Bremelanotide Acetate (PT-141; PT141; PT 141; Vyleesi), the acetatea salt of Bremelanotide, is a peptide analogue of alpha-MSH peptide acting as a melanocortin receptor agonist. It was created to treat hemorrhagic shock, reperfusion injury, and sexual dysfunction. In 2019, bremelanotide received approval to treat premenopausal women with hypoactive sexual desire disorder.
Physicochemical Properties
| Molecular Formula | C₅₂H₇₂N₁₄O₁₂ |
| Molecular Weight | 1085.22 |
| Exact Mass | 1084.545 |
| Elemental Analysis | C, 57.55; H, 6.69; N, 18.07; O, 17.69 |
| CAS # | 1607799-13-2 |
| Related CAS # | Bremelanotide; 189691-06-3 |
| PubChem CID | 91971505 |
| Sequence | Ac-Nle-Asp(1)-His-D-Phe-Arg-Trp-Lys(1)-OH.CH3CO2H |
| Appearance | White to off-white solid powder |
| Hydrogen Bond Donor Count | 14 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 17 |
| Heavy Atom Count | 78 |
| Complexity | 1980 |
| Defined Atom Stereocenter Count | 7 |
| SMILES | O=C1[C@]([H])(C([H])([H])C([H])([H])C([H])([H])/N=C(\N([H])[H])/N([H])[H])N([H])C([C@@]([H])(C([H])([H])C2C([H])=C([H])C([H])=C([H])C=2[H])N([H])C([C@]([H])(C([H])([H])C2=C([H])N=C([H])N2[H])N([H])C([C@]([H])(C([H])([H])C(N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(C(=O)O[H])N([H])C([C@]([H])(C([H])([H])C2=C([H])N([H])C3=C([H])C([H])=C([H])C([H])=C23)N1[H])=O)=O)N([H])C([C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])N([H])C(C([H])([H])[H])=O)=O)=O)=O)=O.O([H])C(C([H])([H])[H])=O |
| InChi Key | MAYUSRUHXFWITM-GBRHMYBBSA-N |
| InChi Code | InChI=1S/C50H68N14O10.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t35-,36-,37-,38+,39-,40-,41-;/m0./s1 |
| Chemical 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;acetic acid |
| Synonyms | PT141 acetate; PT 141 acetate; PT-141 Acetate; PT-141; PT141; PT 141; Vyleesi; Bremelanotide acetate; Bremelanotide |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | Bremelanotide Acetate (50-200 μg/kg; s.c.; once) significantly increases proceptive solicitations in females primed with either estradiol benzoate alone or estradiol benzoate plus progesterone in bilevel chambers[2]. |
| Animal Protocol |
Ovariectomized Long–Evans rats 50, 100, 200 μg/kg s.c.; once |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No information is available on the clinical use of bremelanotide during breastfeeding. Because bremelanotide is a cyclic peptide molecule with a molecular weight of 1025, the amount in milk is likely to be very low and absorption is unlikely because it is probably destroyed in the infant's gastrointestinal tract. Until more data become available, bremelanotide should be used with caution during breastfeeding, especially while nursing a newborn or preterm infant. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. PT-141: a melanocortin agonist for the treatment of sexual dysfunction. Ann N Y Acad Sci. 2003 Jun;994:96-102. [2]. Selective facilitation of sexual solicitation in the female rat by a melanocortin receptor agonist. Proc Natl Acad Sci U S A. 2004 Jul 6;101(27):10201-4. |
| Additional Infomation | See also: Bremelanotide (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
H2O: ≥ 50 mg/mL (~46.1 mM) DMSO: ≥ 36 mg/mL (~33.2 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (1.92 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (1.92 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (1.92 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.9215 mL | 4.6074 mL | 9.2147 mL | |
| 5 mM | 0.1843 mL | 0.9215 mL | 1.8429 mL | |
| 10 mM | 0.0921 mL | 0.4607 mL | 0.9215 mL |