Ormeloxifene
Basic information
- CAS
31477-60-8- Standard SMILES
COc1ccc2c(c1)OC(C)(C)[C@@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1- InChIKey
XZEUAXYWNKYKPL-WDYNHAJCSA-N- Molecular formula
- C30H35NO3
- Average molar mass
- 457.6 g/mol
- Monoisotopic mass
- 457.26169398
Overview
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.
Names & identifiers
- Preferred name
- Ormeloxifene
- IUPAC
- 1-[2-[4-[(3R,4R)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl]phenoxy]ethyl]pyrrolidine
- English name
- Levormeloxifene
- Molecular formula
- C30H35NO3
- Molecular weight
- 457.611
Names & synonyms
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
Show more names
(3R,4R)-CentchromanEntecavir Impurity 971-[2-[4-[[(3R)-3,4-Dihydro-7-methoxy-3β-phenyl-2,2-dimethyl-2H-1-benzopyran]-4α-yl]phenoxy]ethyl]pyrrolidinePyrrolidine, 1-[2-[4-[(3R,4R)-3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2H-1-benzopyran-4-yl]phenoxy]ethyl]-
ormeloxifenumDTXCID9014739681-(2-(4-((3R,4R)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydro-2H-1-benzopyran-4-yl)phenoxy)ethyl)pyrrolidineRefChem:856920G03XC04DTXSID6046844LevormeloxifeneL-CentchroMan
Database identifiers
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 30.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 619
Physicochemical properties
- Melting point
- 197 ° · 197°
- alpha
- 20 · D20 -192.9° (c = 1.0 in CHCl3)
- FDA UNII
- 9512 UKZ352 · 9512UKZ352
Chemistry & industry
Pharmacology
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.
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