Drotaverine hydrochloride

• CAS: 985-12-6
• Catalog Number: ACM985126
• Category: Main Products
• Molecular Weight: 433.97
• Molecular Formula: C₂₄H₃₂ClNO₄
• Synonyms: 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydro-isoquinolin;drotaveriniumchloride;isoquinoline,1,2,3,4-tetrahydro-6,7-diethoxy-1-((3,4-diethoxyphenyl)methylene);no-spa;no-spahydrochloride;tetraspasmin-lefa;DROTAVERINE HYDROCHLORIDE;DROTAVERIN
• IUPAC Name: (1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-3,4-dihydro-2H-i...
• Boiling Point: 564ºC at 760 mmHg
• Melting Point: 208-212ºC
• Flash Point: 240.7ºC
• Density: 1.097 g/cm³
• Appearance: Pale-yellow solid
• Exact Mass: 433.20200

Case Study

Drotaverine Hydrochloride Gastroretentive Floating Mini-Tablets

Louis, Mina M., et al. Journal of Drug Delivery Science and Technology 57 (2020): 101733.

Drotaverine hydrochloride (DRH) is an antispasmodic which has a compromised bioavailability during diarrheal states due to accelerated G.I. transit. The study described the formulation of a gastroretentive floating mini-tablet containing DRH that could potentially enhance gastric residence time and provide sustained drug release to overcome the short intestinal residence and frequent dosing of DRH.
Formulation Development
Nine floating mini-tablet formulations were manufactured by wet granulation using a 32 factorial design to investigate the effects of sodium alginate and sodium bicarbonate levels. The formulation FF9 (sodium alginate 200 mg, sodium bicarbonate 120 mg) emerged as the lead candidate with excellent floating behavior, sustained in-vitro release, and improved systemic exposure vs. a marketed reference.
In-vitro performance
The selected lead, FF9 (200 mg sodium alginate, 120 mg sodium bicarbonate), showed optimal buoyancy with a floating lag time of 49.1 ± 5.3 s and a total floating duration exceeding 24 h. The release profile exhibited a sustained release of DRH: 7.60 ± 1.25% at 0.5 h and 78.14 ± 3.10% at 12 h suggesting a prolonged release which is desired in a gastroretentive dosage form.
In-vivo bioavailability
FF9 was evaluated against a marketed DRH product for systemic exposure. Statistical analysis indicated a significant increase in overall exposure for FF9, with AUC(0-∞) = 3311.31 ± 182.18 ng·h/ml versus 1589.54 ± 127.97 ng·h/ml for the marketed product, along with a delayed Tmax for the floating formulation. The formulation's desirability score in the optimization was 0.942, supporting FF9 as the optimized candidate.

Efficacy and Safety of Drotaverine Hydrochloride for Irritable Bowel Syndrome

Rai, Ramesh R., et al. Saudi Journal of Gastroenterology 20.6 (2014): 378-382.

Drotaverine hydrochloride, a phosphodiesterase-4 inhibitor, has been proposed as a treatment option for irritable bowel syndrome (IBS) due to its smooth muscle relaxant properties. This study evaluated the efficacy and safety of drotaverine hydrochloride, an antispasmodic agent, in alleviating symptoms of IBS.
Methodology
IBS patients that fit the Rome II criteria were enrolled in the study. A total of 180 patients were recruited for the study and randomized to receive 80 mg of Drotaverine Hydrochloride or placebo three times a day for four weeks. The frequency and severity of abdominal pain was recorded by the patients on a weekly basis. Frequency of stools and overall relief of symptoms as recorded by both patients and clinicians was also monitored. Statistical validity of results was confirmed using the Mann-Whitney U-test and the Wilcoxon signed-rank test.
Key Results
· Pain Frequency: 1) Week 2: 25.9% of Drotaverine patients showed significant improvement vs. 9.4% in the placebo group. 2) Week 3: 60% (Drotaverine) vs. 21.2% (placebo). 3) Week 4: 77.7% (Drotaverine) vs. 30.6% (placebo).
· Pain Severity: 77.7% of patients in the Drotaverine group reported reduced pain severity after 4 weeks vs. 30.6% in the placebo group.
· Global Symptom Relief: 1) Patient-reported relief: 85.9% (Drotaverine) vs. 39.5% (placebo). 2) Clinician-assessed relief: 82.4% (Drotaverine) vs. 36.5% (placebo).
· Stool Frequency: Significant improvement was observed in the treatment group compared to placebo (P < 0.01).
· Safety: Drotaverine Hydrochloride was well-tolerated with no major adverse effects reported.

Custom Q&A

What is the molecular formula of Drotaverine hydrochloride?

The molecular formula of Drotaverine hydrochloride is C24H32ClNO4.

What is the molecular weight of Drotaverine hydrochloride?

The molecular weight of Drotaverine hydrochloride is 434.0 g/mol.

What is the IUPAC name of Drotaverine hydrochloride?

The IUPAC name of Drotaverine hydrochloride is (1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-3,4-dihydro-2H-isoquinoline; hydrochloride.

What is the InChI of Drotaverine hydrochloride?

The InChI of Drotaverine hydrochloride is InChI=1S/C24H31NO4.ClH/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;1H/b20-13-.

What is the InChIKey of Drotaverine hydrochloride?

The InChIKey of Drotaverine hydrochloride is JBFLYOLJRKJYNV-MASIZSFYSA-N.

What is the canonical SMILES of Drotaverine hydrochloride?

The canonical SMILES of Drotaverine hydrochloride is CCOC1=C(C=C(C=C1)C=C2C3=CC(=C(C=C3CCN2)OCC)OCC)OCC.Cl.

How many hydrogen bond donor counts does Drotaverine hydrochloride have?

Drotaverine hydrochloride has 2 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does Drotaverine hydrochloride have?

Drotaverine hydrochloride has 5 hydrogen bond acceptor counts.

How many rotatable bond counts does Drotaverine hydrochloride have?

Drotaverine hydrochloride has 9 rotatable bond counts.

What is the topological polar surface area of Drotaverine hydrochloride?

The topological polar surface area of Drotaverine hydrochloride is 49.2.