Ethinyl Estradiol

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==Description==
==Description==
-
A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl  substitution. It has high estrogenic potency when administered orally,  and is often used as the estrogenic component in ORAL  CONTRACEPTIVES.
+
[http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1064&show=SHOW-3D Show 3-D Structure]
-
==General Properties==
+
{{Drugbox|
 +
|IUPAC_name =(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
 +
| CAS_number=57-63-6
 +
|  CASNo_Ref = {{cascite}}
 +
| ATC_suffix=CA01
 +
| ATC_supplemental={{ATC|L02|AA03}}
 +
| PubChem=5991
 +
| DrugBank=APRD00691
 +
|chemical_formula=C20H24O2
 +
| molecular_weight = 296.403
 +
| smile = CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
 +
| bioavailability= 97% is bound
 +
| metabolism = [[Liver]]
 +
| elimination_half-life=36±13 hours
 +
| excretion = Feces and Urine
 +
| pregnancy_category = X ([[United States|USA]])
 +
| legal_status = Rx-only <small>(U.S.)</small>
 +
| routes_of_administration=Oral, [[transdermal]]
 +
}}
 +
'''Ethinylestradiol''' {{pron-en|ˈeθɪnɪlˌiːstrəˈdaɪəl}}, also '''ethinyl estradiol''' (EE), is a [[derivative (chemistry)|derivative]] of [[estradiol]]. Ethinyl estradiol is an orally bio-active [[estrogen]] used in almost all modern [[oral contraceptive formulations|formulations]] of [[combined oral contraceptive pill]]s (the Pill). It is one of the most commonly used [[medication]]s. Most commonly sold as '''NuvaRing'''.
-
<b>*Molecular Weight</b>
+
The first orally active synthetic steroidal estrogen, ethinylestradiol (17α-ethynylestradiol), the 17α-[[ethynyl radical|ethynyl]] analog of [[estradiol]], was [[chemical synthesis|synthesized]] in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at [[Schering|Schering AG]] in [[Berlin]].<!--
 +
--><ref name="Inhoffen 1938">{{cite journal |author=Inhoffen HH, Hohlweg W |month=February 11, |year=1938 |title=Neue per os-wirksame weibliche Keimdrüsenhormon-Derivate: 17-Aethinyl-oestradiol und Pregnen-in-on-3-ol-17 (New female glandular derivatives active per os: 17α-ethynyl-estradiol and pregnen-in-on-3-ol-17) |journal=[[Die Naturwissenschaften|Naturwissenschaften]] |volume=26 |issue=6 |pages=96 |url=http://www.springerlink.com/content/h016u5tg61l00022/?p=6ced2951d3f04b188a3c302670b43768&pi=5}}</ref><!--
 +
--><ref name="Maisel 1965">{{cite book |author=Maisel, Albert Q. |year=1965 |title=The Hormone Quest |location=New York |publisher=Random House |oclc=543168 }}</ref><!--
 +
--><ref name="Petrow 1970">{{cite journal |author=Petrow V |year=1970 |title=The contraceptive progestagens |journal=Chem Rev |volume=70 |issue=6 |pages=713–26 |pmid=4098492 |doi=10.1021/cr60268a004}}</ref><!--
 +
--><ref name="Sneader 2005">{{cite book |author=Sneader, Walter |year=2005 |title=Drug discovery : a history |location=Hoboken, NJ |publisher=John Wiley & Sons |isbn=0471899801 |chapter=Hormone analogues |pages=188–225}}</ref><!--
 +
--><ref name="Djerassi 2006">{{cite journal |author=Djerassi C |year=2006 |title=Chemical birth of the pill |journal=Am J Obstet Gynecol |volume=194 |issue=1 |pages=290–8 |pmid=16389046 |doi=10.1016/j.ajog.2005.06.010}}</ref>
-
296.4
+
Ethinylestradiol was approved by the [[Food and Drug Administration|FDA]] in the [[United States|U.S.]] on June 25, 1943 and marketed by [[Schering-Plough|Schering]] as ''Estinyl''.<!--
 +
--><ref name="Estinyl 1943">{{cite web |author=[[Food and Drug Administration|FDA]] |year=2007 |title=Drug details: Estinyl (ethinyl estradiol) NDA 005292 |url=http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.DrugDetails}} search: Estinyl</ref>
 +
The FDA withdrew approval of ''Estinyl'' effective June 4, 2004 at the request of Schering, who had discontinued marketing ''Estinyl''.<!--
 +
--><ref name="Estinyl 2004">{{cite journal |author=[[Food and Drug Administration|FDA]] |month=May 5, |year=2004 |title=Schering Corp. et al.; Withdrawal of Approval of 92 New Drug Applications and 49 Abbreviated New Drug Applications. Notice |journal=[[Federal Register|Fed Regist]] |volume=69 |issue=87 |pages=25124–30 |url=http://a257.g.akamaitech.net/7/257/2422/14mar20010800/edocket.access.gpo.gov/2004/pdf/04-10194.pdf}}</ref>
-
<b>*Molecular Formula</b>
+
While estradiol is readily absorbed when taken orally, it is also quickly inactivated by the [[liver]]. Substitution at C17 of the estrane steroid with an [[ethyne|ethinyl]] group proved to provide an estrogen that is much more resistant to degradation and paved the way for the development of oral contraceptives.
-
C<sub>2</sub><sub>0</sub>H<sub>2</sub><sub>4</sub>O<sub>2</sub>
+
EE is absorbed  in the small intestine and reaches a serum peak about 2 hours later. It undergoes extensive metabolism in the liver involving the [[cytochrome P450]] 3A4 isoenzyme. EE and its metabolites are in excreted with the bile.  Due to the effect of [[enterohepatic circulation]] a second peak is seen several hours later. Individually, wide variations exist in the overall absorption process, and can be further modified by  drugs (i.e. [[antibiotic]]s) that affect the enterohepatic circulation or [[liver enzyme]]s. In circulation EE is almost fully bound to [[human serum albumin|plasma albumin]]. It is metabolized by [[hydroxylation]]  of the aromatic ring and excreted in both, feces and urine, in part as [[glucuronide]] and [[sulfate]] conjugate. 
-
<b>*IUPAC NAME</b>
+
EE is hormonally effective by activating the [[estrogen receptor]] and thus is an estrogen. It finds its most common use in the estrogen-[[progestin]] combination preparations of oral contraceptives. Over time, formulations have decreased the EE dose from as high as 100 μg to as low as 20 μg.
-
(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
+
The same [[contraindication]]s and precautions apply for EE as with other estrogen medications.
-
<b>*Canonical Smiles</b>
+
''Estinyl'' was a preparation of EE alone that was used for the management of menopausal symptoms and female [[hypogonadism]].<ref>[http://www.rxlist.com/cgi/generic3/estinyl_ids.htm RxList.com] - Estinyl (ethinyl estradiol)</ref>
-
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
+
EE is released into the environment as a [[xenoestrogen]] from the urine and [[feces]] of people who take it as a medication.
 +
===Melting Point===
 +
183 deg C EXP
 +
===log P===
 +
3.67  EXP
 +
===Water Solubility===
 +
11.3 mg/L 27 EXP
 +
===Vapor Pressure===
 +
2.67E-09 mm Hg 25 EST
 +
===Henry's Law Constant===
 +
7.94E-12 atm-m3/mole 25 EST
 +
===Atmospheric OH Rate Constant===
 +
|1.25E-10 cm3/molecule-sec 25 EST
-
<b>*Isomeric Smiles</b>
+
==Adverse Reactions / Side Effects==
 +
Abnormal growth filled with fluid or semisolid material; accidental injury; bladder pain; bloated full feeling; bloody or cloudy urine; body aches or pain; coating or white patches on tongue; congestion; cough producing mucus; decrease in amount of urine; difficult, burning, or painful urination; discouragement; dryness of throat; ear congestion or pain; excess air or gas in stomach or intestines; fear; feeling of warmth; feeling sad or empty; frequent urge to urinate; general feeling of discomfort or illness; headache, severe and throbbing; increased clear or white vaginal discharge; irritability; itching of the vaginal, rectal or genital areas; lack of appetite; lack or loss of strength; loss of interest or pleasure; mild dizziness; neck pain; nervousness; pain; pain during sexual intercourse; painful or difficult urination; pain or tenderness around eyes and cheekbones; passing gas; redness of the face, neck, arms and occasionally, upper chest; runny nose; skin irritation or redness where skin patch was worn; shivering; sleeplessness; sneezing; sore mouth or tongue; stuffy nose; sudden sweating; tender, swollen glands in neck; thick, white vaginal discharge with no odor or with a mild odor; tiredness; trouble concentrating; trouble sleeping; unable to sleep; voice changes
-
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O
+
==Medication Interactions==
 +
'''Ask your doctor before using any of these medicines with Ethinylestradiol:'''
 +
    * [[Acetaminophen]] (e.g., [[Tylenol]]) (with long-term, high-dose use)
 +
    * [[Amiodarone]] (e.g., [[Cordarone]])
 +
    * [[Anabolic steroids]] ([[Nandrolone]] [e.g., [[Anabolin]]], [[Oxandrolone]] [e.g., [[Anavar]]], [[Oxymetholone]] [e.g., [[Anadrol]], [[Stanozolol]] [e.g., [[Winstrol]]])
 +
    * [[Androgens]] (male hormones)
 +
    * Anti-infectives by mouth or by injection (medicine for infection)
 +
    * [[Antithyroid]] agents (medicine for overactive [[thyroid]])
 +
    * [[Carbamazepine]] (e.g., [[Tegretol]])
 +
    * [[Carmustine]] (e.g., [[BiCNU]])
 +
    * [[Chloroquine]] (e.g., [[Aralen]])
 +
    * [[Dantrolene]] (e.g., [[Dantrium]])
 +
    * [[Daunorubicin]] (e.g., [[Cerubidine]])
 +
    * [[Disulfiram]] (e.g., [[Antabuse]])
 +
    * [[Divalproex]] (e.g., [[Depakote]])
 +
    * [[Etretinate]] (e.g., [[Tegison]])
 +
    * [[Gold salts]] (medicine for [[arthritis]])
 +
    * [[Hydroxychloroquine]] (e.g., [[Plaquenil]])
 +
    * [[Isoniazid]]
 +
    * [[Mercaptopurine]] (e.g., [[Purinethol]])
 +
    * [[Methotrexate]] (e.g., [[Mexate]])
 +
    * [[Methyldopa]] (e.g., [[Aldomet]])
 +
    * [[Naltrexone]] (e.g., [[Trexan]]) (with long-term, high-dose use)
 +
    * [[Oral contraceptives]] ([[birth control]] pills) containing [[estrogen]]
 +
    * [[Phenothiazines]] ([[Acetophenazine]] [e.g., [[Tindal]]], [[Chlorpromazine]] [e.g., [[Thorazine]]], [[Fluphenazine]] [e.g., [[Prolixin]]], [[Mesoridazine]] [e.g., [[Serentil]]], [[Perphenazine]] [e.g., [[Trilafon]]], [[Prochlorperazine]] [e.g., [[Compazine]]], [[Promazine]] [e.g., [[Sparine]]], [[Promethazine]] [e.g., [[Phenergan]]], [[Thioridazine]] [e.g., [[Mellaril]]], [[Trifluoperazine]] [e.g., [[Stelazine]]], [[Triflupromazine]] [e.g., [[Vesprin]]], [[Trimeprazine]] [e.g., [[Temaril]]])
 +
    * [[Phenytoin]] (e.g., [[Dilantin]])
 +
    * [[Plicamycin]] (e.g., [[Mithracin]])
 +
    * [[Valproic acid]] (e.g., [[Depakene]])— Use of these medicines with [[estrogens]] may increase the chance of problems occurring that affect the [[liver]]
 +
    * [[Cyclosporine]] (e.g., [[Sandimmune]])— [[Estrogens]] can prevent cyclosporine's removal from the body; this can lead to [[cyclosporine]] causing [[kidney]] or [[liver]] problems
 +
==Dosing==
 +
Depends on needs and age, see [http://www.drugs.com/cons/ethinyl-estradiol.html Consumer Information] for more information.
-
==PhysioChemical Properties==
+
==Toxicity==
 +
{| border="1;width:100%; height:200px;style=text-align:center"
 +
|+'''Table I:'''
 +
|-
 +
! style="background:white; color:blue" |Organism
 +
! style="background:white; color:blue" |Test Type 
 +
! style="background:white; color:blue" |Route 
 +
! style="background:white; color:blue" |Reported Dose (Normalized Dose)
 +
! style="background:white; color:blue" |Effect
 +
! style="background:white; color:blue" |Source
 +
|-
 +
|mouse
 +
|LD50
 +
|intraperitoneal
 +
|250mg/kg (250mg/kg)
 +
|BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
-
<b>*Melting Point</b>
+
BEHAVIORAL: ATAXIA
 +
KIDNEY, URETER, AND BLADDER: OTHER CHANGES
 +
|Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
 +
|-
 +
|mouse
 +
|LD50
 +
|oral
 +
|950mg/kg (950mg/kg)
 +
|  
 +
|Drugs in Japan Vol. -, Pg. 222, 1995.
 +
|-
 +
|mouse
 +
|LD50
 +
|subcutaneous
 +
|> 3gm/kg (3000mg/kg)
 +
|BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
 +
|BLOOD: HEMORRHAGE Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
 +
|-
 +
|rat
 +
|LD50
 +
|intraperitoneal
 +
|471mg/kg (471mg/kg)
 +
|BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
-
183(EXP)
+
BEHAVIORAL: ATAXIA
 +
KIDNEY, URETER, AND BLADDER: OTHER CHANGES
 +
|Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
 +
|-
 +
|rat
 +
|LD50
 +
|oral
 +
|960mg/kg (960mg/kg)
 +
| 
 +
|Drugs in Japan Vol. -, Pg. 222, 1995.
 +
|-
 +
|rat
 +
|LD50
 +
|subcutaneous
 +
|> 2gm/kg (2000mg/kg)
 +
|BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
-
<b>*LogP</b>
+
BLOOD: HEMORRHAGE
 +
|Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
 +
|-
 +
|women
 +
|TDLo
 +
|oral
 +
|21mg/kg/21D-I (21mg/kg)
 +
|LUNGS, THORAX, OR RESPIRATION: DYSPNEA
-
3.67(EXP)
+
GASTROINTESTINAL: NAUSEA OR VOMITING
 +
|Lancet. Vol. 1, Pg. 1479, 1973.
 +
|-
 +
|}
 +
==See also==
 +
* [[Hormonal contraception]]
 +
* [[Oral contraceptive formulations]]
 +
* [[Diethylstilbestrol]]
 +
* [[Esterified Estrogens]]
 +
* [[Estradiol]]
 +
* [[Estrone]]
 +
* [[Estropipate]]
 +
* [[Antineoplastic]]
 +
* [[Osteoporosis prophylactic]]
 +
* [[Ovarian hormone therapy]]
 +
* [[Systemic Estrogen]]
 +
* [[Birth Control]]
-
<b>*Water Solubility</b>
+
==References==
 +
{{reflist}}
-
11.3(EXP) at 27C
+
==External links==
 +
*http://www.drugs.com/sfx/ethinyl-estradiol-side-effects.html
 +
*http://www.drugs.com/cons/ethinyl-estradiol.html
-
==External Links==
 
-
*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5991]Pubchem
 
-
*[http://www.genome.jp/dbget-bin/www_bget?compound+C07534]KEGG Compound
 
-
*[http://www.genome.jp/dbget-bin/www_bget?drug+D00554]KEGG Drug
 
-
*[http://www.drugbank.ca/drugs/DB00977]Drugbank
 
-
[[Categories:Hormones]]
+
[[Category:Hormonal contraception]]
 +
[[Category:Synthetic estrogens]]
 +
[[Category:Alcohols]]
 +
[[Category:Hormones]]

Current revision

Contents

[edit] Description

Show 3-D Structure

Ethinyl Estradiol
Systematic (IUPAC) name
(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Identifiers
CAS number 57-63-6
ATC code  ?
PubChem 5991
DrugBank APRD00691
Chemical data
Formula C20H24O2
Mol. mass 296.403
Pharmacokinetic data
Bioavailability 97% is bound
Metabolism Liver
Half life 36±13 hours
Excretion Feces and Urine
Therapeutic considerations
Pregnancy cat.

X (USA)

Legal status

Rx-only (U.S.)

Routes Oral, transdermal

Ethinylestradiol Template:Pron-en, also ethinyl estradiol (EE), is a derivative of estradiol. Ethinyl estradiol is an orally bio-active estrogen used in almost all modern formulations of combined oral contraceptive pills (the Pill). It is one of the most commonly used medications. Most commonly sold as NuvaRing.

The first orally active synthetic steroidal estrogen, ethinylestradiol (17α-ethynylestradiol), the 17α-ethynyl analog of estradiol, was synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering AG in Berlin.<ref name="Inhoffen 1938">Inhoffen HH, Hohlweg W (February 11, 1938). "Neue per os-wirksame weibliche Keimdrüsenhormon-Derivate: 17-Aethinyl-oestradiol und Pregnen-in-on-3-ol-17 (New female glandular derivatives active per os: 17α-ethynyl-estradiol and pregnen-in-on-3-ol-17)". Naturwissenschaften 26 (6): 96. </ref><ref name="Maisel 1965">Template:Cite book</ref><ref name="Petrow 1970">Petrow V (1970). "The contraceptive progestagens". Chem Rev 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492. </ref><ref name="Sneader 2005">Template:Cite book</ref><ref name="Djerassi 2006">Djerassi C (2006). "Chemical birth of the pill". Am J Obstet Gynecol 194 (1): 290–8. doi:10.1016/j.ajog.2005.06.010. PMID 16389046. </ref>

Ethinylestradiol was approved by the FDA in the U.S. on June 25, 1943 and marketed by Schering as Estinyl.<ref name="Estinyl 1943">Template:Cite web search: Estinyl</ref> The FDA withdrew approval of Estinyl effective June 4, 2004 at the request of Schering, who had discontinued marketing Estinyl.<ref name="Estinyl 2004">FDA (May 5, 2004). "Schering Corp. et al.; Withdrawal of Approval of 92 New Drug Applications and 49 Abbreviated New Drug Applications. Notice". Fed Regist 69 (87): 25124–30. </ref>

While estradiol is readily absorbed when taken orally, it is also quickly inactivated by the liver. Substitution at C17 of the estrane steroid with an ethinyl group proved to provide an estrogen that is much more resistant to degradation and paved the way for the development of oral contraceptives.

EE is absorbed in the small intestine and reaches a serum peak about 2 hours later. It undergoes extensive metabolism in the liver involving the cytochrome P450 3A4 isoenzyme. EE and its metabolites are in excreted with the bile. Due to the effect of enterohepatic circulation a second peak is seen several hours later. Individually, wide variations exist in the overall absorption process, and can be further modified by drugs (i.e. antibiotics) that affect the enterohepatic circulation or liver enzymes. In circulation EE is almost fully bound to plasma albumin. It is metabolized by hydroxylation of the aromatic ring and excreted in both, feces and urine, in part as glucuronide and sulfate conjugate.

EE is hormonally effective by activating the estrogen receptor and thus is an estrogen. It finds its most common use in the estrogen-progestin combination preparations of oral contraceptives. Over time, formulations have decreased the EE dose from as high as 100 μg to as low as 20 μg.

The same contraindications and precautions apply for EE as with other estrogen medications.

Estinyl was a preparation of EE alone that was used for the management of menopausal symptoms and female hypogonadism.<ref>RxList.com - Estinyl (ethinyl estradiol)</ref>

EE is released into the environment as a xenoestrogen from the urine and feces of people who take it as a medication.

[edit] Melting Point

183 deg C EXP

[edit] log P

3.67 EXP

[edit] Water Solubility

11.3 mg/L 27 EXP

[edit] Vapor Pressure

2.67E-09 mm Hg 25 EST

[edit] Henry's Law Constant

7.94E-12 atm-m3/mole 25 EST

[edit] Atmospheric OH Rate Constant

|1.25E-10 cm3/molecule-sec 25 EST

[edit] Adverse Reactions / Side Effects

Abnormal growth filled with fluid or semisolid material; accidental injury; bladder pain; bloated full feeling; bloody or cloudy urine; body aches or pain; coating or white patches on tongue; congestion; cough producing mucus; decrease in amount of urine; difficult, burning, or painful urination; discouragement; dryness of throat; ear congestion or pain; excess air or gas in stomach or intestines; fear; feeling of warmth; feeling sad or empty; frequent urge to urinate; general feeling of discomfort or illness; headache, severe and throbbing; increased clear or white vaginal discharge; irritability; itching of the vaginal, rectal or genital areas; lack of appetite; lack or loss of strength; loss of interest or pleasure; mild dizziness; neck pain; nervousness; pain; pain during sexual intercourse; painful or difficult urination; pain or tenderness around eyes and cheekbones; passing gas; redness of the face, neck, arms and occasionally, upper chest; runny nose; skin irritation or redness where skin patch was worn; shivering; sleeplessness; sneezing; sore mouth or tongue; stuffy nose; sudden sweating; tender, swollen glands in neck; thick, white vaginal discharge with no odor or with a mild odor; tiredness; trouble concentrating; trouble sleeping; unable to sleep; voice changes

[edit] Medication Interactions

Ask your doctor before using any of these medicines with Ethinylestradiol: 

   * Acetaminophen (e.g., Tylenol) (with long-term, high-dose use)
   * Amiodarone (e.g., Cordarone)
   * Anabolic steroids (Nandrolone [e.g., Anabolin], Oxandrolone [e.g., Anavar], Oxymetholone [e.g., Anadrol, Stanozolol [e.g., Winstrol])
   * Androgens (male hormones)
   * Anti-infectives by mouth or by injection (medicine for infection)
   * Antithyroid agents (medicine for overactive thyroid)
   * Carbamazepine (e.g., Tegretol)
   * Carmustine (e.g., BiCNU)
   * Chloroquine (e.g., Aralen)
   * Dantrolene (e.g., Dantrium)
   * Daunorubicin (e.g., Cerubidine)
   * Disulfiram (e.g., Antabuse)
   * Divalproex (e.g., Depakote)
   * Etretinate (e.g., Tegison)
   * Gold salts (medicine for arthritis)
   * Hydroxychloroquine (e.g., Plaquenil)
   * Isoniazid
   * Mercaptopurine (e.g., Purinethol)
   * Methotrexate (e.g., Mexate)
   * Methyldopa (e.g., Aldomet)
   * Naltrexone (e.g., Trexan) (with long-term, high-dose use)
   * Oral contraceptives (birth control pills) containing estrogen
   * Phenothiazines (Acetophenazine [e.g., Tindal], Chlorpromazine [e.g., Thorazine], Fluphenazine [e.g., Prolixin], Mesoridazine [e.g., Serentil], Perphenazine [e.g., Trilafon], Prochlorperazine [e.g., Compazine], Promazine [e.g., Sparine], Promethazine [e.g., Phenergan], Thioridazine [e.g., Mellaril], Trifluoperazine [e.g., Stelazine], Triflupromazine [e.g., Vesprin], Trimeprazine [e.g., Temaril])
   * Phenytoin (e.g., Dilantin)
   * Plicamycin (e.g., Mithracin)
   * Valproic acid (e.g., Depakene)— Use of these medicines with estrogens may increase the chance of problems occurring that affect the liver
   * Cyclosporine (e.g., Sandimmune)— Estrogens can prevent cyclosporine's removal from the body; this can lead to cyclosporine causing kidney or liver problems

[edit] Dosing

Depends on needs and age, see Consumer Information for more information.

[edit] Toxicity

Table I:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA KIDNEY, URETER, AND BLADDER: OTHER CHANGES

Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
mouse LD50 oral 950mg/kg (950mg/kg) Drugs in Japan Vol. -, Pg. 222, 1995.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
rat LD50 intraperitoneal 471mg/kg (471mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA KIDNEY, URETER, AND BLADDER: OTHER CHANGES

Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
rat LD50 oral 960mg/kg (960mg/kg) Drugs in Japan Vol. -, Pg. 222, 1995.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: HEMORRHAGE

Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
women TDLo oral 21mg/kg/21D-I (21mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING

Lancet. Vol. 1, Pg. 1479, 1973.

[edit] See also

[edit] References

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[edit] External links

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