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Bremelanotide

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Chemistry

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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

Bremelanotide Acetate

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 Formula	C₅₀H₆₈N₁₄O₁₀
Molecular Weight	1025.2 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	17
Exact Mass	1024.52428442 g/mol
Monoisotopic Mass	1024.52428442 g/mol
Topological Polar Surface Area	379 Å²
Heavy Atom Count	74
Formal Charge	0
Complexity	1950
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 T_max or 1.0 hour (0.5-1.0 hours) and is 100% bioavailable. The C_max 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.

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