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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H20O5S
Molecular Weight 348.413
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EQUILIN SULFATE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])C2=CCC4=C3C=CC(OS(O)(=O)=O)=C4

InChI

InChIKey=YJBYRYVLFAUXBJ-HFTRVMKXSA-N
InChI=1S/C18H20O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3-5,10,14,16H,2,6-9H2,1H3,(H,20,21,22)/t14-,16+,18+/m1/s1

HIDE SMILES / InChI
Equilin sulfate is one of the main component, which is responsible for the pharmacological action of the PREMARIN, conjugated estrogens tablets. Premarin is used to treat the moderate to severe vasomotor symptoms, vulvar and vaginal atrophy due to menopause. It is also used to treat hypoestrogenism due to hypogonadism, castration or primary ovarian failure; to treat breast cancer and advanced androgen-dependent carcinoma of the prostate (for Palliation Only). In addition, premarin is used to prevent postmenopausal osteoporosis. Equilin sulfate is a prodrug, which is hydrolyzed to the corresponding free estrogen equilin, an inhibitor of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1). Human 17beta-HSD1 catalyzes the reduction of inactive estrone (E1) to the active 17beta-estradiol in breast tissues, is a key enzyme responsible for elevated levels of E2 in breast tumor tissues. Thus equilin reduce the E2 levels in breast tissues and hence the reduce risk of estrogen-dependent breast cancer.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PREMARIN

Approved Use

1.1 Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause 1.2 Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause. 1.3 Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure 1.4 Treatment of Breast Cancer (for Palliation Only) in Appropriately Selected Women and Men with Metastatic Disease 1.5 Treatment of Advanced Androgen-Dependent Carcinoma of the Prostate (for Palliation Only) 1.6 Prevention of Postmenopausal Osteoporosis.
Primary
PREMARIN

Approved Use

1.1 Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause 1.2 Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause. 1.3 Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure 1.4 Treatment of Breast Cancer (for Palliation Only) in Appropriately Selected Women and Men with Metastatic Disease 1.5 Treatment of Advanced Androgen-Dependent Carcinoma of the Prostate (for Palliation Only) 1.6 Prevention of Postmenopausal Osteoporosis.
Primary
PREMARIN

Approved Use

1.1 Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause 1.2 Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause. 1.3 Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure 1.4 Treatment of Breast Cancer (for Palliation Only) in Appropriately Selected Women and Men with Metastatic Disease 1.5 Treatment of Advanced Androgen-Dependent Carcinoma of the Prostate (for Palliation Only) 1.6 Prevention of Postmenopausal Osteoporosis.
Primary
PREMARIN

Approved Use

1.1 Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause 1.2 Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause. 1.3 Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure 1.4 Treatment of Breast Cancer (for Palliation Only) in Appropriately Selected Women and Men with Metastatic Disease 1.5 Treatment of Advanced Androgen-Dependent Carcinoma of the Prostate (for Palliation Only) 1.6 Prevention of Postmenopausal Osteoporosis.
Preventing
PREMARIN

Approved Use

1.1 Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause 1.2 Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause. 1.3 Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure 1.4 Treatment of Breast Cancer (for Palliation Only) in Appropriately Selected Women and Men with Metastatic Disease 1.5 Treatment of Advanced Androgen-Dependent Carcinoma of the Prostate (for Palliation Only) 1.6 Prevention of Postmenopausal Osteoporosis.
PubMed

PubMed

TitleDatePubMed
In vivo metabolism of [3H]equilin in the pregnant mare.
1981 Jan
Biologic effects of equilin sulfate in postmenopausal women.
1988 Feb
Metabolism of [3H]equilin-[35S]sulfate and [3H]equilin sulfate after oral and intravenous administration in normal postmenopausal women and men.
1989 Apr
Patents

Sample Use Guides

In order to determine the relative potency of equilin sulfate (EqS) 15 women received oral doses of EqS (0.15, 0.31, and 0.625 mg) for 25 days. Doses of 0.31 and 0.625 mg significantly stimulated hepatic globulins. This stimulatory effect ranged from being 1.5 to 8 times greater than the effects of comparable doses of estrone sulfate and conjugated equine estrogens.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
EQUILIN SULFATE
WHO-DD  
Common Name English
ESTRA-1,3,5(10),7-TETRAEN-17-ONE, 3-(SULFOOXY)-
Systematic Name English
ESTRA-1,3,5(10),7-TETRAEN-17-ONE, 3-HYDROXY-, HYDROGEN SULFATE
Common Name English
Equilin sulfate [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30872974
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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CAS
27540-07-4
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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FDA UNII
D507VOE6VN
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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PUBCHEM
168708
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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SMS_ID
100000078930
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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MESH
C037875
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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EVMPD
SUB13694MIG
Created by admin on Fri Dec 15 19:45:35 GMT 2023 , Edited by admin on Fri Dec 15 19:45:35 GMT 2023
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