CAS No.76932-56-4,Nafarelin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	76932-56-4
Name:	Nafarelin

Formula:	C₆₆H₈₃N₁₇O₁₃
Molecular Weight:	1322.47
Synonyms:	(D-2-Nal6)-LHRH;Luteinizinghormone-releasing factor (pig), 6-[3-(2-naphthalenyl)-D-alanine]-;NAG;Nafareline;[6-D-(2-naphthyl)-alanine]LH-RH;Luteinizinghormone-releasing factor (swine), 6-[3-(2-naphthalenyl)-D-alanine]-;
EINECS:	686-425-8
Density:	1.493 g/cm³
Appearance:	White or almost white lyophilized powder
PSA:	472.13000
LogP:	3.87190

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Specification

1. Introduction of Nafarelin
Nafarelin is one kind of white or almost white lyophilized powder. The IUPAC Name of this chemical is N-[1-[[1-[[1-[[1-[[1-[[1-[[1-[2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-naphthalen-2-yl-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.

Nafarelin belongs to Hormone and related drugs; Sex hormones and promote the sex hormone; Drug; polypeptide. Besides, the Classification Code of this chemical is Drug / Therapeutic Agent; Fertility Agents; Fertility Agents, Female; Human Data; Reproductive Control Agents. In addition, Nafarelin water solubility is 1.66e-02 g/l.

2. Properties of Nafarelin
Physical properties about Nafarelin are:
(1)Density: 1.49 g/cm³; (2)Index of Refraction: 1.71; (3)Surface Tension: 67.1 dyne/cm; (4)XLogP3-AA: 0.8; (5)H-Bond Donor: 16; (6)H-Bond Acceptor: 15; (7)Rotatable Bond Count: 33; (8)Tautomer Count: 996; (9)Exact Mass: 1321.635626; (10)MonoIsotopic Mass: 1321.635626; (11)Topological Polar Surface Area: 475; (12)Heavy Atom Count: 96; (13)Formal Charge: 0; (14)Complexity: 2730; (15)Isotope Atom Count: 0; (16)Defined Atom Stereocenter Count: 0; (17)Undefined Atom Stereocenter Count: 9; (18)Defined Bond Stereocenter Count: 0; (19)Undefined Bond Stereocenter Count: 0; (20)Covalently-Bonded Unit Count: 1.

3. Structure Descriptors of Nafarelin
(1)InChI: InChI=1S/C66H83N17O13/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71)
(2)InChIKey: RWHUEXWOYVBUCI-UHFFFAOYSA-N
(3)Canonical SMILES: CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CC2=CC3=CC=CC=C3C=C2)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
(4)Smiles: c1(c2c(cccc2)[nH]c1)C[C@@H](NC([C@@H](Cc1c[nH]cn1)NC([C@@H]1CCC(N1)=O)=O)=O)C(N[C@@H](C(N[C@@H](Cc1ccc(O)cc1)C(N[C@@H](Cc1cc2c(cccc2)cc1)C(N[C@@H](C(N[C@@H](C(N1[C@@H](CCC1)C(NCC(N)=O)=O)=O)CCCNC(N)=N)=O)CC(C)C)=O)=O)=O)CO)=O

4. Toxicity of Nafarelin

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
women	TDLo	oral	448ug/kg/8W-I (.448mg/kg)		Lancet. Vol. 347, Pg. 333, 1996.

5. Uses of Nafarelin
Nafarelin may be used in the treatment of estrogen-dependent conditions (such as endometriosis or uterine fibroids), to treat central precocious puberty, and to control ovarian stimulation in IVF. Nafarelin (CAS NO.76932-56-4) is a gonadotropin-releasing hormone agonist (GnRH agonist) which acts as an analog of GnRH. Nafarelin increases the release of FSH and LH by the anterior pituitary, which in turn leads to an increase of estrogen/progesterone. When administered, Nafarelin has the purpose of causing increase estrogen that will negatively feed back upon hypothalamus to decrease GnRH ( negative feedback loop ) Through negative feedback, Nafarelin causes a decrease in pituitary secretion of gonadotropins luteinizing hormone (LH) and follicle stimulating hormone (FSH).

6. Production of Nafarelin
N-acetyl-2-cyano-glycine ethyl ester in ethanol react with 2-(bromomethyl) naphthalene, and then acid hydrolysis to give the compound (I). (I) first acetylated ester-forming, and methanol, to generate the compound (II). (II) were separated to give the D-configuration of the type (III), then with 6mol / L hydrochloric acid hydrolysis to give the compound (IV). (IV) conversion of N-t-butyloxycarbonyl derivative (V), obtained by solid phase synthesis on benzhydrylamine resin nafarelin.

Production of Nafarelin