Oxybutynin

• Catalog No.: DB01062
• CAS Number: 5633-20-5
• M. F.: C22H31NO3
• M. W.: 357.48644

SYNONYMS

• 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: oxybutynin topical gel; Oxybutynine [INN-French]; Oxybutynin Base; oxybutynin; Oxybutinin; Oxibutinina [INN-Spanish]; Oxibutyninum; Oxybutynin Chloride; Oxybutynin Hydrochloride; Oxybutyninum [INN-Latin]; transdermal patch

DATABASE IDS

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

PROPERTIES

• Hydrophobicity(logP): 4.3

DETAILS

Description (English)

• 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

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