Histrelin acetate is a potent LHRH agonist. After a transient increase, continuous administration results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis.
CAT No: 10-101-21
CAS No: 76712-82-8 (net)
Synonyms/Alias: (Des-Gly10,D-His(Bzl)6,Pro-NHEt9)-LHRH; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-1-benzyl-D-histidyl-L-leucyl-L-arginyl-L-proline ethylamide acetic acid
Chemical Name: acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(1-benzylimidazol-4-yl)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
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| M.F/Formula | C66H86N18O12 |
| M.W/Mr. | 1383.6 |
| Sequence | One Letter Code: XHWSYXLRP Three Letter Code: H-Pyr-His-Trp-Ser-Tyr-D-His(1-Bn)-Leu-Arg-Pro-NHEt.CH3CO2H |
| Labeling Target | Gonadotropin-releasing hormone receptor |
| Application | Histrelin is used to treat hormone-sensitive cancers of the prostate in men and uterine fibroids in women. In addition, histrelin has been proven to be highly effective in treating central precocious puberty in children. |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Activity | Agonist |
| Areas of Interest | Cardiovascular System & Diseases Pituitary & Hypothalamic Hormones |
| Target | Gonadotropin-releasing hormone (GnRH) |
| Source# | Synthetic |
| Long-term Storage Conditions | Soluble in DMSO, not in water |
| 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. |
| Short-term Storage Conditions | Dry, dark and at 0 - 4 °C |
| Solubility | -20 °C |
| Organism | Human |
| InChI | InChI=1S/C66H86N18O12.C2H4O2/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47;1-2(3)4/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71);1H3,(H,3,4)/t47-,48-,49-,50-,51-,52-,53+,54-,55-;/m0./s1 |
| InChI Key | OWAUGAMNPZHEOJ-YKZVIGSYSA-N |
| Canonical SMILES | CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC2=CN(C=N2)CC3=CC=CC=C3)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8.CC(=O)O |
| Isomeric SMILES | CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CN(C=N2)CC3=CC=CC=C3)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8.CC(=O)O |
| BoilingPoint | 1800.6ºC at 760 mmHg |
| ShelfLife | >2 years if stored properly |
| References | The once-yearly histrelin implant maintained testosterone suppression for repeated treatment cycles and was generally well tolerated. The histrelin implant provides a clinically attractive option for long-term androgen deprivation therapy in patients with advanced prostate cancer seeking fewer office visits and repeated injections. Shore, N., Cookson, M. S., & Gittelman, M. C. (2012). Long‐term efficacy and tolerability of once‐yearly histrelin acetate subcutaneous implant in patients with advanced prostate cancer. BJU international, 109(2), 226-232. The LHRH agonist histrelin acetate is the only available sustained-release hydrogel implant for once-yearly administration. The once-yearly implant allows patients to receive fewer cycles of implanting and replanting to maintain continuous ADT therapy. The histrelin acetate implant is 3.5 cm long, is 3 mm in diameter, and is administered subcutaneously into the inner aspect of the upper arm or abdomen. The inner aspect of the upper arm can clinically be difficult for the surgeon as it is a mobile insertion site and difficult for elderly patients limited by strength/arthritis to maintain the necessary abducted and extended arm position. Thus, the arm compared to the abdomen site is more difficult for surgeon and is less tolerated by patients. Woolen, S., Holzmeyer, C., Nesbitt, E., & Siami, P. F. (2014). Long-term efficacy and tolerability of abdominal once-yearly histrelin acetate subcutaneous implants in patients with advanced prostate cancer. Prostate cancer, 2014. |
| Melting Point | N/A |
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