4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate

• ChemBase ID: 933
• Molecular Formular: C22H31NO3
• Molecular Mass: 357.48644
• Monoisotopic Mass: 357.23039386
• SMILES: OC(C1CCCCC1)(c1ccccc1)C(=O)OCC#CCN(CC)CC
• Canonical SMILES: CCN(CC#CCOC(=O)C(c1ccccc1)(C1CCCCC1)O)CC
• InChI: InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3
• InChIKey: XIQVNETUBQGFHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate
• IUPAC Traditional name: oxybutynin
• Brand Name: Ditropan; Ditropan Xl; Oxytrol
• Synonyms: Oxibutinina [INN-Spanish]; Oxibutyninum; Oxybutynin Base; Oxybutynin Chloride; Oxybutynin Hydrochloride; Oxybutynine [INN-French]; Oxybutyninum [INN-Latin]; Oxybutinin; oxybutynin; transdermal patch; oxybutynin topical gel; Oxybutynin; Ditropan; Lyrinel XL; Oxytrol

Database IDs

• CAS Number: 5633-20-5
• PubChem SID: 46508005; 160964396
• PubChem CID: 4634

CALCULATED PROPERTIES

JChem

• Lipinski's Rule of Five: true
• Acid pKa: 11.532723
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3698729
• LogD (pH = 7.4): 3.0553124
• Log P: 4.4380755
• Molar Refractivity: 105.2623 cm^3
• Polarizability: 40.873947 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 10

ALOGPS 2.1

• Solubility (Water): 1.00e-02 g/l
• Log P: 4.36
• LOG S: -4.55

PROPERTIES

Physical Property

• Hydrophobicity(logP): 4.3

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01062

• Drug Groups: approved; investigational
• Description: Oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination, by decreasing muscle spasms of the bladder. It competitively antagonizes the M1, M2, and M3 subtypes of the muscarinic acetylcholine receptor.
• Indication: For the treatment of overactive bladder.
• Pharmacology: Oxybutynin is an antispasmodic, anticholinergic agent indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency. Oxybutynin relaxes bladder smooth muscle. Oxybutynin exhibits only one-fifth of the anticholinergic activity of atropine on the rabbit detrusor muscle, but four to ten times the antispasmodic activity. Antimuscarinic activity resides predominantly in the R-isomer.
• Toxicity: LD₅₀=1220 mg/kg (Orally in rats, Goldenthal)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, primarily by CYP3A4
• Absorption: Rapidly absorbed from gastrointestinal tract.
• Half Life: 12.4-13.2 hours
• Protein Binding: 91%-93%
• Elimination: Oxybutynin is metabolized primarily by the cytochrome P450 enzyme systems, particularly CYP3A4, found mostly in the liver and gut wall. Oxybutynin is extensively metabolized by the liver, with less than 0.1% of the administered dose excreted unchanged in the urine.; Also, less than 0.1% of the administered dose is excreted as the metabolite N-desethyloxybutynin.
• Distribution: * 193 L
• References: Tupker RA, Harmsze AM, Deneer VH: Oxybutynin therapy for generalized hyperhidrosis. Arch Dermatol. 2006 Aug;142(8):1065-6. [Pubmed] ; Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC: Oxybutynin: dry days for patients with hyperhidrosis. Neth J Med. 2006 Oct;64(9):326-8. [Pubmed] ; Schollhammer M, Misery L: Treatment of hyperhidrosis with oxybutynin. Arch Dermatol. 2007 Apr;143(4):544-5. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1754

Research Area: Neurological Disease
Biological Activity:
Oxybutynin(Ditropan) is an anticholinergic medication used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination (urge incontinence), by decreasing muscle spasms of the bladder.Oxybutynin contains one stereocenter. The (R)-enantiomer is a more potent anticholinergic than either the racemate or the (S)-enantiomer, which is essentially without anticholinergic activity at the doses used in clinical practice. The other actions (calcium antagonism, local anesthesia) of oxybutynin are not stereospecific. (S)-Oxybutynin has not been clinically tested for its spasmolytic effects, but may be clinically useful for the same indications as the racemate, without the unpleasant anticholinergic side effects. [1]

REFERENCES

• Tupker RA, Harmsze AM, Deneer VH: Oxybutynin therapy for generalized hyperhidrosis. Arch Dermatol. 2006 Aug;142(8):1065-6. Pubmed
• Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC: Oxybutynin: dry days for patients with hyperhidrosis. Neth J Med. 2006 Oct;64(9):326-8. Pubmed
• Schollhammer M, Misery L: Treatment of hyperhidrosis with oxybutynin. Arch Dermatol. 2007 Apr;143(4):544-5. Pubmed
• http://en.wikipedia.org/wiki/Oxybutynin