| Supplier |
Creative Peptides |
| Product # |
10-101-17 |
| CAS # |
66002-66-2 |
| Pricing |
Inquire
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| LabelingTarget |
Gonadotropin-releasing hormone (GNRH) Receptor
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| Synonyms |
(Des-Gly10,Pro-NHEt9)-LHRH; Fertirelin; Fertirelina; Fertireline; Fertirelinum
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| MolecularFormula |
C55H74N16O13
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| MolecularWeight |
1166.56
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| Source |
Synthetic
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| Sequence |
- One Letter Code: XHWSYGLRP
- Three Letter Code: H-Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-NHEt.CH3CO2H
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| Explanation |
Fertirelin 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.
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| ChemicalName |
acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]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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| Application |
In veterinary medicine fertirelin acetate is used in the treatment of ovarian follicular cysts in cattle and for the improvement of conception rates in cows.
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| Activity |
Agonist
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| InChI |
InChI=1S/C55H76N16O12.C2H4O2/c1-4-59-53(82)44-12-8-20-71(44)54(83)38(11-7-19-60-55(56)57)66-49(78)39(21-30(2)3)65-46(75)27-62-47(76)40(22-31-13-15-34(73)16-14-31)67-52(81)43(28-72)70-50(79)41(23-32-25-61-36-10-6-5-9-35(32)36)68-51(80)42(24-33-26-58-29-63-33)69-48(77)37-17-18-45(74)64-37;1-2(3)4/h5-6,9-10,13-16,25-26,29-30,37-44,61,72-73H,4,7-8,11-12,17-24,27-28H2,1-3H3,(H,58,63)(H,59,82)(H,62,76)(H,64,74)(H,65,75)(H,66,78)(H,67,81)(H,68,80)(H,69,77)(H,70,79)(H4,56,57,60);1H3,(H,3,4)/t37-,38-,39-,40-,41-,42-,43-,44-;/m0./s1
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| InChIKey |
ZVTCYOIDKTXKGH-UYRFKBGYSA-N
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| CanonicalSMILES |
CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6.CC(=O)O
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| IsomericSMILES |
CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O
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| Target |
Gonadotropin-releasing hormone (GnRH)
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| Reference |
- The effect of using a dose of 50 micro g rather than 100 micro g fertirelin in an ovulation/fixed-time insemination protocol for Holstein-Friesian dairy cows was investigated in three experiments. In each experiment, fertirelin was administered at the beginning of the protocol followed 7 days later by 500 micro g cloprosterol. Two days later, a second dose of fertirelin was given and AI performed 16-19 h later regardless of the incidence of behavioral oestrus. The effect on conception rate was studied in experiment 1 using 114 postpartum anoestrus cows. There was no significant difference in the age, parity or number of days after parturition in each treatment groups. The conception rate did not differ between the 50 micro g fertirelin group (61.1%; n=72) and the 100 micro g group (59.5%; n=42; NS). In experiment 2, a further 12 cows at 40-60 days postpartum were treated with 100 or 50 micro g fertirelin (n=6 per dose) with treatment commencing in the follicular or luteal phase of the oestrous cycle. The plasma concentration of luteinizing hormone (LH) reached similar peaks of over 5 ng/ml 120 min after the intramuscular administration of fertirelin in both groups. There were no significant differences in LH levels between treatments or phase of the oestrous cycle when treatment commenced. Doses of 50 and 100 micro g fertirelin were compared in experiment 3 using 17 cows to study follicular wave development and synchronization by transrectal ultrasonography, conception rate and corpus luteum function. There were no significant differences between treatments for these factors. It was concluded that using a dose of 50 micro g fertirelin enabled the drug costs to be reduced without affecting the efficiency of a synchronization of ovulation/fixed-time AI protocol for dairy cows.
- Yamada, K., Nakao, T., Nakada, K., & Matsuda, G. (2002). Influence of GnRH analogue (fertirelin acetate) doses on synchronization of ovulation and fixed-time artificial insemination in lactating dairy cows. Animal reproduction science, 74(1), 27-34.
- The optimum dose for establishing superovulation in mice of Fertirelin Acetate (FA), an LH-RH analogue, was examined. Mice were subcutaneously injected with 5 IU of hCG at 17:00 (Day 0), and with various doses of FA (0.001 to 1.0 microg) five times at 4 h intervals on and after 22:00 on Day 0. To induce ovulation, 5 IU of hCG was again injected subcutaneously at 17:00 on Day 2. In the groups administered with doses ranging from 0.01 to 0.5 microg of FA, the number of ovulated eggs was significantly (p<0.05) larger than in the control group (12.9 +/- 5.9). The greatest number of ovulated eggs (22.6 +/- 7.3) was obtained in the group administered with 0.025 microg of FA. The results indicate that the effective dose of LH-RH analogue, FA, is between 0.1 and 0.5 microg for superovulation induction in mice.
- Nariai, K., Ishinazaka, T., Suzuki, K., UCHIYAMA, H., SATO, K., ASANO, R., ... & KANAYAMA, K. (2005). Optimum dose of LH-RH analogue Fertirelin Acetate for the induction of superovulation in mice. Experimental animals, 54(1), 97-99.
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| AreasOfInterest |
- Pituitary & Hypothalamic Hormones
- Veterinary Medicine
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| LongTermStorageConditions |
−20°C
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