LEVORMELOXIFENE FUMARATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H35NO3.C4H4O4
Molecular Weight	573.676
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.COC1=CC2=C(C=C1)[C@H]([C@H](C3=CC=CC=C3)C(C)(C)O2)C4=CC=C(OCCN5CCCC5)C=C4

InChI

InChIKey=CKDZFQCZLXNLRD-JJGRXVLVSA-N

InChI=1S/C30H35NO3.C4H4O4/c1-30(2)29(23-9-5-4-6-10-23)28(26-16-15-25(32-3)21-27(26)34-30)22-11-13-24(14-12-22)33-20-19-31-17-7-8-18-31;5-3(6)1-2-4(7)8/h4-6,9-16,21,28-29H,7-8,17-20H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t28-,29+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C30H35NO3
Molecular Weight	457.6038
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23895678 | http://adisinsight.springer.com/drugs/800009670 | https://www.ncbi.nlm.nih.gov/pubmed/25619124 | http://www.drugsupdate.com/generic/view/367/Ormeloxifenehttps://www.ncbi.nlm.nih.gov/pubmed/12841887
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24468615 | https://www.ncbi.nlm.nih.gov/pubmed/11738564

Levormeloxifene (INN) is an experimental selective estrogen receptor modulator (SERM) that was being developed as an alternative to estrogen replacement therapy for the treatment and prevention of postmenopausal bone loss. Levormeloxifene is the levorotatory enantiomer of non-hormonal, non-steroidal oral contraceptive -- ormeloxifene (trade names Novex-DS, Centron, and Sevista). The development of Levormeloxifene was stopped because of a high incidence of gynecologic adverse events during clinical trials.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11410933 \| http://www.kegg.jp/entry/D08301 \| https://www.ncbi.nlm.nih.gov/pubmed/18279543 \| http://gynaeonline.com/centchroman.htm	Modulator 846
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11738564	Partial Agonist 297		13.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ovarian cancer 160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25306892	Primary	Preclinical	Unknown Approved Use Unknown
Dysfunctional uterine bleeding 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24392393	Primary	Approved 8583	SEVISTA Approved Use Dysfunctional uterine bleeding Launch Date 1992
Pregnancy 65 Sources: http://www.drugsupdate.com/generic/view/367/Ormeloxifene https://www.ncbi.nlm.nih.gov/pubmed/11257249	Preventing	Approved 8583	SEVISTA Approved Use Contraceptive Launch Date 1992
Postmenopausal bone loss 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12841887	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
5.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
27 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
128 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
443 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
1115 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2737 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	320 mg single, oral dose: 320 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
254 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
387 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
1081 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
769 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2031 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
182 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
477 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
377 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
879 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
147 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
141 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Analyte	Population
3.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
10 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
26 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
64 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
129 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	320 mg single, oral dose: 320 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
4.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
4.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
19.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
33.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
8.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
4.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
15.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
9771 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
12181 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	320 mg single, oral dose: 320 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	160 mg 1 times / day multiple, oral dose: 160 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	40 mg 1 times / day multiple, oral dose: 40 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11874392/	80 mg 1 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
126 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
151 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11219480/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.1% EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0940299398800018#page=114			LEVORMELOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 1 times / day steady-state, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: steady-state Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	Other AEs: Edema, Endometrial polyps... Other AEs: Edema (75%) Endometrial polyps (6%) Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	Other AEs: leukorrhea, Endometrial disorder... Other AEs: leukorrhea (30%) Endometrial disorder (19%) enlarged uterus (17%) uterovaginal prolapse (7%) urinary incontinence (17%) increased micturition frequency (9%) lower abdominal pain (17%) hot flushes (10%) leg cramps (6%) Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	Other AEs: Edema, Endometrial polyps... Other AEs: Edema (74%) Endometrial polyps (11%) Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	Other AEs: Hot flushes, Breast pain... Other AEs: Hot flushes (17%) Breast pain (0.5%) Leukorrhea (19%) Bleeding (13%) Endometrial Disorder (26%) Uterovaginal prolaps (6%) Cervical polyp (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	Other AEs: Edema, Endometrial polyps... Other AEs: Edema (70%) Endometrial polyps (10%) Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
5 mg 1 times / day steady-state, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: steady-state Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	Other AEs: Edema... Other AEs: Edema (73%) Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/

AEs

PubMed

Title	Date	PubMed
Effects of estrogen, raloxifene, and levormeloxifene on the expression of Rho-kinase signaling molecules in urethral smooth muscle cells.	2010-12	20970835
The effect of long-term hormonal treatment on voiding patterns during filling cystometry and on urethral histology in a postpartum, ovariectomized female rat.	2010-12	20201831
Long-term progestin contraceptives (LTPOC) induce aberrant angiogenesis, oxidative stress and apoptosis in the guinea pig uterus: A model for abnormal uterine bleeding in humans.	2010-04-27	20423489
Clinical pharmacokinetics and interaction of centchroman--a mini review.	2010-04	20227542
Expression of estrogen receptor co-regulators SRC-1, RIP140 and NCoR and their interaction with estrogen receptor in rat uterus, under the influence of ormeloxifene.	2009-08	19460436
Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study.	2009-08	19751337
Effect of ormeloxifene, a selective estrogen receptor modulator, on biomarkers of endometrial receptivity and pinopode development and its relation to fertility and infertility in Indian subjects.	2009-06	18675966
Expression of alphaVbeta3 integrin in rat endometrial epithelial cells and its functional role during implantation.	2009-01-15	19027743
Effect of centchroman on cellular and humoral immunity.	2008-05-15	18476393
In silico elucidation of the molecular mechanism defining the adverse effect of selective estrogen receptor modulators.	2007-11	18052534
Role of centchroman in regression of mastalgia and fibroadenoma.	2007-06	17431715
Modulation of AP-1 mediated estrogenic response by ormeloxifene in rat uterus.	2007-05	17553677
Expression of oestrogen receptors alpha and beta during the period of uterine receptivity in rat: effect of ormeloxifene, a selective oestrogen receptor modulator.	2007-01	17280556
Modulation of estrogen receptor transactivation and estrogen-induced gene expression by ormeloxifene-a triphenylethylene derivative.	2006-11	16965798
Effect of ormeloxifene on ovariectomy-induced bone resorption, osteoclast differentiation and apoptosis and TGF beta-3 expression.	2006-08	16797179
Antioxidant defense system during endometrial receptivity in the guinea pig: effect of ormeloxifene, a selective estrogen receptor modulator.	2006-01	16394181
Modulation of estrogen action during preimplantation period and in immature estradiol-primed rat uterus by anti-implantation agent, ormeloxifene.	2005-06	15914137
Differential effects of estrogen and raloxifene on messenger RNA and matrix metalloproteinase 2 activity in the rat uterus.	2005-04	15576828
In vitro anti-resorptive activity and prevention of ovariectomy-induced osteoporosis in female Sprague-Dawley rats by ormeloxifene, a selective estrogen receptor modulator.	2004-06	15261309
Evaluation of interaction potential of certain concurrently administered drugs with pharmacological and pharmacokinetic profile of centchroman in rats.	2002-07	12169381
Effects of 3-phenyl-4-[[4-[2-(1-piperidinyl)ethoxy]phenyl]methyl]- 2H-1-benzopyran-7-ol (CHF 4056), a novel nonsteroidal estrogen agonist/antagonist, on reproductive and nonreproductive tissue.	2002-03	11861784
Interaction with anti-implantation and estrogen antagonistic activities of dl-ormeloxifene, a selective estrogen receptor modulator, by tetracycline in female Sprague-Dawley rats.	2001-10	11747877
Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders.	2001-07	11410933
Optimization of contraceptive dosage regimen of Centchroman.	2001-01	11257249

Patents

Sample Use Guides

In Vivo Use Guide

Dosage Oral Dysfunctional uterine bleeding Adult: 60 mg twice a week for the 1st 12 weeks and then 60 mg once a week for up to next 12 weeks. Oral Contraception Adult: Take 1 tablet (30 mg) twice a week for the 1st 12 weeks then 1 tablet (30 mg) once a week from 13th weeks onwards. Take 1st tablet on the 1st day of menstrual cycle. Follow dose irrespective of menstrual periods.

Route of Administration: Oral

In Vitro Use Guide

Ormeloxifene (10(-6) and 10(-8)M) significantly inhibited osteoclastogenesis (P<0.001 versus vehicle control) as evidenced by lower number of TRAP-positive osteoclasts in bone marrow cultures and caused apoptosis of osteoclasts from adult Balb/c mice.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:43:21 GMT 2025` Edited by `admin` on `Mon Mar 31 19:43:21 GMT 2025`
Record UNII	2XFK7X56Q3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRROLIDINE, 1-(2-(4-((3R,4R)-3,4-DIHYDRO-7-METHOXY-2,2-DIMETHYL-3-PHENYL-2H-1-BENZOPYRAN-4-YL)PHENOXY)ETHYL)-, (2E)-2-BUTENEDIOATE (1:1)

Preferred Name

English

LEVORMELOXIFENE FUMARATE

Common Name

English

LEVORMELOXIFENE FUMARATE [JAN]

Common Name

English

Code System Code Type Description

PUBCHEM

9938031

Created by admin on Mon Mar 31 19:43:21 GMT 2025 , Edited by admin on Mon Mar 31 19:43:21 GMT 2025

PRIMARY

FDA UNII

2XFK7X56Q3

Created by admin on Mon Mar 31 19:43:21 GMT 2025 , Edited by admin on Mon Mar 31 19:43:21 GMT 2025

PRIMARY

CAS

199583-01-2

Created by admin on Mon Mar 31 19:43:21 GMT 2025 , Edited by admin on Mon Mar 31 19:43:21 GMT 2025

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					88XHZ13131

Fumaric acid

PARENT -> SALT/SOLVATE


					9512UKZ352

LEVORMELOXIFENE

PARENT -> SALT/SOLVATE

Related Record Type Details


					9512UKZ352

LEVORMELOXIFENE

ACTIVE MOIETY

AE	Significance	Dose	Population
Endometrial polyps	6%	20 mg 1 times / day steady-state, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: steady-state Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Edema	75%	20 mg 1 times / day steady-state, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: steady-state Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
hot flushes	10%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
enlarged uterus	17%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
lower abdominal pain	17%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
urinary incontinence	17%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
Endometrial disorder	19%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
leukorrhea	30%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
leg cramps	6%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
uterovaginal prolapse	7%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
increased micturition frequency	9%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12237621/
Endometrial polyps	11%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Edema	74%	1.25 mg 1 times / day steady-state, oral Studied dose Dose: 1.25 mg, 1 times / day Route: oral Route: steady-state Dose: 1.25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Breast pain	0.5%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Cervical polyp	1%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Bleeding	13%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Hot flushes	17%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Leukorrhea	19%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Endometrial Disorder	26%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Uterovaginal prolaps	6%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Endometrial polyps	10%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Edema	70%	10 mg 1 times / day steady-state, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: steady-state Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/
Edema	73%	5 mg 1 times / day steady-state, oral Studied dose Dose: 5 mg, 1 times / day Route: oral Route: steady-state Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12648882/

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