Bremelanotide
Identification
- Brand Names
- Vyleesi
- Generic Name
- Bremelanotide
- DrugBank Accession Number
- DB11653
- Background
Bremelanotide is a 7 amino acid peptide used to treat hypoactive sexual desire disorder in premenopausal women.5 Bremelanotide does not interact with alcohol.2 The mechanism by which bremelanotide's action on receptors translates to a clinical effect is still unknown.5
Bremelanotide was first described in the literature in 2003 when it was known by the investigational code PT-141.1 Since then it was investigated for its place in treating sexual dysfunction in men and women but is now only indicated for women.1,2,5 Other drugs used to treat female sexual dysfunction include flibanserin, estrogen, ospemifene, and prasterone.3
Bremelanotide was granted FDA approval on 21 June 2019.5
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Bremelanotide (DB11653)
- Weight
- Average: 1025.182
Monoisotopic: 1024.524284446 - Chemical Formula
- C50H68N14O10
- Synonyms
- Bremelanotida
- Bremelanotide
- Brémelanotide
- Bremelanotidum
- External IDs
- PT 141
- PT-141
Pharmacology
- Indication
Bremelanotide is indicated to treat premenopausal women with hypoactive sexual desire disorder that is not due to a medical or psychiatric condition, problems with the relationship, or the effects of a medication or drug.5
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- Contraindications & Blackbox Warnings
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Bremelanotide is a melanocortin receptor agonist injected 45 minutes before anticipated sexual activity.5 Agonism of the melanocortin receptor MC1R also leads to increased melanin expression.5 Patients taking bremelanotide may also experience nausea, headache, and vomiting.5
- Mechanism of action
Bremelanotide is an agonist of many melanocortin receptors which in order of potency are MC1R, MC4R, MC3R, MC5R, and MC2R.5 The mechanism by which agonism of these receptors translates to an improvement in hypoactive sexual desire disorder is currently unknown, however MC4R receptors are present in many areas of the central nervous system.5 MC3R and MC4R are found in the hypothalamus and are involved in food intake and energy homeostasis.1
One theory is that bremelanotide stimulates dopamine in the medial preoptic area, which is involved in the sexual behaviour of a number of organisms.4
Target Actions Organism UMelanocyte-stimulating hormone receptor agonistHumans UMelanocortin receptor 4 agonistHumans UMelanocortin receptor 3 agonistHumans UMelanocortin receptor 5 agonistHumans UAdrenocorticotropic hormone receptor agonistHumans - Absorption
Bremelanotide has a Tmax or 1.0 hour (0.5-1.0 hours) and is 100% bioavailable.5 The Cmax is 72.8ng/mL and the AUC is 276hr*ng/mL.5
- Volume of distribution
The mean volume of distribution of bremelanotide is 25.0±5.8L.5
- Protein binding
Bremelanotide is 21% protein bound in serum.5
- Metabolism
Bremelanotide is a 7 amino acid and so its metabolism consists of multiple hydrolysis reactions.5
- Route of elimination
64.8% of a radiolabelled dose is excreted in the urine and 22.8% of the dose is recovered in the feces.5
- Half-life
The half life of bremelanotide is 2.7 hours (1.9-4.0 hours).5
- Clearance
The mean clearance of bremelanotide is 6.5±1.0L/hr.5
- Adverse Effects
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Currently there are no reports of overdoses of bremelanotide.5 Patients taking higher doses are more likely to experience nausea, focal hyperpigmentation, and increases in blood pressure.5 In the event of an overdose, supportive measures should be used to address the associated symptoms.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
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interactions in your softwareNaltrexone The serum concentration of Naltrexone can be decreased when it is combined with Bremelanotide. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bremelanotide acetate PV2WI7495P 1607799-13-2 MAYUSRUHXFWITM-GBRHMYBBSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vyleesi Injection 1.75 mg/0.3mL Subcutaneous Palatin Technologies 2019-06-21 Not applicable US 
Vyleesi Injection 1.75 mg/0.3mL Subcutaneous AMAG Pharmaceuticals, Inc. 2019-06-21 Not applicable US
Categories
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hypothalamic Hormones
- Melanocortins
- Melanocyte-Stimulating Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Peptide Hormones
- Peptides
- Pituitary Hormones
- Pituitary Hormones, Anterior
- Pro-Opiomelanocortin
- Protein Precursors
- Proteins
- Receptor, Melanocortin, Type 3, agonists
- Receptor, Melanocortin, Type 4, agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / N-acyl-alpha amino acids and derivatives / Macrolactams / Alpha amino acid amides / 3-alkylindoles / Imidazolyl carboxylic acids and derivatives / Benzene and substituted derivatives / Substituted pyrroles / N-acyl amines / Acetamides show 12 more
- Substituents
- 3-alkylindole / Acetamide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group show 31 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6Y24O4F92S
- CAS number
- 189691-06-3
- InChI Key
- FFHBJDQSGDNCIV-MFVUMRCOSA-N
- InChI
- InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1
- IUPAC Name
- (3S,6S,9R,12S,15S,23S)-9-benzyl-6-(3-carbamimidamidopropyl)-15-[(2S)-2-acetamidohexanamido]-12-[(1H-imidazol-5-yl)methyl]-3-[(1H-indol-3-yl)methyl]-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexaazacyclotricosane-23-carboxylic acid
- SMILES
- CCCC[C@H](NC(C)=O)C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CN=CN2)NC1=O)C(O)=O
References
- General References
- Molinoff PB, Shadiack AM, Earle D, Diamond LE, Quon CY: PT-141: a melanocortin agonist for the treatment of sexual dysfunction. Ann N Y Acad Sci. 2003 Jun;994:96-102. doi: 10.1111/j.1749-6632.2003.tb03167.x. [Article]
- Clayton AH, Lucas J, DeRogatis LR, Jordan R: Phase I Randomized Placebo-controlled, Double-blind Study of the Safety and Tolerability of Bremelanotide Coadministered With Ethanol in Healthy Male and Female Participants. Clin Ther. 2017 Mar;39(3):514-526.e14. doi: 10.1016/j.clinthera.2017.01.018. Epub 2017 Feb 9. [Article]
- Miller MK, Smith JR, Norman JJ, Clayton AH: Expert opinion on existing and developing drugs to treat female sexual dysfunction. Expert Opin Emerg Drugs. 2018 Sep;23(3):223-230. doi: 10.1080/14728214.2018.1527901. Epub 2018 Oct 11. [Article]
- Both S: Recent Developments in Psychopharmaceutical Approaches to Treating Female Sexual Interest and Arousal Disorder. Curr Sex Health Rep. 2017;9(4):192-199. doi: 10.1007/s11930-017-0124-3. Epub 2017 Oct 19. [Article]
- FDA Approved Drug Products: Bremelanotide Injection [Link]
- External Links
- PubChem Compound
- 9941379
- PubChem Substance
- 347828024
- ChemSpider
- 8116997
- BindingDB
- 50389769
- 2176312
- ChEMBL
- CHEMBL2070241
- Wikipedia
- Bremelanotide
- MSDS
- Download (526 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Recruiting Treatment Hypoactive Sexual Desire Disorder (HSDD) 1 3 Active Not Recruiting Treatment Hypoactive Sexual Desire Disorder (HSDD) 1 3 Completed Treatment Hypoactive Sexual Desire Disorder (HSDD) 2 2 Completed Not Available Arousal Disorders, Sexual 1 2 Completed Treatment Hypoactive Sexual Desire Disorder (HSDD) / Sexual; Disorder, Arousal, Female 1 1 Completed Treatment Nausea 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Subcutaneous 1.75 mg/0.3mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9700592 No 2017-07-11 2033-11-05 US US9352013 No 2016-05-31 2033-11-05 US US10286034 No 2019-05-14 2033-11-05 US US6794489 No 2004-09-21 2020-06-28 US US6579968 No 2003-06-17 2020-06-28 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 230 MSDS - Predicted Properties
Property Value Source Water Solubility 0.0251 mg/mL ALOGPS logP 0.69 ALOGPS logP -3.2 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 3.45 ChemAxon pKa (Strongest Basic) 11.96 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 14 ChemAxon Hydrogen Donor Count 14 ChemAxon Polar Surface Area 376.47 Å2 ChemAxon Rotatable Bond Count 17 ChemAxon Refractivity 278.91 m3·mol-1 ChemAxon Polarizability 106.06 Å3 ChemAxon Number of Rings 5 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
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Receptor for MSH (alpha, beta and gamma) and ACTH. The activity of this receptor is mediated by G proteins which activate adenylate cyclase.
- Gene Name
- MC1R
- Uniprot ID
- Q01726
- Uniprot Name
- Melanocyte-stimulating hormone receptor
- Molecular Weight
- 34705.04 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Receptor specific to the heptapeptide core common to adrenocorticotropic hormone and alpha-, beta-, and gamma-MSH. Plays a central role in energy homeostasis and somatic growth. This receptor is mediated by G proteins that stimulate adenylate cyclase (cAMP).
- Specific Function
- Melanocortin receptor activity
- Gene Name
- MC4R
- Uniprot ID
- P32245
- Uniprot Name
- Melanocortin receptor 4
- Molecular Weight
- 36942.325 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Receptor for MSH (alpha, beta and gamma) and ACTH. This receptor is mediated by G proteins which activate adenylate cyclase. Required for expression of anticipatory patterns of activity and wakefulness during periods of limited nutrient availability and for the normal regulation of circadian clock activity in the brain.
- Specific Function
- Melanocortin receptor activity
- Gene Name
- MC3R
- Uniprot ID
- P41968
- Uniprot Name
- Melanocortin receptor 3
- Molecular Weight
- 36042.75 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Receptor for MSH (alpha, beta and gamma) and ACTH. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. This receptor is a possible mediator of the immunomodulation properties of melanocortins.
- Specific Function
- Hormone binding
- Gene Name
- MC5R
- Uniprot ID
- P33032
- Uniprot Name
- Melanocortin receptor 5
- Molecular Weight
- 36600.21 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Melanocortin receptor activity
- Specific Function
- Receptor for corticotropin (ACTH). This receptor is mediated by G proteins (G(s)) which activate adenylate cyclase (cAMP).
- Gene Name
- MC2R
- Uniprot ID
- Q01718
- Uniprot Name
- Adrenocorticotropic hormone receptor
- Molecular Weight
- 33926.28 Da
Drug created on October 20, 2016 20:37 / Updated on February 21, 2021 18:53