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Danazol

HCID 28417
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
17230-88-5
표준 SMILES
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C
InChIKey
POZRVZJJTULAOH-LHZXLZLDSA-N
분자식
C22H27NO2
평균 분자량
337.5 g/mol
단동위원소 질량
337.2041791

개요

Danazol can cause developmental toxicity according to state or federal government labeling requirements.

이름 및 식별자

우선 이름
Danazol
IUPAC
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
영어명
Danazol
분자식
C22H27NO2
분자량
337.46

이름 및 동의어

danazol17230-88-5DanocrineChronogynDanolWinobaninDanazolumCyclomenLadogalBonzolDanatrolWIN 17757
이름 더 보기
danazoleDanazol Usp17α-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol4-ANDROSTEN-[2,3-D]ISOXAZOLE-17-ALPHA-ETHYNYL-17-BETA-OL1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl- (7CI)DanoDANZOL
WIN-17757WIN 17,757DTXSID2022880N29QWW3BUO17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-olNSC-270916CHEBI:4315DTXCID202880

데이터베이스 식별자

CAS
17230-88-5
PubChem CID
28417
DTXSID
DTXSID2022880
ChEMBL
CHEMBL1479
ChEBI
CHEBI:4315
UNII
N29QWW3BUO
EC Number
241-270-1

물성

구조 계산 물성

XLogP
3.8
극성 표면적
46.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
1
무거운 원자 수
25
형식 전하
0
복잡도
677

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2건

4.081

4.21

Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Estrogen Antagonists

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2건

224.2-226.8

225.6 °C

Physical DescriptionSolid
Collision Cross Section · 2건

193.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID2022880]

170.25 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
224.4 · 224.4-226.80C
끓는 점
473.76 °C · 473.76°C (rough estimate)

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H312 (95.2%): Harmful in contact with skin [Warning Acute toxicity, dermal]

P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationHazard Traits - Developmental Toxicity
Other Safety InformationIMAP assessments - Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17.alpha.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (95.2%)

독성 정보

Adverse Effects · 1건

As a synthetic steroid, danazol has many adverse effects in line with other androgens, making its adverse effects broad and systemic. The most commonly reported adverse effects of danazol include weight gain, gastrointestinal symptoms including bloating, nausea, vomiting, gastroenteritis, elevated liver function tests, joint pain, muscle spasms, lethargy, headache, and depression. Other than these, gynecologic adverse effects such as intermenstrual bleeding, breast atrophy, flushes, and androgenic adverse effects such as hirsutism, decreased breast size, acne, hair loss, oily skin, oily hair, menstrual irregularities, and hoarseness, adverse effects due to weak mineralocorticoid activity such as swelling and edema have also been reported.

Toxicity SummaryToxicity discussion generally revolves around the virilizing effects of danazol in females. Symptoms of overdose may include yellowing of the skin and eyes, abdominal pain, and dark urine. There is no antidote for danazol.

화학 및 산업

약리 정보

ATC Code · 2건

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Pharmacodynamics · 1건

Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.

Mechanism of Action · 1건

As a gonadotropin inhibitor, danazol suppresses the pituitary-ovarian axis possibly by inhibiting the output of pituitary gonadotropins. Danazol also depresses the preovulatory surge in output of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibits ovarian steroidogenesis; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex-hormone-binding globulin and corticosteroid-binding globulin; and increases the metabolic clearance rate of progesterone. Another mechanism of action by which danazol may use to facilitate regression of endometriosis is by decreasing IgG, IgM, and IgA concentrations, as well as phospholipid and IgG isotope autoantibodies. In the treatment of endometriosis, as a consequence of suppression of ovarian function, danazol causes both normal and ectopic endometrial tissues to become inactive and atrophic. This leads to anovulation and associated amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unknown, but may be related to suppressed estrogenic stimulation as a result of decreased ovarian production of estrogen. A direct effect on steroid receptor sites in breast tissue is also possible. This leads to a disappearance of nodularity, relief of pain and tenderness, and possibly changes in the menstrual pattern. In terms of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing serum concentrations of the deficient C1 esterase inhibitor, resulting in increased serum concentrations of the C4 component of the complement system. (Source: PharmGKB)

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Nikkaji
J24.462G
밀도
1.0909 · 1.0909 (rough estimate)
굴절률
1.5614 · 1.5614 (estimate)
저장 조건
-20 °C · -20°C Freezer
용해도
Acetonitrile (Slightly), Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
산도 계수 (pKa)
13.1 · 13.10±0.60(Predicted)
물리적 상태
고체
색상
흰색에서 연한 노란색
수용성
물에 부분적으로 용해됩니다. 클로로포름(25 mg/ml), 아세톤, 아세토니트릴 및 에탄올에 용해됩니다.
InChI
1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16,17,18,20,21,22-/m0/s1
InChIKey
POZRVZJJTULAOH-QLPJIZEUNA-N
SMILES
[C@]12([H])CC[C@]3(C)[C@](CC[C@@]3([H])[C@]1([H])CCC1=CC3ON=CC=3C[C@]21C)(O)C#C |&1:0,4,6,9,11,23,r|
EPA
Danazol (17230-88-5)

화학적 성질

White Solid

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Danazol

vMost-DILI-concern

8

Box warning

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
TU4157070
독성
dog,LD50,oral,> 5gm/kg (5000mg/kg),Journal of International Medical Research. Vol. 5(Suppl,
HS 번호
29372900
risk_code
20/21/22-63-36/37/38
hazard_code
Xn,Xi
safety_code
22-36-37/39-26
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationRepr. 2
스토리지 클래스
11 - Combustible Solids
Biological Half-Life
Approximately 24 hours.
Metabolism/MetabolitesHepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.
FDA Pharmacological Classification · 6건

N29QWW3BUO

DANAZOL

Established Pharmacologic Class [EPC] - Androgen

Mechanisms of Action [MoA] - Androgen Receptor Agonists

Chemical Structure [CS] - Androstanes

Danazol is an Androgen. The mechanism of action of danazol is as an Androgen Receptor Agonist.

MeSH Pharmacological ClassificationCompounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.
Cellular LocationsExtracellular

용도 및 제조

Use ClassificationPharmaceuticals
응용 분야 · 2건

용도Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

일반 설명Danazol, 17α-pregna-2,4-dien-20-yno-[2,3-d]isoxazol-17-ol, is a weak androgen that, in spite ofthe 17α-ethinyl group, has little estrogenic or progestogenicactivity. Danazol has been called a synthetic steroidwith diverse biological effects. Danazol binds to sexhormone–binding globulin (SHBG) and decreases the hepaticsynthesis of this estradiol and testosterone carrier.Free testosterone thus increases. Danazol inhibits FSH andLH production by the hypothalamus and pituitary. It bindsto PRs, GRs, ARs, and ERs. Although the exact mechanismof action is unclear, danazol alters endometrial tissueso that it becomes inactive and atrophic, which allowsdanazol to be an effective treatment for endometriosis.Danazol is also used to treat hereditary angioedema and fibrocysticbreast disease.

상·하류 제품 정보

상류 원료

아세트산(빙초산)아세트산 나트륨

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