Identification
- Summary
Buserelin is a LHRH agonist used for the palliative treatment of hormone-dependent advanced carcinoma of the prostate gland in males and treatment of endometriosis in females.
- Brand Names
- Suprefact
- Generic Name
- Buserelin
- DrugBank Accession Number
- DB06719
- Background
Buserelin is a synthetic peptide analog of the luteinizing hormone-releasing hormone (LHRH) agonist, which stimulates the pituitary gland's gonadotrophin-releasing hormone receptor (GnRHR). It is used in prostate cancer treatment.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Buserelin (DB06719)
- Weight
- Average: 1239.447
Monoisotopic: 1238.656026893 - Chemical Formula
- C60H86N16O13
- Synonyms
- Buserelin
- Buserelina
- Busereline
- Buserelinum
- Etilamide
- Tiloryth
- External IDs
- HOE 766
- S 746766
Pharmacology
- Indication
Buserelin may be used in the treatment of hormone-responsive cancers such as prostate cancer or breast cancer, estrogen-dependent conditions (such as endometriosis or uterine fibroids), and in assisted reproduction.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of D prostate cancer •••••••••••• ••••••••• ••••••••• Treatment of Endometriosis •••••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
The substitution of glycine in position 6 by D-serine, and that of glycinamide in position 10 by ethylamide, leads to a nonapeptide with a greatly enhanced LHRH effect. The effects of buserelin on FSH and LH release are 20 to 170 times greater than those of LHRH. Buserelin also has a longer duration of action than natural LHRH. Investigations in healthy adult males and females have demonstrated that the increase in plasma LH and FSH levels persist for at least 7 hours and that a return to basal values requires about 24 hours. Clinical inhibition of gonadotropin release, and subsequent reduction of serum testosterone or estradiol to castration level, was found when large pharmacologic doses (50-500 mcg SC/day or 300-1200 mcg IN/day) were administered for periods greater than 1 to 3 months. Chronic administration of such doses of buserelin results in sustained inhibition of gonadotropin production, suppression of ovarian and testicular steroidogenesis and, ultimately, reduced circulating levels of gonadotropin and gonadal steroids. These effects form the basis for buserelin use in patients with hormone-dependent metastatic carcinoma of the prostate gland as well as in patients with endometriosis.
- Mechanism of action
Buserelin stimulates the pituitary gland's gonadotrophin-releasing hormone receptor (GnRHR). Buserelin desensitizes the GnRH receptor, reducing the amount of gonadotropin. In males, this results in a reduction in the synthesis and release of testosterone. In females, estrogen secretion is inhibited. While initially, there is a rise in FSH and LH levels, chronic administration of Buserelin results in a sustained suppression of these hormones.
Target Actions Organism ALutropin-choriogonadotropic hormone receptor Not Available Humans AGonadotropin-releasing hormone receptor Not Available Humans - Absorption
Buserelin is water soluble and readily absorbed after subcutaneous injection (70% bioavailable). However, bioavailability after oral absorption. When administered correctly via the nasal route, it may be absorbed in the nasal mucosa to achieve sufficient plasma levels.
- Volume of distribution
Buserelin circulates in serum predominantly in intact active form. Preferred accumulation is preferentially in the liver and kidneys as well as in the anterior pituitary lobe, the biological target organ.
- Protein binding
15%
- Metabolism
It is metabolized and subsequently inactivated by peptidase (pyroglutamyl peptidase and chymotrypsin-like endopeptidase) in the liver and kidneys as well as in the gastrointestinal tract. In the pituitary gland, it is inactivated by membrane-located enzymes.
- Route of elimination
Buserelin and its inactive metabolites are excreted via the renal and biliary routes. In man it is excreted in urine at 50% in its intact form.
- Half-life
The elimination half-life is approximately 50 to 80 minutes following intravenous administration, 80 minutes after subcutaneous administration and approximately 1 to 2 hours after intranasal administration.
- Clearance
Not Available
- Adverse Effects
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Buserelin may induce early, transient increase in serum testosterone or estradiol which can lead in the exacerbation of signs and symptoms of metastatic prostate cancer or endometriosis. Adverse reactions reported at more than 10% occurrence include headache, loss of libido in patients with prostate cancer, hot flashes, hypermenorrhea, decreased libido in prostate cancer and endometriosis, flatulence, impotence, vaginal dryness, back pain and nasal mucosa irritation.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Buserelin. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Buserelin. Acrivastine The risk or severity of QTc prolongation can be increased when Buserelin is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Buserelin is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Buserelin. - Food Interactions
- No interactions found.
Products
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Ingredient UNII CAS InChI Key Buserelin acetate 13U86G7YSP 68630-75-1 PYMDEDHDQYLBRT-DRIHCAFSSA-N - International/Other Brands
- Cinnafact (Cinnagen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Suprefact Solution 1 mg / mL Subcutaneous Cheplapharm Arzneimittel Gmbh 1998-05-05 Not applicable Canada 
Suprefact Solution 100 mcg / act Nasal Cheplapharm Arzneimittel Gmbh 1998-02-03 2022-04-29 Canada Suprefact Depot 2 Months Implant 6.3 mg Subcutaneous Cheplapharm Arzneimittel Gmbh 1997-02-10 Not applicable Canada Suprefact Depot 3 Months Implant 9.45 mg Subcutaneous Cheplapharm Arzneimittel Gmbh 2000-02-24 Not applicable Canada Suprefact Inj 1mg/ml Liquid 1 mg / mL Subcutaneous Hoechst Canada Inc. 1988-12-31 1998-08-25 Canada
Categories
- ATC Codes
- L02AE01 — Buserelin
- Drug Categories
- Adrenal Cortex Hormones
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Endocrine Therapy
- Fertility Agents
- Fertility Agents, Female
- Gonadotropin-releasing hormone agonist
- Hormones
- Hormones and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Hypothalamic Hormones
- Miscellaneous Therapeutic Agents
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary Hormone-Releasing Hormones
- Potential QTc-Prolonging Agents
- Proteins
- QTc Prolonging Agents
- Reproductive Control Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- PXW8U3YXDV
- CAS number
- 57982-77-1
- InChI Key
- CUWODFFVMXJOKD-UVLQAERKSA-N
- InChI
- InChI=1S/C60H86N16O13/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65)/t40-,41-,42-,43-,44-,45-,46-,47+,48-/m0/s1
- IUPAC Name
- (2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido]-5-carbamimidamidopentanoyl]-N-ethylpyrrolidine-2-carboxamide
- SMILES
- CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@@H]1CCC(=O)N1
References
- General References
- Link [Link]
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Fertility / Optimal Stimulation Protocol / Reproductive Endocrinology 1 4 Completed Treatment Infertility 2 4 Completed Treatment OHSS (Ovarian Hyperstimulation) 1 4 Completed Treatment Ovarian Stimulation 1 4 Completed Treatment Pregnancy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Spray Nasal 0.15 mg Implant Parenteral 6.3 MG Implant Parenteral 9.45 MG Injection, solution 1 MG/ML Solution Nasal 100 mcg / act Solution Subcutaneous 1 mg / mL Spray Nasal 0.1 MG Injection Parenteral 1 mg/ml Implant; injection Subcutaneous 9.9 mg Implant Subcutaneous 6.3 mg Implant Subcutaneous 9.45 mg Liquid Subcutaneous 1 mg / mL Injection Subcutaneous 1 mg/ml Spray Nasal 1 mg / mL Liquid Nasal 1 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP -3.3 Chemaxon pKa (Strongest Acidic) 9.49 Chemaxon pKa (Strongest Basic) 11.85 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 17 Chemaxon Hydrogen Donor Count 16 Chemaxon Polar Surface Area 438.27 Å2 Chemaxon Rotatable Bond Count 33 Chemaxon Refractivity 334.23 m3·mol-1 Chemaxon Polarizability 131.48 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Luteinizing hormone receptor activity
- Specific Function
- Receptor for lutropin-choriogonadotropic hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase.
- Gene Name
- LHCGR
- Uniprot ID
- P22888
- Uniprot Name
- Lutropin-choriogonadotropic hormone receptor
- Molecular Weight
- 78642.01 Da
References
- Kirby RS, Fitzpatrick JM, Clarke N: Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Peptide binding
- Specific Function
- Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
- Gene Name
- GNRHR
- Uniprot ID
- P30968
- Uniprot Name
- Gonadotropin-releasing hormone receptor
- Molecular Weight
- 37730.355 Da
References
- Kirby RS, Fitzpatrick JM, Clarke N: Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Maeda K, Kitawaki J, Yokota K, Noguchi T, Urabe M, Yamamoto T, Honjo H: [Effects of gonadotropin-releasing hormone and its analogue (buserelin) on aromatase in cultured human granulosa cells]. Nihon Sanka Fujinka Gakkai Zasshi. 1996 Feb;48(2):89-95. [Article]
Drug created at June 07, 2010 22:44 / Updated at February 20, 2024 23:54