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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 Acetate
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 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.


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ABOUT THIS PAGE

Bremelanotide Acetate Manufacturers

A Bremelanotide Acetate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Bremelanotide Acetate, including repackagers and relabelers. The FDA regulates Bremelanotide Acetate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Bremelanotide Acetate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Bremelanotide Acetate manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Bremelanotide Acetate Suppliers

A Bremelanotide Acetate supplier is an individual or a company that provides Bremelanotide Acetate active pharmaceutical ingredient (API) or Bremelanotide Acetate finished formulations upon request. The Bremelanotide Acetate suppliers may include Bremelanotide Acetate API manufacturers, exporters, distributors and traders.

click here to find a list of Bremelanotide Acetate suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Bremelanotide Acetate NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Bremelanotide Acetate as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Bremelanotide Acetate API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Bremelanotide Acetate as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Bremelanotide Acetate and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Bremelanotide Acetate NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Bremelanotide Acetate suppliers with NDC on PharmaCompass.

Bremelanotide Acetate GMP

Bremelanotide Acetate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Bremelanotide Acetate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Bremelanotide Acetate GMP manufacturer or Bremelanotide Acetate GMP API supplier for your needs.

Bremelanotide Acetate CoA

A Bremelanotide Acetate CoA (Certificate of Analysis) is a formal document that attests to Bremelanotide Acetate's compliance with Bremelanotide Acetate specifications and serves as a tool for batch-level quality control.

Bremelanotide Acetate CoA mostly includes findings from lab analyses of a specific batch. For each Bremelanotide Acetate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Bremelanotide Acetate may be tested according to a variety of international standards, such as European Pharmacopoeia (Bremelanotide Acetate EP), Bremelanotide Acetate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Bremelanotide Acetate USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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