基本情報
- CAS
31477-60-8- 標準SMILES
COc1ccc2c(c1)OC(C)(C)[C@@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1- InChIKey
XZEUAXYWNKYKPL-WDYNHAJCSA-N- 分子式
- C30H35NO3
- 平均分子量
- 457.6 g/mol
- 単同位体質量
- 457.26169398
概要
Ormeloxifene is a third-generation selective estrogen receptor (ER) modulator. In India, ormeloxifene has been marketed since the 1990s as a non-hormonal, non-steroidal oral contraceptive taken once a week, and it was later introduced for the treatment of dysfunctional uterine bleeding. Similar to other selective estrogen receptor modulators (SERMs), ormeloxifene has estrogenic activity in the vagina, bone, cardiovascular, and central nervous system tissues, and anti-estrogenic activity in the uterus and breast. The use of ormeloxifene for the treatment of perimenopausal bleeding and the management of menorrhagia has also been investigated. Ormeloxifene is marketed in India as a racemic mixture of the l- (levormeloxifene) and d-isomers (d-ormeloxifene) of trans-ormeloxifene. The use of levormeloxifene for the treatment of reduced bone turnover and the prevention of atherosclerosis has been evaluated; however, drug development was discontinued due to adverse events.
名称と識別子
- 優先名称
- Ormeloxifene
- IUPAC
- 1-[2-[4-[(3R,4R)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl]phenoxy]ethyl]pyrrolidine
- 現地名
- 2,2-ジメチル-7-メトキシ-3β-フェニル-4α-[4-[2-(1-ピロリジニル)エトキシ]フェニル]-3,4-ジヒドロ-2H-1-ベンゾピラン
- 英語名
- Levormeloxifene
- 分子式
- C30H35NO3
- 分子量
- 457.611
名称と別名
OrmeloxifeneCENTCHROMANCentronSaheli31477-60-8trans-Centchroman44AXY5VE90Pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)-, trans-Ormeloxifeno1-(2-{4-[(3R,4R)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydro-2H-1-benzopyran-4-yl]phenoxy}ethyl)pyrrolidineCompound 6720Compound 67 20
名称をさらに表示
3,4-ジヒドロ-7-メトキシ-2,2-ジメチル-3β-フェニル-4α-[4-[2-(1-ピロリジニル)エトキシ]フェニル]-2H-1-ベンゾピラン(3R,4R)-セントクロマンレボルメロキシフェン1-[2-[4-[(3,4-ジヒドロ-7-メトキシ-2,2-ジメチル-3β-フェニル-2H-1-ベンゾピラン)-4α-イル]フェノキシ]エチル]ピロリジン2,2-ジメチル-7-メトキシ-3β-フェニル-4α-[4-[2-(1-ピロリジニル)エトキシ]フェニル]-3,4-ジヒドロ-2H-1-ベンゾピラン1-[2-[4-[[(3R)-3,4-ジヒドロ-7-メトキシ-3β-フェニル-2,2-ジメチル-2H-1-ベンゾピラン]-4α-イル]フェノキシ]エチル]ピロリジン2,2-ジメチル-3β-フェニル-4α-[4-(2-ピロリジノエトキシ)フェニル]-7-メトキシクロマン1-(2-{4-[(3R,4R)-7-メトキシ-2,2-ジメチル-3-フェニル-3,4-ジヒドロ-2H-1-ベンゾピラン-4-イル]フェノキシ}エチル)ピロリジン(3R,4R)-CentchromanEntecavir Impurity 97
物性
構造計算による物性
- XLogP
- 6.2
- 極性表面積
- 30.9 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 7
- 重原子数
- 34
- 形式電荷
- 0
- 複雑度
- 619
物理化学的性質
- 融点
- 197 ° · 197°
- 比旋光度
- 20 · D20 -192.9° (c = 1.0 in CHCl3)
化学と産業
薬理情報
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Protein BindingApproximately 90% of ormeloxifene is bound to albumin.
Pharmacodynamics
Ormeloxifene is a selective estrogen receptor modulator (SERMs) with contraceptive activity. Also, it has been suggested that it may be beneficial in the treatment of breast cancer, osteoporosis, dermatitis, restenosis, endometriosis and uterine fibroids.
Mechanism of Action
Ormeloxifene has both estrogenic and anti-estrogenic activity. As a contraceptive, ormeloxifene inhibits endometrial receptivity to blastocyst signals. This mechanism inhibits implantation without affecting nidatory estrogen and progesterone, the hypothalamo-pituitary-ovarian axis, follicle maturation, ovulation, mating behavior, gamete transport or fertilization, and the preimplantation development of embryos.
Biological Half-LifeIn healthy, non-lactating volunteers given 30 mg of ormeloxifene (n=11), the half-life is 165 h.
Metabolism/Metabolites_In vivo_ studies suggest that ormeloxifene is quickly metabolized by the liver. In rats, the active metabolite of this drug is 7-desmethylated ormeloxifene.
MeSH Pharmacological Classification
Postcoital contraceptives which owe their effectiveness to synthetic preparations.
Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.
Absorption, Distribution and Excretion
In healthy, non-lactating volunteers given 30 mg of ormeloxifene (n=11), the Cmax, tmax and AUC0-∞ were 55.5 ng/mL, 5.2 h, and 5199 ng⋅h/mL, respectively.
_In vivo_ studies suggest that ormeloxifene is excreted from the body primarily via feces.
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…