Histrelin

Histrelin
Clinical data
Trade names	Vantas, Supprelin LA, others
Other names	ORF-17070, RWJ-17070
AHFS/Drugs.com	Monograph
MedlinePlus	a601146
License data	US DailyMed: Histrelin;
Routes of; administration	Subcutaneous implant
Drug class	GnRH analogue; GnRH agonist; Antigonadotropin
ATC code	L02AE05 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	92%
Protein binding	70%
Metabolism	Liver
Elimination half-life	4.0 hours
Identifiers
	IUPAC name 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-1-benzyl-D-histidyl-L-leucyl-N5-(diaminomethylene)-L-ornithyl-N-ethyl-L-prolinamide;
CAS Number	76712-82-8 ; as salt: 220810-26-4;
PubChem CID	25077993; as salt: 56927879;
IUPHAR/BPS	3884;
DrugBank	DB06788 ; as salt: DBSALT001172;
ChemSpider	10482012 ; as salt: 26606349;
UNII	H50H3S3W74; as salt: QMG7HLD1ZE;
KEGG	D02369 ;
ChEBI	CHEBI:5739; as salt: CHEBI:63530;
ChEMBL	ChEMBL1201255 ; as salt: ChEMBL1200509;
CompTox Dashboard (EPA)	DTXSID50227543 ;
ECHA InfoCard	100.163.860
Chemical and physical data
Formula	C66H86N18O12
Molar mass	1323.528 g·mol−1
3D model (JSmol)	Interactive image; as salt: Interactive image;
	SMILES CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2cn(Cc3ccccc3)cn2)NC(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc5c[nH]c6ccccc56)NC(=O)[C@H](Cc7c[nH]cn7)NC(=O)[C@@H]8CCC(=O)N8; ; as salt: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2cn(Cc3ccccc3)cn2)NC(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc5c[nH]c6ccccc56)NC(=O)[C@H](Cc7c[nH]cn7)NC(=O)[C@@H]8CCC(=O)N8.CC(=O)O.CC(=O)O;
	InChI InChI=1S/C66H86N18O12/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/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)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1 ; Key:HHXHVIJIIXKSOE-QILQGKCVSA-N ; ; as salt: InChI=1S/C66H86N18O12.2C2H4O2/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;21-2(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);21H3,(H,3,4)/t47-,48-,49-,50-,51-,52-,53+,54-,55-;;/m0../s1; Key:BKEMVGVBBDMHKL-VYFXDUNUSA-N;
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Histrelin acetate, sold under the brand name Supprelin among others, is a nonapeptide analogue of gonadotropin-releasing hormone (GnRH) with added potency.^[2] When present in the bloodstream, it acts on particular cells of the pituitary gland called gonadotropes. Histrelin stimulates these cells to release luteinizing hormone and follicle-stimulating hormone. Thus it is considered a gonadotropin-releasing hormone agonist or GnRH agonist.

^ "Supprelin LA- histrelin acetate implant". DailyMed. 30 April 2022. Retrieved 25 September 2024.
^ Davis M (25 February 2005). Chandramouli J (ed.). "Histrelin acetate (Vantas)". New Drug Bulletins. University of Utah Hospitals & Clinics. Archived from the original on 10 May 2006.

[1] "Supprelin LA- histrelin acetate implant". DailyMed. 30 April 2022. Retrieved 25 September 2024.

[def-2] Davis M (25 February 2005). Chandramouli J (ed.). "Histrelin acetate (Vantas)". New Drug Bulletins. University of Utah Hospitals & Clinics. Archived from the original on 10 May 2006.

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