Drotaverine
Identification
- Name
- Drotaverine
- Accession Number
- DB06751
- Description
Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, structurally related to papaverine. Drotaverine is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects. Drotaverine has been shown to possess dose-dependant analgesic effects in animal models. One small study has shown drotaverine to be eliminated mainly non-renally.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Drotaverine (DB06751)
- Weight
- Average: 397.5072
Monoisotopic: 397.225308485 - Chemical Formula
- C24H31NO4
- Synonyms
- Drotaverin
- Drotaverina
- Drotaverine
- Drotaverinum
Pharmacology
- Indication
Used in the treatment of functional bowel disorders and alleviating pain in renal colic.
- Associated Conditions
- Abdominal Pain caused by Gall Stones
- Abdominal Pain caused by Kidney Stones
- Muscle Spasms
- Spastic Pain
- Spastic Pain caused by Cystitis
- Spastic Pain caused by Funicular Nephritis
- Spastic Pain caused by Gallbladder disorders
- Spastic Pain caused by Physical Examination
- Spastic Pain caused by cholecysitis
- Spastic Pain of the Gastrointestinal Tract
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Drotaverine is a spasmolytic agent by inhibiting PDE4 in smooth muscle cells.
- Mechanism of action
Drotaverine inhibits phosphodiesterases hydrolysing cAMP, thereby increasing cAMP concentration, decreasing Ca uptake of the cells and changing the distribution of calcium among the cells. It may also have minor allosteric calcium channel blocking properties.
Target Actions Organism AcAMP-specific 3',5'-cyclic phosphodiesterase 4A inhibitorHumans UVoltage-dependent L-type calcium channel subunit alpha-1C inhibitorHumans - Absorption
Bioavailability is highly variable
- Volume of distribution
- Not Available
- Protein binding
80 to 95%
- Metabolism
Hepatic
- Route of elimination
- Not Available
- Half-life
7 to 12 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Unlock Additional DataIsosorbide mononitrate Drotaverine may increase the vasodilatory activities of Isosorbide mononitrate. Patent Blue The therapeutic efficacy of Drotaverine can be decreased when used in combination with Patent Blue. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Drotaverine hydrochloride 24ZVH4C669 985-12-6 JBFLYOLJRKJYNV-MASIZSFYSA-N - International/Other Brands
- Drotin / No-Spa (Sanofi-Aventis) / Taverin
Categories
- ATC Codes
- A03AD02 — Drotaverine
- Drug Categories
- Alimentary Tract and Metabolism
- Alkaloids
- Analgesics
- Autonomic Agents
- Benzylisoquinolines
- Cardiovascular Agents
- Central Nervous System Agents
- Drugs for Functional Gastrointestinal Disorders
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Opiate Alkaloids
- Papaverine and Derivatives
- Parasympatholytics
- Peripheral Nervous System Agents
- Sensory System Agents
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Tetrahydroisoquinolines
- Sub Class
- Not Available
- Direct Parent
- Tetrahydroisoquinolines
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Aralkylamines / Alkyl aryl ethers / Enamines / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Enamine / Ether / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 98QS4N58TW
- CAS number
- 14009-24-6
- InChI Key
- OMFNSKIUKYOYRG-MOSHPQCFSA-N
- InChI
- InChI=1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13-
- IUPAC Name
- (1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline
- SMILES
- CCOC1=C(OCC)C=C(\C=C2/NCCC3=CC(OCC)=C(OCC)C=C23)C=C1
References
- General References
- Bolaji OO, Onyeji CO, Ogundaini AO, Olugbade TA, Ogunbona FA: Pharmacokinetics and bioavailability of drotaverine in humans. Eur J Drug Metab Pharmacokinet. 1996 Jul-Sep;21(3):217-21. [PubMed:8980918]
- External Links
- Human Metabolome Database
- HMDB0015669
- PubChem Compound
- 1712095
- PubChem Substance
- 99443287
- ChemSpider
- 1361582
- BindingDB
- 50237620
- 23684
- ChEBI
- 135630
- ChEMBL
- CHEMBL551978
- ZINC
- ZINC000100011979
- PharmGKB
- PA165958398
- Wikipedia
- Drotaverine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Terminated Treatment Menstrual Cramps 1 3 Completed Prevention Bile Duct Diseases / ERCP / Pancreatic Diseases 1 2 Unknown Status Diagnostic Effect of Meperidine or Drotaverine on Effacement and Dilatation of the Cervix During Labor in Full Term Primigravidae 1 2, 3 Completed Treatment Failure of Cervical Dilation as Antepartum Condition / Mild Birth Asphyxia, APGAR 4-7 / Pain, Labor / Prolonged First Stage of Labor 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 40 mg Injection, solution 40 mg/2mL Tablet, coated Oral 40 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.002 mg/mL ALOGPS logP 5.35 ALOGPS logP 4.19 ChemAxon logS -5.3 ALOGPS pKa (Strongest Basic) 7.4 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 48.95 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 117.99 m3·mol-1 ChemAxon Polarizability 46.99 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.753 Caco-2 permeable + 0.6023 P-glycoprotein substrate Substrate 0.8447 P-glycoprotein inhibitor I Inhibitor 0.7972 P-glycoprotein inhibitor II Non-inhibitor 0.8544 Renal organic cation transporter Non-inhibitor 0.625 CYP450 2C9 substrate Non-substrate 0.7958 CYP450 2D6 substrate Non-substrate 0.6116 CYP450 3A4 substrate Substrate 0.6738 CYP450 1A2 substrate Inhibitor 0.6812 CYP450 2C9 inhibitor Inhibitor 0.5672 CYP450 2D6 inhibitor Non-inhibitor 0.6789 CYP450 2C19 inhibitor Non-inhibitor 0.6475 CYP450 3A4 inhibitor Inhibitor 0.7906 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8634 Ames test Non AMES toxic 0.8205 Carcinogenicity Non-carcinogens 0.9164 Biodegradation Not ready biodegradable 0.9421 Rat acute toxicity 2.5733 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6798 hERG inhibition (predictor II) Inhibitor 0.7085
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4A
- Uniprot ID
- P27815
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4A
- Molecular Weight
- 98142.155 Da
References
- Muravyov AV, Yakusevich VV, Chuchkanov FA, Maimistova AA, Bulaeva SV, Zaitsev LG: Hemorheological efficiency of drugs, targeting on intracellular phosphodiesterase activity: in vitro study. Clin Hemorheol Microcirc. 2007;36(4):327-34. [PubMed:17502703]
- Romics I, Molnar DL, Timberg G, Mrklic B, Jelakovic B, Koszegi G, Blasko G: The effect of drotaverine hydrochloride in acute colicky pain caused by renal and ureteric stones. BJU Int. 2003 Jul;92(1):92-6. [PubMed:12823389]
- Pareek A, Chandurkar NB, Patil RT, Agrawal SN, Uday RB, Tambe SG: Efficacy and safety of aceclofenac and drotaverine fixed-dose combination in the treatment of primary dysmenorrhoea: a double-blind, double-dummy, randomized comparative study with aceclofenac. Eur J Obstet Gynecol Reprod Biol. 2010 Sep;152(1):86-90. doi: 10.1016/j.ejogrb.2010.05.007. Epub 2010 Jun 15. [PubMed:20554370]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Tomoskozi Z, Finance O, Aranyi P: Drotaverine interacts with the L-type Ca(2+) channel in pregnant rat uterine membranes. Eur J Pharmacol. 2002 Aug 2;449(1-2):55-60. [PubMed:12163106]
- Romics I, Molnar DL, Timberg G, Mrklic B, Jelakovic B, Koszegi G, Blasko G: The effect of drotaverine hydrochloride in acute colicky pain caused by renal and ureteric stones. BJU Int. 2003 Jul;92(1):92-6. [PubMed:12823389]
Drug created on September 07, 2010 15:21 / Updated on June 12, 2020 10:52
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