Bremelanotide

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MedKoo CAT#: 597534

CAS#: 189691-06-3 (free base)

Description: Bremelanotide is a melanocortin receptor (MCR) agonist that nonselectively activates several receptor subtypes with the following order of potency: MC1R, MC4R, MC3R, MC5R, MC2R. At therapeutic dose levels, binding to MC1R and MC4R is most relevant. Neurons expressing MC4R are present in many areas of the central nervous system (CNS). The mechanism by which VYLEESI improves HSDD in women is unknown. The MC1R is expressed on melanocytes; binding at this receptor leads to melanin expression and increased pigmentation. Bremelanotide was approved in 6/21/2018 To treat hypoactive sexual desire disorder in premenopausal women.

Chemical Structure

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Bremelanotide
CAS# 189691-06-3 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 597534
Name: Bremelanotide
CAS#: 189691-06-3 (free base)
Chemical Formula: C50H68N14O10
Exact Mass: 1,024.52
Molecular Weight: 1,025.180
Elemental Analysis: C, 58.58; H, 6.69; N, 19.13; O, 15.61

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 1607799-13-2 (acetate)   189691-06-3 (free base)    

Synonym: Bremelanotide; PT 141; PT-141; PT141;

IUPAC/Chemical Name: (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

InChi Key: FFHBJDQSGDNCIV-MFVUMRCOSA-N

InChi Code: 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

SMILES Code: CCCC[C@@H](C(N[C@H]1CC(NCCCC[C@@H](C(O)=O)NC([C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC1=O)Cc2[nH]cnc2)=O)Cc3ccccc3)=O)CCCNC(N)=N)=O)Cc(c[nH]4)c5c4cccc5)=O)=O)=O)NC(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,025.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Simon JA, Kingsberg SA, Portman D, Williams LA, Krop J, Jordan R, Lucas J, Clayton AH. Long-Term Safety and Efficacy of Bremelanotide for Hypoactive Sexual Desire Disorder. Obstet Gynecol. 2019 Nov;134(5):909-917. doi: 10.1097/AOG.0000000000003514. PubMed PMID: 31599847; PubMed Central PMCID: PMC6819023.

2: Kingsberg SA, Clayton AH, Portman D, Williams LA, Krop J, Jordan R, Lucas J, Simon JA. Bremelanotide for the Treatment of Hypoactive Sexual Desire Disorder: Two Randomized Phase 3 Trials. Obstet Gynecol. 2019 Nov;134(5):899-908. doi: 10.1097/AOG.0000000000003500. PubMed PMID: 31599840; PubMed Central PMCID: PMC6819021.

3: Dhillon S, Keam SJ. Bremelanotide: First Approval. Drugs. 2019 Sep;79(14):1599-1606. doi: 10.1007/s40265-019-01187-w. Review. PubMed PMID: 31429064.

4: Bremelanotide (Vyleesi) for hypoactive sexual desire disorder. Med Lett Drugs Ther. 2019 Jul 29;61(1577):114-116. Review. PubMed PMID: 31381550.

5: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK544629/ PubMed PMID: 31369224.

6: Althof S, Derogatis LR, Greenberg S, Clayton AH, Jordan R, Lucas J, Spana C. Responder Analyses from a Phase 2b Dose-Ranging Study of Bremelanotide. J Sex Med. 2019 Aug;16(8):1226-1235. doi: 10.1016/j.jsxm.2019.05.012. Epub 2019 Jul 2. PubMed PMID: 31277966.

7: Nappi RE, Gardella B. What are the challenges in prescribing pharmacotherapy for female sexual dysfunctions? Expert Opin Pharmacother. 2019 May;20(7):777-779. doi: 10.1080/14656566.2019.1582644. Epub 2019 Feb 26. PubMed PMID: 30806100.

8: 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. Review. PubMed PMID: 30251897.

9: Weinberger JM, Houman J, Caron AT, Patel DN, Baskin AS, Ackerman AL, Eilber KS, Anger JT. Female Sexual Dysfunction and the Placebo Effect: A Meta-analysis. Obstet Gynecol. 2018 Aug;132(2):453-458. doi: 10.1097/AOG.0000000000002733. PubMed PMID: 29995725.

10: Pyke RE, Clayton AH. Effect Size in Efficacy Trials of Women With Decreased Sexual Desire. Sex Med Rev. 2018 Jul;6(3):358-366. doi: 10.1016/j.sxmr.2018.01.003. Epub 2018 Mar 22. Review. PubMed PMID: 29576442.

11: Clayton AH, Kingsberg SA, Goldstein I. Evaluation and Management of Hypoactive Sexual Desire Disorder. Sex Med. 2018 Jun;6(2):59-74. doi: 10.1016/j.esxm.2018.01.004. Epub 2018 Mar 6. Review. PubMed PMID: 29523488; PubMed Central PMCID: PMC5960024.

12: 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. Review. PubMed PMID: 29225554; PubMed Central PMCID: PMC5711968.

13: Croft HA. Understanding the Role of Serotonin in Female Hypoactive Sexual Desire Disorder and Treatment Options. J Sex Med. 2017 Dec;14(12):1575-1584. doi: 10.1016/j.jsxm.2017.10.068. Review. PubMed PMID: 29198512.

14: Petherick A. Sexual arousal: Sex matters. Nature. 2017 Oct 4;550(7674):S2-S3. doi: 10.1038/550S2a. PubMed PMID: 28976951.

15: Gelman F, Atrio J. Flibanserin for hypoactive sexual desire disorder: place in therapy. Ther Adv Chronic Dis. 2017 Jan;8(1):16-25. doi: 10.1177/2040622316679933. Epub 2017 Jan 18. Review. PubMed PMID: 28203348; PubMed Central PMCID: PMC5298357.

16: 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. PubMed PMID: 28189361.

17: White WB, Myers MG, Jordan R, Lucas J. Usefulness of ambulatory blood pressure monitoring to assess the melanocortin receptor agonist bremelanotide. J Hypertens. 2017 Apr;35(4):761-768. doi: 10.1097/HJH.0000000000001221. PubMed PMID: 27977473; PubMed Central PMCID: PMC5338879.

18: Seftel AD. Re: Bremelanotide for Female Sexual Dysfunctions in Premenopausal Women: A Randomized, Placebo-Controlled Dose-Finding Trial. J Urol. 2016 Nov;196(5):1516-1517. doi: 10.1016/j.juro.2016.08.063. Epub 2016 Aug 23. PubMed PMID: 27751477.

19: Clayton AH, Althof SE, Kingsberg S, DeRogatis LR, Kroll R, Goldstein I, Kaminetsky J, Spana C, Lucas J, Jordan R, Portman DJ. Bremelanotide for female sexual dysfunctions in premenopausal women: a randomized, placebo-controlled dose-finding trial. Womens Health (Lond). 2016 Jun;12(3):325-37. doi: 10.2217/whe-2016-0018. Epub 2016 May 16. PubMed PMID: 27181790; PubMed Central PMCID: PMC5384512.

20: Kingsberg SA, Clayton AH, Pfaus JG. The Female Sexual Response: Current Models, Neurobiological Underpinnings and Agents Currently Approved or Under Investigation for the Treatment of Hypoactive Sexual Desire Disorder. CNS Drugs. 2015 Nov;29(11):915-33. doi: 10.1007/s40263-015-0288-1. Review. PubMed PMID: 26519340.