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Synopsis

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Chemistry

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Also known as: 5633-20-5, Ditropan, Oxytrol, Oxibutyninum, Kentera, Oxybutyninum

Molecular Formula

C₂₂H₃₁NO₃

Molecular Weight

357.5 g/mol

InChI Key

XIQVNETUBQGFHX-UHFFFAOYSA-N

FDA UNII

K9P6MC7092

Oxybutynin is a tertiary amine possessing antimuscarinic and antispasmodic properties. Oxybutynin blocks muscarinic receptors in smooth muscle, hence inhibiting acetylcholine binding and subsequent reduction of involuntary muscle contractions. Oxybutynin is used to reduce bladder contractions by relaxing bladder smooth muscle.

Oxybutynin is a Cholinergic Muscarinic Antagonist. The mechanism of action of oxybutynin is as a Cholinergic Muscarinic Antagonist.

1 2D Structure

Oxybutynin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

2.1.2 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

2.1.3 InChI Key

XIQVNETUBQGFHX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC)CC#CCOC(=O)C(C1CCCCC1)(C2=CC=CC=C2)O

2.2 Other Identifiers

2.2.1 UNII

K9P6MC7092

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(diethylamino)-2-butynyl-alpha-cyclohexyl-alpha-hydroxybenzeneacetate

2. 4-(diethylamino)-2-butynyl-alpha-phenylcyclohexaneglycolate

3. Apo-oxybutynin

4. Contimin

5. Cystonorm

6. Cystrin

7. Ditropan

8. Dresplan

9. Dridase

10. Driptane

11. Gelnique

12. Gen-oxybutynin

13. Novo-oxybutynin

14. Nu-oxybutyn

15. Oxyb Abz

16. Oxybugamma

17. Oxybutin Holsten

18. Oxybuton

19. Oxybutynin Al

20. Oxybutynin Azu

21. Oxybutynin Chloride

22. Oxybutynin Heumann

23. Oxybutynin Hexal

24. Oxybutynin Hydrochloride

25. Oxybutynin Stada

26. Oxybutynin Von Ct

27. Oxybutynin-puren

28. Oxybutynin-ratiopharm

29. Oxymedin

30. Oxytrol

31. Pms-oxybutynin

32. Pollakisu

33. Renamel

34. Ryol

35. Spasmex Oxybutynin

36. Spasyt

37. Tavor

38. Zatur

2.3.2 Depositor-Supplied Synonyms

1. 5633-20-5

2. Ditropan

3. Oxytrol

4. Oxibutyninum

5. Kentera

6. Oxybutyninum

7. Oxybutinin

8. Oxybutynine

9. Oxibutinina

10. Oxybutynine [inn-french]

11. Oxybutyninum [inn-latin]

12. Oxibutinina [inn-spanish]

13. 4-diethylamino-2-butinyl Alpha-cyclohexylmandelat

14. Ditropan Xl

15. Oxybutynin (ditropan)

16. 4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

17. 4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate

18. 4-diethylamino-2-butynyl Alpha-phenylcyclohexaneglycolate

19. Chembl1231

20. Chebi:7856

21. 4-(diethylamino)-2-butynyl Alpha-phenylcyclohexaneglycolic Acid Ester

22. K9p6mc7092

23. 5633-20-5 (free)

24. Cyclohexaneglycolic Acid, Alpha-phenyl-, 4-(diethylamino)-2-butynyl Ester

25. Benzeneacetic Acid, Alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl Ester

26. Cystrin

27. 4-(diethylamino)but-2-yn-1-yl Cyclohexyl(hydroxy)phenylacetate

28. Oxybutynin Base

29. Anturol

30. Transdermal Patch

31. Lyrinel Xl

32. Oxytrol For Women

33. Oxybutynin [usan:inn:ban]

34. Ccris 1923

35. Oxybutynin Transdermal

36. Oxybutynin Topical Gel

37. Hsdb 3270

38. Oxybutynin Transdermal Patch

39. Oxybutinyn

40. Unii-k9p6mc7092

41. (rs)-oxybutynin

42. Anturol (tn)

43. Oxytrol (tn)

44. Mfcd00865252

45. Oxybutynin [mi]

46. Oxybutynin [inn]

47. Oxybutynin (usan/inn)

48. Prestwick0_000287

49. Prestwick1_000287

50. Prestwick2_000287

51. Prestwick3_000287

52. Oxybutynin [hsdb]

53. Oxybutynin [usan]

54. Oxybutynin [vandf]

55. Oxybutynin [mart.]

56. Schembl2992

57. Oxybutynin [who-dd]

58. Lopac0_000923

59. Bspbio_000194

60. Gtpl359

61. Mls006010052

62. Oxybutynin [ema Epar]

63. Spbio_002413

64. Bpbio1_000214

65. Dtxsid0023406

66. Oxybutynin [orange Book]

67. Oxybutynin, Oxybutynin Chloride

68. Chebi:144551

69. Hms3884k08

70. Bcp12179

71. Hy-b0267

72. Ab7701

73. Bdbm50165019

74. S1754

75. Akos015896242

76. Cyclohexaneglycolic Acid, .alpha.-phenyl-, 4-(diethylamino)-2-butynyl Ester

77. Ac-2153

78. Ccg-205005

79. Db01062

80. Ks-5221

81. Sdccgsbi-0050898.p003

82. Benzeneacetic Acid, .alpha.-cyclohexyl-.alpha.-hydroxy-, 4-(diethylamino)-2-butynyl Ester

83. Mrf-0000601

84. (+/-)-oxybutynin(hydrochloride Form)

85. Ncgc00015767-03

86. Ncgc00015767-04

87. Ncgc00015767-06

88. Ncgc00015767-07

89. Ncgc00015767-09

90. Ncgc00015767-10

91. Ncgc00015767-21

92. Ncgc00089795-02

93. Smr001550466

94. Sbi-0050898.p002

95. Ft-0603679

96. Sw196787-3

97. C07360

98. D00465

99. 633o205

100. A831004

101. L000923

102. Q1060922

103. Brd-a65013509-003-03-8

104. Brd-a65013509-003-13-7

105. 4-(diethylamino)-2-butynyl .alpha.-phenylcyclohexaneglycolate

106. 4-(diethylamino)-2-butynyl Cyclohexyl(hydroxy)phenylacetate #

107. 4-diethylaminobut-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

108. Rac-4-(diethylamino)but-2-yn-1-yl Cyclohexyl(hydroxy)phenylacetate

109. (r)-4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

110. (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetic Acid 4-(diethylamino)but-2-ynyl Ester

111. 4-(diethylamino)-2-butynyl .alpha.-phenylcyclohexaneglycolic Acid Ester

112. Alpha-cyclohexyl-alpha-hydroxybenzeneacetic Acid 4-(diethylamino)-2-butynyl Ester

113. Benzeneacetic Acid, A-cyclohexyl-a-hydroxy-,4-(diethylamino)-2-butynyl Ester

114. 119579-36-1

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₁NO₃
Molecular Weight	357.5 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Exact Mass	357.23039385 g/mol
Monoisotopic Mass	357.23039385 g/mol
Topological Polar Surface Area	49.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	490
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Oxybutynin
PubMed Health	Oxybutynin
Drug Classes	Urinary Antispasmodic
Drug Label	Oxybutynin chloride tablets USP are a debossed, very pale blue, round, biconvex, scored tablet containing 5 mg of oxybutynin chloride, USP. Chemically, oxybutynin chloride is d,l (racemic) 4-diethylamino-2-butynyl phenylcyclohexylglycolate hydrochlor...
Active Ingredient	Oxybutynin
Dosage Form	Film, extended release
Route	Transdermal
Strength	3.9mg/24hr
Market Status	Prescription
Company	Barr Labs Div Teva

2 of 4
Drug Name	Oxytrol
PubMed Health	Oxybutynin (Absorbed through the skin)
Drug Classes	Urinary Antispasmodic
Drug Label	OXYTROL (oxybutynin transdermal system) is designed to deliver oxybutynin over a 3- to 4-day interval after application to intact skin. OXYTROL is available as a 39 cm2 system containing 36 mg of oxybutynin. OXYTROL has a nominal in vivo delivery rat...
Active Ingredient	Oxybutynin
Dosage Form	Film, extended release
Route	Transdermal
Strength	3.9mg/24hr
Market Status	Prescription
Company	Watson Labs (utah)

3 of 4
Drug Name	Oxybutynin
PubMed Health	Oxybutynin
Drug Classes	Urinary Antispasmodic
Drug Label	Oxybutynin chloride tablets USP are a debossed, very pale blue, round, biconvex, scored tablet containing 5 mg of oxybutynin chloride, USP. Chemically, oxybutynin chloride is d,l (racemic) 4-diethylamino-2-butynyl phenylcyclohexylglycolate hydrochlor...
Active Ingredient	Oxybutynin
Dosage Form	Film, extended release
Route	Transdermal
Strength	3.9mg/24hr
Market Status	Prescription
Company	Barr Labs Div Teva

4 of 4
Drug Name	Oxytrol
PubMed Health	Oxybutynin (Absorbed through the skin)
Drug Classes	Urinary Antispasmodic
Drug Label	OXYTROL (oxybutynin transdermal system) is designed to deliver oxybutynin over a 3- to 4-day interval after application to intact skin. OXYTROL is available as a 39 cm2 system containing 36 mg of oxybutynin. OXYTROL has a nominal in vivo delivery rat...
Active Ingredient	Oxybutynin
Dosage Form	Film, extended release
Route	Transdermal
Strength	3.9mg/24hr
Market Status	Prescription
Company	Watson Labs (utah)

4.2 Therapeutic Uses

Parasympatholytics; Cholinegeric Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

OXYBUTYNIN IS AN ANTISPASMODIC USED IN TREATMENT OF UNINHIBITED OR REFLEX-TYPE NEUROGENIC BLADDER. ON BASIS OF ANIMAL PHARMACOLOGIC STUDIES, IT IS THOUGHT TO HAVE BOTH ANTICHOLINERGIC AND MUSCULOTROPIC PROPERTIES. /CHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1200

...OXYBUTYNIN IMPROVED SYMPTOMS OF NEUROGENIC BLADDER SUCH AS URINARY URGENCY, URGE INCONTINENCE, NOCTURIA, & PAIN. ...IN CHILDREN WITH ENURESIS, THERE WAS REDN IN INCIDENCE OF BEDWETTING, URINARY FREQUENCY, & DAYTIME ACCIDENTS. ... ITS EFFECTIVENESS IS COMPARABLE TO THAT OF OTHER ANTISPASMODIC AGENTS... /CHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1200

4.3 Drug Indication

Oxybutynin is indicated for the symptomatic treatment of overactive bladder, which causes urge urinary incontinence and frequency, and urgency. Oxybutynin may also be used for children aged 6 and above for the symptomatic management of detrusor muscle overactivity which has been found to be related to a neurological condition. Spina bifida is an example of a neurological condition in which oxybutynin may be used to control urinary symptoms. On occasion, oxybutynin may be used off-label to relieve bladder spasms associated with ureteral stents or urinary catheters.

Symptomatic treatment of urge incontinence and/or increased urinary frequency and urgency as may occur in adult patients with unstable bladder.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxybutynin exerts antispasmodic actions on the bladder, relieving the uncomfortable symptoms of overactive bladder, including urinary urgency and frequency. These actions occur through the inhibition of muscarinic receptors. **A note on angioedema and anticholinergic effects** Symptoms of angioedema may occur with oxybutynin therapy. If angioedema is suspected, discontinue oxybutynin immediately and provide appropriate medical treatment. In addition, anticholinergic effects may occur with the administration of this drug. Some symptoms may include hallucinations, confusion, agitation, and drowsiness. It is advisable to avoid operating heavy machinery before the response to oxybutynin has been monitored. Dose adjustments may be required.

5.2 MeSH Pharmacological Classification

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

OXYBUTYNIN

5.3.2 FDA UNII

K9P6MC7092

5.3.3 Pharmacological Classes

Cholinergic Muscarinic Antagonists [MoA]; Cholinergic Muscarinic Antagonist [EPC]

5.4 ATC Code

G04BD04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BD - Drugs for urinary frequency and incontinence

G04BD04 - Oxybutynin

5.5 Absorption, Distribution and Excretion

Absorption

Oxybutynin should be swallowed whole with the help of liquids. A pharmacokinetic study revealed that oxybutynin was rapidly absorbed, and peak concentrations were reached within about 1 hour of administration, measured at 8.2 ngml-1 and AUC was 16 ngml-1. The biovailability of oxybutynin is about 6%, and the plasma concentration of the active metabolite, desethyloxybutynin is 5 to 12 times greater than that of oxybutynin. Bioavailability is increased in the elderly. Food has been shown to increase the exposure to controlled-release oxybutynin.

Route of Elimination

Oxybutynin is heavily cleared by the liver. Under 0.1% of an administered dose is found as unchanged drug in the urine. Less than 0.1% of a single dose of oxybutynin is excreted as desethyloxybutynin.

Volume of Distribution

Oxybutynin has a wide volume of distribution of 193 L. In rats, oxybutynin penetrates the central nervous system.

5.6 Metabolism/Metabolites

Oxybutynin is heavily metabolized by the CYP3A4 enzyme system in both the liver and the wall of the intestine. It undergoes first-pass metabolism, and its resulting primary active metabolite, N-desethyloxybutynin circulates. It is active at the muscarinic receptors in both the bladder and the salivary gland. Hepatic biotransformation also produces its major inactive metabolite, phenylcyclohexylglycolic acid.

5.7 Biological Half-Life

The plasma elimination half-life is about 2 hours. In the elderly, the elimination half-life is prolonged up to 5 hours.

5.8 Mechanism of Action

Oxybutynin acts to relax the bladder by inhibiting the muscarinic action of acetylcholine on smooth muscle, and not skeletal muscle. The active of oxybutynin is metabolite is N-desethyloxybutynin. It competitively inhibits the postganglionic type 1, 2 and 3 muscarinic receptors. The above actions lead to increased urine capacity in the bladder, decreasing urinary urgency and frequency. In addition, oxybutynin delays the initial desire to void.

RESULTS OF CYSTOMETRIC STUDIES SHOWED THAT THE DRUG INCR BLADDER CAPACITY @ ONSET OF FIRST CONTRACTION & FIRST DESIRE TO VOID, AS WELL AS @ END OF CYSTOMETRY. /CHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1200

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euroPLX 86 Munich

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 3.9MG/24HR

USFDA APPLICATION NUMBER - 202211

DOSAGE - GEL, METERED;TRANSDERMAL - 3%

USFDA APPLICATION NUMBER - 202513

DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 3.9MG/24HR

USFDA APPLICATION NUMBER - 21351

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FILM, EXTENDED RELEASE;TRANSDERMAL - 3.9MG/24HR

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FILM, EXTENDED RELEASE;TRANSDERMAL - 3.9MG/24HR

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API REF. PRICE (USD/KG)

$ 653

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01

01

02

02

03

03

04

Seloc Ag

04

Seloc Ag

Average Price (USD/KGS)

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Total Quantity (KGS)