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Identification
NameBuserelin
Accession NumberDB06719
TypeBiotech
GroupsApproved
Description

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.

Protein structureDb06719
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Protein chemical formulaC62H90N16O15
Protein average weightNot Available
SequencesNot Available
Synonyms
(Des-Gly10,D-Ser(tBu)6,Pro-NHEt9)-LHRH
D-Ser(Tbu)6EA10LHRH
Etilamide
Tiloryth
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Suprefactsolution1 mgnasalSanofi Aventis Canada Inc1998-02-03Not applicableCanada
Suprefactsolution1 mgsubcutaneousSanofi Aventis Canada Inc1998-05-05Not applicableCanada
Suprefact Depot 2 Monthsimplant6.3 mgsubcutaneousSanofi Aventis Canada Inc1997-02-10Not applicableCanada
Suprefact Depot 3 Monthsimplant9.45 mgsubcutaneousSanofi Aventis Canada Inc2000-02-24Not applicableCanada
Suprefact Inj 1mg/mlliquid1 mgsubcutaneousHoechst Canada Inc.1988-12-311998-08-25Canada
Suprefact Intranasal Solution 1mg/mlspray1 mgnasalHoechst Canada Inc.1988-12-311996-08-29Canada
Suprefact Liq 1mg/mlliquid1 mgnasalHoechst Roussel Canada Inc.1993-12-312000-07-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CinnafactCinnagen
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Buserelin acetate
ThumbNot applicableDBSALT001170
Categories
UNIIPXW8U3YXDV
CAS number57982-77-1
Taxonomy
DescriptionNot Available
KingdomOrganic Compounds
Super ClassOrganic Acids
ClassCarboxylic Acids and Derivatives
Sub ClassAmino Acids, Peptides, and Analogues
Direct ParentPeptides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Pharmacology
IndicationBuserelin 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.
PharmacodynamicsThe 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 actionBuserelin 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.
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AbsorptionBuserelin 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 binding15%
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 eliminationBuserelin 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 lifeThe 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.
ClearanceNot Available
ToxicityBuserelin 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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionnasal1 mg
Solutionsubcutaneous1 mg
Implantsubcutaneous6.3 mg
Implantsubcutaneous9.45 mg
Liquidsubcutaneous1 mg
Spraynasal1 mg
Liquidnasal1 mg
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental PropertiesNot Available
References
Synthesis ReferenceNot Available
General References
  1. Link [Link]
External Links
ATC CodesL02AE01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Buserelin.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Buserelin.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Buserelin.
CapromabBuserelin may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Buserelin.
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Buserelin.
CitalopramBuserelin may increase the QTc-prolonging activities of Citalopram.
Corifollitropin AlfaThe therapeutic efficacy of Corifollitropin Alfa can be increased when used in combination with Buserelin.
DofetilideBuserelin may increase the QTc-prolonging activities of Dofetilide.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Buserelin.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Buserelin.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Buserelin.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Buserelin.
GoserelinBuserelin may increase the QTc-prolonging activities of Goserelin.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Buserelin.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Buserelin.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Buserelin.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Buserelin.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Buserelin.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Buserelin.
LeuprolideBuserelin may increase the QTc-prolonging activities of Leuprolide.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Buserelin.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Buserelin.
MifepristoneMifepristone may increase the QTc-prolonging activities of Buserelin.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Buserelin.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Buserelin.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Buserelin.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Buserelin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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
Molecular Weight:
78642.01 Da
References
  1. 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. [PubMed:20053189 ]
Kind
Protein
Organism
Human
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 (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol-calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling.
Gene Name:
GNRHR
Uniprot ID:
P30968
Molecular Weight:
37730.355 Da
References
  1. 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. [PubMed:20053189 ]

Enzymes

Kind
Protein
Organism
Human
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
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 07, 2010 16:44 / Updated on August 17, 2016 12:24