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Anastrozole

Anastrozole
Clinical data
Trade namesArimidex, Aremed, others[1]
Other namesAnastrazole; anastrozol; ICI-D1033; ZD-1033
AHFS/Drugs.comMonograph
MedlinePlusa696018
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
Drug classAromatase inhibitor; Antiestrogen
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
BioavailabilityUnknown (but well-absorbed in animals)[2]
Protein binding40%[3][4]
MetabolismLiver (~85%) (N-dealkylation, hydroxylation, glucuronidation)[3][2][4]
Elimination half-life40–50 hours[3][2][4]
ExcretionUrine (11%)[3][2][4]
Identifiers
  • 2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]bis(2-methylpropanenitrile)[5]
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.129.723 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N5
Molar mass293.374 g·mol−1
3D model (JSmol)
  • N#CC(C)(C)c1cc(Cn2cncn2)cc(c1)C(C)(C)C#N
  • InChI=1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3 checkY
  • Key:YBBLVLTVTVSKRW-UHFFFAOYSA-N checkY
  (verify)

Anastrozole, sold under the brand name Arimidex among others, is an antiestrogenic medication used in addition to other treatments for breast cancer.[6][7] Specifically it is used for hormone receptor-positive breast cancer.[7] It has also been used to prevent breast cancer in those at high risk.[7] It is taken by mouth.[7]

Common side effects of anastrozole include hot flashes, altered mood, joint pain, and nausea.[7][6] Severe side effects include an increased risk of heart disease and osteoporosis.[7] Use during pregnancy may harm the baby.[7] Anastrozole is in the aromatase-inhibiting family of medications.[7] It works by blocking the production of estrogens in the body, and hence has antiestrogenic effects.[7]

Anastrozole was patented in 1987 and was approved for medical use in 1995.[8][9] It is on the World Health Organization's List of Essential Medicines.[10] Anastrozole is available as a generic medication.[7] In 2021, it was the 182nd most commonly prescribed medication in the United States, with more than 2 million prescriptions.[11][12]

Medical uses

Breast cancer

Anastrozole is used in the treatment and prevention of breast cancer in women.[7] The Arimidex, Tamoxifen, Alone or in Combination (ATAC) trial was of localized breast cancer and women received either anastrozole, the selective estrogen receptor modulator tamoxifen, or both for five years, followed by five years of follow-up.[13] After more than 5 years the group that received anastrozole had better results than the tamoxifen group.[13] The trial suggested that anastrozole is the preferred medical therapy for postmenopausal women with localized estrogen receptor-positive breast cancer.[13]

Early puberty

Anastrozole is used at a dosage of 0.5 to 1 mg/day in combination with the antiandrogen bicalutamide in the treatment of peripheral precocious puberty, for instance due to familial male-limited precocious puberty (testotoxicosis) and McCune–Albright syndrome, in boys.[14][15][16][17][18][19][20][21][22][23]

Available forms

Anastrozole is available in the form of 1 mg oral tablets.[6][24] No alternative forms or routes are available.[24]

Contraindications

Contraindications of anastrozole include hypersensitivity to anastrozole or any other component of anastrozole formulations, pregnancy, and breastfeeding.[6] Hypersensitivity reactions to anastrozole including anaphylaxis, angioedema, and urticaria have been observed.[6]

Side effects

Common side effects of anastrozole (≥10% incidence) include hot flashes, asthenia, arthritis, pain, arthralgia, hypertension, depression, nausea and vomiting, rash, osteoporosis, bone fractures, back pain, insomnia, headache, bone pain, peripheral edema, coughing, dyspnea, pharyngitis, and lymphedema.[6] Serious but rare adverse effects (<0.1% incidence) include skin reactions such as lesions, ulcers, or blisters; allergic reactions with swelling of the face, lips, tongue, and/or throat that may cause difficulty swallowing or breathing; and abnormal liver function tests as well as hepatitis.[6]

Interactions

Anastrozole is thought to have clinically negligible inhibitory effects on the cytochrome P450 enzymes CYP1A2, CYP2A6, CYP2D6, CYP2C8, CYP2C9, and CYP2C19.[3][2][4][6] As a result, it is thought that drug interactions of anastrozole with cytochrome P450 substrates are unlikely.[4] No clinically significant drug interactions have been reported with anastrozole as of 2003.[3]

Anastrozole does not affect circulating levels of tamoxifen or its major metabolite N-desmethyltamoxifen.[3][2] However, tamoxifen has been found to decrease steady-state area-under-the-curve levels of anastrozole by 27%.[3][2] But estradiol levels were not significantly different in the group that received both anastrozole and tamoxifen compared to the anastrozole alone group, so the decrease in anastrozole levels is not thought to be clinically important.[4]

Pharmacology

Pharmacodynamics

Anastrozole works by reversibly binding to the aromatase enzyme, and through competitive inhibition blocks the conversion of androgens to estrogens in peripheral (extragonadal) tissues.[25] The medication has been found to achieve 96.7% to 97.3% inhibition of aromatase at a dosage of 1 mg/day and 98.1% inhibition of aromatase at a dosage of 10 mg/day in humans.[3][2] As such, 1 mg/day is considered to be the minimal dosage required to achieve maximal suppression of aromatase with anastrozole.[3] This decrease in aromatase activity results in an at least 85% decrease in estradiol levels in postmenopausal women.[3] Levels of corticosteroids and other adrenal steroids are unaffected by anastrozole.[3]

Pharmacodynamics of aromatase inhibitors
Generation Medication Dosage % inhibitiona Classb IC50c
First Testolactone 250 mg 4x/day p.o. ? Type I ?
100 mg 3x/week i.m. ?
Rogletimide 200 mg 2x/day p.o.
400 mg 2x/day p.o.
800 mg 2x/day p.o.		 50.6%
63.5%
73.8%		 Type II ?
Aminoglutethimide 250 mg mg 4x/day p.o. 90.6% Type II 4,500 nM
Second Formestane 125 mg 1x/day p.o.
125 mg 2x/day p.o.
250 mg 1x/day p.o.		 72.3%
70.0%
57.3%		 Type I 30 nM
250 mg 1x/2 weeks i.m.
500 mg 1x/2 weeks i.m.
500 mg 1x/1 week i.m.		 84.8%
91.9%
92.5%
Fadrozole 1 mg 1x/day p.o.
2 mg 2x/day p.o.		 82.4%
92.6%		 Type II ?
Third Exemestane 25 mg 1x/day p.o. 97.9% Type I 15 nM
Anastrozole 1 mg 1x/day p.o.
10 mg 1x/day p.o.		 96.7–97.3%
98.1%		 Type II 10 nM
Letrozole 0.5 mg 1x/day p.o.
2.5 mg 1x/day p.o.		 98.4%
98.9%–>99.1%		 Type II 2.5 nM
Footnotes: a = In postmenopausal women. b = Type I: Steroidal, irreversible (substrate-binding site). Type II: Nonsteroidal, reversible (binding to and interference with the cytochrome P450 heme moiety). c = In breast cancer homogenates. Sources: See template.

Pharmacokinetics

The bioavailability of anastrozole in humans is unknown, but it was found to be well-absorbed in animals.[2][6] Absorption of anastrozole is linear over a dosage range of 1 to 20 mg/day in humans and does not change with repeated administration.[3][4][6] Food does not significantly influence the extent of absorption of anastrozole.[4][6] Peak levels of anastrozole occur a median 3 hours after administration, but with a wide range of 2 to 12 hours.[2][4] Steady-state levels of anastrozole are achieved within 7 to 10 days of continuous administration, with 3.5-fold accumulation.[3][2][4] However, maximal suppression of estradiol levels occurs within 3 or 4 days of therapy.[3]

Active efflux of anastrozole by P-glycoprotein at the blood–brain barrier has been found to limit the central nervous system penetration of anastrozole in rodents, whereas this was not the case with letrozole and vorozole.[26][27][28] As such, anastrozole may have peripheral selectivity in humans, although this has yet to be confirmed.[28] In any case, estradiol is synthesized peripherally and readily crosses the blood–brain barrier, so anastrozole would still expected to reduce estradiol levels in the central nervous system to a certain degree. The plasma protein binding of anastrozole is 40%.[3][4]

The metabolism of anastrozole is by N-dealkylation, hydroxylation, and glucuronidation.[3] Inhibition of aromatase is due to anastrozole itself rather than to metabolites, with the major circulating metabolite being inactive.[6] The elimination half-life of anastrozole is 40 to 50 hours (1.7 to 2.1 days).[3][2][4] This allows for convenient once-daily administration.[4] The medication is eliminated predominantly by metabolism in the liver (83 to 85%) but also by residual excretion by the kidneys unchanged (11%).[3][2][4] Anastrozole is excreted primarily in urine but also to a lesser extent in feces.[4]

Chemistry

Anastrozole is a nonsteroidal benzyl triazole.[3][4] It is also known as α,α,α',α'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrile.[1] Anastrozole is structurally related to letrozole, fadrozole, and vorozole, with all being classified as azoles.[29][30][31][32]

History

Anastrozole was patented by Imperial Chemical Industries (ICI) in 1987 and was approved for medical use, specifically the treatment of breast cancer, in 1995.[8][9]

Society and culture

Generic names

Anastrozole is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name.[1]

Brand names

Anastrozole is primarily sold under the brand name Arimidex.[1] However, it is also marketed under a variety of other brand names throughout the world.[1]

Availability

Anastrozole is available widely throughout the world.[1]

Research

Anastrozole is surprisingly ineffective at treating gynecomastia, in contrast to selective estrogen receptor modulators like tamoxifen.[33][34]

Anastrozole was under development for the treatment of female infertility but did not complete development and hence was never approved for this indication.[35]

An anastrozole and levonorgestrel vaginal ring (developmental code name BAY 98–7196) was under development for use as a hormonal contraceptive and treatment for endometriosis, but development was discontinued in November 2018 and the formulation was never marketed.[36]

Anastrozole increases testosterone levels in males and has been studied as an alternative method of androgen replacement therapy in men with hypogonadism.[37][38] However, there are concerns about its long-term influence on bone mineral density in this patient population, as well as other adverse effects.[37]

References

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  2. ^ a b c d e f g h i j k l m Lønning P (2003). "Clinical pharmacokinetics of aromatase inhibitors and inactivators". Clinical Pharmacokinetics. 42 (7): 619–631. doi:10.2165/00003088-200342070-00002. PMID 12844324. S2CID 9585901.
  3. ^ a b c d e f g h i j k l m n o p q r s t Lønning P, Pfister C, Martoni A, Zamagni C (August 2003). "Pharmacokinetics of third-generation aromatase inhibitors". Seminars in Oncology. 30 (4 Suppl 14): 23–32. doi:10.1016/S0093-7754(03)00305-1. PMID 14513434.
  4. ^ a b c d e f g h i j k l m n o p q Sanford M, Plosker GL (2008). "Anastrozole: a review of its use in postmenopausal women with early-stage breast cancer". Drugs. 68 (9): 1319–1340. doi:10.2165/00003495-200868090-00007. PMID 18547136. S2CID 195687223.
  5. ^ "anastrozole". Chemical Entities of Biological Interest (ChEBI). European Molecular Biology Laboratory. Archived from the original on 22 September 2011. Retrieved 14 August 2011.
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  8. ^ a b Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 516. ISBN 9783527607495. Archived from the original on 20 December 2016.
  9. ^ a b Dukes M (1997). "The relevance of preclinical models to the treatment of postmenopausal breast cancer". Oncology. 54 (2): 6–10. doi:10.1159/000227748. PMID 9394853.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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  13. ^ a b c Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, et al. (2005). "Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer". Lancet. 365 (9453): 60–62. doi:10.1016/S0140-6736(04)17666-6. PMID 15639680. S2CID 8350282. [non-primary source needed]
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  22. ^ Mauras N (October 2011). "Strategies for maximizing growth in puberty in children with short stature". Pediatric Clinics of North America. 58 (5): 1167–79, x. doi:10.1016/j.pcl.2011.07.007. PMID 21981954.
  23. ^ Fuqua JS (June 2013). "Treatment and outcomes of precocious puberty: an update". The Journal of Clinical Endocrinology and Metabolism. 98 (6): 2198–2207. doi:10.1210/jc.2013-1024. PMID 23515450.
  24. ^ a b White R, Bradnam V (11 March 2015). Handbook of Drug Administration via Enteral Feeding Tubes, 3rd edition. Pharmaceutical Press. pp. 108–. ISBN 978-0-85711-162-3.
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  26. ^ Costa R, Carneiro BA, Wainwright DA, Santa-Maria CA, Kumthekar P, Chae YK, et al. (January 2017). "Developmental therapeutics for patients with breast cancer and central nervous system metastasis: current landscape and future perspectives". Annals of Oncology. 28 (1): 44–56. doi:10.1093/annonc/mdw532. PMC 7360139. PMID 28177431.
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  28. ^ a b Miyajima M, Kusuhara H, Takahashi K, Takashima T, Hosoya T, Watanabe Y, et al. (September 2013). "Investigation of the effect of active efflux at the blood-brain barrier on the distribution of nonsteroidal aromatase inhibitors in the central nervous system". Journal of Pharmaceutical Sciences. 102 (9): 3309–3319. doi:10.1002/jps.23600. PMID 23712697.
  29. ^ Thurston DE (22 November 2006). Chemistry and Pharmacology of Anticancer Drugs. CRC Press. pp. 136–. ISBN 978-1-4200-0890-6.
  30. ^ Roy, Kunal (28 February 2015). Quantitative Structure-Activity Relationships in Drug Design, Predictive Toxicology, and Risk Assessment. IGI Global. pp. 437–. ISBN 978-1-4666-8137-8.
  31. ^ Smith DA, Allerton C, Kalgutkar AS, van de Waterbeemd H, Walker DK (13 September 2012). Pharmacokinetics and Metabolism in Drug Design. John Wiley & Sons. pp. 197–. ISBN 978-3-527-64529-9.
  32. ^ Environmental Health Perspectives: Supplements. U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, National Institute of Environmental Health Sciences. 1993. pp. 256–260.
  33. ^ Fagerlund A, Cormio L, Palangi L, Lewin R, Santanelli di Pompeo F, Elander A, et al. (2015). "Gynecomastia in Patients with Prostate Cancer: A Systematic Review". PLOS ONE. 10 (8): e0136094. Bibcode:2015PLoSO..1036094F. doi:10.1371/journal.pone.0136094. PMC 4550398. PMID 26308532.
  34. ^ Bedognetti D, Rubagotti A, Zoppoli G, Boccardo F (2010). "Gynaecomastia: the anastrozole paradox". Journal of Pediatric Endocrinology & Metabolism. 23 (1–2): 205–206. doi:10.1515/JPEM.2010.23.1-2.205. PMID 20432826. S2CID 41999854.
  35. ^ "Anastrozole - AstraZeneca". Adis Insight.
  36. ^ "Anastrozole/levonorgestrel intravaginal ring - Bayer HealthCare". Adis Insight.
  37. ^ a b Serefoglu EC, Gokce A, Hellstrom WJ, Guay AT (2013). "Alternate Therapies for Testosterone Replacement". Androgen Deficiency and Testosterone Replacement. Current Clinical Urology. Humana Press. pp. 141–147. doi:10.1007/978-1-62703-179-0_11. ISBN 978-1-62703-178-3.
  38. ^ Khera M, Adaikan G, Buvat J, Carrier S, El-Meliegy A, Hatzimouratidis K, et al. (December 2016). "Diagnosis and Treatment of Testosterone Deficiency: Recommendations From the Fourth International Consultation for Sexual Medicine (ICSM 2015)". The Journal of Sexual Medicine. 13 (12): 1787–1804. doi:10.1016/j.jsxm.2016.10.009. PMID 27914560.
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