Cleviprex Emulsion 0.5 mg/1mL Intravenous Chiesi USA, Inc. 2008-09-15 Not applicable US Cleviprex Emulsion 0.5 mg / mL Intravenous Chiesi Farmaceutici S.P.A. 2023-08-04 Not applicable Canada 
Cleviprex Emulsion 0.5 mg/1mL Intravenous Chiesi USA, Inc. 2008-09-15 Not applicable US
Categories
- ATC Codes
- C08CA16 — Clevidipine
- Drug Categories
- Agents causing hyperkalemia
- Antiarrhythmic agents
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Calcium Channel Blockers (Dihydropyridine)
- Calcium-Regulating Hormones and Agents
- Cardiovascular Agents
- Cholinesterase substrates
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dihydropyridine Derivatives
- Dihydropyridines
- Drugs that are Mainly Renally Excreted
- Hypotensive Agents
- Membrane Transport Modulators
- Selective Calcium Channel Blockers With Mainly Vascular Effects
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. These are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Hydropyridines
- Direct Parent
- Dihydropyridinecarboxylic acids and derivatives
- Alternative Parents
- Tricarboxylic acids and derivatives / Dichlorobenzenes / Acylals / Fatty acid esters / Aryl chlorides / Vinylogous amides / Methyl esters / Enoate esters / Amino acids and derivatives / Acetals show 8 more
- Substituents
- 1,2-dichlorobenzene / Acetal / Acylal / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle show 26 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 19O2GP3B7Q
- CAS number
- 167221-71-8
- InChI Key
- KPBZROQVTHLCDU-UHFFFAOYSA-N
- 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
- IUPAC Name
- methyl 5-{[(butanoyloxy)methoxy]carbonyl}-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate
- SMILES
- CCCC(=O)OCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC(Cl)=C1Cl)C(=O)OC
References
- General References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Nordlander M, Sjoquist PO, Ericsson H, Ryden L: Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine, an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc Drug Rev. 2004 Fall;22(3):227-50. [Article]
- Wang QD, Segawa D, Ericsson H, Sjoquist PO, Johansson L, Ryden L: Time-dependent cardioprotection with calcium antagonism and experimental studies with clevidipine in ischemic-reperfused pig hearts: part I. J Cardiovasc Pharmacol. 2002 Aug;40(2):228-34. [Article]
- Stephens CT, Jandhyala BS: Effects of fenoldopam, a dopamine D-1 agonist, and clevidipine, a calcium channel antagonist, in acute renal failure in anesthetized rats. Clin Exp Hypertens. 2002 May;24(4):301-13. [Article]
- FDA Approved Drug Products: Cleviprex (clevidipine) injection [Link]
- External Links
- KEGG Drug
- D08892
- PubChem Compound
- 153994
- PubChem Substance
- 175426904
- ChemSpider
- 135722
- BindingDB
- 50088387
- 233603
- ChEBI
- 135738
- ChEMBL
- CHEMBL1237132
- Wikipedia
- Clevidipine
- FDA label
- Download (381 KB)
- MSDS
- Download (568 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Diagnostic Pulmonary Hypertension (PH) 1 4 Completed Treatment Brain Neoplasm / Epilepsy / Hypertension 1 4 Not Yet Recruiting Treatment Hypertension 1 4 Suspended Treatment Pediatric Perioperative Blood Pressure Management 1 4 Terminated Treatment Aortic Aneurysms / Aortic Diseases 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Emulsion Intravenous 0.5 mg / mL Emulsion Intravenous 0.5 mg/1mL Emulsion Parenteral 0.5 MG/ML Injection, emulsion Intravenous 0.5 MG/ML Emulsion Intravenous 25.000 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5739152 No 1998-04-14 2015-04-14 US US5856346 No 1999-01-05 2021-01-05 US US8658676 No 2014-02-25 2031-10-10 US US10010537 No 2018-07-03 2031-10-10 US US11103490 No 2021-08-31 2031-10-10 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00267 mg/mL ALOGPS logP 4.98 ALOGPS logP 4.09 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 16.95 Chemaxon pKa (Strongest Basic) -6.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 90.93 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 113.93 m3·mol-1 Chemaxon Polarizability 45.14 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9887 Blood Brain Barrier - 0.5892 Caco-2 permeable + 0.6566 P-glycoprotein substrate Substrate 0.5787 P-glycoprotein inhibitor I Inhibitor 0.8948 P-glycoprotein inhibitor II Non-inhibitor 0.6827 Renal organic cation transporter Non-inhibitor 0.8312 CYP450 2C9 substrate Non-substrate 0.8879 CYP450 2D6 substrate Non-substrate 0.8693 CYP450 3A4 substrate Substrate 0.693 CYP450 1A2 substrate Inhibitor 0.6871 CYP450 2C9 inhibitor Inhibitor 0.6818 CYP450 2D6 inhibitor Non-inhibitor 0.8455 CYP450 2C19 inhibitor Inhibitor 0.7456 CYP450 3A4 inhibitor Inhibitor 0.9187 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9098 Ames test Non AMES toxic 0.7527 Carcinogenicity Non-carcinogens 0.8407 Biodegradation Not ready biodegradable 0.9403 Rat acute toxicity 2.6248 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7841 hERG inhibition (predictor II) Non-inhibitor 0.8148
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.57634 predictedDeepCCS 1.0 (2019) [M+H]+ 203.93434 predictedDeepCCS 1.0 (2019) [M+Na]+ 210.34546 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
- Gene Name
- CACNA1F
- Uniprot ID
- O60840
- Uniprot Name
- Voltage-dependent L-type calcium channel subunit alpha-1F
- Molecular Weight
- 220675.9 Da
References
- Nordlander M, Sjoquist PO, Ericsson H, Ryden L: Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine, an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc Drug Rev. 2004 Fall;22(3):227-50. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
- Gene Name
- CACNA1S
- Uniprot ID
- Q13698
- Uniprot Name
- Voltage-dependent L-type calcium channel subunit alpha-1S
- Molecular Weight
- 212348.1 Da
References
- Nordlander M, Sjoquist PO, Ericsson H, Ryden L: Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine, an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc Drug Rev. 2004 Fall;22(3):227-50. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated calcium channel activity involved sa node cell action potential
- Specific Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
- Gene Name
- CACNA1D
- Uniprot ID
- Q01668
- Uniprot Name
- Voltage-dependent L-type calcium channel subunit alpha-1D
- Molecular Weight
- 245138.75 Da
References
- Nordlander M, Sjoquist PO, Ericsson H, Ryden L: Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine, an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc Drug Rev. 2004 Fall;22(3):227-50. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
- Gene Name
- CACNA1C
- Uniprot ID
- Q13936
- Uniprot Name
- Voltage-dependent L-type calcium channel subunit alpha-1C
- Molecular Weight
- 248974.1 Da
References
- Nordlander M, Sjoquist PO, Ericsson H, Ryden L: Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine, an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc Drug Rev. 2004 Fall;22(3):227-50. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Clevidipine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
- Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Ericsson H, Tholander B, Regardh CG: In vitro hydrolysis rate and protein binding of clevidipine, a new ultrashort-acting calcium antagonist metabolised by esterases, in different animal species and man. Eur J Pharm Sci. 1999 Apr;8(1):29-37. [Article]
Drug created at October 21, 2007 22:23 / Updated at October 05, 2023 12:19