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

• ChemBase ID: 4472
• Molecular Formular: C24H31NO4
• Molecular Mass: 397.50724
• Monoisotopic Mass: 397.22530848
• SMILES: O(c1cc2CCN/C(=C\c3cc(OCC)c(OCC)cc3)/c2cc1OCC)CC
• Canonical SMILES: CCOc1cc(ccc1OCC)/C=C/1\NCCc2c1cc(OCC)c(c2)OCC
• 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-
• InChIKey: OMFNSKIUKYOYRG-MOSHPQCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline
• IUPAC Traditional name: drotaverine
• Brand Name: No-Spa; Drotin
• Synonyms: drotaverin; Drotaverine; (Z)-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline

Database IDs

• CAS Number: 985-12-6
• PubChem SID: 160967904; 99443287
• PubChem CID: 1712095

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.3096476
• LogD (pH = 7.4): 3.892906
• Log P: 4.191375
• Molar Refractivity: 117.994 cm^3
• Polarizability: 44.95594 Å^3
• Polar Surface Area: 48.95 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.35
• LOG S: -5.3
• Solubility (Water): 2.00e-03 g/l

DETAILS

DrugBank - DB06751

• Drug Groups: approved
• 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.
• Indication: Used in the treatment of functional bowel disorders and alleviating pain in renal colic.
• Pharmacology: Drotaverine is a spasmolytic agent by inhibiting PDE4 in smooth muscle cells.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Bioavailability is highly variable
• Half Life: 7 to 12 hours
• Protein Binding: 80 to 95%
• 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]
• External Links: Wikipedia

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