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17-beta estradiol (E2, Estrace, Estinyl, Delestrogen, Elestrin, Evamist, Imvexxy)

Tradenames: Estrace, Delestrogen Delestrogen. Estradiol cypionate & estradiol valerate. Indications: - symptoms of menopause - moderate to severe vasomotor symptoms, hot flashes - treatment of atrophic vaginitis - atrophic dystrophy of the vulva - atrophic urethritis - estradiol vaginal inserts (Imvexxy) for dyspareunia resulting from menopause [7] - female hypogonadism - ovariectomy - primary ovarian failure - polycystic ovary disease - endometriosis [6] - dysmenorrhea - menorrhagia - acne [6] - inoperable breast cancer - inoperable prostate cancer - prevention of postmenopausal osteoporosis - may be useful for depression in perimenopausal women Dosage: 1) moderate to severe vasomotor symptoms a) cypionate 1-5 mg IM every 3-4 weeks b) valerate 10-20 mg IM every 4 weeks 2) osteoporosis prevention -> 1-2 mg PO QD for 1st 3 weeks of month 3) hypogonadism: a) 1-2 mg PO QD for 1st 3 weeks of month b) cypionate: 1.5-2 mg/month IM c) valerate: 10-20 mg/month 4) prostate cancer: a) > 30 mg estradiol valerate every 1-2 weeks b) 1-2 mg PO TID Tabs: 0.5, 1, 2 mg. Injection (cypionate): 5 mg/mL (5 mL) (valerate): 20 mg/mL, 40 mg/mL syringe 2.5-3 mL, needle 22 g, 1.5 inch Topical:vaginal cream (Estrace) 42 gram tube atrophic vaginitis: 1) 2-4 g/day for 2 weeks 2) reduce to 1-2 g for 2 weeks 3) maintenance 1 g 3x/week Gel: Elestrin (bioidentica) postmenopausal vasomotor symptoms Evamist: transdermal spray, 1.53 mg/spray Vaginal rings: see Estring, Femring Pharmacokinetics: 1) 1st pass metabolism 2) metabolized to estrone Adverse effects: 1) common (> 10%) - nausea, peripheral edema, enlargement of the breasts, breast tenderness, anorexia, bloating 2) less common (1-10%) - vomiting, diarrhea, headache, increased libido (females), decreased libido (males) 3) uncommon (< 1%) - intolerance to contact lenses, breast tumors, amenorrhea, alterations in frequency & flow of menses, hypertension, thrombophlebitis & venous thrombosis, stroke, myocardial infarction, edema, depression, dizziness, anxiety, chloasma, melasma, rash, hyperglycemia, GI distress, increased serum triglycerides, increased LDL, cholestatic jaundice, increased susceptibility to Candida infection 4) other a) breakthrough bleeding b) induction of estrogen-sensitive neoplasms - endometrial cancer - breast cancer ? Drug interactions: 1) estradiol increases effects of: a) antidepressants b) beta blockers c) corticosteroids d) theophylline 2) agents that decrease effectiveness of estrogens a) antibiotics b) barbiturates c) phenytoin d) rifampin Laboratory: - estradiol in tissue - estradiol in body fluid - estradiol in amniotic fluid - estradiol in saliva - estradiol in semen - estradiol in serum - free estradiol in serum - estradiol.albumin bound in serum/plasma - estradiol.bioavailable in serum/plasma - estradiol in urine - estradiol unconjugated in urine Mechanism of action: 1) most potent & major secretory product of the ovary 2) development & maintenance of female reproductive system

Interactions

molecular events drug adverse effects of estrogens

Related

estradiol in serum estrone (E1) ethinyl estradiol gonadal steroid biosynthesis

Specific

estradiol vaginal (Vagifem) estradiol-3-benzoate

General

adrenal cortex hormone; corticosteroid estrane estrogen

Properties

MISC-INFO: elimination route LIVER KIDNEY pregnancy-category X safety in lactation -

Database Correlations

PUBCHEM correlations

References

  1. The Pharmacological Basis of Therapeutics, 9th ed. Gilman et al, eds. Permagon Press/McGraw Hill, 1996
  2. Drug Information & Medication Formulary, Veterans Affairs, Central California Health Care System, 1st ed., Ravnan et al eds, 1998 Department of Veterans Affairs, VA National Formulary
  3. Kaiser Permanente Northern California Regional Drug Formulary, 1998
  4. Prescriber's Letter 8(7):41 2001
  5. Prescriber's Letter 15(4): 2008 Estrogen-Containing Hormone Replacement Products for Postmenopausal Women Detail-Document#: 240407 (subscription needed) http://www.prescribersletter.com
  6. Deprecated Reference
  7. Brown T FDA Approves Imvexxy for Moderate to Severe Dyspareunia. Medscape - May 31, 2018. https://www.medscape.com/viewarticle/897436

Substructure-of

estriol (E3)

Component-of

Activella Angeliq (drospirenone, estradiol) benzoate/estradiol benzoate/estradiol/testosterone Climara Pro contraceptive/estradiol/ethinyl estradiol/levonorgestrel desogestrel/estradiol/ethinyl estradiol drospirenone/estradiol drospirenone/estradiol/ethinyl estradiol estradiol/ethinyl estradiol estradiol/ethinyl estradiol/ferrous fumarate/iron/norethindrone estradiol/ethinyl estradiol/ferrous fumarate/norethindrone estradiol/ethinyl estradiol/levonorgestrel estradiol/ethinyl estradiol/norethindrone estradiol/ethinyl estradiol/norgestimate estradiol/ethinyl estradiol/norgestrel estradiol/etonogestrel estradiol/levonorgestrel estradiol/methoxyprogesterone estradiol/norethindrone estradiol/norethindrone/relugolix estradiol/norgestimate estradiol/oxytetracycline estradiol/progesterone estradiol/testosterone estradiol/trenbolone (Revalor) estramustine (Emcyt) Estrasorb Estring Femring Lunelle Ortho-Prefest transdermal estradiol