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Oxybutynin

HCID 4634
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
5633-20-5
표준 SMILES
CCN(CC)CC#CCOC(=O)C(O)(c1ccccc1)C1CCCCC1
InChIKey
XIQVNETUBQGFHX-UHFFFAOYSA-N
분자식
C22H31NO3
평균 분자량
357.5 g/mol
단동위원소 질량
357.23039385

개요

Oxybutynin is a racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder. It has a role as a local anaesthetic, a calcium channel blocker, a muscarinic antagonist, a parasympatholytic, a muscle relaxant and an antispasmodic drug. It is a tertiary amino compound and a racemate. It contains a (R)-oxybutynin and an esoxybutynin.

이름 및 식별자

우선 이름
Oxybutynin
IUPAC
4-(diethylamino)but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
영어명
Oxybutynin
분자식
C22H31NO3
분자량
357.49

이름 및 동의어

oxybutynin5633-20-5OxytrolOxybutyninekenteraOxibutininaOxybutyninumAnturolCystrinOxytrol for Women4-Diethylamino-2-butinyl alpha-cyclohexylmandelat4-Diethylamino-2-butynyl alpha-phenylcyclohexaneglycolate
이름 더 보기
OXYBUTININOxibutyninOxibutyninum(RS)-OxybutyninOXYBUTYNIN BASE(+/-)-OXYBUTYNINOxybutynin(Ditropan)Oxybutynin USP/EP/BP
K9P6MC7092Cyclohexaneglycolic acid, alpha-phenyl-, 4-(diethylamino)-2-butynyl esterBenzeneacetic acid, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl esterCHEBI:7856DTXSID0023406Dridase4-diethylaminobut-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetateLyrinel XL

데이터베이스 식별자

CAS
5633-20-5
PubChem CID
4634
DTXSID
DTXSID0023406
ChEMBL
CHEMBL1231
ChEBI
CHEBI:7856

물성

구조 계산 물성

XLogP
4.2
극성 표면적
49.8 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
4
회전 가능 결합 수
8
무거운 원자 수
26
형식 전하
0
복잡도
490

실험 및 물리화학적 성질

DrugsPharmaceuticals
LogP · 2건

4.3

4.68

Solubility1.00e-02 g/L
Human Drugs · 4건

Breast Feeding; Lactation; Muscarinic Antagonists; Parasympatholytics

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Melting Point · 3건

122-124

CRYSTALS; MP: 129-130 °C /CHLORIDE/

129 - 130 °C

Physical DescriptionSolid
Dissociation Constants8.04
Collision Cross Section192.2 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

끓는 점
494.4 · 494.4±45.0 °C(Predicted)
밀도
1.097 · 1.097±0.06 g/cm3(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationOxybutynin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Hepatotoxicity · 1건

In multiple, large clinical trials of oxybutynin therapy for overactive bladder syndrome, serum enzyme elevations were rare and no more frequent than with placebo, and there were no episodes of clinically apparent liver injury. Since its approval and widespread use for more than four decades, there has been only a single published case of suspected liver injury attributed to oxybutynin – a report of transient serum enzyme elevations without jaundice or apparent symptoms in a patient with a severe ischemic stroke arising within weeks of starting oxybutynin. Thus, clinically apparent liver injury from oxybutynin is very rare if it occurs at all.

Adverse Effects · 1건

The immediate-release form of oxybutynin can cause various adverse effects in patients, including dry mouth (71.4%), dizziness (16.6%), constipation (15.1%), somnolence (14.0%), and nausea (11.6%). Some of the less common adverse effects of immediate-release oxybutynin include blurred vision (9.6%), urinary hesitation (8.5%), urinary retention (6.0%), and dyspepsia (6.0%). Notably, a dry mouth is considered a dose-related adverse effect of oxybutynin. Oxybutynin hydrochloride has a more favorable profile than other antimuscarinic drugs regarding adverse effects on heart rate increase.

화학 및 산업

약리 정보

ATC Code · 3건

G04BD04

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingOxybutynin enantiomers are more than 97% bound to plasma proteins, primarily to alpha-1 acid glycoprotein.
Pharmacodynamics · 1건

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.

Mechanism of Action · 2건

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/

Biological Half-LifeThe plasma elimination half-life is about 2 hours. In the elderly, the elimination half-life is prolonged up to 5 hours.
Metabolism/Metabolites · 1건

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.

관련 반응

13건
반응 기록 만들기
HRID 219491 반응식
HRID 219491생성물로uspto-grants-2012_06
HRID 333519 반응식
HRID 333519생성물로uspto-grants-2014_11
HRID 403104 반응식
HRID 403104생성물로uspto-grants-2014_06
HRID 1060511 반응식
HRID 1060511생성물로uspto-grants-2003_02
HRID 1408260 반응식
HRID 1408260생성물로uspto-grants-2014_12
HRID 1496677 반응식
HRID 1496677생성물로uspto-grants-2015_12
HRID 1532921 반응식
HRID 1532921생성물로uspto-grants-2001_03
HRID 1629650 반응식
HRID 1629650생성물로uspto-grants-2014_07
1 / 2 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
UNII
K9P6MC7092
EC Number
630-332-7
Nikkaji
J8.038A
저장 조건
Inert atmosphere,Room Temperature
용해도
17.9 mg/mL · ≥ 17.9mg/mL in DMSO
산도 계수 (pKa)
8.04 · 8.04(at 25℃)
물리적 상태
가루
색상
White to off-white
Toxicity Summary · 1건

If an overdose of oxybutynin is suspected, a medical professional should be sought for immediate care. Symptoms of oxybutynin overdose may include central nervous system overactivity, fever, cardiac arrhythmias, vomiting, respiratory failure, paralysis, and coma. The treatment for oxybutynin overdose typically involves supportive care from healthcare providers. In some cases, medical professionals may consider administering activated charcoal to patients to help absorb the excess medication in their digestive system. Alternatively, a cathartic agent might be used to promote bowel movements in patients to facilitate the elimination of the drug from the body.

Human Toxicity ExcerptsADVERSE REACTIONS REFLECT THIS AGENT'S ANTICHOLINERGIC ACTIVITY. DRYNESS OF MOUTH IS MOST COMMON; NAUSEA, BLURRED VISION, FLUSHING, & TACHYCARDIA ALSO HAVE BEEN REPORTED. /CHLORIDE/
Drug Induced Liver Injury · 6건

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

oxybutynin

Ditropan®

Antispasmodics

Not Applicable

no-DILI-concern

Non-Human Toxicity Excerpts · 1건

IN CONSCIOUS DOG EFFECT OF 0.10-10.0 MG/KG, IV WAS DOSE-RELATED TACHYCARDIA, SLIGHT ELEVATION IN DIASTOLIC PRESSURE & INSIGNIFICANT INCR IN SYSTOLIC PRESSURE. UNDER PENTOBARBITAL ANESTHESIA, PRESSURE RESPONSES WERE REVERSED & SHOWED SYSTOLIC & DIASTOLIC HYPOTENSION.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

유해 물질 데이터
5633-20-5(Hazardous Substances Data)
FDA Pharmacological Classification · 6건

K9P6MC7092

OXYBUTYNIN

Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Antagonist

Mechanisms of Action [MoA] - Cholinergic Muscarinic Antagonists

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

OXYBUTYNIN

MeSH Pharmacological Classification · 3건

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the 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.

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.

Absorption, Distribution and Excretion · 3건

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.

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.

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

Cellular LocationsMembrane

용도 및 제조

Uses · 2건

MEDICATION

Use (kg; approx.) in Germany (2009): >100

Methods of ManufacturingBRITISH PATENT 940,540 (1963 TO MEAD JOHNSON). /CHLORIDE/
Formulations/Preparations · 2건

OXYBUTYNIN CHLORIDE; ALPHA-CYCLOHEXYL-ALPHA-HYDROXYBENZENEACETIC ACID 4-(DIETHYLAMINO)-2-BUTYNYL ESTER HYDROCHLORIDE; ALPHA-PHENYLCYCLOHEXANEGLYCOLIC ACID 4-(DIETHYLAMINO)-2-BUTYNYL ESTER HYDROCHLORIDE; 4-DIETHYLAMINO-2-BUTYNYL PHENYLCYCLOHEXYLGLYCOLATE HYDROCHLORIDE; OXIBUTININA HYDROCHLORIDE.../CHLORIDE/

DITROPAN, TROPAX. /CHLORIDE/

응용 분야 · 3건

용도Oxybutynin(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

용도Oxybutynin is intended for relieving unpleasant symptoms associated with emptying the intestine or urinary bladder. A

일반 설명Oxybutynin, 4-Diethylaminobut- 2-ynyl2-cyclohexyl-2- hydroxy-2-phenyl-ethanoate, (Oxytrol) wasone of the first agents specifically developed to exploit the effectsthat cholinergic blocking agents have on the bladder. Bycompetitively blocking the muscarinic receptors, it has directspasmolytic effects on bladder smooth muscle. This reductionin smooth muscle tone allows for greater volumes of urine tobe stored in the bladder, which results in less urinary incontinence,urgency, and frequency. Oxybutynin acts as a competitiveantagonist on M1, M2, and M3 receptor subtypes.

상·하류 제품 정보

상류 원료

[4-(Diethylamino)-2-butynyl] acetate메틸시클로헥실페닐글리콜레이트메틸산 나트륨

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