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Drotaverine

July 24, 2017
Common Name

Drotaverine 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source DrotinKegg DrotaverinHMDB NospanMeSH IsodihydroperparineMeSH NO-ShpaMeSH DihydroisoperparineMeSH Drotaverin hydrochlorideMeSH NO-SpaMeSH NospanumMeSH

Chemical Formlia

C24H31NO4 Average Molecliar Weight

397.5072 Monoisotopic Molecliar Weight

397.225308485 IUPAC Name

(1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline Traditional Name

drotaverine CAS Registry Number

985-12-6 SMILES

CCOC1=C(OCC)C=C(C=C2/NCCC3=CC(OCC)=C(OCC)C=C23)C=C1

InChI Identifier

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-

InChI Key

OMFNSKIUKYOYRG-MOSHPQCFSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Tetrahydroisoquinolines Direct Parent

Tetrahydroisoquinolines Alternative Parents

  • Phenoxy compounds
  • Phenol ethers
  • Aralkylamines
  • Alkyl aryl ethers
  • Enamines
  • Dialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Tetrahydroisoquinoline
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary aliphatic amine
  • Enamine
  • Ether
  • Secondary amine
  • Azacycle
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.002 mg/mLALOGPS logP5.35ALOGPS logP4.19ChemAxon logS-5.3ALOGPS pKa (Strongest Basic)7.4ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area48.95 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity117.99 m3·mol-1ChemAxon Polarizability46.99 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06751

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06751

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06751 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    1361582 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Drotaverine NuGOwiki Link

    HMDB15669 Metagene Link

    HMDB15669 METLIN ID

    Not Available PubChem Compound

    1712095 PDB ID

    Not Available ChEBI ID

    665387

    Product: Atovaquone

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. 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 ]

    Enzymes

    General function:
    Involved in 3,5-cyclic-nucleotide phosphodiesterase activity
    Specific function:
    Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
    Gene Name:
    PDE4A
    Uniprot ID:
    P27815
    Molecular weight:
    98142.155
    References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    General function:
    Involved in ion 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, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the high-voltage activated (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
    Gene Name:
    CACNA1C
    Uniprot ID:
    Q13936
    Molecular weight:
    248974.1
    References
    1. 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 ]
    2. 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 ]

    PMID: 23911321

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