기본 정보
- CAS
129260-79-3- 표준 SMILES
C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)OCCl- InChIKey
YPZVAYHNBBHPTO-MXRBDKCISA-N- 분자식
- C21H27ClO5
- 평균 분자량
- 394.9 g/mol
- 단동위원소 질량
- 394.1547017
개요
Loteprednol is a 17alpha-hydroxy steroid, an 11beta-hydroxy steroid, an organochlorine compound, a steroid acid ester, an androstanoid and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an antilipemic drug.
이름 및 식별자
- 우선 이름
- Loteprednol
- IUPAC
- chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
- 영어명
- Loteprednol
- 분자식
- C21H27ClO5
- 분자량
- 394.89
이름 및 동의어
loteprednol129260-79-3Z8CBU6KR16CHEBI:50848DTXSID10156128Loteprednolumchloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-diene-14-carboxylatechloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-14-carboxylateRefChem:58138DTXCID0078619S01BA14Loteprednol [INN:BAN]
이름 더 보기
Loteprednol APILoteprednol base17a-Hydroxy-11b-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid chloromethyl esterAndrosta-1,4-diene-17-carboxylic acid, 11,17-dihydroxy-3-oxo-, chloromethyl ester, (11β,17α)-
UNII-Z8CBU6KR16Loteprednol (INN)chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylateLOTEPREDNOL [INN]chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylatechloromethyl 11beta,17alpha-dihydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylateLoteprednol Impurity 8LOTEPREDNOL [VANDF]
물성
구조 계산 물성
- XLogP
- 2.6
- 극성 표면적
- 83.8 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 745
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.4
Solubility3.36e-02 g/L
Melting Point220 - 224 °C
Physical DescriptionSolid
물리화학적 성질
- 끓는 점
- 531.2 · 531.2±50.0 °C(Predicted)
- 밀도
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- 산도 계수 (pKa)
- 12.39 · 12.39±0.70(Predicted)
- InChIKey
- DMKSVUSAATWOCU-PCGATYFFNA-N
- SMILES
- [C@]1(C(=O)OCCl)(OC(=O)OCC)CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C |&1:0,14,16,26,28,30,33,r|
화학 및 산업
약리 정보
ATC Code
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.
Mechanism of Action
The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.
FDA Pharmacological Classification
Z8CBU6KR16
LOTEPREDNOL
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Loteprednol is a Corticosteroid. The mechanism of action of loteprednol is as a Corticosteroid Hormone Receptor Agonist.
MeSH Pharmacological Classification
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Cellular LocationsCytoplasm
응용 분야
Antiinflammatory (topical).
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