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    Bremelanotide

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    PATENTS & EXCLUSIVITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 322,960Xls

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    2D Structure
    Also known as: 189691-06-3, Pt-141, Pt-141 free base, 6y24o4f92s, Vyleesi (tn), (3s,6s,9r,12s,15s,23s)-15-[[(2s)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1h-imidazol-5-ylmethyl)-3-(1h-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxylic acid
    Molecular Formula
    C50H68N14O10
    Molecular Weight
    1025.2  g/mol
    InChI Key
    FFHBJDQSGDNCIV-MFVUMRCOSA-N
    FDA UNII
    6Y24O4F92S
    Bremelanotide is a 7 amino acid peptide used to treat hypoactive sexual desire disorder in premenopausal women. Bremelanotide does not interact with alcohol. The mechanism by which bremelanotide's action on receptors translates to a clinical effect is still unknown. Bremelanotide was first described in the literature in 2003 when it was known by the investigational code PT-141. Since then it was investigated for its place in treating sexual dysfunction in men and women but is now only indicated for women. Other drugs used to treat female sexual dysfunction include [flibanserin], [estrogen], [ospemifene], and [prasterone]. Bremelanotide was granted FDA approval on 21 June 2019.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1H-imidazol-5-ylmethyl)-3-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxylic acid
    2.1.2 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
    2.1.3 InChI Key
    FFHBJDQSGDNCIV-MFVUMRCOSA-N
    2.1.4 Canonical SMILES
    CCCCC(C(=O)NC1CC(=O)NCCCCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)O)NC(=O)C
    2.1.5 Isomeric SMILES
    CCCC[C@@H](C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC2=CN=CN2)CC3=CC=CC=C3)CCCN=C(N)N)CC4=CNC5=CC=CC=C54)C(=O)O)NC(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    6Y24O4F92S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Pt-141

    2. Vyleesi

    2.3.2 Depositor-Supplied Synonyms

    1. 189691-06-3

    2. Pt-141

    3. Pt-141 Free Base

    4. 6y24o4f92s

    5. Vyleesi (tn)

    6. (3s,6s,9r,12s,15s,23s)-15-[[(2s)-2-acetamidohexanoyl]amino]-9-benzyl-6-[3-(diaminomethylideneamino)propyl]-12-(1h-imidazol-5-ylmethyl)-3-(1h-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexazacyclotricosane-23-carboxylic Acid

    7. (3s,6s,9r,12s,15s,23s)-12-((1h-imidazol-5-yl)methyl)-3-((1h-indol-3-yl)methyl)-15-((s)-2-acetamidohexanamido)-9-benzyl-6-(3-guanidinopropyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexaazacyclotricosane-23-carboxylic Acid

    8. Bremelanotide [usan:inn]

    9. Unii-6y24o4f92s

    10. Bremelanotide, Pt-141

    11. Bremelanotide [mi]

    12. Bremelanotide [inn]

    13. Pt-141 (bremelanotide)

    14. Bremelanotide (usan/inn)

    15. Bremelanotide [usan]

    16. Bremelanotide [who-dd]

    17. Chembl2070241

    18. Schembl13574795

    19. Schembl20337333

    20. Gtpl10408

    21. Dtxsid40893711

    22. Chebi:177849

    23. Pt141

    24. 189691-06-3 (free Base)

    25. Bdbm50389769

    26. Akos005145807

    27. Db11653

    28. Hs-2024

    29. Hy-18678

    30. Cs-0013839

    31. D06569

    32. Q415353

    33. Q-200747

    34. (1z,3s,4z,6s,7z,9r,10e,12s,13z,15s,17e,23s)-12-((1h-imidazol-5-yl)methyl)-3-((1h-indol-3-yl)methyl)-9-benzyl-6-(3-guanidinopropyl)-2,5,8,11,14,17-hexahydroxy-15-(((s,z)-1-hydroxy-2-(((z)-1-hydroxyethylidene)amino)hexylidene)amino)-1,4,7,10,13,18-hexaazacyclotricosa-1,4,7,10,13,17-hexaene-23-carboxylic Acid

    35. L-lysine, N-acetyl-l-norleucyl-l-.alpha.-aspartyl-l-histidyl-d-phenylalanyl-l-arginyl-l-tryptophyl-, (2->7)-lactam

    36. L-lysine, N-acetyl-l-norleucyl-l-alpha-aspartyl-l-histidyl-d-phenylalanyl-l-arginyl-l-tryptophyl-, (2->7)-lactam

    37. N-acetyl-l-2-aminohexanoyl-l-.alpha.-aspartyl-l-histidyl-d-phenylalanyl-l-arginyl-l-tryptophyl-l-lysine-(2->7)-lactam

    38. N-acetyl-l-2-aminohexanoyl-l-alpha-aspartyl-l-histidyl-d-phenylalanyl-l-arginyl-l-tryptophyl-l-lysine-(2->7)-lactam

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 1025.2 g/mol
    Molecular Formula C50H68N14O10
    XLogP30.7
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count17
    Exact Mass1024.52428442 g/mol
    Monoisotopic Mass1024.52428442 g/mol
    Topological Polar Surface Area379 Ų
    Heavy Atom Count74
    Formal Charge0
    Complexity1950
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug 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 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bremelanotide is a melanocortin receptor agonist injected 45 minutes before anticipated sexual activity. Agonism of the melanocortin receptor MC1R also leads to increased melanin expression. Patients taking bremelanotide may also experience nausea, headache, and vomiting.

    5.2 ATC Code

    G - Genito urinary system and sex hormones

    G02 - Other gynecologicals

    G02C - Other gynecologicals

    G02CX - Other gynecologicals

    G02CX05 - Bremelanotide

    5.3 Absorption, Distribution and Excretion

    Absorption

    Bremelanotide has a Tmax or 1.0 hour (0.5-1.0 hours) and is 100% bioavailable. The Cmax is 72.8ng/mL and the AUC is 276hr\*ng/mL.

    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.

    Volume of Distribution

    The mean volume of distribution of bremelanotide is 25.05.8L.

    Clearance

    The mean clearance of bremelanotide is 6.51.0L/hr.

    5.4 Metabolism/Metabolites

    Bremelanotide is a 7 amino acid and so its metabolism consists of multiple hydrolysis reactions.

    5.5 Biological Half-Life

    The half life of bremelanotide is 2.7 hours (1.9-4.0 hours).

    5.6 Mechanism of Action

    Bremelanotide is an agonist of many melanocortin receptors which in order of potency are MC1R, MC4R, MC3R, MC5R, and MC2R. 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. MC3R and MC4R are found in the hypothalamus and are involved in food intake and energy homeostasis. One theory is that bremelanotide stimulates dopamine in the medial preoptic area, which is involved in the sexual behaviour of a number of organisms.